Nothing Special   »   [go: up one dir, main page]

EP0035684A1 - Process for the production of aromatic substances - Google Patents

Process for the production of aromatic substances Download PDF

Info

Publication number
EP0035684A1
EP0035684A1 EP81101286A EP81101286A EP0035684A1 EP 0035684 A1 EP0035684 A1 EP 0035684A1 EP 81101286 A EP81101286 A EP 81101286A EP 81101286 A EP81101286 A EP 81101286A EP 0035684 A1 EP0035684 A1 EP 0035684A1
Authority
EP
European Patent Office
Prior art keywords
tobacco
extract
irradiated
diterpenes
irradiation
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP81101286A
Other languages
German (de)
French (fr)
Other versions
EP0035684B1 (en
Inventor
Ursula Brümmer
Volker Heeman
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
British American Tobacco Germany GmbH
Original Assignee
BAT Cigarettenfabriken GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BAT Cigarettenfabriken GmbH filed Critical BAT Cigarettenfabriken GmbH
Publication of EP0035684A1 publication Critical patent/EP0035684A1/en
Application granted granted Critical
Publication of EP0035684B1 publication Critical patent/EP0035684B1/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
    • A24B15/26—Use of organic solvents for extraction
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/305—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances of undetermined constitution characterised by their preparation

Definitions

  • the invention relates to a process for the production of flavorings by UV irradiation of an alcoholic extract containing diterpenes, which was obtained from the surface resin of fresh tobacco plants or parts thereof or from the "gum" derived from tobacco flowers, in the presence of oxygen.
  • the surface resin of fresh tobacco plants contains diterpenes, in particular Duvane, which influence the tobacco aroma as smoke aroma precursors.
  • diterpenes in particular Duvane
  • Numerous processes are known for isolating these diterpenes from the surface resin, in particular undesirable lipids also present in resin being separated off. Such a method is known for example from DE-OS 29 18 920.
  • the resulting diterpene fraction is added to finished tobacco after isolation and purification,
  • Nicotinia species such as N. tomentosiformis, glutinosa or sylvestris or known tobacco hybrids and tobacco plants from conventional tobacco crops are used as the starting material for obtaining the alcoholic diterpene fraction.
  • those types of tobacco can be used which are unsuitable as smoking tobacco, but which form large amounts of surface resin. The otherwise unsuitable tobacco plants can then be discarded after the diterpenes have been removed.
  • Tobacco flowers can also be used to produce the diterpene fraction.
  • Lower alcohols in particular methanol and ethanol, can be used as solvents for the diterpene fraction to be irradiated.
  • the irradiated extracts can, if necessary after prior concentration, be applied directly to finished tobacco, for example by spraying.
  • the photooxidation is preferably carried out by passing a stream of air or oxygen through the extract and simultaneously irradiating it with a suitable UV source which delivers a wavelength of 220-580 nm.
  • UV lamps e.g. High pressure mercury vapor lamps or the like can be used.
  • the photooxidation according to the invention can take place at room temperature, but other temperatures are also possible, e.g. Temperatures between -20 ° C and the boiling point of the solvent used.
  • the duration of the radiation depends on the size of the radiation approach, the respective type of diterpenes, which can vary depending on the tobacco plants, and the power of the UV source. It is generally one hour to 10 days, especially 6-24 hours.
  • the irradiated extract is fractionated onto the tobacco before being fed in. This can cause undesired by-products, e.g. very volatile constituents and polymers, which adversely affect the aroma or can do nothing to improve it, are separated off.
  • the aforementioned fractionation can be done in different ways.
  • a suitable method is column chromatography, e.g. on silica gel.
  • the irradiated solution is concentrated and placed on a silica gel column.
  • Another fractionation process is distillation. Even the concentration of the methanol extract at room temperature in a vacuum leads to the removal of unwanted low-boiling components.
  • the residue can then be subjected to high vacuum distillation, in a typical case collecting the distillate and using it as a flavoring which transitions at 0.02 Torr to a temperature of 100 ° C.
  • the residue obtained after removal of the methanol can also be subjected to steam distillation, the water vapor-volatile products being collected and used as flavorings.
  • the diterpene fraction thus obtained is mixed with methanol so that a solution with a concentration of 1-100 g solid / 1 methanol is obtained.
  • 300 ml of an extract obtained above are placed in a 500 ml reactor and irradiated for 10 hours at room temperature with stirring using a high-pressure mercury lamp (Philips high-pressure burner HPK 125), a constant stream of synthesis air being bubbled through the solution.
  • a high-pressure mercury lamp Philips high-pressure burner HPK 125
  • the irradiated extract obtained above is concentrated to a small volume and placed on a column loaded with silica gel (dimensions: 2.5 ⁇ 50 cm). The column is then eluted with hexane; the hexane fraction obtained is discarded. The column is then eluted with ether and finally with methanol, to which 1% acetic acid has been added. The eluates obtained here are collected and evaporated in vacuo at room temperature. The residue is taken up in ethanol and sprayed onto ready-made tobacco; the solvent is allowed to evaporate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Aromastoffe für Tabak werden erhalten, indem man einen aus frischen Tabakpflanzen gewonnenen, Diterpene enthaltenden alkoholischen Extrakt herstellt und diesen Extrakt in Gegenwart von Sauerstoff und in Abwesenheit von Sensibilisatoren unter UV-Bestrahlung oxidiert.Flavorings for tobacco are obtained by producing an alcoholic extract obtained from fresh tobacco plants and containing diterpenes and oxidizing this extract in the presence of oxygen and in the absence of sensitizers under UV radiation.

Description

Die Erfindung betrifft ein Verfahren zur Herstellung von Aromastoffen durch UV-Bestrahlung eines alkoholischen, Diterpene enthaltenden Extrakts, der aus dem Oberflächenharz von frischen Tabakpflanzen bzw. deren Teilen oder aus dem von Tabakblüten stammenden "Gum" erhalten wurde, in Gegenwart von Sauerstoff.The invention relates to a process for the production of flavorings by UV irradiation of an alcoholic extract containing diterpenes, which was obtained from the surface resin of fresh tobacco plants or parts thereof or from the "gum" derived from tobacco flowers, in the presence of oxygen.

