EP1900800A2 - 4-phenyl-pentan-2-ol as odorous and aromatic substance - Google Patents

Abstract

Fragrance or flavoring, comprises 4-phenylpentan-2-ol (I). Independent claims are included for: (1) a perfumed or flavored article comprising (I) and 1-3 or more other fragrances or flavorings; (2) a process for imparting, modifying and/or intensifying an odor or flavor with one or more or all of the notes green, fruity, comprising brought into contact or mixing (I) or the fragrance or flavoring composition comprising (I) with a product; and (3) preparation of (I) or a mixture containing (I) comprising catalytic cleavage of a substituted 1,3-dioxane of formula (A). Y 1>H or 1-10C acyl residue. [Image].

Description

The present invention relates to the use of 4-phenyl-pentan-2-ol as a fragrance and flavoring. The invention also relates to perfumed or flavored articles comprising this compound and corresponding methods for imparting, modifying and / or enhancing certain odor and / or flavor notes. Also described are processes for the preparation of 4-phenyl-pentan-2-ol.

Despite a large number of already existing fragrances, there is still a general need in the perfume industry for new fragrances. Thus, there is a need for fragrances with interesting green notes, which are able (in fragrance compositions) in addition to a green fragrance note other interesting odor notes, such as fruity notes to produce and expand with their novel or original fragrance properties, the possibilities of perfumers. In particular, there is an interest in fragrances with green and fruity scents, which are able to enter into a harmonious combination with floral-scented fragrances.

Preferably, a superimposition of the different odoriferous aspects and notes should take place in order thereby to produce an overall complex olfactory impression.

For the creation of novel modern compositions there is a constant need for fragrances with special odor properties, which are suitable to serve as the basis for the composition of novel modern perfumes with a complex odor character. Preferred fragrances sought after should have, in addition to a green, fruity scent, further notes and aspects that give them an odor character and complexity.

• Die Mechanismen der Geruchswahrnehmung sind nicht ausreichend bekannt.
• Die Zusammenhänge zwischen der speziellen Geruchswahrnehmung einerseits und der chemischen Struktur des zugehörigen Riechstoffs andererseits sind nicht hinreichend erforscht.
• Häufig bewirken bereits geringfügige Änderungen am strukturellen Aufbau eines bekannten Riechstoffs starke Änderungen der sensorischen Eigenschaften und beeinträchtigen die Verträglichkeit für den menschlichen Organismus.

The search for suitable fragrances which led to the present invention was hampered by the following facts:

• The mechanisms of smell perception are not sufficiently known.
• The connections between the special smell perception on the one hand and the chemical structure of the corresponding fragrance on the other hand, have not been sufficiently researched.
• Often, even minor changes in the structural makeup of a known fragrance cause significant changes in sensory properties and affect tolerability to the human organism.

The success of finding suitable fragrances therefore depends heavily on the intuition of the searcher.

Therefore, the object underlying this invention was essentially to find fragrances with green, fruity notes, which are preferably paired with other interesting and original odor properties, allowing the fragrances sought novel and original fragrance compositions with specific odor notes and aspects. In particular, fragrances with green, fruity notes should be found, which in particular are suitable for combination with fragrances which have a woody and / or floral scent.

In addition, the perfumes that accomplish this main purpose should also preferably have additional positive secondary properties beyond their primary, namely, odoriferous, properties, such as, e.g. a higher stability under certain conditions of use, a higher yield, a better adhesion, a high substantivity, a remarkable booster effect or a strong blooming, so that sensory remarkable effects or else better dermatological and toxicological properties can be achieved compared to similar fragrances.

als Riech- oder Aromastoff.According to the invention, the primary object is achieved by the use of 4-phenyl-pentan-2-ol of the formula (I)

as a scent or flavoring.

The 4-phenyl-pentan-2-ol of the formula (I) to be used according to the invention has two chiral centers. The compound of formula (I) may be syn- or anticonfigured, as (R, R) -configured enantiomer, (R, S) -configured enantiomer, (S, R) -configured enantiomer, (S, S) -configured or as any mixture of the enantiomers, in particular as a racemate, or else as any desired mixture of the corresponding diastereomers.

The stated object is also achieved by the use of 4-phenyl-pentan-2-ol of the formula (I) as a fragrance or aroma with green, fruity notes.

Further aspects of the invention will become apparent from the appended claims and the description below; In particular, these aspects concern new perfumed or flavored articles and related procedures.

The odor properties of the compound 4-phenyl-pentan-2-ol of the formula (I) to be used according to the invention are described by the perfumers as follows: very strong, interesting green, fruity scent in the direction of grapefruit and rhubarb, very natural odor impression.

In particular, the compound of formula (I) can be used for imparting, modifying and / or enhancing a green, fruity odor and / or flavor note.

In J. Chem. Soc., Chem. Commun. (1982), 348 describes the synthesis of (R, S) -4-phenyl-pentan-2-ol by hydrogenation of chiral homoallylic alcohols.

Eur. J. Org. Chem. 2002, 16, 2472-2757 . J.Org. Chem. 2000, 65, 4281-4288 . Chem. Commun. 1998, 19, 2127-2128 and Tetrahedron Lett. 1998, 39, 8829-8832 are concerned with the stereoselective radical aryl migration, whereby the preparation of 4-phenyl-pentan-2-ol of formula (I) has been studied in detail.

A sensory description of 4-phenyl-pentan-2-ol of the formula (I) has not yet been given.

in the Journal f. Prakt. Chemie volume 319, No. 4, 1977, 601 the catalytic cleavage of substituted 1,3-dioxanes is described, but the compound 4-phenyl-pentan-2-ol to be used according to the invention is not mentioned in this article.

• 5-Phenyl-pentan-1-ol: süß-krautig, Citrus-Note, Verbena-Note
• 5-Phenyl-pentan-3-ol: balsamisch, blumig, erdig-grün-würzig
• 1-Phenyl-pentan-2-ol: leicht grün, süß, feucht-erdig

The odor descriptions from own investigations and from the literature ( S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published ) phenylpentanols can be summarized as follows:

• 5-phenyl-pentan-1-ol: sweet-herbaceous, citrus note, verbena note
• 5-Phenyl-pentan-3-ol: balsamic, flowery, earthy-green-spicy
• 1-phenylpentan-2-ol: slightly green, sweet, moist earthy

A certain structural similarity of the compound of the formula (I) to be used according to the invention also exists for the tertiary alcohol 4-phenyl-2-methyl-2-butanol (α, α-dimethylphenylethylcarbinol) which is known as a fragrance but which has a dry, rosy-floral, lily-like odor.

• Dihydrozimtalkohol (3-Phenylpropanol) besitzt einen fruchtigen Zimtgeruch.
• 2-Methyl-5-phenylpentanol (unter dem Namen Rosaphen kommerziell erhältlich) verfügt über einen Duft von Rosenblüten mit einer leicht wachsigen Note.
• 3-Methyl-5-phenylpentanol (unter dem Namen Phenoxanol kommerziell erhältlich) ist für seinen langanhaltenden diffusiven, frischen, floralen Rosengeruch bekannt.

Other phenylalkanols which have side chains with more or fewer carbon atoms than the compound of the formula (I) to be used according to the invention also show a different odor characteristic than these (see Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001 ):

• Dihydrocinnamyl alcohol (3-phenylpropanol) has a fruity smell of cinnamon.
• 2-methyl-5-phenylpentanol (commercially available under the name Rosaphen) has a scent of rose petals with a slightly waxy note.
• 3-Methyl-5-phenylpentanol (commercially available under the name Phenoxanol) is known for its long lasting, diffusive, fresh, floral rose smell.

According to the prior art described, the field of phenylpentanols has been well studied, and therefore it is particularly unexpected that another valuable fragrance could be found in this field. The compound of the formula (I) has completely independent olfactory properties, which stand out clearly from the known fragrances of similar structure. The suitability of the compound of the formula (I) to be used according to the invention as a fragrance or flavoring agent for use in the olfactory and flavor industry has hitherto not been known and is surprising.

It is particularly surprising that the 4-phenyl-pentan-2-ol to be used according to the invention has, in addition to the green-fruity aspects, an expressive rhubarb note with additional, sometimes very complex and multi-faceted aspects, because it differs due to the presence of these additional additional aspects the compound to be used according to the invention is very distinct from structurally comparable and known substances (see above) and gives a very complex and varied odor and taste impression that can otherwise be achieved only by complex mixtures of several components (such as essential oils or herbal or spice mixtures).

In mixtures with other fragrances, the 4-phenylpentan-2-ol to be used according to the invention can intensify the intensity of a fragrance mixture even at low dosages and round off and harmonize the overall appearance of the fragrance mixture and impart more (off) radiation and naturalness to the mixture ,

In the context of the use according to the invention of 4-phenylpentan-2-ol as a fragrance or flavoring substance (in particular with a green fruity note), the present invention also relates to the use for providing (a) hair, (b) skin or (c) textile fibers with a fragrance, in particular a green fruity fragrance (with regard to further odor or taste notes, see above). The present invention also relates to corresponding processes and (preferably surfactant-containing) mixtures. According to a related aspect, the present invention also relates to the use of 4-phenyl-pentan-2-ol as an agent for increasing the substantivity and / or retention of a fragrance mixture and / or fixator and / or as an agent for increasing the surfactant-containing aqueous Solution of perceived odor of other fragrances.

In connection with the preferred use for modifying and / or enhancing an odor and / or flavor, there is also the recognition that the 4-phenyl-pentan-2-ol to be used according to the invention can function excellently as a so-called booster (enhancer).

The 4-phenyl-pentan-2-ol to be used according to the invention has, in addition to its primary, namely olfactory properties, additional positive secondary properties, such as, for example, B. a high stability under certain conditions of use, high yield, good adhesion, high substantivity. 4-phenyl-pentan-2-ol of the formula (I) can be used in particular to impart radiation, rounding off and / or harmony to an odor or aroma composition (off) and / or to intensify existing odor and / or taste notes.

1. (a) die Verwendung von 4-Phenyl-pentan-2-ol der Formel (I), vorzugsweise in einer Menge, die ausreicht, eine Geruchs- oder Geschmacksnote des Typs grün, fruchtig, insbesondere in Richtung Grapefruit und Rhabarber, zu vermitteln, zu modifizieren und/oder zu verstärken sowie
2. (b) einen, zwei, drei oder mehr weitere Riech- oder Aromastoffe wobei der oder die weiteren Riech- oder Aromastoffe vorzugsweise einen holzigen und/oder blumigen Geruch und/oder Geschmack vermitteln.

The present invention also relates to perfumed or flavored articles comprising

1. (a) the use of 4-phenyl-pentan-2-ol of the formula (I), preferably in an amount sufficient to impart an odor or flavor note of the green, fruity type, in particular towards grapefruit and rhubarb, to modify and / or reinforce as well
2. (b) one, two, three or more other fragrances or flavorings, wherein the one or more other fragrances or flavorings preferably impart a woody and / or floral odor and / or flavor.

