KR920005369B1 - Process for making antioxidant composition having herb flavoring - Google Patents

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Description

Extraction method of antioxidant extract from Lamitae herb and separation of less polar antioxidant part from more polar part of the extract

The present invention relates to a method of extracting an antioxidant extract from rosemary and other Lamiaceae and Labiatae herb and to a method of separating the less polar antioxidant portion from the more polar portion of the extract.

Lamiaceae plants, including well-known flavoring plants such as sage, rosemary, thyme and peppermint, individuals of the genus Mint, delay the fading of paprika and other natural colors, especially pork oil. It has been known for many years to slow down the rate of decay of pork sausages and to contain fat-resistant antioxidants in poultry, other meats, baked goods and other foods.

The use of spices, flavoring plants and their various forms for such purposes is known in the art. Maveety described this in US Patent No. 2,124,706 in 1938. The crude extract of these flavoring plants or the flavoring plants themselves were used to achieve the intended effect. However, there was no easy and practical way to measure the effectiveness of these perfumed plants or extracts, and their use was limited, especially in relation to their fragrances.

More recently, various techniques have been developed to provide extracts with less fragrance in both liquid and powder forms.

The powder form (Kimura U.S. Pat. No. 4,363,823) extracts fresh flavoring plants, or previously steam-distilled flavoring residues with alcohol, and then evaporates the alcohol into a pasty substance. Alternatively, the desolvated extract can be added to the breaking water to dissolve the water-soluble substances in the extract and to leave insoluble substances, including antioxidants, as crystals that can be filtered out and dried to form a powder. If the crystals are well washed in water, the hygroscopic material is removed and the remaining dry powder, which contains some fragrance, antioxidants, fats and waxes, will not harden under moist air. Non-polar solvents are not selected because they are required for drying of the spent perfume residues.

Viani shows in US Pat. No. 4,012,531 a direct extraction of dried perfumed plant material (rosemary and sage) with a basic aqueous solution of pH about 7 to 11.5, preferably about 9, to recover antioxidants from the perfumed plant. Viani points out that the upper pH limit is important because it impedes the removal of strongly acidic oxidant substances from rosemary, particularly in column 2 above. The alkaline extract may be dried or extracted with a solvent which is not mixed with water such as methylene chloride and then acidified. The extract of Viani has very little rosemary flavor (see Example 1, column 5, line 57).

Nakatani first extracts the fragrance plants dried in US Pat. No. 4,450,097 with a nonpolar organic solvent such as hexane, removes hexane, removes volatile essential oils from the aqueous dispersion by steam distillation, and cools them in water. The extraction method was modified by isolating extracts from insoluble rosemary. The deodorized extract is dissolved in ether and pickled, and then the ether solution is treated with sodium hydrogen carbonate and extracted at least at pH 10.5. The oxidant moiety, a weak acid described by Viani, is obviously not extracted from ether into water when using bicarbonate. Nakatani also showed that the extracts were purified as above by first steam distillation to remove essential oils from rosemary leaves and then treated with a nonpolar solvent (the purified extracts of the present invention had reduced emulsions and specific substances and simplified pH separation by This is a very simplified process and should be emphasized).

Berner used edible fats to extract the dried perfumed plants in US Pat. No. 3,732,111, removed essential oils from the fat-soluble extracts and used the deodorant extracts in these fats as antioxidants. This method has the distinct disadvantage of wasting large amounts of edible fat on the consuming plants and the inability to concentrate the extract.

Chang extracts the dried rosemary leaves in US Pat. No. 3,950,266 with an organic solvent, removes the solvent, mixes it with a non-volatile soybean oil-like cooking oil with a high breaking point, and vaporizes the resulting mixture by steam distillation. One small amount of antioxidant left. He also molecularly distilled the fluid to obtain concentrated antioxidants before and after deodorizing with charcoal. Chang has also shown that the antioxidant portion is concentrated in larger polar solvents by contacting the extract with large and small polar solvents using column chromatography. Chang's method has a distinct advantage over Berner as it provides a concentrated antioxidant that can be used in many cases where the fat used by Berner is inadequate.