Es ist bekannt, daß das Oberflächenharz von frischen Tabakpflanzen Diterpene, insbesondere Duvane, enthält, die als Raucharomaprecursoren das Tabakaroma beeinflussen. Es sind zahlreiche Verfahren bekannt, diese Diterpene aus dem Oberflächenharz zu isolieren, wobei insbesondere ebenfalls in Harz vorhandene unerwünschte Lipide abgetrennt werden. Ein derartiges Verfahren ist beispielsweise aus der DE-OS 29 18 920 bekannt.It is known that the surface resin of fresh tobacco plants contains diterpenes, in particular Duvane, which influence the tobacco aroma as smoke aroma precursors. Numerous processes are known for isolating these diterpenes from the surface resin, in particular undesirable lipids also present in resin being separated off. Such a method is known for example from DE-OS 29 18 920.

Die dabei erhaltene Diterpenfraktion wird nach Isolierung und Reinigung fertigkonfektioniertem Tabak zugesetzt,The resulting diterpene fraction is added to finished tobacco after isolation and purification,

Die Eigenschaften von aus Tabakpflanzen isolierten Diterpenen als Raucharomaprecursoren hat in der Vergangenheit mehrere-Arbeitsgruppen veranlaßt, sich mit der Aufklärung der chemischen Struktur der Diterpene und ihren chemischen Reaktionen, insbesondere hinsichtlich ihrer Photoreaktionen mit Singulett-Sauerstoff, zu befassen, vgl. Acta Chemica Scandinavica 1979, Seite 437-442. Bei diesen Untersuchungen wurde die Photooxydation in Gegenwart von Sensibilatoren, z.B. Bengalrosa, durchgeführt.The properties of isolated from tobacco plants diterpenes as Raucharomaprecursoren has several in the past - led working groups to deal with the elucidation of the chemical structure of the diterpenes and their chemical reactions, in particular in terms of their photochemical reactions with singlet oxygen, see. Acta Chemica Scandinavica 1979, pages 437-442. In these investigations, the photooxidation was carried out in the presence of sensitizers, for example rose Bengal.

Es wurde nun gefunden, daß man aus einer Diterpenfraktion der oben genannten Art ein erheblich verbessertes Tabakaroma erhalten kann, wenn man den alkoholischen Diterpenextrakt in Abwesenheit von Sensibilisatoren bestrahlt, d.h. einer Photooxydation unterwirft. Infolge der Abwesenheit von Sensibilisatoren erfolgt die Photo- _ oxydation der Diterpene nicht mehr durch Singulett-Sauerstoff, sondern vielmehr nach einem üblichen Radikalmechanismus. Demgemäß weisen die erfindungsgemäß erhaltenen Aromastoffe, wie eine erste Analyse ergeben hat, Produkte mit zahlreichen freien Carboxylgruppen bei im übrigen unbekannter Konstitution auf.It has now been found that a significantly improved tobacco aroma can be obtained from a diterpene fraction of the type mentioned above if the alcoholic di terpene extract irradiated in the absence of sensitizers, ie subject to photooxidation. As a result of the absence of sensitizers, the photo-oxidation of the diterpenes is no longer carried out by singlet oxygen, but rather by a conventional radical mechanism. Accordingly, the aroma substances obtained according to the invention have, as a first analysis has shown, products with numerous free carboxyl groups with an otherwise unknown constitution.

Die mit dem erfindungsgemäß behandelten Diterpenextrakt erreichten Geschmacksverbesserungen im Aroma des mit dem bestrahlten Extrakt erhaltenen Tabaks sind überraschend, da man unter den Verfahrensbedingungen eine erheblich stärkere Zerstörung der Aromastoffe als bei der Photooxydation mit Singulett-Sauerstoff annehmen mußte.The taste improvements achieved in the aroma of the tobacco obtained with the irradiated extract obtained with the diterpene extract treated according to the invention are surprising, since under the process conditions a considerably greater destruction of the aroma substances than in photooxidation with singlet oxygen had to be assumed.

Als Ausgangsmaterial für die Gewinnung der alkoholischen Diterpenfraktion dienen Nicotinia-Arten, wie N. tomentosiformis, glutinosa oder sylvestris oder bekannte Tabak-Hybride sowie Tabakpflanzen aus üblichen Tabakkulturen. Dabei können insbesondere solche Tabakarten verwendet werden, die an sich als Rauchtabak ungeeignet sind, jedoch große Mengen an Oberflächenharz bilden. Die im übrigen ungeeigneten Tabakpflanzen können dann nach Abtrerinung der Diterpene verworfen werden. Weiterhin können zur Herstellung der Diterpenfraktion Tabakblüten eingesetzt werden.Nicotinia species such as N. tomentosiformis, glutinosa or sylvestris or known tobacco hybrids and tobacco plants from conventional tobacco crops are used as the starting material for obtaining the alcoholic diterpene fraction. In particular, those types of tobacco can be used which are unsuitable as smoking tobacco, but which form large amounts of surface resin. The otherwise unsuitable tobacco plants can then be discarded after the diterpenes have been removed. Tobacco flowers can also be used to produce the diterpene fraction.

Als Lösungsmittel für die zu bestrahlende Diterpenfraktion können niedere Alkohole, insbesondere Methanol und Ethanol, eingesetzt werden. Die bestrahlten Extrakte können, ggf. nach vorheriger Konzentrierung, direkt auf fertigkonfektionierten Tabak, z.B. durch Sprühen, aufgegeben werden.Lower alcohols, in particular methanol and ethanol, can be used as solvents for the diterpene fraction to be irradiated. The irradiated extracts can, if necessary after prior concentration, be applied directly to finished tobacco, for example by spraying.