The preferred embodiments of the invention described above and below with a view to the uses according to the invention accordingly also apply to perfumed or flavored articles according to the invention.

4-phenyl-pentan-2-ol is usually used in sensory effective amounts in the context of the use according to the invention. Frequently, the 4-phenyl-pentan-2-ol to be used according to the invention should be mixed or combined with other fragrances or flavorings. The weight ratio of the total amount of 4-phenylpentan-2-ol to the total amount of further odorants or aromatic substances is then preferably in the range from 1: 1000 to 1: 0.5, preferably 1: 100 to 1: 0.5 ,

• (i) Extrakte aus natürlichen Rohstoffen wie Etherische Öle, Concretes, Absolues, Resine, Resinoide, Balsame, Tinkturen wie z. B.
  Ambratinktur; Amyrisöl; Angelicasamenöl; Angelicawurzelöl; Anisöl; Baldrianöl; Basilikumöl; Baummoos -Absolue; Bayöl; Beifußöl; Benzoeresin; Bergamotteöl; Bienenwachs-Absolue; Birkenteeröl; Bittermandelöl; Bohnenkrautöl; Buccoblätteröl; Cabreuvaöl; Cadeöl; Calmusöl; Campheröl; Canangaöl; Cardamomenöl; Cascarillaöl; Cassiaöl; Cassie-Absolue; Castoreum-absolue; Cedernblätteröl; Cedernholzöl; Cistusöl; Citronellöl; Citronenöl; Copaivabalsam; Copaivabalsamöl; Corianderöl; Costuswurzelöl; Cuminöl; Cypressenöl; Davanaöl; Dillkrautöl; Dillsamenöl; Eau de brouts-Absolue; Eichenmoos-Absolue; Elemiöl; Estragonöl; Eucalyptus-citriodora-Öl; Eucalyptusöl; Fenchelöl ; Fichtennadelöl; Galbanumöl; Galbanumresin; Geraniumöl; Grapefruitöl; Guajakholzöl; Gurjunbalsam; Gurjunbalsamöl; Helichrysum-Absolue; Helichrysumöl; Ingweröl; Iriswurzel-Absolue; Iriswurzelöl; Jasmin-Absolue; Kalmusöl; Kamillenöl blau; Kamillenöl römisch; Karottensamenöl; Kaskarillaöl; Kiefernadelöl; Krauseminzöl; Kümmelöl; Labdanumöl; Labdanum-Absolue; Labdanumresin; Lavandin-Absolue; Lavandinöl ; Lavendel-Absolue; Lavendelöl; Lemongrasöl; Liebstocköl; Limetteöl destilliert; Limetteöl gepreßt; Linaloeöl; Litsea-cubeba-Öl; Lorbeerblätteröl; Macisöl; Majoranöl; Mandarinenöl; Massoirindenöl; Mimosa-Absolue; Moschuskörneröl; Moschustinktur; Muskateller-Salbei-Öl; Muskatnußöl; Myrrhen-Absolue; Myrrhenöl; Myrtenöl; Nelkenblätteröl; Nelkenblütenöl; Neroliöl; Olibanum-Absolue; Olibanumöl; Opopanaxöl; Orangenblüten-Absolue; Orangenöl; Origanumöl; Palmarosaöl; Patchouliöl; Perillaöl; Perubalsamöl; Petersilienblätteröl; Petersiliensamenöl; Petitgrainöl; Pfefferminzöl; Pfefferöl; Pimentöl; Pineöl; Poleyöl; Rosen-Absolue; Rosenholzöl; Rosenöl; Rosmarinöl; Salbeiöl dalmatinisch; Salbeiöl spanisch; Sandelholzöl; Selleriesamenöl; Spiklavendelöl; Sternanisöl; Styraxöl; Tagetesöl; Tannennadelöl; Tea-tree-Öl; Terpentinöl; Thymianöl; Tolubalsam; Tonka-Absolue; Tuberosen-Absolue; Vanilleextrakt; Veilchenblätter-Absolue; Verbenaöl; Vetiveröl; Wacholderbeeröl; Weinhefenöl; Wermutöl; Wintergrünöl; Ylangöl; Ysopöl; Zibet-Absolue; Zimtblätteröl; Zimtrindenöl sowie Fraktionen davon, bzw. daraus isolierten Inhaltsstoffen;
• (ii) Einzel-Riechstoffe aus der Gruppe der Kohlenwasserstoffe, wie z.B. 3-Caren; α-Pinen; β-Pinen; α-Terpinen; γ-Terpinen; p-Cymol; Bisabolen; Camphen; Caryophyllen; Cedren; Farnesen; Limonen; Longifolen; Myrcen; Ocimen; Valencen; (E,Z)-1,3,5-Undecatrien; Styrol; Diphenylmethan;
  • der aliphatischen Alkohole wie z.B. Hexanol; Octanol; 3-Octanol; 2,6-Dimethylheptanol; 2-Methyl-2-heptanol; 2-Methyl-2-octanol; (E)-2-Hexenol; (E)- und (Z)-3-Hexenol; 1-Octen-3-ol; Gemisch von 3,4,5,6,6-Pentamethyl-3/4-hepten-2-ol und 3,5,6,6-Tetramethyl-4-methyleneheptan-2-ol; (E,Z)-2,6-Nonadienol; 3,7-Dimethyl-7-methoxyoctan-2-ol; 9-Decenol; 10-Undecenol; 4-Methyl-3-decen-5-ol;
  • der aliphatischen Aldehyde und deren Acetale wie z.B. Hexanal; Heptanal; Octanal; Nonanal; Decanal; Undecanal; Dodecanal; Tridecanal; 2-Methyloctanal; 2-Methylnonanal; (E)-2-Hexenal; (Z)-4-Heptenal; 2,6-Dimethyl-5-heptenal; 10-Undecenal; (E)-4-Decenal; 2-Dodecenal; 2,6,10-Trimethyl-9-undecenal; 2,6,10-Trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-Dimethoxy-2,2,5-trimethyl-4-hexen; Citronellyloxyacetaldehyd; 1-(1-Methoxy-propoxy)-(E/Z)-3-hexen;
  • der aliphatischen Ketone und deren Oxime wie z.B. 2-Heptanon; 2-Octanon; 3-Octanon; 2-Nonanon; 5-Methyl-3-heptanon ; 5-Methyl-3-heptanonoxim; 2,4,4,7-Tetramethyl-6-octen-3-on; 6-Methyl-5-hepten-2-on;
  • der aliphatischen schwefelhaltigen Verbindungen wie z.B. 3-Methylthio-hexanol; 3-Methylthiohexylacetat; 3-Mercaptohexanol; 3-Mercaptohexylacetat; 3-Mercaptohexylbutyrat; 3-Acetylthiohexylacetat; 1-Menthen-8-thiol;
  • der aliphatischen Nitrile wie z.B. 2-Nonensäurenitril; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-Dimethyl-2,6-octadien-säurenitril; 3,7-Dimethyl-6-octensäurenitril;
  • der Ester von aliphatischen Carbonsäuren wie z.B. (E)- und (Z)-3-Hexenylformiat; Ethylacetoacetat; Isoamylacetat; Hexylacetat; 3,5,5-Trimethylhexylacetat; 3-Methyl-2-butenylacetat; (E)-2-Hexenylacetat; (E)- und (Z)-3-Hexenylacetat; Octylacetat; 3-Octylacetat; 1-Octen-3-ylacetat; Ethylbutyrat; Butylbutyrat, ; Isoamylbutyrat; Hexylbutyrat; (E)- und (Z)-3-Hexenyl-isobutyrat; Hexylcrotonat; Ethylisovalerianat; Ethyl-2-methylpentanoat; Ethylhexanoat; Allylhexanoat; Ethylheptanoat; Allylheptanoat; Ethyloctanoat; Ethyl-(E,Z)-2,4-decadienoat; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoat;4-Methyl-2-pentyl-crotonat;
  • der acyclischen Terpenalkohole wie z. B. Citronellol; Geraniol; Nerol; Linalool; Lavandulol; Nerolidol; Farnesol; Tetrahydrolinalool; Tetrahydrogeraniol; 2,6-Dimethyl-7-octen-2-ol; 2,6-Dimethyloctan-2-ol; 2-Methyl-6-methylen-7-octen-2-ol; 2,6-Dimethyl-5,7-octadien-2-ol; 2,6-Dimethyl-3,5-octadien-2-ol; 3,7-Dimethyl-4,6-octadien-3-ol; 3,7-Dimethyl-1,5,7-octatrien-3-ol 2,6-Dimethyl-2,5,7-octatrien-1-ol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate;
  • der acyclischen Terpenaldehyde und -ketone wie z. B. Geranial; Neral; Citronellal; 7-Hydroxy-3,7-dimethyloctanal; 7-Methoxy-3,7-dimethyloctanal; 2,6,10-Trimethyl-9-undecenal; Geranylaceton; sowie die Dimethyl- und Diethylacetale von Geranial, Neral, 7-Hydroxy-3,7-dimethyloctanal;
  • der cyclischen Terpenalkohole wie z. B. Menthol; Isopulegol; alpha-Terpineol; Terpinenol-4; Menthan-8-ol; Menthan-1-ol; Menthan-7-ol; Borneol; Isoborneol; Linalooloxid; Nopol; Cedrol; Ambrinol; Vetiverol; Guajol; sowie deren Formiate, Acetate, Propionate, Isobutyrate, Butyrate, Isovalerianate, Pentanoate, Hexanoate, Crotonate, Tiglinate und 3-Methyl-2-butenoate;
  • der cyclischen Terpenaldehyde und -ketone wie z. B. Menthon; Isomenthon ; 8-Mercaptomenthan-3-on ; Carvon; Campher; Fenchon; alpha-lonon; beta-lonon; alphan-Methylionon; beta-n-Methylionon; alpha-lsomethylionon; beta-lsomethylionon; alpha-lron; alpha-Damascon; beta-Damascon; beta-Damascenon; delta-Damascon; gamma-Damascon; 1-(2,4,4-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-on; 1,3,4,6,7,8a-Hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8(5H)-on;2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-butenal; Nootkaton ; Dihydronootkaton ; 4,6,8-Megastigmatrien-3-on; alpha-Sinensal ; beta-Sinensal ; acetyliertes Cedernholzöl (Methylcedrylketon);
  • der cyclischen Alkohole wie z.B. 4-tert.-Butylcyclohexanol ; 3,3,5-Trimethylcyclohexanol; 3-Isocamphylcyclohexanol; 2,6,9-Trimethyl-Z2,Z5,E9-cyclododecatrien-1-ol; 2-Isobutyl-4-methyltetrahydro-2H-pyran-4-ol;
  • der cycloaliphatischen Alkohole wie z.B. alpha,3,3-Trimethylcyclohexylmethanol;1-(4-Isopropylcyclohexyl)ethanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)butanol; 2-Methyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 2-Ethyl-4-(2,2,3-trimethyl-3-cyclopent-1-yl)-2-buten-1-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-pentan-2-ol; 3-Methyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopent-1-yl)-4-penten-2-ol; 1-(2,2,6-Trimethylcyclohexyl)pentan-3-ol; 1-(2,2,6-Trimethylcyclohexyl)hexan-3-ol;