Bracco applied both Chang and Berner methods in US Pat. No. 4,352,746 to provide a suitable method for both fatty extracts and extracts in solvents of perfume plants. This preparation is also suitable for both steamed distilled rosemary leaves and rosemary containing essential oils. In Bracco's method, the extract in oil or extract in solvent is ultra finely ground after desolvation and suspension in oil and then carbonized in the presence of water by heat treatment. The carbonized suspension is filtered to remove the carbonized material and the fluid portion is molecularly distilled according to Chang's method to obtain a concentrated antioxidant portion. Bracco found his invention to use less oil than Chang in terms of spices. Thus, in contrast to Chang's method (step 4, line 65, above), in the case of Bracco, the oil may comprise 20% equivalent of the plant starting material. The advance is made by carbonization, which removes the substances that would interfere with the molecular distillation apparatus.

In a more recent patent, Kimura (US Pat. No. 4,380,506) describes a method for separating the active ingredient in oil- and oil-insoluble parts from extracts from perfumed plants. He used an ethanol-hexane mixture of ethanol in the range of 2% to 95% in hexane to extract salvia, all of which showed a very effective extraction solvent. By adding the extract dissolved in the extraction solvent mixture to water, he was able to separate the rosemary extract into hexane soluble and hexane insoluble portions. The hexane soluble portion was also fat soluble and had strong antioxidant power. The crystals produced when the extract dissolved in the solvent is added to water are insoluble in fat and have weak antioxidant properties (as a result of treating hexane solubles), but are useful as antibacterial agents. This crystal is not an acetone-insoluble substance without the antibacterial properties according to the invention. Kimura had the same disadvantages as Berner in the loss of solvent (ethanol) to the mixed aqueous phase, and had the disadvantage of using ten times the solvent weight of the fragrance to purify extracts (Examples 1 and 2), The "acetone-insoluble" material was effectively dissolved in the hexanes, but the acetone insoluble material was removed by the present invention. Kimura never removed the acetone-insoluble impurities from his hexane phase.

It is an object of the present invention to enhance the effects of natural antioxidants present in rosemary and other lamiaceae and plants; Increase the yield of antioxidant extract from the fragrance plant material; Removing unwanted or detoxified substances from antioxidant extracts; It provides a method for extracting a totally fat-soluble natural extract containing a natural antioxidant of flavor plants; Adjusting the ratio of the antioxidant activity and the flavor of the extract to a certain ratio so as to be suitable for use in various kinds of foods and various preparation methods thereof; Providing antioxidant extracts from nectar and flavoring plants that are compatible with a broad range of antioxidants that act synergistically; Providing an antioxidant extract from which the intended color is removed from the extract without loss of antioxidant activity; It is to provide an extraction method suitable for this purpose under a series of suitable food solvents and various extraction conditions.

The present invention is a method of extracting the antioxidant extract from rosemary and other perfume plants by maximizing the extraction rate and yield by using a solvent commonly used such as hexane, ethanol and acetone and chlorinated solvent such as methylene chloride Or separating the desired antioxidant extract from the extract solution by post-extraction crystallization using a solvent comprising methyl ethyl ketone preferentially, which has no antioxidant effect and only forms cloudy particles in the finally obtained vegetable oil. It provides a new extraction method to remove other insoluble substances and unwanted toxic promoters.

Embodiments of the present invention relate to the following.

1. Separation of unwanted substances and (a) enhancement of the effect of the desired substances, and (b) their increased solubility and flow.

2. Enhanced removal of unwanted acetone insolubles which will be deodorized according to Chang's method, including steam distillation and molecular distillation.

3. Separation method of petroleum ether soluble and insoluble substances and each formulation type for specific purposes.

4. Measure the effect of antioxidants and strength of fragrances and control their proportions

5. A method for preparing an antioxidant that is compatible with an aqueous water-based system, ie, well dispersed in water alone.

6. Eliminating many of the steps required for purification of antioxidants.

7. Overall recovery of edible or volatile solvents.

8. A process for the separation of antioxidant moieties in polar substances (including nonpolar and other substances) which are dissolved under extraction conditions and insoluble under purification conditions.