Vorzugsweise erfolgt die Photooxydation, indem man einen Luft- bzw. Sauerstoffstrom durch den Extrakt leitet und diesen gleichzeitig mit einer geeigneten UV-Quelle, die eine Wellenlänge von 220-580 nm liefert, bestrahlt.The photooxidation is preferably carried out by passing a stream of air or oxygen through the extract and simultaneously irradiating it with a suitable UV source which delivers a wavelength of 220-580 nm.

Für die Bestrahlung können übliche UV-Lampen, z.B. Hochdruck-Quecksilberdampflampen oder dergl. verwendet werden.Conventional UV lamps, e.g. High pressure mercury vapor lamps or the like can be used.

Die Photooxydation gemäß der Erfindung kann bei Raumtemperatur erfolgen, es sind jedoch auch andere Temperaturen möglich, z.B. Temperaturen zwischen -20° C und dem Siedepunkt des verwendeten Lösungsmittels.The photooxidation according to the invention can take place at room temperature, but other temperatures are also possible, e.g. Temperatures between -20 ° C and the boiling point of the solvent used.

Die Dauer der Bestrahlung richtet sich nach der Größe des Bestrahlungsansatzes, der jeweiligen Art der Diterpene, die in Abhängigkeit von den Tabakpflanzen schwanken kann, und der Leistung der UV-Quelle. Sie beträgt im allgemeinen eine Stunde bis 10 Tage, insbesondere 6-24 Stunden.The duration of the radiation depends on the size of the radiation approach, the respective type of diterpenes, which can vary depending on the tobacco plants, and the power of the UV source. It is generally one hour to 10 days, especially 6-24 hours.

Gemäß einer weiteren vorteilhaften Ausführungsform der Erfindung wird der bestrahlte Extrakt vor der Aufgabe auf den Tabak fraktioniert. Hierdurch können Unerwünschte Nebenprodukte, z.B. sehr flüchtige Bestandteile und Polymere, die das Aroma nachteilig beeinflussen oder nichts zu seiner Verbesserung beitragen können, abgetrennt werden.According to a further advantageous embodiment of the invention, the irradiated extract is fractionated onto the tobacco before being fed in. This can cause undesired by-products, e.g. very volatile constituents and polymers, which adversely affect the aroma or can do nothing to improve it, are separated off.

Die vorgenannte Fraktionierung kann auf verschiedenen Wegen erfolgen. Eine geeignete Methode ist die Säulenchromatographie, z.B. an Kieselgel. Hierzu wird die bestrahlte Lösung eingeengt und auf eine Kieselgel-Säule gegeben.The aforementioned fractionation can be done in different ways. A suitable method is column chromatography, e.g. on silica gel. For this purpose, the irradiated solution is concentrated and placed on a silica gel column.

Anschließend wird mit verschiedenen Lösungsmitteln mit steigender Polarität eluiert. Als erstes Eluierungsmittel kann z.B. Hexan verwendet werden; dieses Eluat, das unpolare Kohlenwasserstoffe enthält, wird verworfen. Anschließend wird mit Ether eluiert; dieses Eluat wird gesammelt. Schließlich können durch Eluierung mit Methanol, dem ggf. eine geringe Menge, z.B. ≤ 1%o Essigsäure zugesetzt wurde, die während der Bestrahlung gebildeten wertvollen Carbonsäuren isoliert und gesammelt werden. Die Ether- und Methanoleluate werden anschließend im Vakuum eingeengt; der Rückstand kann in einem anderen Lösungsmittel aufgenommen und anschließend auf den Tabak aufgegeben werden.Then elute with various solvents with increasing polarity. As a first eluent e.g. Hexane can be used; this eluate, which contains non-polar hydrocarbons, is discarded. The mixture is then eluted with ether; this eluate is collected. Finally, by elution with methanol, which may contain a small amount, e.g. ≤ 1% o acetic acid was added, the valuable carboxylic acids formed during the irradiation are isolated and collected. The ether and methanol eluates are then concentrated in vacuo; the residue can be taken up in another solvent and then added to the tobacco.

Ein weiteres Fraktionierungsverfahren ist die Destillation. Bereits die-Einengung des Methanolextraktes bei Raumtemperatur im Vakuum führt zu einer Entfernung unerwünschter leicht siedender Bestandteile. Der Rückstand kann anschließend einer Hochvakuumdestillation unterworfen werden, wobei in einem typischen Fall das Destillat gesammelt und als Aromastoff verwendet wird, das bei 0,02 Torr bis zu einer Temperatur von 100° C übergeht.Another fractionation process is distillation. Even the concentration of the methanol extract at room temperature in a vacuum leads to the removal of unwanted low-boiling components. The residue can then be subjected to high vacuum distillation, in a typical case collecting the distillate and using it as a flavoring which transitions at 0.02 Torr to a temperature of 100 ° C.

Schließlich kann man den nach der Entfernung des Methanols erhaltenen Rückstand auch einer Wasserdampfdestillation unterwerfen, wobei die wasserdampfflüchtigen Produkte gesammelt und als Aromastoffe eingesetzt werden.Finally, the residue obtained after removal of the methanol can also be subjected to steam distillation, the water vapor-volatile products being collected and used as flavorings.

Das Verfahren der Erfindung wird im folgenden anhand eines bevorzugten Ausführungsbeispiels näher erläutert.The method of the invention is explained in more detail below with the aid of a preferred exemplary embodiment.

Herstellun einer alkoholischen Diter enfraktionProduction of an alcoholic diter fraction

Teile von frischen grünen Tabakpflanzen, nämlich Stengel, Blüten und Blätter, werden 2 x 30 Sekunden lang mit Methylenchlorid in einer Menge von 1' 1/kg Tabakteile gewaschen. Die anschließende Abtrennung der Diterpene von Begleitstoffen aus der Methylenchloridfraktion erfolgt in üblicher Weise durch Chromatographie an-Kieselgel oder durch Phasenverteilung.Parts of fresh green tobacco plants, namely stems, flowers and leaves, are washed 2 × 30 seconds with methylene chloride in an amount of 1 ′ 1 / kg parts of tobacco. The subsequent separation of the diterpenes from accompanying substances from the methylene chloride fraction is carried out in the usual way by chromatography on silica gel or by Phase distribution.