  • der cyclischen und cycloaliphatischen Ether wie z.B. Cineol; Cedrylmethylether; Cyclododecylmethylether;1,1-Dimethoxycyclododecan; (Ethoxymethoxy)cyclododecan; alpha-Cedrenepoxid; 3a,6,6,9a-Tetramethyldodecahydronaphtho[2,1 -b]furan; 3a-Ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan; 1,5,9-Trimethyl-13-oxabicyclo[10.1.0]trideca-4,8-dien; Rosenoxid; 2-(2,4-Dimethyl-3-cyclohexen-1-yl)-5-methyl-5-(1-methylpropyl)-1,3-dioxan; 2,4,6-Trimethyl-4-phenyl-1,3-dioxan (Vertacetal^®; bevorzugte Kombination, siehe unten)
  • der cyclischen und makrocyclischen Ketone wie z.B. 4-tert.-Butylcyclohexanon; 2,2,5-Trimethyl-5-pentylcyclopentanon; 2-Heptylcyclopentanon; 2-Pentylcyclopentanon; 2-Hydroxy-3-methyl-2-cyclopenten-1-on; 3-Methyl-cis-2-penten-1-yl-2-cyclopenten-1-on; 3-Methyl-2-pentyl-2-cyclopenten-1-on; 3-Methyl-4-cyclopentadecenon; 3-Methyl-5-cyclopentadecenon; 3-Methylcyclopentadecanon; 4-(1 -Ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanon; 4-tert.-Pentylcyclohexanon; 5-Cyclohexadecen-1-on; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4(5H)-indanon; 8-Cyclohexadecen-1-on; 9-Cycloheptadecen-1-on; Cyclopentadecanon; Cyclohexadecanon;
  • der cycloaliphatischen Aldehyde wie z.B. 2,4-Dimethyl-3-cyclohexencarbaldehyd; 2-Methyl-4-(2,2,6-trimethyl-cyclohexen-1-yl)-2-butenal; 4-(4-Hydroxy-4-methylpentyl)-3-cyclohexencarbaldehyd; 4-(4-Methyl-3-penten-1-yl)-3-cyclohexencarbaldehyd;
  • der cycloaliphatischen Ketone wie z. B. 1-(3,3-Dimethylcyclohexyl)-4-penten-1-on; 2,2-Dimethyl-1-(2,4-dimethyl-3-cyclohexen-1-yl)-1-propanon; 1-(5,5-Dimethyl-1-cyclohexen-1-yl)-4-penten-1-on; 2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert.-Butyl-(2,4-dimethyl-3-cyclohexen-1-yl)keton;
  • der Ester cyclischer Alkohole wie z.B. 2-tert-Butylcyclohexylacetat; 4-tert-Butylcyclohexylacetat; 2-tert-Pentylcyclohexylacetat; 4-tert-Pentylcyclohexylacetat; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthylacetat;2-Cyclopentylcyclopentylcrotonat; 3-Pentyltetrahydro-2H-pyran-4-ylacetat; Decahydro-2,5,5,8a-tetramethyl-2-naphthylacetat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylacetat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylpropionat; 4,7-Methano-3a,4,5,6,7,7a-hexahydro-5, bzw. 6-indenylisobutyrat; 4,7-Methanooctahydro-5, bzw. 6-indenylacetat;
  • der Ester cycloaliphatischer Alkohole wie z.B.1-Cyclohexylethylcrotonat;
  • der Ester cycloaliphatischer Carbonsäuren wie z. B. Allyl-3-cyclohexylpropionat; Allylcyclohexyloxyacetat; cis- und trans-Methyldihydrojasmonat; cis- und trans-Methyljasmonat; Methyl-2-hexyl-3-oxocyclopentancarboxylat; Ethyl-2-ethyl-6,6-dimethyl-2-cyclohexencarboxylat; Ethyl-2,3,6,6-tetramethyl-2-cyclohexencarboxylat; Ethyl-2-methyl-1,3-dioxolan-2-acetat;
  • der araliphatischen Alkohole wie z.B. Benzylalkohol; 1-Phenylethylalkohol; 2-Phenylethylalkohol; 3-Phenylpropanol; 2-Phenylpropanol; 2-Phenoxyethanol; 2,2-Dimethyl-3-phenylpropanol; 2,2-Dimethyl-3-(3-methylphenyl)propanol; 1,1-Dimethyl-2-phenylethylalkohol; 1,1-Dimethyl-3-phenylpropanol; 1-Ethyl-1-methyl-3-phenylpropanol; 2-Methyl-5-phenylpentanol; 3-Methyl-5-phenylpentanol; 3-Phenyl-2-propen-1-ol; 4-Methoxybenzylalkohol; 1-(4-Isopropylphenyl)ethanol;
  • der Ester von araliphatischen Alkoholen und aliphatischen Carbonsäuren wie z.B. Benzylacetat; Benzylpropionat; Benzylisobutyrat; Benzylisovalerianat; 2-Phenylethylacetat; 2-Phenylethylpropionat; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-Phenylethylacetat; alpha-Trichlormethylbenzylacetat; alpha,alpha-Dimethylphenylethylacetat; alpha,alpha-Dimethylphenylethylbutyrat; Cinnamylacetat; 2-Phenoxyethylisobutyrat; 4-Methoxybenzylacetat;
  • der araliphatischen Ether wie z.B. 2-Phenylethylmethylether; 2-Phenylethylisoamylether; 2-Phenylethyl-1-ethoxyethylether; Phenylacetaldehyddimethylacetal; Phenylacetaldehyddiethylacetal; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-Trimethyl-4-phenyl-1,3-dioxan; 4,4a,5,9b-Tetrahydroindeno[1,2-d]-m-dioxin; 4,4a,5,9b-Tetrahydro-2,4-dimethylindeno[1,2-d]-m-dioxin;
  • der aromatischen und araliphatischen Aldehyde wie z. B. Benzaldehyd; Phenylacetaldehyd; 3-Phenylpropanal; Hydratropaaldehyd; 4-Methylbenzaldehyd; 4-Methylphenylacetaldehyd; 3-(4-Ethylphenyl)-2,2-dimethylpropanal; 2-Methyl-3-(4-isopropylphenyl)propanal; 2-Methyl-3-(4-tert.-butylphenyl)propanal; 2-Methyl-3-(4-isobutylphenyl)propanal; 3-(4-tert.-Butylphenyl)propanal; Zimtaldehyd; alpha-Butylzimtaldehyd; alpha-Amylzimtaldehyd; alpha-Hexylzimtaldehyd; 3-Methyl-5-phenylpentanal; 4-Methoxybenzaldehyd; 4-Hydroxy-3-methoxybenzaldehyd; 4-Hydroxy-3-ethoxybenzaldehyd; 3,4-Methylendioxybenzaldehyd; 3,4-Dimethoxybenzaldehyd; 2-Methyl-3-(4-methoxyphenyl)propanal; 2-Methyl-3-(4-methylendioxyphenyl)propanal;
  • der aromatischen und araliphatischen Ketone wie z.B. Acetophenon; 4-Methylacetophenon; 4-Methoxyacetophenon; 4-tert.-Butyl-2,6-dimethylacetophenon; 4-Phenyl-2-butanon; 4-(4-Hydroxyphenyl)-2-butanon; 1-(2-Naphthalenyl)ethanon;2-Benzofuranylethanon;(3-Methyl-2-benzofuranyl)ethanon; Benzophenon; 1,1,2,3,3,6-Hexamethyl-5-indanylmethylketon; 6-tert.-Butyl-1,1-dimethyl-4-indanylmethylketon; 1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methylethyl)-1H-5-indenyl]ethanon; 5',6',7',8'-Tetrahydro-3',5',5',6',8',8'-hexamethyl-2-acetonaphthon;
  • der aromatischen und araliphatischen Carbonsäuren und deren Ester wie z.B. Benzoesäure; Phenylessigsäure; Methylbenzoat; Ethylbenzoat; Hexylbenzoat; Benzylbenzoat; Methylphenylacetat; Ethylphenylacetat; Geranylphenylacetat; Phenylethylphenylacetat; Methylcinnmat; Ethylcinnamat; Benzylcinnamat; Phenylethylcinnamat; Cinnamylcinnamat; Allylphenoxyacetat; Methylsalicylat; Isoamylsalicylat; Hexylsalicylat; Cyclohexylsalicylat; Cis-3-Hexenylsalicylat; Benzylsalicylat; Phenylethylsalicylat; Methyl-2,4-dihydroxy-3,6-dimethylbenzoat; Ethyl-3-phenylglycidat; Ethyl-3-methyl-3-phenylglycidat;
  • der stickstoffhaltigen aromatischen Verbindungen wie z.B. 2,4,6-Trinitro-1,3-dimethyl-5-tert.-butylbenzol; 3,5-Dinitro-2,6-dimethyl-4-tert.-butylacetophenon; Zimtsäurenitril; 3-Methyl-5-phenyl-2-pentensäurenitril; 3-Methyl-5-phenylpentansäurenitril; Methylanthranilat; Methy-N-methylanthranilat; Schiff'sche Basen von Methylanthranilat mit 7-Hydroxy-3,7-dimethyloctanal, 2-Methyl-3-(4-tert.-butylphenyl)propanal oder 2,4-Dimethyl-3-cyclohexencarbaldehyd; 6-Isopropylchinolin; 6-Isobutylchinolin; 6-sec.-Butylchinolin;2-(3-Phenylpropyl)pyridin; Indol; Skatol; 2-Methoxy-3-isopropylpyrazin; 2-Isobutyl-3-methoxypyrazin;
  • der Phenole, Phenylether und Phenylester wie z.B. Estragol; Anethol; Eugenol; Eugenylmethylether; Isoeugenol; Isoeugenylmethylether; Thymol; Carvacrol; Diphenylether; beta-Naphthylmethylether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-Dimethoxybenzol; Eugenylacetat; 2-Methoxy-4-methylphenol; 2-Ethoxy-5-(1-propenyl)phenol; p-Kresylphenylacetat;
  • der heterocyclischen Verbindungen wie z.B. 2,5-Dimethyl-4-hydroxy-2H-furan-3-on; 2-Ethyl-4-hydroxy-5-methyl-2H-furan-3-on; 3-Hydroxy-2-methyl-4H-pyran-4-on; 2-Ethyl-3-hydroxy-4H-pyran-4-on;
  • der Lactone wie z.B. 1,4-Octanolid; 3-Methyl-1,4-octanolid; 1,4-Nonanolid; 1,4-Decanolid; 8-Decen-1,4-olid; 1,4-Undecanolid; 1,4-Dodecanolid; 1,5-Decanolid; 1,5-Dodecanolid;4-Methyl-1,4-decanolid; 1,15-Pentadecanolid; cis- und trans-11-Pentadecen-1,15-olid; cis- und trans-12-Pentadecen-1,15-olid; 1,16-Hexadecanolid; 9-Hexadecen-1,16-olid; 10-Oxa-1,16-hexadecanolid; 11-Oxa-1,16-hexadecanolid; 12-Oxa-1,16-hexadecanolid; Ethylen-1,12-dodecandioat; Ethylen-1,13-tridecandioat; Cumarin; 2,3-Dihydrocumarin; Octahydrocumarin.