9. A description of the use of the invention as a method of extracting purified extracts from various flavoring plants.

The following examples are not intended to limit the scope of the invention, but merely to illustrate the invention in detail, for example.

In these examples, the containing resin and the extract are synonymous. These are substances which are dissolved in the solvent from the perfume plant, and are quantitatively analyzed by removing the solvent from the extract dissolved in the solvent, and are called "miscella". For example, when rosemary is fully extracted with acetone from a soxhlet, after extraction the acetone is removed from the micellar in a distillation flask, and the residual material is a rosemary-containing resin or raw extract. When the original extract is treated with acetone according to the invention, the acetone soluble portion is considered to be a "purified extract" after removal of acetone.

Example 1

Rosemary-Purified Colorless Antioxidant Extract

120gms of fine Portuguese Rosemary was extracted from Soxhle with acetone to give 19.6g. A portion of this "crude oleoresin" that was solid at room temperature was left as it is. The rest was 17.4 g, which was warmed and stirred with 100 ml acetone and then cooled to ambient temperature for 5 hours. After filtration, the solid mass was washed with acetone to remove some of the acetone solubles attached to it. After removal of the solvent, the acetone soluble antioxidant fraction was measured to be 12.3 g, which is 71% of the original resin. Solids were 5.0 g or 28% and losses were 0.1 g or 0.6%.

The acetone soluble portion (7.61 g) was redissolved in acetone and stirred with activated carbon (0.76 g) for 5 hours. After filtration, evaporation with a water aspirator on a 70 ° C. rotary evaporator recovered 7.2 g, meaning that 63.5% of the original resin was obtained. The decrease from 71.0% is due to the loss of the lighter portion of rosemary oil on the tumble dryer, the loss of tissue and the absorption of the coloring material into charcoal.

Each of these portions was diluted with soybean oil to a concentration that provided the same amount of raw resin. The resin was not premixed with the liquid vehicle, but was first stirred with hot oil and then cooled by stirring with a greater amount of hot oil. Precipitates and clarities were observed: (1) Acetone-soluble resins were clear and free of precipitates; (2) raw resins, acetone-insoluble fractions, and (3) products and market products according to Viani's method.

A more preferred method of preparing rosemary formulations or other flavored plant products is to add an edible liquid such as mono or di-glycerides to the solvent prior to removal of the extractant. This prevents the extract from becoming a hard rosin that is difficult to maintain and re-dissolve in the form of a paste or liquid when cooled. This edible liquid can be added at any point in extraction and purification.

This also indicates that the decolorization and solid removal steps can be done simultaneously. This step was carried out continuously for the purposes of this example, thereby avoiding the rubbery secretion of the char which makes filtration more difficult. Furthermore, it should be pointed out that chlorophyll breaks down into brown pigment, which dissolves very little in fat over time. Since this pigment is removed by charcoal, a more preferred form of the invention is a depigmented extract from which cold acetone insolubles have been removed.

The level of antioxidant activity of the extract is determined by instrumental ranchmat (TM), which induces the time of induction under accelerated ripening conditions using an oil sample containing a measurand, i.e., 0.1% or the same amount of extract. Degree trend). Induction time is measured as a sharp change in the conductivity of the solution into the air passing through the oil sample. The oil is kept at 120 ° C and passes through 18 liters of air per minute.

In addition, the control experiment was performed at the same time, the induction time of the control experiment (184 minutes) is subtracted from the 254 minutes, the induction time of the tested sample 70 minutes, indicating the increase in stability affected by the sample. At the same concentration, the second sample was compared as the ratio of other induction time to the induction time of the first sample. If the induction time of the second sample is increased to 80 minutes at the same concentration, it has an efficiency of 114% of the reference sample.

In this case, the stability of the ranch mat of the raw resin at 0.1% concentration was 95 minutes compared with the control experiment. Acetone insolubles were oxidation promoters with 21 minutes less induction time than the control experiment at 0.033% concentration. The decolored acetone soluble resin showed a stability increase of 111 minutes at a concentration of 0.0635% and 117% of the original resin. Since the bleached resin accounted for 63.5% of the original resin, this tablet increased the antioxidant activity of the extract by 17%.