Die so erhaltene Diterpenfraktion wird so mit Methanol versetzt, daß eine Lösung mit einer Konzentration von 1-100 g Feststoff/1 Methanol erhalten wird.The diterpene fraction thus obtained is mixed with methanol so that a solution with a concentration of 1-100 g solid / 1 methanol is obtained.

PhotooxidationPhotooxidation

300 ml eines vorstehend erhaltenen Extrakts werden in einen 500 ml Reaktor gegeben und bei Raumtemperatur unter Rühren mit einer Quecksilber-Hochdrucklampe (Philips-Hochdruckbrenner HPK 125) 10 Stunden lang bestrahlt, wobei man durch die Lösung einen ständigen Strom von Syntheseluft durchperlen läßt.300 ml of an extract obtained above are placed in a 500 ml reactor and irradiated for 10 hours at room temperature with stirring using a high-pressure mercury lamp (Philips high-pressure burner HPK 125), a constant stream of synthesis air being bubbled through the solution.

Fraktionierung des bestrahlten ExtraktesFractionation of the irradiated extract

Der vorstehend erhaltene bestrahlte Extrakt wird auf ein geringes Volumen eingeengt und auf eine mit Kieselgel beschickte Säule (Abmessungen: 2,5 x 50 cm) gegeben. Anschließend wird die Säule mit Hexan eluiert; die erhaltene Hexanfraktion wird verworfen. Danach wird die Säule mit Ether und schließlich mit Methanol, dem 1%o Essigsäure zugesetzt ist, eluiert. Die hier erhaltenen Eluate werden gesammelt und bei Raumtemperatur im Vakuum eingedampft. Der Rückstand wird in Ethanol aufgenommen und auf fertigkonfektionierten Tabak gesprüht; das Lösungsmittel läßt man verdunsten.The irradiated extract obtained above is concentrated to a small volume and placed on a column loaded with silica gel (dimensions: 2.5 × 50 cm). The column is then eluted with hexane; the hexane fraction obtained is discarded. The column is then eluted with ether and finally with methanol, to which 1% acetic acid has been added. The eluates obtained here are collected and evaporated in vacuo at room temperature. The residue is taken up in ethanol and sprayed onto ready-made tobacco; the solvent is allowed to evaporate.

Claims (6)

1. Verfahren zur Herstellung von Aromastoffen durch UV-Bestrahlung eines alkoholischen, Diterpene enthal- tenden Extrakts, der aus dem Oberflächenharz von frischen Tabakpflanzen bzw. deren Teilen oder aus dem von Tabakblüten stammenden "Gum" erhalten wurde, in Gegenwart von Sauerstoff, dadurch gekennzeichnet, daß man den Extrakt in Abwesenheit von Sensibilisatoren bestrahlt.1. A process for the preparation of aroma substances by UV irradiation of an alcoholic, diterpenes contained t ends extract obtained from the surface resin of fresh tobacco plants or parts thereof or from the originating from tobacco flowers "Gum", in the presence of oxygen, characterized characterized in that the extract is irradiated in the absence of sensitizers. 2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man die Bestrahlung bei einer Wellenlänge von 220-580 nm vornimmt.2. The method according to claim 1, characterized in that one carries out the irradiation at a wavelength of 220-580 nm. 3. Verfahren nach Anspruch 1 oder 2, dadurch gekennzeichnet, daß man die Bestrahlung bei Raumtemperatur vornimmt.3. The method according to claim 1 or 2, characterized in that one carries out the irradiation at room temperature. 4. Verfahren nach einem der Ansprüche 1-3, dadurch ge- kennzeichnet, daß man den Extrakt eine Stunde bis 10 Tage, insbesondere 6-24 Stunden, bestrahlt.4. The method according to any one of claims 1-3, characterized in that the extract is irradiated for one hour to 10 days, in particular 6-24 hours. 5. Verfahren nach einem der Ansprüche 1-4, dadurch gekennzeichnet, daß man den bestrahlten Extrakt auf fertig konfektionierten Tabak aufgibt.5. The method according to any one of claims 1-4, characterized in that the irradiated extract is placed on ready-made tobacco. 6. Verfahren nach einem der Ansprüche 1-5, dadurch gekennzeichnet, daß man den bestrahlten Extrakt vor der Aufgabe auf den Tabak fraktioniert.6. The method according to any one of claims 1-5, characterized in that the irradiated extract is fractionated on the tobacco before the task.
EP81101286A 1980-03-08 1981-02-23 Process for the production of aromatic substances Expired EP0035684B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3009032A DE3009032C2 (en) 1980-03-08 1980-03-08 Process for the production of flavorings for smoking products
DE3009032 1980-03-08

Publications (2)

Publication Number Publication Date
EP0035684A1 true EP0035684A1 (en) 1981-09-16
EP0035684B1 EP0035684B1 (en) 1983-09-21

Family

ID=6096680

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81101286A Expired EP0035684B1 (en) 1980-03-08 1981-02-23 Process for the production of aromatic substances

Country Status (7)

Country Link
US (1) US4359059A (en)
EP (1) EP0035684B1 (en)
AU (1) AU538822B2 (en)
BR (1) BR8101306A (en)
CA (1) CA1160029A (en)
DE (1) DE3009032C2 (en)
ZA (1) ZA81867B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0127010A2 (en) * 1983-05-20 1984-12-05 B.A.T. Cigarettenfabriken GmbH Process for preparing flavouring agents from diterpenic fractions
CN101381653B (en) * 2008-10-24 2012-02-01 华宝食用香精香料（上海）有限公司 Method for preparing spice for cigarette by pressurized oxidation of terpenoid
CN103190693A (en) * 2013-04-19 2013-07-10 安徽中烟工业有限责任公司 Extracting method for tobacco flower extract and application thereof
CN104824837A (en) * 2015-03-31 2015-08-12 川渝中烟工业有限责任公司 Method for applying tobacco flavor extracted from tobacco flowers to suns