Preferably, a perfumed or flavored article of the invention is a fragrance or flavoring composition. By combining 4-phenyl-pentan-2-ol with one, two, three or more other fragrances or flavorings (preferably having a woody and / or floral odor or taste), new fragrance or flavor compositions can be formed. In this way you can create particularly interesting and natural new and original fragrances. Fragrances (as component (b)), which for combination with 4-phenyl-pentan-2-ol are advantageously suitable, z. In S. Arctander, Perfume and Flavor Materials, Vol. I and II, Montclair, NJ 1969, self-published , or K. Bauer et al., Common Fragrance and Flavor Materials, 4th Edition, Wiley-VCH, Weinheim 2001 , Specifically, may be mentioned:

• (i) extracts of natural raw materials such as essential oils, concretes, absolues, resines, resinoids, balsams, tinctures such. B.
  ambergris tincture; Amyrisöl; Angelica seed oil; Angelica root oil; anise oil; Valerian oil; Basil oil; Tree Moss -Absolue; Bay oil; Mugwort oil; Benzoeresin; Bergamot oil; Beeswax absolute; birch tar; Bitter almond oil; Savory oil; Buccoblätteröl; Cabreuvaöl; cade oil; calamus; camphor oil; Cananga oil; cardamom; Cascarillaöl; cassia; Cassie absolute; Beaver-absolue; Cedernblätteröl; cedarwood; cistus; citronella; lemon; copaiba balsam; Copaivabalsamöl; Coriander oil; costus root; Cuminöl; Cypress oil; Davanaöl; Dill herb oil; Dill seed oil; Eau de Brouts absolute; Oak moss absolute; elemi; Tarragon oil; Eucalyptus citriodora oil; eucalyptus oil; Fennel oil; Pine needle oil; galbanum; Galbanumresin; geranium; Grapefruit oil; guaiac wood; gurjun balsam; gurjun balsam oil; Helichrysum absolute; Helichrysumöl; Ginger oil; Iris root absolute; Orris root oil; Jasmine absolute; calamus; Chamomile oil blue; Camomile oil Roman; Carrot seed oil; Kaskarillaöl; Pine needle oil; spearmint; Seed oil; labdanum; Labdanum absolute; Labdanumresin; Lavandin absolute; Lavandin oil; Lavender absolute; Lavender oil; Lemongrass oil; Lovage oil; Distilled lime oil; Pressed lime oil; linaloe; Litsea cubeba oil; Bay leaf oil; Macisöl; Marjoram oil; Mandarin oil; Massoirindenöl; Mimosa absolute; Musk seed oil; musk tincture; Clary sage oil; nutmeg; Myrrh absolute; Myrrh oil; myrtle; Clove leaf oil; Clove flower oil; neroli; Olibanum absolute; olibanum; Opopanaxöl; Orange blossom absolute; Orange oil; oregano; Palmarosa oil; patchouli oil; perilla oil; Peruvian balsam oil; Parsley leaf oil; Parsley seed oil; Petitgrain oil; Peppermint oil; Pepper oil; chilli; pine oil; Poleyöl; Rose absolute; Rosewood oil; Rose oil; Rosemary oil; Sage oil Dalmatian; Sage oil spanish; sandalwood; Celery seed oil; spike lavender oil; star anise; Styraxöl; tagetes; Pine needle oil; Tea-tree oil; turpentine; Thyme oil; Tolu; Tonka absolute; Tuberose absolute; Vanilla extract; Violet leaf absolute; verbena; vetiver; Juniper berry oil; Wine yeast oil; Wormwood oil; Wintergreen oil; ylang oil; hyssop oil; Civet absolute; cinnamon leaf; Cinnamon bark oil and fractions thereof, or ingredients isolated therefrom;
• (ii) individual fragrances from the group of hydrocarbons, such as 3-carene; α-pinene; β-pinene; α-terpinene; γ-terpinene; p-cymene; bisabolene; camphene; caryophyllene; cedrene; farnesene; limonene; longifolene; myrcene; ocimene; valencene; (E, Z) -1,3,5-undecatriene; styrene; diphenylmethane;
  • the aliphatic alcohols such as hexanol; octanol; 3-octanol; 2,6-dimethylheptanol; 2-methyl-2-heptanol; 2-methyl-2-octanol; (E) -2-hexenol; (E) - and (Z) -3-hexenol; 1-octene-3-ol; Mixture of 3,4,5,6,6-pentamethyl-3/4-hepten-2-ol and 3,5,6,6-tetramethyl-4-methyleneheptan-2-ol; (E, Z) -2,6-Nonadienol; 3,7-dimethyl-7-methoxyoctane-2-ol; 9-decenol; 10-undecenol; 4-methyl-3-decen-5-ol;
  • the aliphatic aldehydes and their acetals such as hexanal; heptanal; octanal; nonanal; decanal; undecanal; dodecanal; tridecanal; 2-methyloctanal; 2-methyl nonanal; (E) -2-hexenal; (Z) -4-heptenal; 2,6-dimethyl-5-heptenal; 10-undecenal; (E) -4-decenal; 2-dodecenal; 2,6,10-trimethyl-9-undecenal; 2,6,10-trimethyl-5,9-undecadienal; Heptanaldiethylacetal; 1,1-dimethoxy-2,2,5-trimethyl-4-hexene; citronellyloxyacetaldehyde; (1-methoxy-propoxy) 1- - 3-ene (E / Z);
  • the aliphatic ketones and their oximes such as 2-heptanone; 2-octanone; 3-octanone; 2-nonanone; 5-methyl-3-heptanone; 5-methyl-3-heptanone oxime; 2,4,4,7-tetramethyl-6-octen-3-one; 6-methyl-5-hepten-2-one;
  • the aliphatic sulfur-containing compounds such as 3-methylthio-hexanol; 3-Methylthiohexylacetat; 3-mercaptohexanol; 3-mercaptohexyl acetate; 3-mercaptohexyl butyrate; 3-acetylthiohexyl acetate; 1-menthene-8-thiol;
  • the aliphatic nitriles such as 2-nonenitrile; 2-Undecensäurenitril; 2-Tridecensäurenitril; 3,12-Tridecadiensäurenitril; 3,7-dimethyl-2,6-octadiene-acid nitrile; 3,7-dimethyl-6-octensäurenitril;
  • the ester of aliphatic carboxylic acids such as (E) - and (Z) -3-hexenylformate; ethylacetoacetate; isoamyl; hexyl acetate; 3,5,5-trimethylhexyl acetate; 3-methyl-2-butenyl acetate; (E) -2-hexenyl acetate; (E) - and (Z) -3-hexenylacetate; octyl acetate; 3-octyl acetate; 1-octen-3-yl acetate; ethyl butyrate; Butyl butyrate, isoamyl; hexyl butyrate; (E) - and (Z) -3-hexenyl isobutyrate; hexyl crotonate; Ethylisovalerianat; Ethyl 2-methylpentanoate; ethylhexanoate; allyl hexanoate; ethyl heptanoate; allyl heptanoate; ethyl octanoate; Ethyl (E, Z) -2,4-decadienoate; Methyl-2-octinat; Methyl-2-noninat; Allyl-2-isoamyloxyacetat; Methyl-3,7-dimethyl-2,6-octadienoate; 4-methyl-2-pentyl-crotonate;
  • the acyclic terpene alcohols such. Citronellol; geraniol; nerol; linalool; lavandulol; nerolidol; farnesol; tetrahydrolinalool; tetrahydrogeraniol; 2,6-dimethyl-7-octene-2-ol; 2,6-dimethyl octane-2-ol; 2-methyl-6-methylene-7-octen-2-ol; 2,6-dimethyl-5,7-octadiene-2-ol; 2,6-dimethyl-3,5-octadiene-2-ol; 3,7-dimethyl-4,6-octadiene-3-ol; 3,7-dimethyl-1,5,7-octatrien-3-ol 2,6-dimethyl-2,5,7-octatrien-1-ol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
  • the acyclic terpene aldehydes and ketones such. B. Geranial; neral; citronellal; 7-hydroxy-3,7-dimethyloctanal; 7-methoxy-3,7-dimethyloctanal; 2,6,10-trimethyl-9-undecenal; geranyl acetone; and the dimethyl and diethyl acetals of geranial, neral, 7-hydroxy-3,7-dimethyloctanal;
  • the cyclic terpene alcohols such. Menthol; isopulegol; alpha-terpineol; Terpinenol-4; Menthane-8-ol; Menthane-1-ol; Menthane-7-ol; borneol; soborneol; linalool; monopoly; cedrol; ambrinol; Vetyverol; guaiol; as well as their formates, acetates, propionates, isobutyrates, butyrates, isovalerates, pentanoates, hexanoates, crotonates, tiglinates and 3-methyl-2-butenoates;
  • the cyclic terpene aldehydes and ketones such. Eg menthone; Isomenthone; 8-mercaptomenthan-3-one; carvone; camphor; fenchon; alpha-ionone; beta-ionone; Alphan-methyl ionone; beta-n-methylionone; alpha-isomethylionone; beta-isomethylionone; alpha-lron; alpha-damascone; beta-damascone; beta-damascenone; delta-damascone; gamma-damascone; 1- (2,4,4-trimethyl-2-cyclohexen-1-yl) -2-buten-1-one; 1,3,4,6,7,8a-hexahydro-1,1,5,5-tetramethyl-2H-2,4a-methanonaphthalen-8 (5H) -one; 2-methyl-4- (2,6, 6-trimethyl-1-cyclohexen-1-yl) -2-butenal; Nootkatone; Dihydronootkaton; 4,6,8-Mega stigma triene-3-one; alpha-sinensal; beta-Sinensal; acetylated cedarwood oil (methyl cedryl ketone);
  • the cyclic alcohols such as 4-tert-butylcyclohexanol; 3,3,5-trimethylcyclohexanol; 3-isocamphylcyclohexanol; 2,6,9-trimethyl-Z2, Z5, E9-cyclododecatrien-1-ol; 2-isobutyl-4-methyl tetrahydro-2H-pyran-4-ol;
  • the cycloaliphatic alcohols such as alpha, 3,3-trimethylcyclohexylmethanol; 1- (4-isopropylcyclohexyl) ethanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) butanol; 2-methyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 2-ethyl-4- (2,2,3-trimethyl-3-cyclopent-1-yl) -2-buten-1-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) pentan-2-ol; 3-methyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 3,3-Dimethyl-5- (2,2,3-trimethyl-3-cyclopent-1-yl) -4-penten-2-ol; 1- (2,2,6-trimethylcyclohexyl) pentan-3-ol; 1- (2,2,6-trimethylcyclohexyl) hexan-3-ol;