In conclusion, these results demonstrate that the method of the present invention provides a product with greater solubility and also enhances rosemary efficiency of a given weight by removing the oxidant material present in the insoluble portion.

Example 2

Removal of Rosemary-oxidizer Substance

Rosemary was extracted using a mixture of hexane and acetone at about 50 to 50 to prepare a standard rosemary-containing resin. A solvent portion comprising the extract (micella) was obtained in the laboratory. This Michela is divided into three parts: Leave 1) intact; 2) was cut off until the solvent content was about 10-20%, reconstituted with acetone so that the resin content was about 12%, and cooled to ambient temperature for several hours and filtered; 3), acetone was added as in (2), and charcoal was added at a 12% w / w ratio of the resin, followed by stirring for several hours and filtered. Solvent was removed from each sample. The product weight was recorded and the weight recovered was recorded in Table 1 as weight percent based on the weight of the sample (1). This table shows that 13% weight is reduced by treatment (2) and 4.5% is reduced by treatment (3). The ranch mat induction time of each completed extract was measured. The yield from the crude extract (1) was considered to have 100% activity. It is noted that the antioxidant activity increases with the removal of unwanted antioxidants or antagonists in steps (2) and (3). In other words, the sample 3 at 0.083% concentration in oil has a stability of 123% compared to the sample 1 at 0.1% concentration in oil.

TABLE 1

It is noted that the amount of acetone insoluble matter (13%) of this example is much less than that of Example 1 (33%). These two values generally represent the maximum concentrations of these substances encountered in the fragrance plant and may be related to freshness, specialty culture, harvest, or geographic categories.

This example shows that the preferred effects of the present invention are not limited to certain rosemary flavor plants.

Acetone insolubles can be removed using food solvents such as petroleum ethers such as hexane or heptane, lower alcohols, lower esters such as ethyl acetate, and lower alkyl ketones such as methyl ethyl ketone. It does not dissolve when scratched. Acetone is a preferred solvent in coordination with common solvents required for its price, ease of handling and extraction convenience. The present invention is not intended to specifically use only the container solvent for extracting the raw extract, it will be clear that any suitable food solvent can be used.

Example 3

Effect of Different Solvent Mixtures on Extraction

The fine rosemary was extracted almost exclusively from a Soxhlet extractor using hexane, either alone as acetone, or using a mixture of 50% hexane and 50% acetone or a mixture of 80% hexane and 20% acetone. These represent a wide range of solvent particles and exhibit the flexibility of the extraction solvent that can be used in the present invention. In the next extraction, the solvent was removed and the crude extract was mixed with hot acetone (8 parts), cooled and filtered. Both the acetone insoluble portion and the soluble portion are desolvated and Table 2 shows the percentage of acetone insoluble portion in the extract. The antioxidant activity of the acetone soluble portion is the same and the polarity of the extract solvent is not critical for the acetone insoluble substance, even though hot hexane is the better solvent, and appears to be less polar than the acetone soluble substance.

In Example 2, it was mentioned that the maximum amount of acetone insolubles commonly encountered in extracts from rosemary was 13% and 33% yarn. This example describes a rare case where rosemary powder at the start of extraction has almost twice the presence of acetone insolubles than usual due to unknown reasons. This shows that the present invention is applicable to a wide variety of rosemary and its extracts.

TABLE 2

Example 4

Extraction and Purification Methods of Extracts from Salvia

Fine Daltion sage was extracted from Soxhle using a mixture solvent with a hexane and acetone ratio of 70:30 and the extract was separated from the solvent. It was redissolved with hot acetone, cooled and stirred for 5 hours with 14% w / w of the extract of charcoal and filtered, and the filtrate was separated from the solvent. 84% of the original weight of the resin was recovered, demonstrating that Salvia's sample contains much less "acetone insolubles" than the typical rosemary sample. The antioxidant activity of the bleached and purified resin contained was 110% of its original activity at the same basis weight. Dilution of this extract with vegetable oil frees it and blurs it like a haze.

This example points out the diversity of the invention as the age, season, location of leaves, special cultures, as well as insolubles depending on the type of flavoring plant are clearly varied. Two samples of sage, harvested in early autumn and late autumn in 1985, contain 25% and 27% acetone insolubles in the original extract, respectively.