Families Citing this family (136)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7222079B1 (en) * 1994-06-23 2007-05-22 Ingenix, Inc. Method and system for generating statistically-based medical provider utilization profiles
CA2638038A1 (en) 2006-02-28 2007-09-07 Tyco Healthcare Group Lp Tissue adhesives and sealants comprising biotin and avidin polymers
US8955523B2 (en) 2010-01-15 2015-02-17 R.J. Reynolds Tobacco Company Tobacco-derived components and materials
US20130014771A1 (en) 2011-01-13 2013-01-17 R. J. Reynolds Tobacco Company Tobacco-derived components and materials
US9039839B2 (en) 2010-04-08 2015-05-26 R.J. Reynolds Tobacco Company Smokeless tobacco composition comprising tobacco-derived material and non-tobacco plant material
US9402415B2 (en) 2010-04-21 2016-08-02 R. J. Reynolds Tobacco Company Tobacco seed-derived components and materials
US9155321B2 (en) 2010-08-11 2015-10-13 R.J. Reynolds Tobacco Company Meltable smokeless tobacco composition
US9675102B2 (en) 2010-09-07 2017-06-13 R. J. Reynolds Tobacco Company Smokeless tobacco product comprising effervescent composition
US20120125354A1 (en) 2010-11-18 2012-05-24 R.J. Reynolds Tobacco Company Fire-Cured Tobacco Extract and Tobacco Products Made Therefrom
US9775376B2 (en) 2010-12-01 2017-10-03 R.J. Reynolds Tobacco Company Smokeless tobacco pastille and moulding process for forming smokeless tobacco products
US9204667B2 (en) 2010-12-01 2015-12-08 R.J. Reynolds Tobacco Company Smokeless tobacco pastille and injection molding process for forming smokeless tobacco products
US9220295B2 (en) 2010-12-01 2015-12-29 R.J. Reynolds Tobacco Company Tobacco separation process for extracting tobacco-derived materials, and associated extraction systems
US20120152265A1 (en) 2010-12-17 2012-06-21 R.J. Reynolds Tobacco Company Tobacco-Derived Syrup Composition
US8893725B2 (en) 2011-01-28 2014-11-25 R. J. Reynolds Tobacco Company Polymeric materials derived from tobacco
US9458476B2 (en) 2011-04-18 2016-10-04 R.J. Reynolds Tobacco Company Method for producing glycerin from tobacco
US9254001B2 (en) 2011-04-27 2016-02-09 R.J. Reynolds Tobacco Company Tobacco-derived components and materials
US9192193B2 (en) 2011-05-19 2015-11-24 R.J. Reynolds Tobacco Company Molecularly imprinted polymers for treating tobacco material and filtering smoke from smoking articles
US9629392B2 (en) 2011-09-22 2017-04-25 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US20130078307A1 (en) 2011-09-22 2013-03-28 Niconovum Usa, Inc. Nicotine-containing pharmaceutical composition
US9084439B2 (en) 2011-09-22 2015-07-21 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US9474303B2 (en) 2011-09-22 2016-10-25 R.J. Reynolds Tobacco Company Translucent smokeless tobacco product
US20130118512A1 (en) 2011-11-16 2013-05-16 R.J. Reynolds Tobacco Company Smokeless tobacco products with starch component
US20130125907A1 (en) 2011-11-17 2013-05-23 Michael Francis Dube Method for Producing Triethyl Citrate from Tobacco
US20130125904A1 (en) 2011-11-18 2013-05-23 R.J. Reynolds Tobacco Company Smokeless tobacco product comprising pectin component
US10881132B2 (en) 2011-12-14 2021-01-05 R.J. Reynolds Tobacco Company Smokeless tobacco product comprising effervescent composition
US20130206150A1 (en) 2012-02-10 2013-08-15 R.J. Reynolds Tobacco Company Multi-layer smokeless tobacco composition
US9763928B2 (en) 2012-02-10 2017-09-19 Niconovum Usa, Inc. Multi-layer nicotine-containing pharmaceutical composition
US9420825B2 (en) 2012-02-13 2016-08-23 R.J. Reynolds Tobacco Company Whitened tobacco composition
CN104284605B (en) 2012-03-19 2018-02-23 R.J.雷诺兹烟草公司 For the tobacco product for handling the method for the tobacco pulp extracted and thus preparing
US20130269719A1 (en) 2012-04-11 2013-10-17 R.J. Reynolds Tobacco Company Method for treating plants with probiotics
US9339058B2 (en) 2012-04-19 2016-05-17 R. J. Reynolds Tobacco Company Method for producing microcrystalline cellulose from tobacco and related tobacco product
US9485953B2 (en) 2012-07-19 2016-11-08 R.J. Reynolds Tobacco Company Method for treating tobacco plants with enzymes
MX356657B (en) * 2012-08-28 2018-06-06 Philip Morris Products Sa Tobacco composition comprising tobacco flower.
US9289011B2 (en) 2013-03-07 2016-03-22 R.J. Reynolds Tobacco Company Method for producing lutein from tobacco
US9155334B2 (en) 2013-04-05 2015-10-13 R.J. Reynolds Tobacco Company Modification of bacterial profile of tobacco
US20150034109A1 (en) 2013-08-02 2015-02-05 R.J. Reynolds Tobacco Company Process for Producing Lignin from Tobacco
US11503853B2 (en) 2013-09-09 2022-11-22 R.J. Reynolds Tobacco Company Smokeless tobacco composition incorporating a botanical material
US10357054B2 (en) 2013-10-16 2019-07-23 R.J. Reynolds Tobacco Company Smokeless tobacco pastille
US9265284B2 (en) 2014-01-17 2016-02-23 R.J. Reynolds Tobacco Company Process for producing flavorants and related materials
US9375033B2 (en) 2014-02-14 2016-06-28 R.J. Reynolds Tobacco Company Tobacco-containing gel composition
US10881133B2 (en) 2015-04-16 2021-01-05 R.J. Reynolds Tobacco Company Tobacco-derived cellulosic sugar
WO2016193755A1 (en) * 2015-06-04 2016-12-08 Synshark Llc Process for recovering terpenes from plant material