  • the cyclic and cycloaliphatic ethers such as cineole; cedryl methyl ether; Cyclododecyl; 1,1-Dimethoxycyclododecan; (Ethoxymethoxy) cyclododecane; alpha-Cedrenepoxid; 3a, 6,6,9a-tetramethyldodecahydronaphtho [2,1-b] furan; 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho [2,1-b] furan; 1,5,9-trimethyl-13-oxabicyclo [10.1.0] trideca-4,8-diene; rose oxide; 2- (2,4-dimethyl-3-cyclohexen-1-yl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane; 2,4,6-trimethyl-4-phenyl-1,3-dioxane (Vertacetal ^®; preferred combination, see below)
  • the cyclic and macrocyclic ketones such as 4-tert-butylcyclohexanone; 2,2,5-trimethyl-5-pentylcyclopentanone; 2-heptylcyclopentanone; 2-pentylcyclopentanone; 2-hydroxy-3-methyl-2-cyclopenten-1-one; 3-methyl-cis-2-penten-1-yl-2-cyclopenten-1-one; 3-methyl-2-pentyl-2-cyclopenten-1-one; 3-methyl-4-cyclopentadecenone; 3-methyl-5-cyclopentadecenone; 3-methylcyclopentadecanone; 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone; 4-tert.-pentylcyclohexanone; 5-cyclohexadecen-1-one; 6,7-Dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanon; 8-cyclohexadecen-1-one; 9-cycloheptadecen-1-one; cyclopentadecanone; cyclohexadecanone;
  • the cycloaliphatic aldehydes such as 2,4-dimethyl-3-cyclohexene carbaldehyde; 2-methyl-4- (2,2,6-trimethyl-cyclohexen-1-yl) -2-butenal; 4- (4-hydroxy-4-methylpentyl) -3-cyclohexene carbaldehyde; 4- (4-methyl-3-penten-1-yl) -3-cyclohexene carbaldehyde;
  • the cycloaliphatic ketones such. B. 1- (3,3-dimethylcyclohexyl) -4-penten-1-one; 2,2-dimethyl-1- (2,4-dimethyl-3-cyclohexen-1-yl) -1-propanone; 1- (5,5-dimethyl-1-cyclohexen-1-yl) -4-penten-1-one; 2,3,8,8-tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon; Methyl-2,6,10-trimethyl-2,5,9-cyclododecatrienylketon; tert-butyl (2,4-dimethyl-3-cyclohexen-1-yl) ketone;
  • the ester of cyclic alcohols such as 2-tert-butylcyclohexyl acetate; 4-tert-butylcyclohexyl acetate; 2-tert-pentylcyclohexyl acetate; 4-tert-pentylcyclohexyl acetate; 3,3,5-Trimethylcyclohexylacetat; Decahydro-2-naphthyl acetate, 2-Cyclopentylcyclopentylcrotonat; 3-pentyltetrahydro-2H-pyran-4-yl acetate; Decahydro-2,5,5,8a-tetramethyl-2-naphthyl acetate; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl acetate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenylpropionate, respectively; 4,7-methano-3a, 4,5,6,7,7a-hexahydro-5, and 6-indenyl isobutyrate, respectively; 4,7-Methanooctahydro-5, or 6-indenyl acetate;
  • the ester of cycloaliphatic alcohols such as 1-cyclohexylethyl crotonate;
  • the esters of cycloaliphatic carboxylic acids such as. For example, allyl-3-cyclohexylpropionate; Allylcyclohexyloxyacetat; cis- and trans-methyldihydrojasmonate; cis- and trans-methyl jasmonate; Methyl-2-hexyl-3-oxocyclopentanecarboxylate; Ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate; Ethyl 2,3,6,6-tetramethyl-2-cyclohexenecarboxylate; Ethyl-2-methyl-1,3-dioxolan-2-acetate;
  • the araliphatic alcohols such as benzyl alcohol; 1-phenylethyl; 2-phenylethyl; 3-phenylpropanol; 2-phenylpropanol; 2-phenoxyethanol; 2,2-dimethyl-3-phenylpropanol; 2,2-dimethyl-3- (3-methylphenyl) propanol; 1,1-dimethyl-2-phenylethyl; 1,1-dimethyl-3-phenylpropanol; 1-ethyl-1-methyl-3-phenylpropanol; 2-methyl-5-phenylpentanol; 3-methyl-5-phenylpentanol; 3-phenyl-2-propen-1-ol; 4-methoxybenzyl; 1- (4-isopropylphenyl) ethanol;
  • the ester of araliphatic alcohols and aliphatic carboxylic acids such as benzyl acetate; benzylpropionate; benzyl isobutyrate; Benzylisovalerianat; 2-phenylethyl acetate; 2-phenylethyl propionate; 2-Phenylethylisobutyrat; 2-Phenylethylisovalerianat; 1-phenylethyl acetate; alpha-Trichlormethylbenzylacetat; alpha, alpha-Dimethylphenylethylacetat; alpha, alpha-Dimethylphenylethylbutyrat; cinnamyl; 2-phenoxyethyl isobutyrate; 4-methoxybenzyl acetate;
  • the araliphatic ethers such as 2-phenylethyl methyl ether; 2-Phenylethylisoamylether; 2-phenylethyl-1-ethoxyethyl ether; phenylacetaldehyde; phenylacetaldehyde; Hydratropaaldehyddimethylacetal; Phenylacetaldehydglycerinacetal; 2,4,6-trimethyl-4-phenyl-1,3-dioxane; 4,4a, 5,9b-tetrahydroindeno [1,2-d] -m-dioxin; 4,4a, 5,9b-tetrahydro-2,4-dimethylindeno [1,2-d] -m-dioxin;
  • the aromatic and araliphatic aldehydes such. B. benzaldehyde; phenylacetaldehyde; 3-phenylpropanal; Hydratropaaldehyd; 4-methylbenzaldehyde; 4-methylphenylacetaldehyde; 3- (4-ethylphenyl) -2,2-dimethylpropanal; 2-methyl-3- (4-isopropylphenyl) propanal; propanal, 2-methyl-3- (4-tert-butylphenyl); 2-methyl-3- (4-isobutylphenyl) propanal; 3- (4-tert-butylphenyl) propanal; cinnamic aldehyde; alpha-Butylzimtaldehyd; alpha amyl cinnamic aldehyde; alpha-hexylcinnamaldehyde; 3-methyl-5-phenylpentanal; 4-methoxybenzaldehyde; 4-Hydroxy-3-methoxybenzaldehyde; 4-hydroxy-3-ethoxybenzaldehyde; 3,4-methylenedioxybenzaldehyde; 3,4-dimethoxybenzaldehyde; 2-methyl-3- (4-methoxyphenyl) propanal; 2-methyl-3- (4-methylenedioxyphenyl) propanal;
  • the aromatic and araliphatic ketones such as acetophenone; 4-methylacetophenone; 4-methoxyacetophenone; 4-tert-butyl-2,6-dimethylacetophenone; 4-phenyl-2-butanone; 4- (4-hydroxyphenyl) -2-butanone; 1- (2-naphthalenyl) ethanone; 2-Benzofuranylethanon; (3-methyl-2-benzofuranyl) ethanone; benzophenone; 1,1,2,3,3,6-hexamethyl-5-indanyl methyl ketone; 6-tert-butyl-1,1-dimethyl-4-indanyl methyl ketone; 1- [2,3-dihydro-1,1,2,6-tetramethyl-3- (1-methylethyl) -1H-5-indenyl] ethanone; 8'-hexamethyl-2-acetonaphthone, 5 ', 6', 7 ', 8'-tetrahydro-3', 5 ', 5', 6 ', 8';
  • the aromatic and araliphatic carboxylic acids and their esters such as benzoic acid; phenylacetic acid; methylbenzoate; ethyl benzoate; hexyl benzoate; benzyl benzoate; methyl phenylacetate; ethyl phenylacetate; geranyl phenylacetate; phenylethyl phenylacetate; Methylcinnmat; ethylcinnamate; Benzyl; Phenylethylcinnamat; cinnamyl cinnamate; allyl phenoxyacetate; methyl salicylate; isoamyl; hexyl salicylate; cyclohexyl; Cis-3-hexenyl salicylate; benzyl; phenylethyl; Methyl-2,4-dihydroxy-3,6-dimethylbenzoate; Ethyl 3-phenylglycidate; Ethyl-3-methyl-3-phenylglycidate;
  • the nitrogen-containing aromatic compounds such as 2,4,6-trinitro-1,3-dimethyl-5-tert-butylbenzene; 3,5-dinitro-2,6-dimethyl-4-tert.-butylacetophenone; cinnamic acid; 3-methyl-5-phenyl-2-pentensäurenitril; 3-methyl-5-phenylpentansäurenitril; methyl anthranilate; Methyl N-methylanthranilate; Schiff bases of methyl anthranilate with 7-hydroxy-3,7-dimethyloctanal, 2-methyl-3- (4-tert-butylphenyl) propanal or 2,4-dimethyl-3-cyclohexene carbaldehyde; 6-Isopropyl; 6-Isobutylchinolin; 6-sec.-butylquinoline; 2- (3-phenylpropyl) pyridine; indole; skatol; 2-methoxy-3-isopropylpyrazine; 2-isobutyl-3-methoxypyrazine;
  • the phenols, phenyl ethers and phenyl esters such as estragole; anethole; eugenol; Eugenylmethylether; isoeugenol; Isoeugenylmethylether; thymol; carvacrol; diphenyl ether; beta-naphthyl methyl ether; beta-Naphthylethylether; beta-Naphthylisobutylether; 1,4-dimethoxybenzene; Eugenylacetat; 2-methoxy-4-methyl phenol; 2-ethoxy-5- (1-propenyl) phenol; p-Kresylphenylacetat;
  • heterocyclic compounds such as 2,5-dimethyl-4-hydroxy-2H-furan-3-one; 2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one; 3-hydroxy-2-methyl-4H-pyran-4-one; 2-ethyl-3-hydroxy-4H-pyran-4-one;
  • the lactones such as 1,4-octanolide; 3-methyl-1,4-octanolide; 1,4-nonanolide; 1,4-decanolide; 8-decen-1,4-olide; 1,4-undecanolide; 1,4-dodecanolide; 1,5-decanolide; 1,5-dodecanolide, 4-methyl-1,4-decanolide; 1.15 pentadecanolide; cis- and trans-11-pentadecene-1,15-olide; cis and trans-12-pentadecene-1,15-olide; 1,16-hexadecanolide; 9-hexadecene-1,16-olide; 10-oxa-1,16-hexadecanolide; 11-oxa-1,16-hexadecanolide; 12-oxa-1,16-hexadecanolide; Ethylene-1,12-dodecanedioate; Ethylene-1,13-tridecandioat; coumarin; 2,3-dihydrocoumarin; Octahydrocoumarin.