As used herein, the term "acetone insolubles" refers to a group of inert and / or toxic (including oxidation promoters) substances that can be separated from the active elements of extracts from flavoring plants by precipitating acetone with a predominantly cold solvent. it means. It can also be used as a lower alcohol such as ethyl alcohol, methyl ethyl ketone, lower ester, petroleum ether and mixtures thereof.

Example 5

How to separate active ingredients into more soluble and more water-soluble parts

A more advanced form of the present invention involves separating the active ingredient of the refined containing resin into portions that are more soluble in liquid oil and more soluble in solvents such as propylene-glycol. The rosemary-containing resin obtained by removing the acetone insoluble substance is mixed with two to five times hot hexane or heptane, stirred well, cooled and precipitated. The solvent phase is separated by decantation from the solid phase and the two phases are desolvated. 37% of the product is solid and 63% is the solvent portion. The bleached solid fraction is readily soluble in propylene glycol, for example, in its vegetable oil its solubility is maintained and its antioxidant properties are retained. Secondly, the solvent soluble portion is readily soluble in vegetable oil, less soluble in propylene-glycol, and contains both antioxidant properties and fragrance and residual carotenoids. The recombined portion has the same activity as the purified containing resin. The two parts have essentially the same antioxidant activity, which distinguishes them from the part obtained by Kimura. The present invention is not intended for the preparation of conservative fungicide moieties and includes two antioxidant moieties, one containing fragrance and antioxidant activity, the other being fragrance free and soluble in vegetable oil and propylene glycol. Both parts can be steam sorted and mixed with mono or diglycerides as in other embodiments.

Those skilled in the art, as a desirable result that can be achieved by first stirring hot extract with hot hydrocarbon solvent and hot hydrocarbon, cooling and separating the solvent phase from the solid phase, acetone insoluble before separating the oil soluble portion It will be clearly understood that there is no need to remove the portion ". Acetone insolubles are also insoluble in hydrocarbon solvents and can be separated from the remainder of the containing resin by stirring this portion with acetone as in the previous examples. In this form the steps of the reaction process are reversed. Various other applications will also be possible for those skilled in the art.

Some are more polar and can therefore be formulated in propylene glycol or glycerin to be supplied as an antioxidant in aqueous solutions, and secondly, those that are more soluble in oil are useful as oil systems. This fractional technique makes the invention even more diverse. Part of the propylene glycol soluble portion and better soluble portion of oil have a constant antioxidant property by using a compatible soluble solvent such as oil or other suitable edible solvents that can standardize the activity of the parent purified extract. Dilute to strength. Likewise, perfume formulations of certain formulations can be controlled by the amount of essential oil to be removed or used to solidify the purified extract. Therefore, the present invention provides this extract to food production by standardizing extracts that do not form hazy particles in each extract and both when diluted with vegetable oil, and by standardizing antioxidant activity and flavor levels.

Example 6

Solubility properties of "acetone insolubles" in acetone and vegetable oils and the most suitable level in purified extracts.

As pointed out in Example 1, cold acetone insolubles usually account for 30-40% of the perfume plant-containing resin extracted with a suitable food organic solvent and sometimes reach 2/3. A portion of the precipitate of Example 1 (2.6 g) was refluxed with about 40 ml of acetone to be sufficiently dissolved. The hot acetone was filtered off and evaporated to recover 2.18 g of solid material. 1.84 g of this solid was stirred with 500 ml of acetone at 40 ° C. and remained a slightly cloudy solution. The solution was cooled to 19 ° C., stirred for one hour to one and a half hours, and filtered. A total of 0.38 g was removed by filtration and the filtrate remained a slightly cloudy solution.

100 ml of this solution was placed in capped containers of different temperatures as recorded below and left for 5 hours. In addition, one sample was diluted 1: 1 with acetone and the other sample was diluted 1: 1 with hexane and left for five hours as follows. The undiluted samples were filtered through Whatman's first filter paper to remove diatomaceous earth and almost all cloudy particles. In each case, however, very little particles passed through the paper. Acetone was then evaporated to determine the solubility of the "insolubles" at the specified temperature.