US20170059554A1 (en) 2015-09-02 2017-03-02 R. J. Reynolds Tobacco Company Method for monitoring use of a tobacco product
US10869497B2 (en) 2015-09-08 2020-12-22 R.J. Reynolds Tobacco Company High-pressure cold pasteurization of tobacco material
US10532046B2 (en) 2015-12-03 2020-01-14 Niconovum Usa, Inc. Multi-phase delivery compositions and products incorporating such compositions
US11612183B2 (en) 2015-12-10 2023-03-28 R.J. Reynolds Tobacco Company Protein-enriched tobacco composition
US20170165252A1 (en) 2015-12-10 2017-06-15 Niconovum Usa Inc. Protein-enriched therapeutic composition
US10499684B2 (en) 2016-01-28 2019-12-10 R.J. Reynolds Tobacco Company Tobacco-derived flavorants
CN105686070A (en) * 2016-04-28 2016-06-22 湖南中烟工业有限责任公司 Preparation method for tobacco source raw material with basic cigarette smell
US10721957B2 (en) 2016-10-04 2020-07-28 R.J. Reynolds Tobacco Company Tobacco-derived colorants and colored substrates
US10813383B2 (en) 2016-12-12 2020-10-27 R.J. Reynolds Tobacco Company Dehydration of tobacco and tobacco-derived materials
US11091446B2 (en) 2017-03-24 2021-08-17 R.J. Reynolds Tobacco Company Methods of selectively forming substituted pyrazines
US10470487B2 (en) 2017-04-06 2019-11-12 R.J. Reynolds Tobacco Company Smoke treatment
US10757964B2 (en) 2017-07-20 2020-09-01 R.J. Reynolds Tobacco Company Purification of tobacco-derived protein compositions
US11278050B2 (en) 2017-10-20 2022-03-22 R.J. Reynolds Tobacco Company Methods for treating tobacco and tobacco-derived materials to reduce nitrosamines
US20190307082A1 (en) 2018-04-05 2019-10-10 R.J. Reynolds Tobacco Company Oriental tobacco production methods
US20200196658A1 (en) 2018-12-20 2020-06-25 R.J. Reynolds Tobacco Company Method for whitening tobacco
US11523623B2 (en) 2019-01-18 2022-12-13 R.J. Reynolds Tobacco Company Plant-derived protein purification
US20210068447A1 (en) 2019-09-11 2021-03-11 R. J. Reynolds Tobacco Company Pouched products with enhanced flavor stability
US20210068446A1 (en) 2019-09-11 2021-03-11 R. J. Reynolds Tobacco Company Oral product with cellulosic flavor stabilizer
CA3150662A1 (en) 2019-09-11 2021-03-18 Michael Andrew Zawadzki Alternative methods for whitening tobacco
US12063953B2 (en) 2019-09-11 2024-08-20 Nicoventures Trading Limited Method for whitening tobacco
US11369131B2 (en) 2019-09-13 2022-06-28 Nicoventures Trading Limited Method for whitening tobacco
US11903406B2 (en) 2019-09-18 2024-02-20 American Snuff Company, Llc Method for fermenting tobacco
EP4051020A1 (en) 2019-10-31 2022-09-07 Nicoventures Trading Limited Oral product and method of manufacture
US20210169121A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Liquid oral composition
EP4072851A1 (en) 2019-12-09 2022-10-19 Nicoventures Trading Limited Layered fleece for pouched product
WO2021116895A2 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Stimulus-responsive pouch
US20210169123A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Pouched products with enhanced flavor stability
US20210169132A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral composition including gels
US20210169126A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral composition with salt inclusion
US11672862B2 (en) 2019-12-09 2023-06-13 Nicoventures Trading Limited Oral products with reduced irritation
US20210169137A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Pouched products
JP2023504916A (en) 2019-12-09 2023-02-07 ニコベンチャーズ トレーディング リミテッド Pouch product with heat-sealable binder
US20210169129A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Lipid-containing oral composition
US11793230B2 (en) 2019-12-09 2023-10-24 Nicoventures Trading Limited Oral products with improved binding of active ingredients
WO2021116865A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Agents for oral composition
BR112022010877A2 (en) 2019-12-09 2022-08-23 Nicoventures Trading Ltd NANOEMULSION FOR ORAL USE
WO2021116842A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Oral products with controlled release
US20210169783A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral products with controlled release
US20210169788A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral product and method of manufacture
WO2021116916A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Oral product with multiple flavors having different release profiles
CA3159813A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Oral product with dissolvable component
US11617744B2 (en) 2019-12-09 2023-04-04 Nico Ventures Trading Limited Moist oral compositions
US20210169890A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral composition with polymeric component
US20210170031A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral composition with nanocrystalline cellulose
WO2021116856A2 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Oral products
US20210169868A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral compositions with reduced water content
WO2021116919A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Fleece for oral product with releasable component
US20210169784A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Buffered oral compositions
US20210169138A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Fibrous fleece material