An odoriferous or aromatic substance composition according to the invention can be prepared, for example, by mixing 4-phenylpentan-2-ol as component (a) with one or more further odoriferous or aromatic substances (as component (b)). The component (a) is used regularly in an amount sufficient to impart, modify and / or enhance an odor or flavor note of the type green, fruity in the finished composition.

A fragrance or flavoring composition according to the invention preferably comprises a total amount of 4-phenylpentan-2-ol (component (a)) in the range of 0.01 to 50 wt .-%, preferably 0.1 to 25 wt .-% and particularly preferably from 0.5 to 20% by weight, based on the total amount of the fragrance or flavoring composition.

If the 4-phenyl-pentan-2-ol to be used according to the invention is mainly used to impart more (aus) radiation, rounding off and / or harmony to an odorant or flavoring composition and / or to reinforce certain notes, its total amount is preferably comparatively low and more preferably in the range of 0.01 to 5 wt .-%, preferably in the range of 0.1 to 2 wt .-%, based on the total amount of the fragrance or flavoring composition. If a comparatively low concentration is selected within the preferred concentration ranges, depending on the other components of the particular composition, in some cases the mediation of the abovementioned odor or taste notes does not yet occur.

The preparation of the 4-phenyl-pentan-2-ol to be used according to the invention can be carried out by means of known reactions and processes.

wobei Y entweder Wasserstoff oder einen Alkylrest mit 1 bis 10 C-Atomen bedeutet, vorzugsweise bedeutet Y Methyl oder Ethyl.For example, 4-phenyl-pentan-2-ol of the formula (I) can be prepared on the basis of the literature ( Journal f. Prakt. Chemie volume 319, No. 4, 1977, 601-610 ) are prepared via a catalytic cleavage of substituted 1,3-dioxanes of the formula (A) (see the following equation).

where Y is either hydrogen or an alkyl radical having 1 to 10 C atoms, preferably Y is methyl or ethyl.

Preferred starting material of the formula (A) is 2,4,6-trimethyl-4-phenyl-1,3-dioxane (formula (A) where Y = methyl), which in US 6,114,301 described under the name Vertacetal ^® or Vertacetal ^® Coeur (Symrise GmbH & Co. KG, Germany) is commercially available. This educt itself has a scent towards grapefruit and rhubarb and can be excellently combined with 4-phenylpentan-2-ol to provide new articles such as fragrance or flavor compositions.

The catalytic hydrogenation is preferably carried out in the presence of a hydrogenation catalyst in the range of 160-240 ° C at a hydrogen pressure in the range of 20 to 50.

Suitable hydrogenation catalysts may include, for example, ruthenium, rhodium, iridium, nickel, palladium or platinum. Advantageous hydrogenation catalysts include palladium, platinum, ruthenium or rhodium, particularly preferred hydrogenation catalyst is (elemental) palladium.

The hydrogenation catalysts to be used according to the invention can be applied to organic or inorganic support materials. The hydrogenation catalysts may contain a carrier material or mixtures of carrier materials. As advantageous support materials may be mentioned: activated carbon, coal, aluminum oxides, Metal oxides, silica gels, zeolites, clays, clay granules, amorphous aluminosilicates and other inorganic carriers. A preferred carrier material is activated carbon.

Very particularly preferred catalysts are palladium on activated carbon and palladium on alumina. The product mixture comprising 4-phenyl-pentan-2-ol can comprise residues of the dioxane of the formula (A) which, in particular in the case of the vertacetal, can contribute positively to the sensory overall impression.

4-phenyl-pentan-2-ol can also be prepared starting from 3-phenylbutyraldehyde via Grignard reaction with MeMgX (X = Cl, Br or I), as illustrated by the equation below.

Fragrance or flavoring compositions according to the invention which contain 4-phenylpentan-2-ol of the formula (I) can be used in liquid form, undiluted or diluted with a solvent for perfuming or aromatization. Suitable solvents for this are e.g. Ethanol, isopropanol, diethylene glycol monoethyl ether, glycerin, propylene glycol, 1,2-butylene glycol, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, triacetin, etc.

Fragrance or flavoring compositions according to the invention containing 4-phenylpentan-2-ol of the formula (I) may be adsorbed on a carrier which promotes both a fine distribution of the odoriferous or aromatic substances in the product and a controlled release the application ensures. Such carriers can be porous inorganic materials such as light sulphate, silica gels, zeolites, gypsum, clays, clay granules, aerated concrete, etc. or organic materials such as woods, cellulosic substances, sugars, dextrins (eg maltodextrin) or plastics such as PVC, polyvinyl acetates or polyurethanes. The combination of inventive Composition and carrier is an exemplary article of the invention.

Inventive fragrance or flavor compositions containing 4-phenyl-pentan-2-ol of formula (I) may also be microencapsulated, spray dried, as inclusion complexes or as extrusion products (i.e., inventive articles) and in this form e.g. B. to be perfumed or flavored product.

Optionally, the properties of the compositions modified in this way can be further optimized by so-called "coating" with suitable materials with a view to a more targeted release of fragrance, to which end preferably wax-like plastics, such as e.g. Polyvinyl alcohol can be used. The resulting products are in turn articles of the invention.

The microencapsulation of the odoriferous or flavoring compositions according to the invention to articles according to the invention can be carried out, for example, by the so-called coacervation method with the aid of capsule materials, e.g. made of polyurethane-like substances or soft gelatin. The spray-dried odoriferous or flavoring compositions can be prepared, for example, by spray-drying an emulsion or dispersion containing the fragrance or aroma composition, it being possible to use modified starches, proteins, dextrin and vegetable gums as carriers. Inclusion complexes can be e.g. by incorporating dispersions of the fragrance or flavoring composition and cyclodextrins or urea derivatives into a suitable solvent, e.g. Water, to be produced. Extrusion products may be made by fusing the fragrance or flavor compositions together with a suitable waxy substance and by extrusion followed by solidification, optionally in a suitable solvent, e.g. Isopropanol.

4-phenyl-pentan-2-ol of formula (I) and fragrance or flavor compositions containing 4-phenyl-pentan-2-ol can be used in concentrated form, in solutions or in modified form as described above for the preparation of inventive perfumed articles such. B. Perfume Extraits, Eau de Parfums, Eau de toilettes, shaving waters, eau de colognes, pre-shave products, splash colognes and scented refreshing wipes, as well as the perfuming of acidic, alkaline and neutral detergents, such as floor cleaners, window glass cleaners, dishwashing detergents, bathroom and sanitary cleaners, scouring creams, fixed and liquid toilet cleaners, powder and foam carpet cleaners, textile removers, ironing aids, liquid detergents, powder detergents, laundry pretreatment agents such as bleach, soaking and stain removers, laundry conditioners, laundry soap, washing tablets, disinfectants, surface disinfectants and air fresheners in liquid, gel or solid support applied form, aerosol sprays, waxes and polishes such as furniture polishes, floor waxes, shoe creams and personal care products such as solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, ko oil-in-water, water-in-oil and water-in-oil-in-water type smectic emulsions such as skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after -sun creams and lotions, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning lotions and lotions, hair care products such as hair sprays, hair gels, firming hair lotions, hair conditioners, permanent ones and semipermanent hair dyes, hair styling agents such as cold waving and hair straightening agents, hair lotions, hair creams and lotions, deodorants and antiperspirants such as underarm sprays, roll-ons, deodorants, deodorants, decorative cosmetics such as eyeshadows, nail polishes, make-ups, lipsticks, mascara and others candles, lamp oils, incense sticks, insecticides, repellents and fuels.

4-phenyl-pentan-2-ol of the formula (I) can be incorporated into flavored or flavored articles, in particular in the diet, oral care or pleasure-serving preparations.

The diet or pleasure-serving preparations are, for example, baked goods (eg bread, dry biscuits, cakes, other pastry), confectionery (eg chocolates, chocolate bar products, other bar products, fruit gums, hard and soft caramels, chewing gum), alcoholic or non-alcoholic beverages (eg Coffee, tea, wine, wine-based beverages, beer, beer-based drinks, liqueurs, schnapps, brandies, fruit-based sodas, isotonic drinks, soft drinks, nectars, fruit and vegetable juices, fruit or vegetable juice preparations), instant drinks (eg instant cocoa drinks, instant tea drinks, instant coffee drinks), meat products (eg ham, fresh sausage or raw sausage preparations) , spiced or marinated fresh or cured meat products), eggs or egg products (dry egg, egg whites, egg yolks), cereal products (eg breakfast cereals, muesli bars, pre-cooked finished rice products), dairy products (eg milk drinks, milk ice cream, yoghurt, kefir, cream cheese, soft cheese, hard cheese , Dried milk powder, whey, butter, buttermilk, partially or completely hydrolysed milk protein-containing products), products of soy protein or other soybean fractions (eg soymilk and products made thereof, soy lecithin-containing preparations, fermented products such as tofu or tempe or products thereof , Soy sauces), fruit preparations (eg jams, fruit is, fruit sauces, fruit fillings), vegetable preparations (eg ketchup, sauces, dried vegetables, frozen vegetables, pre-cooked vegetables, pickled vegetables, cooked vegetables), snacks (eg baked or fried potato chips or potato dough products, bread dough products, corn or peanut based extrudates), Products based on fat and oil or emulsions thereof (eg mayonnaise, remoulade, dressings, spice preparations), other ready meals and soups (eg dry soups, instant soups, pre-gassed soups), spices, spice mixtures and in particular seasoning seasonings, for example to be used in the snack area. After incorporation of the compound of formula (I) according to the invention, these preparations are preparations according to the invention (as an example of inventive articles).

Formulations according to the invention can be applied, for example, to B. present as a semi-finished product or as seasoning mixture.

Preparations according to the invention can serve, in particular, as semi-finished goods for the production of further preparations for nutrition or enjoyment, in particular in spray-dried form. Formulations according to the invention may also be in the form of capsules, tablets (non-coated and coated tablets, eg enteric coatings), dragees, granules, pellets, solid mixtures, dispersions in liquid phases, as emulsions, as powders, as solutions, as Pastes or other swallowable or chewable preparations as dietary supplements.