First, although the greatest benefit can be obtained by reducing the temperature of the extract solution below 20 ° C or, if possible, below 10 ° C, this result suggests that the superiority of the lower temperature in the removal of insolubles plays a secondary role. To present.

Second, acetone is more useful than hexane because it is apparent that cold insolubles are slightly more soluble in hexane than acetone. If the extraction solvent is chosen to contain abundant amounts of hexane due to large volume and cost requirements, it is desirable to remove enough hexane prior to forming and removing insoluble matter.

Third, this points to prior technical deficiencies as exemplified in Kimura's Example 2. In this example he extracts 50 g of rosemary with a 500 ml total volume solvent consisting of a mixture of 50 ml ethanol and 450 ml hexane. Following decolorization, ethanol is removed by mixing water and Miracel to obtain hexane soluble precipitate and its bactericidal precipitate. As shown in Example 3, hexane is a good solvent for "acetone insolubles" and they are extracted from rosemary. After removing ethanol by treatment with water, at least about 0.3% or 1.25g of 1.94g of hexane soluble residue is left in 450ml of hexane solution. According to the invention, 1.94 g of hexane soluble residue is redissolved in acetone, cooled and filtered to remove insolubles and the acetone soluble antioxidant portion is recovered. This is the part with high solubility in oil and will not form cloudy particles.

When a portion of 2.18 g of the prepared solid acetone insoluble substance is added to soybean oil at a concentration of 0.042%, it must be heated to 140 ° C. in order to see the dissolution effect within about 30 minutes. After two to two and a half hours of cooling, a precipitate is formed and the solution becomes milky overnight. A portion of this solution is diluted 1: 1 with soybean oil, heated to 100 ° C. and cooled overnight to redissolve the precipitate. Very coarse cloudy solutions will be suitable for the use of more or less commercial extracts, indicating that 0.02% to 0.03% concentrations of acetone insolubles are resistant to clear cooling oils.

Yajima (US Pat. No. 4,525,306) stabilizes capsules using conventional discolored solvent extracts without removing acetone insolubles (patent third) and having better extract levels of 0.1% to 1% w. / w (the fourth patent column 11-12). The comparable level for purified extracts in the present invention is 0.5% or less. At this level, the extract may be resistant to the use of 0.03 / 0.5 × 100% = 6% of insolubles and 0.4%, 7.5% of acetone insolubles. This is, in the present invention, set as the practical upper limit of the refined perfume extract extract fluid when diluting the extract with acetone concentration at 15% w / w at about 20 ° C.

As the concentration of the raw extract in acetone increases, and also as the temperature of the precipitation decreases, more insolubles are precipitated to reduce the amount of insolubles remaining in the purified extract. The upper limit of the actual concentration is determined by the viscosity, the intersolvent effect of other substances, the activity, the acetone soluble composition of the extract, and the like. For practical purposes the upper concentration limit of the rough extract in the solvent is 50%. The operating concentration is preferably controlled between 20% and 40%, gives sufficient cooling time and sufficient settling time, and insolubles will be mostly removed even at 5% to 10% concentrations.

Example 7

Commercial extraction of rosemary, purification of extracts and determination of insolubles in purified extracts.

After crushing the rosemary leaves were extracted by continuously treating with a solvent mixture of about half of hexane and acetone at an elevated temperature.

Some of the micelles pointing to the extract in the solvent were distilled to raise the extract concentration to 50-60%. Acetone was then added, diluted to a concentration of about 15%, cooled to 20 ° C. and filtered to remove acetone insolubles. After adding glyceride (20% w / w of soluble acetone extract) and cottonseed oil (80% w / w of soluble acetone extract), the solvent was removed. Acetone was added to the extract at 15% concentration, diluted, heated, cooled and filtered to recover 1.3% to 1.6% of acetone insoluble material from the extract in oil. The liquid extract (as in Chang's method) was steam distilled to remove the basic fragrance. The resulting extract provided a 0.5% clear solution in oil and did not require heat to turn into a solution. The other part of the micellar was directly desolvated without filtration of insoluble materials, followed by steam distillation after addition of glycerides and cottonseed oil. It takes three hours to remove insoluble substances and to remove essential essential oils, which result in a decrease in the viscosity of the extract, which is a great advantage compared to the processes of Chang and Yajima, for example. The extract is clouded when added to the oil at the 0.5% level and when heating is required to dissolve. It is not possible to determine from this example whether a commercial extract prepared according to the method of the invention will contain less than 1.6% insolubles. If the filter paper is not fine enough, it will pass further and the result will not be satisfactory if the diluted coarse extract is not sufficiently cooled or not sufficiently crystallized. The upper limit of the acetone insoluble substance in the extract for the purpose of the present invention is 7.5%, which is taken as the practical upper limit.