WO2021116881A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Oral product in a pourous pouch comprising a fleece material
WO2021116855A1 (en) 2019-12-09 2021-06-17 Nicoventures Trading Limited Oral compositions and methods of manufacture
US11889856B2 (en) 2019-12-09 2024-02-06 Nicoventures Trading Limited Oral foam composition
US20210169786A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral composition with beet material
US20210169785A1 (en) 2019-12-09 2021-06-10 Nicoventures Trading Limited Oral compositions with reduced water activity
US20210195938A1 (en) 2019-12-27 2021-07-01 Nicoventures Trading Limited Substrate with multiple aerosol forming materials for aerosol delivery device
US12016369B2 (en) 2020-04-14 2024-06-25 Nicoventures Trading Limited Regenerated cellulose substrate for aerosol delivery device
CN113633017B (en) * 2020-05-11 2023-06-30 中国烟草总公司郑州烟草研究院 Tobacco extract, preparation method and application thereof, and tobacco product
WO2021250516A1 (en) 2020-06-08 2021-12-16 Nicoventures Trading Limited Effervescent oral composition comprising an active ingredient
US11937626B2 (en) 2020-09-04 2024-03-26 Nicoventures Trading Limited Method for whitening tobacco
US20220104532A1 (en) 2020-10-07 2022-04-07 NIlCOVENTURES TRADING LIMITED Methods of making tobacco-free substrates for aerosol delivery devices
US20240008522A1 (en) 2020-11-18 2024-01-11 Nicoventures Trading Limited Oral products
US20220232881A1 (en) 2021-01-28 2022-07-28 Nicoventures Trading Limited Method for sealing pouches
KR20230159518A (en) 2021-03-19 2023-11-21 니코벤처스 트레이딩 리미티드 Extruded substrates for aerosol delivery devices
BR112023018982A2 (en) 2021-03-19 2023-12-05 Nicoventures Trading Ltd GRANULATED SUBSTRATES FOR AEROSOL DISTRIBUTION DEVICES
WO2022224197A1 (en) 2021-04-22 2022-10-27 Nicoventures Trading Limited Effervescent oral composition
CA3216265A1 (en) 2021-04-22 2022-10-27 Michael Andrew Zawadzki Orally dissolving films
US20220354785A1 (en) 2021-04-22 2022-11-10 Nicoventures Trading Limited Oral lozenge products
MX2023012537A (en) 2021-04-22 2024-01-24 Nicoventures Trading Ltd Oral compositions and methods of manufacture.
WO2022229929A1 (en) 2021-04-30 2022-11-03 Nicoventures Trading Limited Oral products with high-density load
US20220354155A1 (en) 2021-04-30 2022-11-10 Nicoventures Trading Limited Multi-compartment oral pouched product
BR112023023129A2 (en) 2021-05-06 2024-02-06 Nicoventures Trading Ltd ORAL COMPOSITIONS AND RELATED METHODS TO REDUCE THROAT IRRITATION
MX2023015515A (en) 2021-06-16 2024-01-23 Nicoventures Trading Ltd Pouched product comprising dissolvable composition.
CA3223460A1 (en) 2021-06-21 2022-12-29 Nicoventures Trading Limited Oral product tablet and method of manufacture
EP4358748A1 (en) 2021-06-25 2024-05-01 Nicoventures Trading Limited Oral products and method of manufacture
MX2024000201A (en) 2021-06-30 2024-01-29 Nicoventures Trading Ltd Substrate with multiple aerosol forming materials for aerosol delivery device.
KR20240036696A (en) 2021-07-30 2024-03-20 니코벤처스 트레이딩 리미티드 Aerosol-generating substrate comprising microcrystalline cellulose
US20230098503A1 (en) 2021-09-30 2023-03-30 Nicoventures Trading Limited Oral gum composition
WO2023053062A1 (en) 2021-09-30 2023-04-06 Nicoventures Trading Limited Oral product with a basic amine and an ion pairing agent
WO2023084499A1 (en) 2021-11-15 2023-05-19 Nicoventures Trading Limited Products with enhanced sensory characteristics
KR20240116845A (en) 2021-12-20 2024-07-30 니코벤처스 트레이딩 리미티드 Base materials containing beads for aerosol delivery devices
US20230309603A1 (en) 2022-03-31 2023-10-05 R.J. Reynolds Tobacco Company Agglomerated botanical material for oral products
WO2023194959A1 (en) 2022-04-06 2023-10-12 Nicoventures Trading Limited Pouched products with heat sealable binder
WO2024069544A1 (en) 2022-09-30 2024-04-04 Nicoventures Trading Limited Reconstituted tobacco substrate for aerosol delivery device
WO2024069542A1 (en) 2022-09-30 2024-04-04 R. J. Reynolds Tobacco Company Method for forming reconstituted tobacco
WO2024079722A1 (en) 2022-10-14 2024-04-18 Nicoventures Trading Limited Capsule-containing pouched products
WO2024089588A1 (en) 2022-10-24 2024-05-02 Nicoventures Trading Limited Shaped pouched products
WO2024095164A1 (en) 2022-11-01 2024-05-10 Nicoventures Trading Limited Products with spherical filler
WO2024095162A1 (en) 2022-11-01 2024-05-10 Nicoventures Trading Limited Method of preparing a pouched product comprising a nicotine salt
WO2024161256A1 (en) 2023-01-31 2024-08-08 Nicoventures Trading Limited Aerosol generating materials including a botanical material
WO2024161353A1 (en) 2023-02-02 2024-08-08 Nicoventures Trading Limited Capsule-containing aerosol-generating substrate for aerosol delivery device
WO2024171117A1 (en) 2023-02-15 2024-08-22 Nicoventures Trading Limited Oral products with high-density load
WO2024171119A1 (en) 2023-02-17 2024-08-22 Nicoventures Trading Limited Fibrous material for aerosol delivery device
WO2024180481A1 (en) 2023-02-28 2024-09-06 Nicoventures Trading Limited Caffeine-containing oral product
WO2024201300A1 (en) 2023-03-30 2024-10-03 Rai Strategic Holdings, Inc. Aerosol precursor composition comprising monomenthyl ester