Oral preparations according to the invention are, in particular, oral and / or dental care products such as toothpastes, tooth gels, tooth powders, mouthwashes, chewing gums and other oral hygiene products.

Other customary active substances, basic substances, auxiliaries and additives for nutrition, oral care or pleasure-use preparations according to the invention can be used in amounts of 5 to 99.999999% by weight, preferably 10 to 80% by weight, based on the Total weight of the preparation to be included. Furthermore, the preparations may comprise water in an amount of up to 99.999999% by weight, preferably 5 to 80% by weight, based on the total weight of the preparation.

Preparations according to the invention (as examples of articles according to the invention) containing 4-phenyl-pentan-2-ol are prepared according to a preferred embodiment by reacting the 4-phenyl-pentan-2-ol of the formula (I) as a substance, as a solution (eg B. in ethanol, water or 1,2-propylene glycol) or in the form of a mixture with a solid or liquid carrier (eg maltodextrin, starch, silica gel), other flavors or flavorings and optionally other auxiliaries and / or stabilizers (eg natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic) are incorporated into a nutritional, oral care or pleasure base preparation. Advantageously, preparations according to the invention present as solution and / or suspension or emulsion can also be converted by spray-drying into a solid preparation according to the invention (semi-finished product).

The spray-dried solid preparations according to the invention (as an example of inventive articles) are particularly suitable as semi-finished goods for the production of further preparations according to the invention. The spray-dried solid preparations according to the invention preferably contain 50 to 95% by weight of excipients, in particular maltodextrin and / or starch, 5 to 40% adjuvants, preferably natural or artificial polysaccharides and / or vegetable gums such as modified starches or gum arabic.

According to a further preferred embodiment, to prepare preparations according to the invention, the 4-phenyl-pentan-2-ol and optionally other constituents of the preparation according to the invention are initially dissolved in emulsions, in liposomes, e.g. starting from phosphatidylcholine, in microspheres, in nanospheres or even in capsules, granules or extrudates of a matrix suitable for food and beverage, e.g. from starch, starch derivatives (eg modified starch), cellulose or cellulose derivatives (eg hydroxypropylcellulose), other polysaccharides (eg dextrin, alginate, curdlan, carageenan, chitin, chitosan, pullulan), natural fats, natural waxes (eg beeswax, carnauba wax) Proteins, eg Gelatin or other natural products (e.g., shellac). Depending on the matrix, the products may be obtained by spray drying, spray granulation, melt granulation, coacervation, coagulation, extrusion, melt extrusion, emulsion processes, coating or other suitable encapsulation processes and optionally a suitable combination of the abovementioned processes. In a further preferred preparation process for a preparation according to the invention, the 4-phenylpentan-2-ol is first complexed with one or more complexing agents, for example cyclodextrins or cyclodextrin derivatives, preferably α- or β-cyclodextrin, and used in this complexed form.

Particular preference is given to a preparation according to the invention in which the matrix is selected so that the 4-phenylpentan-2-ol of the formula (I) is released from the matrix in a delayed manner, so that a long-lasting effect is achieved. In this respect, a fat, wax, polysaccharide or protein matrix is particularly preferred.

As further constituents for preparations according to the invention, which are used for nutrition or pleasure, it is possible to use customary bases, auxiliaries and additives for foods or luxury foods, for example water, mixtures of fresh or processed, vegetable or animal raw materials or raw materials (eg raw, roasted , dried, fermented, smoked and / or cooked meat, bones, cartilage, fish, vegetables, fruits, herbs, nuts, vegetable or fruit juices or pastes or their mixtures), digestible or non-digestible carbohydrates (eg sucrose, maltose, fructose , Glucose, dextrins, amylose, amylopectin, inulin, xylans, cellulose, tagatose), sugar alcohols (eg sorbitol, erythritol), natural or hardened fats (eg, tallow, lard, palm fat, coconut fat, hardened vegetable fat), oils (eg, sunflower oil, peanut oil, corn oil, olive oil, fish oil, soybean oil, sesame oil), fatty acids or their salts (eg, potassium stearate), proteinogenic or nonproteinogenic amino acids, and related compounds (eg γ-aminobutyric acid, taurine), peptides (eg glutathione), native or processed proteins (eg gelatin), enzymes (eg peptidases), nucleic acids, nucleotides, taste-correcting agents for unpleasant taste impressions, further taste modulators for further, generally not unpleasant taste impressions other flavor modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), emulsifiers (eg lecithins, diacylglycerols, gum arabic), stabilizers (eg carageenan, alginate), preservatives (eg benzoic acid, sorbic acid) , Antioxidants (eg tocopherol, ascorb acid), chelators (eg citric acid), organic or inorganic acidulants (eg malic acid, acetic acid, citric acid, tartaric acid, phosphoric acid), bitter substances (eg quinine, caffeine, limonin, amarogentin, humolone, lupolone, catechins, tannins), mineral salts (eg Sodium chloride, potassium chloride, magnesium chloride, sodium phosphates), enzymatic browning inhibiting substances (eg sulfite, ascorbic acid), essential oils, plant extracts, natural or synthetic dyes or color pigments (eg carotenoids, flavonoids, anthocyanins, chlorophyll and their derivatives), spices, trigeminally active Substances or plant extracts containing such trigeminal active substances, synthetic, natural or nature-identical flavorings or fragrances and odor remedies.

Dentifrices (as a base for oral care preparations) containing 4-phenylpentan-2-ol generally comprise an abrasive system (abrasives or abrasives) such as silicic acids, calcium carbonates, calcium phosphates, aluminas and / or hydroxyapatites. surfactants such as sodium lauryl sulfate, sodium lauryl sarcosinate and / or cocamidopropyl betaine, humectants, such as glycerol and / or sorbitol, thickeners, such as carboxymethyl cellulose, polyethylene glycols, carrageenan and / or Laponite ^®, sweeteners such as saccharin, flavor correcting agents for unpleasant taste impressions, taste corrigents for further , usually not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, Nucleotides such as guanosine monophosphate, adenosine monophosphate or other substances such as sodium glutamate or 2-phenoxypropionic acid), cooling agents such as menthol, menthol derivatives (eg L-menthol, L-menthyl lactate, L-menthyl alkyl carbonates, menthone ketals, menthane carboxylic acid amides), 2,2,2-trialkylacetic acid amides (eg 2,2-diisopropylpropionic acid methylamide), icilin and icilin derivatives, stabilizers and active agents such as sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulfate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphates, triclosan, cetylpyridinium chloride, aluminum lactate, potassium citrate, potassium nitrate , Potassium chloride, strontium chloride, hydrogen peroxide, flavors and / or sodium bicarbonate or odoriferous.

Chewing gums (as another example of oral care preparations) containing 4-phenylpentan-2-ol generally comprise a chewing gum base, i. chewing gum that becomes plastic during chewing, sugar of various types, sugar substitutes, other sweet tasting substances, sugar alcohols, flavoring agents for unpleasant taste impressions, other flavor modulators for further, generally not unpleasant taste impressions, taste modulating substances (eg inositol phosphate, nucleotides such as guanosine monophosphate, adenosine monophosphate or others Substances such as monosodium glutamate or 2-phenoxypropionic acid), humectants, thickeners, emulsifiers, flavors and stabilizers or odor remedies.

In addition to 4-phenyl-pentan-2-ol, the preparations according to the invention preferably contain an aroma composition in order to round off and refine the taste and / or smell of the preparation. Suitable (additional) flavoring compositions include e.g. synthetic, natural or nature-identical flavorings, fragrances and flavorings as well as suitable excipients and carriers.

Other aspects of the present invention will be apparent from the following examples and the appended claims.

The invention will be explained in more detail by way of examples. Unless otherwise indicated, all data are by weight.

Example 1: Preparation of 4-phenyl-pentan-2-ol formula (I) (based on the method according to literature Journal f. Prakt. Chemie volume 319, No. 4, 1977, 601-610 )

In a 1 L stirred autoclave 206 g (1 mol) of 2,4,6-trimethyl-4-phenyl- (1,3) dioxan (Vertacetal ^®) in 250 ml ethanol / water 9: 1, with 0.2 g Palladium (5% on activated carbon) submitted. The mixture was then hydrogenated at 180 ° C and a pressure of 20 bar for 8 hours with stirring until 2 mol of hydrogen. It was then cooled to room temperature, the reaction solution was filtered and concentrated. The crude product (165 g) was fractionated on a 30 cm Vigreux column in vacuo.
Yield: 150.9 g (92% of theory) bp .: 130 ° -135 ° C./8 mbar
Purity to GC 99.5%, diastereomer ratio (about 1: 1)

Example 2: Preparation of 4-phenyl-pentan-2-ol of the formula (I) via Grignard reaction

In a 2 l stirrer 148 g (1 mol) of 3-phenylbutyraldehyde in 500 ml of THF abs. submitted. 81.8 g of methylmagnesium chloride (22% strength solution in THF (1.1 mol)) were then added over one hour with stirring and cooling at 0 ° C. Thereafter, stirring was continued for 1.5 hours under reflux. After cooling to room temperature, the reaction solution was carefully decomposed with 300 ml of 10% NaOH, the aqueous phase separated, the organic phase washed neutral with water and concentrated. The crude product (167.8 g) was fractionated on a 30 cm Vigreux column in vacuo.
Yield: 147 g (89.6% of theory) bp .: 130 ° -135 ° C./8 mbar.
Purity to GC 99.5%, diastereomer ratio (about 1: 1)

The spectroscopic data of 4-phenyl-pentan-2-ol of the formula (I) were determined. The data of the diastereomers (about 1: 1) are given below.
¹ H-NMR _(CDCl3, 400 MHz, TMS = 0): 1.12, 1.18 (d, J = 6.2, 3H); 1.26, 1.27 (d, J = 7, 3H); 1.61-1.86 (m, 2H); 2.81-3.01 (m, 1H); 3.53-3.59 (m, 1H); 7.18-7.32 (m, aromat. 5H).
¹³ C-NMR (CDCl _3, 100 MHz): 147.3 (s), 146.8 (s); 128.6 (d), 128.5 (d), 127.1 (d), 126.9 (d); 126.2 (d), 126.1 (d); 66.4 (d), 65.9 (d); 47.9 (t), 47.7 (t); 37.0 (d), 36.6 (d); 24.2 (q), 23.7 (q); 23.1 (q), 22.3 (q).
MS: m / z (%) = 164 (3, M ⁺ ), 146 (32), 131 (89), 106 (49), 105 (100), 91 (55), 78 (20), 77 (24 ), 45 (18).
MS: m / z (%) = 164 (3, M ⁺ ), 146 (34), 131 (98), 106 (45), 105 (100), 91 (55), 78 (20), 77 (25 ), 45 (18).