Example 8

A method for and extracting an extract from musk vine and other nectar and plants in the presence of an edible carrier.

Musk vinegar (150 g), harvested in October 1985 in Carama, Michigan, USA, was extracted using acetone in Soxhle. After adding 3 g of mono or diglycerides, acetone was removed to obtain 15.1 g of a raw resin. This indicates that 8% of the resin was obtained from the civet with the characteristic fragrance. Resin and glycerides (15.1 g) were redissolved in 50 ml of hot acetone and then cooled for several hours and filtered. The mass was washed with acetone and dried to give 20% or 3.4 g of solids of the weight of resin (12.1 g). The filtrate was desolvated, all dissolved in 0.2% oil.

This example illustrates the versatility of the present invention by showing that ordinary edible solvents, such as glycerides, may be present during the purification step if advantageous in production. It is a further embodiment for other flavoring plants and can be improved in solubility in oil in the same way by subsequent treatment of the raw resin from the extraction solvent. The resin may also be discolored as described above and become dark brown. Through this purification process, the pleasant odor of the characteristic musk vine is present if desired and can be removed prior to steam distillation of the volatile scent if not desired. Extracts from other lamiaceae and plants also change in the same fashion when treated as described above. The extract from marjoram contains 26% acetone insolubles; Oregano is 37%; 11% spearmint: 12.5% peppermint; Monarda contains 18.3%.

Example 9

Purification of the raw extract.

In some cases the original extract can be prepared in an embodiment according to the method of Viani or Kimura after the removal of the inerts and oxidation promoters by the method of the invention. This can be done very easily by refluxing the original extract with acetone, which is then cooled and separated by filtering or decanting the liquid phase from the solid phase and then collecting the purified extract as above. It is to be understood that acetone is only a preferred solvent and that other volatile organic solvents are also suitable, as noted above.

For example, an extract from 5 g of rosemary produced by Viani's method was refluxed, stirred with 50 ml of acetone for 30 minutes, cooled and filtered. As a result, 3.53 g of acetone solubles and 1.45 g of acetone insolubles were recovered. Acetone solubles were mixed with 5.4 g soybean oil and 3.2 g mono and diglycerides, added to soybean oil at the same level as 0.1% of the starting extract, and left at 12 ° C. during the night to not cloud.

In contrast, the source extract requires 150 ° C. for a complete dispersion effect at the 0.1% level, and the dispersion causes the extract to flow at the 0.05% level. Filtrate the hot dispersion solution with diatomaceous earth and keep it at 12 ° C. overnight to clear and produce a precipitate.

Example 10

Synergistic Mixture of Natural Substances Treated with Purified Extracts

And about 1 part extract, 0.8 parts vegetable oil, 0.2 parts mono or diglycerides. Since the amount of diluted liquefied edible oil and glycerides is not critical, the concentration of extracts from rosemary or other lamiaceae and plants in liquid mixtures can be easily increased or decreased in particular applications. This form allows mixing into liquids of different materials, which can have synergistic effects on particular fat and food systems. It is therefore one of the objects of the present invention to provide a homogeneous mixture of synergists and extracts from rosemary.

Metals such as iron and copper have been found to promote rancidity even when present in fats and foods. Often metal trapping agents such as citric acid or EDTA are used for chelating compounds and inert metals. In the following examples, fat is added to reduce the odor effect of the indicator metal ion of the chelating agent.