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2918920A1 (en) * 1978-05-12 1980-01-17 British American Tobacco Co METHOD FOR PRODUCING AN ADDITIVE FOR TOBACCO

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE857624C (en) * 1948-10-02 1952-12-01 Reemtsma Cigarettenfabriken G Process to prevent mold formation in tobacco and tobacco products
US2586701A (en) * 1949-02-05 1952-02-19 Sereno G Norton Tobacco
US3870053A (en) * 1972-06-06 1975-03-11 Brown & Williamson Tobacco Enhancement of flavor and aroma by microwave treatment
GB2020538B (en) * 1978-05-12 1983-01-12 British American Tobacco Co Smoking material additives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2918920A1 (en) * 1978-05-12 1980-01-17 British American Tobacco Co METHOD FOR PRODUCING AN ADDITIVE FOR TOBACCO

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Acta Chemica Scandinavica, Band B33, 1979, Teil II, series B Denmark, Finland, Norway & Sweden INGER WAHLBERG et al.: "Tobacco Chemistry. 48. Synthesis of Tobacco Labdanoids by Sensitized Photo-Oxygenation of (12E)-Abienol" *seite 441, zeilen 22-39* *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0127010A2 (en) * 1983-05-20 1984-12-05 B.A.T. Cigarettenfabriken GmbH Process for preparing flavouring agents from diterpenic fractions
EP0127010A3 (en) * 1983-05-20 1986-08-06 B.A.T. Cigarettenfabriken GmbH Process for preparing flavouring agents from diterpenic fractions
CN101381653B (en) * 2008-10-24 2012-02-01 华宝食用香精香料（上海）有限公司 Method for preparing spice for cigarette by pressurized oxidation of terpenoid
CN103190693A (en) * 2013-04-19 2013-07-10 安徽中烟工业有限责任公司 Extracting method for tobacco flower extract and application thereof
CN103190693B (en) * 2013-04-19 2015-03-25 安徽中烟工业有限责任公司 Extracting method for tobacco flower extract and application thereof
CN104824837A (en) * 2015-03-31 2015-08-12 川渝中烟工业有限责任公司 Method for applying tobacco flavor extracted from tobacco flowers to suns

Also Published As

Publication number Publication date
EP0035684B1 (en) 1983-09-21
US4359059A (en) 1982-11-16
AU538822B2 (en) 1984-08-30
DE3009032C2 (en) 1983-11-24
DE3009032A1 (en) 1981-09-17
AU6805181A (en) 1981-09-17
BR8101306A (en) 1981-09-08
CA1160029A (en) 1984-01-10
ZA81867B (en) 1982-03-31

Similar Documents

Publication Publication Date Title
EP0035684B1 (en) Process for the production of aromatic substances
EP0035683B1 (en) Process for the production of aromatic substances
Roberts et al. Isolation and identification of flavor components of burley tobacco
EP0144934A2 (en) Smoking product containing nicotine-N'-oxide
DE2808710B2 (en) 1- [3- (Methylthio) - butyryl] -2,6,6trimethylcyclohexene and the 13-cyclohexadiene analog, process for their preparation and their use
DE2630392A1 (en) DIMERIC ANHYDROVINCA ALKALOIDS AND THE METHOD OF MANUFACTURING THEREOF
EP0075134B1 (en) Process for the extraction of fragrances from the vanilla capsule
DE69805933T2 (en) METHOD FOR PRODUCING IRONS
EP0560291A1 (en) Process for preparing natural antioxidants
DE2338680A1 (en) ALIPHATIC OR CYCLOALIPHATIC MERKAPTODERIVATES, THEIR PRODUCTION AND USE
DE1517129C3 (en) Process for flavoring food
DE69708338T2 (en) METHOD FOR PRODUCING NATURAL 1,3 DIOL DERIVATIVES AND CORRESPONDING NATURAL 1,3 DIOXAN DERIVATIVES
DE69225942T2 (en) Diterpenoid alcohols for flavoring
EP0010142A1 (en) Sesquiterpenoid tetrahydrofuran derivatives (I) as isolated compounds or in the form of mixtures, process and starting materials (V) for their preparation, application of (I) as perfumes and/or flavors and perfume and/or flavor compositions with an amount of (I)
DE3874468T2 (en) METHOD FOR PRODUCING A JASMINE EXTRACT AND THE EXTRACT SO OBTAINED.
DE2229269A1 (en)
DE1642646A1 (en) Process for the production of coenzymes Q9, Q10, Q11 and Q12
DE2725247C2 (en) Process for the production of verbenone or myrtenal
DE2507385B2 (en) Process for the production of a fumigant
EP2018870B1 (en) Method for extracting flavonoids from horse chestnuts
Ogawa et al. Ds-erythro-2-amino-4-ethoxy-3-hydroxybutanoic acid from the fruiting bodies of the edible mushroom, Lyophyllum ulmarium
EP0127010A2 (en) Process for preparing flavouring agents from diterpenic fractions
DE1593086C3 (en) Process for the isolation of peruvoside from plant materials
CH476661A (en) Process for the preparation of 4,4a, 5,6-tetrahydro-4,4,7-trimethyl-2 (3H) -naphthalenone
DE2259388A1 (en) Isolation of vincristine from vinca rosa l - in improved yields

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): BE CH FR GB NL SE

17P Request for examination filed

Effective date: 19811002

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH FR GB LI NL SE

ET Fr: translation filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19840305

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: SE

Payment date: 19840331

Year of fee payment: 4

Ref country code: BE

Payment date: 19840331

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19840425

Year of fee payment: 4

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19860228

Year of fee payment: 6

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19870224

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Effective date: 19870228

Ref country code: CH

Effective date: 19870228

BERE Be: lapsed

Owner name: BAT CIGARETTEN-FABRIEKEN G.M.B.H.

Effective date: 19870228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19870901

GBPC Gb: european patent ceased through non-payment of renewal fee
NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19871030

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881118

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19890228

EUG Se: european patent has lapsed

Ref document number: 81101286.3

Effective date: 19880215