Example 3: Perfume Composition (Fragrance Composition)

parts by weight Agrumex LC 10.00 Amarocit® 10% in DPG 10.00 Ambroxid 10.00 basil oil 10.00 Calone 1951 10% in DPG 10.00 cedarwood 10.00 cedrol 50,00 Citral 10% in DPG 10.00 Citronellol 5.00 coumarin 10.00 Cyclogalbanat® 10% in DPG 15.00 dihydromyrcenol 80,00 Farenal® 10% in DPG 5.00 Galbex 10% in DPG 25,00 Globalide® 80,00 Globanone® 40,00 Hedion 90.00 helional 20.00 heliotropin 5.00 Hexenol cis-3 10% in DPG 15.00 Hexenyl salicylate cis-3 10.00 Beta-ionone 5.00 Iso E Super 180.00 Isodamascon® 10% in DPG 10.00 Isomuscone (cyclohexadecanone) 20.00 Isoraldein 70 20.00 Ketamber 10% in TEC 25,00 Lavandin oil Grosso Nat. 15.00 lilial 20.00 linalool 20.00 Linalylacetat 40,00 Tangerine oil brasil. green 50,00 Timberol® 40,00 vanillin 5.00 Veloutone 10% in DPG 20.00 Ysamber K® 10.00 total 1,000.00 DPG: dipropylene glycol, TEC = triethyl citrate

Odor description of the perfume composition without addition of compound of the formula (I): woody, floral, dry

In the opinion of the perfumers, this perfume composition becomes fresher, brighter, more rounded and more harmonious with the addition of 3% by weight of 4-phenylpentan-2-ol from Example 2, adding a green-fruity and sweet note and the woody and floral notes Aspects are reinforced. The used 4-phenyl-pentan-2-ol of formula (I) gives the composition by its own odor and by its modifying and reinforcing effect (booster effect) has its own character and combines the different odoriferous elements.

Example 4: Perfume Composition (Fragrance Composition)

parts by weight Allylcyclohexylpropionat 3.00 amylsalicylate 2.00 benzyl 64,00 Citronellol 122.00 Citral 10% in DPG 2.00 Cyclamenaldehyd 10.00 dihydromyrcenol 3.00 dimethyl benzyl 3.00 Ethyl salicylate 10% in DPG 2.00 eugenol 3.00 Indoflor 10% in DPG 16.00 Galaxolide 50% in DPG 164.00 geraniol 35,00 dihydromethyl 6.00 heliotropin 4.00 hexyl cinnamic aldehyde 121.00 Vertocitral 4.00 Hedion 42,00 indole 2.00 isobutyl 6.00 Lavandin oil Grosso Nat. 6.00 Acetyl 10.00 Majantol 190.00 linalool 35,00 Linalylacetat 10.00 Methyl anthranilate 10% in DPG 5.00 nerol 10.00 orange oil 6.00 Phantolide 4.00 phenylacetaldehyde 6.00 phenylethyl 75.00 Florol 6.00 sandalwood 3.00 sandranol 16.00 trifernal 2.00 tonalide 2.00 total 1,000.00 DPG: dipropylene glycol

Odor description of the perfume composition without addition of compound of formula (I): flowery, lily of the valley.

In the opinion of the perfumers, this perfume composition comes to life with the addition of 6% by weight of 4-phenylpentan-2-ol of the formula (I) from Example 1. The impression of flowery is greatly enhanced. The composition looks brighter, more rounded and more harmonious, adding a green-fruity and natural touch. The used 4-phenyl-pentan-2-ol of formula (I) gives the composition by its own odor and by its modifying and reinforcing effect (booster effect) has its own character and combines the different odoriferous elements.

The aspects mentioned are ^® by further addition of 0.1 wt .-% Vertacetal further emphasized in a harmonious fashion.

Example 5: Shampoo 4-phenyl-pentan-2-ol of the formula (I) from Example 1 was incorporated in a dosage of 0.5% by weight into a shampoo base of the following composition:

Sodium lauryl ether sulfate (e.g., Texapon NSO, Cognis Deutschland GmbH) 12% Cocamidopropylbetaine (for example Dehyton K, Cognis Deutschland GmbH) 2% sodium chloride 1.4% citric acid 1.3% Phenoxyethanol, methyl, ethyl, butyl, and propylparaben 0.5% water 82.8%

The pH of the shampoo base was about 6. From this, 100 ml of a 20 wt .-% aqueous shampoo solution were prepared. In this shampoo solution, 2 hair slides were washed together for 2 minutes and then rinsed for 20 seconds under running lukewarm water. One strand of hair was wet wrapped in aluminum foil and dried the second strand of hair with a hair dryer. Both strands of hair were judged by a panel odor.

Odor description respectively: radiant, interesting green scent towards grapefruit and rhubarb, very natural aura.

Example 6: fabric softener

The perfume composition of Example 3 (after addition of 3 wt .-% 4-phenyl-pentan-2-ol formula (I) from Example 2) was in a dosage of 0.5 wt .-% in a fabric softener base of the following composition incorporated: Quaternary ammonium methosulfate (esterquat), about 90% (eg Rewoquat WE 18, Fa. Witco Surfactants GmbH) 5.5% Alkyldimethylbenzylammonium chloride, about 50% (eg Preventol R50, Fa. Bayer AG) 0.2% Color solution, about 1% 0.3% water 94.0%

The pH of the fabric softener base was in the range of 2 to 3. Two pieces of fabric were mixed with 370 g of a 1% aqueous fabric softener solution based on the fabric softener comprising 0.5% by weight of compound formula (I) -Ground mass in a Linetest machine in the softening program 30 minutes at 20 ° C rinsed. The flaps were wrung out and then spun for 20 seconds. A rag was wet-sealed, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor.

Odor description: flowery, woody, fresh, radiant, green-fruity aspects with light sweet undertones, rounded and harmonious olfactory impression.

Example 7: Washing powder

The perfume composition from Example 4 (after addition of 6% by weight of compound of formula (I) from Example 1) was incorporated in a dosage of 0.4% by weight into a base powder of the following formulation: Linear Na-alkylbenzenesulfonate 8.8% Ethoxylated fatty alcohol C12-18 (7 EO) 4.7% Na-soap 3.2% defoamers DOW CORNING (R) 2-4248S POWDERED ANTIFOAM, Silicone oil on zeolite as carrier material 3.9% Zeolite 4A 28.3% Na carbonate 11.6% Na salt of a copolymer of acrylic and maleic acid (Sokalan CP5) 2.4% Na silicate 3.0% carboxymethylcellulose 1.2% Dequest 2066 2.8% ([[(Phosphonomethyl) imino] bis [(ethylenitrilo) bis (methylene)]] tetrakisphosphonic acid, sodium salt) Optical brightener 0.2% Na sulfate 6.5% protease 0.4% sodium perborate 22.0% TAED 1.0%

Two cloths were washed with 370 g of a 1% aqueous Waschpulauge on the basis of 0.4 wt .-% of the perfume oil composition of Example 4 comprising washing powder base (the pH of Waschpulaugeauge is clearly in the basic range) in a Linetest machine washed in the main wash for 45 minutes at 60 ° C. The flaps were first rinsed with cold water for 5 minutes, wrung out and then spun for 20 seconds. A rag was wet-sealed, and one hung up to dry. Subsequently, both flaps were assessed by a panel odor.

Odor description in each case: strongly flowery, radiant, green-fruity and natural note with slight sweet and woody undertones, rounded and harmonious olfactory impression.

Claims (16)

Use of 4-phenyl-pentan-2-ol (I)

as a scent or flavoring. Use of 4-phenyl-pentan-2-ol (I)

as a scent or flavoring with a green, fruity note. Use according to one of the preceding claims, for imparting, modifying and / or enhancing an odor and / or flavor with the following aspects: green, fruity. Perfumed or flavored article comprising (a) 4-phenylpentan-2-ol (I)

such as (b) one, two, three or more other fragrances or flavorings. Perfumed or flavored article according to claim 4, wherein the one or more other fragrances or flavorings (component (b)) impart a woody and / or floral odor and / or flavor. Perfumed or flavored article according to claim 4 or 5, comprising as further fragrance 2,4,6-trimethyl-4-phenyl-1,3-dioxane. Perfumed or flavored article according to any one of claims 4 to 6, wherein the weight ratio of the total amount of 4-phenyl-pentan-2-ol to the total amount of other fragrances or flavorings is in the range of 1: 1000 to 1: 0.5. Perfumed or flavored article according to any one of claims 4 to 7, wherein the article is a fragrance or flavoring composition. A fragrance or flavoring composition according to claim 8 comprising 4-phenyl-pentan-2-ol in an amount sufficient to impart, modify and / or enhance an odor or flavor note of the green, fruity type. Fragrance or flavoring composition according to any one of claims 8 or 9, characterized in that the olfactory or Aromastoffkomposition a total amount of 4-phenyl-pentan-2-ol in the range of 0.01 to 50 wt .-%, preferably 0.01 to 25% by weight, and more preferably 0.5 to 20% by weight, based on the total amount of the fragrance or flavoring composition. A perfumed or flavored article according to any one of claims 4 to 7, preferably comprising a fragrance or flavoring composition according to any one of claims 6 to 8, said article being selected from the group consisting of: perfume extracts, eau de parfums, eau de toilettes, Shaving lotions, Eau de Colognes, Pre-shave products, Splash colognes, Perfumed refreshing wipes, Acid, Alkaline and neutral detergents, Textile fresheners, Ironing aids, Liquid detergents, Powdered detergents, Laundry pretreatment preparations, Dishwashing detergents, Washing soaps, Washing tablets, Disinfectants, Surface disinfectants, Air fresheners, Aerosol sprays, waxes and polishes, body care products, hand creams and lotions, foot creams and lotions, depilatory creams and lotions, after-shave creams and lotions, tanning lotions and lotions, hair care products, deodorants and antiperspirants, decorative cosmetics products, candles, L ampen oils, incense sticks, insecticides, repellents and fuels. A method for imparting, modifying and / or enhancing an odor or flavor with one, several or all of the notes green, fruity, wherein a sensory effective amount of (i) 4-phenylpentan-2-ol of the formula (I)

or (ii) a fragrance or flavoring composition comprising 4-phenyl-pentan-2-ol according to any one of claims 8 to 10
is contacted or mixed with a product. Process for the preparation of (i)

or (ii) a mixture comprising 4-phenyl-pentan-2-ol, comprising the following step: catalytic cleavage of a substituted 1,3-dioxane of the formula (A)

where Y is hydrogen or an acyl radical having 1 to 10 carbon atoms. The method of claim 13, wherein Y is methyl or ethyl. The method of claim 13 or 14, wherein Y is methyl. A process according to any one of claims 13 to 15, wherein the mixture (ii) comprising 4-phenyl-pentan-2-ol comprises a portion of the substituted 1,3-dioxane of formula (A).