In determining the effect of the synergist, a known amount of a substance selected from ascorbic acid, topopherol and urumic acid compound is mixed with the rosemary-containing resin as in Example 7 above and the mixture is added to the fat to obtain fat. 0.05% rosemary-containing resin in the resin. The amount of synergist present is expressed as percentage of rosemary extract present. For example, if the mixed fluid contains 18% rosemary extract and 9% tocopherol, the synergist will be present at the rosemary 50% level.

BHA (butyrated hydroxyanisole) most commonly used as synthetic antioxidants is shown in the table for comparison purposes.

The test results were measured using a lanci mat as above.

This table shows that extracts from purified rosemary are more effective than BHA at the same concentration, and in particular cases their usefulness increases even more when combined with synergists. The preparation of the fluid according to the invention is carried out in a single phase, which is compatible with the synergists listed above, and tablet extracts comprising or combined with what are designated synergists are also considered part of the invention.

The output by the extraction method of the present invention is an extract from the new enhanced flavoring plant with little formation of cloudy particles or little oxidation promoter and is easily separated into a part that is better dissolved in fat or oil and better dissolved in water as a whole. can do. The extract according to the present invention retains the original antioxidant power of the original extract and can be further processed using known techniques in the art used to separate volatile essential oils. It can also be used in combination with synergists and can be diluted with an edible solvent such as vegetable oil or glycerin to form a liquid form that can be easily applied to food preparation.

The extracts according to the invention can be prepared from perfumed plants which have been steam distilled beforehand to remove essential oils and if the whole fragrance of the perfumed plants is required in the purified extract, it can also preserve the essential oils (as in Example 8) Alternatively, essential oils can be added directly in accordance with the present invention. The preparation of this new product is simpler and less expensive than the previous methods of Nakatani, Viani, Bracco, Kimura and Berner, and it is possible to obtain extracts which are much improved than the extracts by these prior arts.

The extraction method according to the invention comprises a conventional extraction step, which allows the use of a wide range of volatile food solvents and does not require the recovery of certain substances from the water system which create annoying emulsions. All of the volatile solvents can be reused because they will be mainly reused in the extraction process, and there is no loss to water or consuming plants as in Berner.

Claims (11)

In the method of extracting antioxidant extract from Lamiaceae, the extract is extracted from the Lamiaceae plant using a certified food solvent that melts when warm insoluble in acetone and does not melt when warm. The solvent is removed so that the concentration of the extract in the solvent is between about 5% and 50% until the solvent is no more than about 20 times the weight of the extract, so that the concentration of the extract in the remaining solvent is about 5% to 50%. After cooling the mixture of to remove the acetone insoluble matter, the solvent is removed, when dilution of the extract to 15% w / v concentration in acetone at about 20 ℃, less than 7.5% by weight of the oxidation promoter material insoluble in acetone A method of extracting antioxidant extracts from Lamiaceae and fragrance plants, which have an excellent antioxidant effect. Using acetone as an essential ingredient and petroleum ether as an optional ingredient, the extract is extracted from the fragrance plant with Lamiaceae, the solvent is removed until the extract concentration is about 5% or more and less than 50%, and then the mixture is A method of extracting antioxidant extracts from Lamiaceae and flavoring plants, characterized by cooling to temperature to remove insoluble matters. The method of claim 1, wherein the solvent is a single solvent selected from edible solvents such as acetone, methyl ethyl ketone, lower alcohol, lower ester and petroleum ether, or a mixture thereof. Extraction method. The method of claim 1, wherein the charcoal is added before removing the insoluble material. The method of claim 1, wherein the insoluble material is separated in the presence of an edible solvent. The method of extracting antioxidant extracts from Lamiaceae and fragrance plants according to claim 1, wherein the fragrance plant essential oil is removed in whole or in part after removing acetone insoluble substances. The method of claim 1, wherein the solvent is acetone. The method of claim 1, wherein at least one of an ascorbic acid compound, tocopherol and urumic acid is mixed with the antioxidant extract. A mixture of purified and unpurified extracts with petroleum ether solvents, removing the solvent phase from the solid phase, and then desolvating both phases with an optional edible solvent, further extracting from the extracts of nectar and spices A method of separating the less polar antioxidant part from the polar part. After mixing the petroleum ether solvent and the extract and removing the solvent phase and its desolvent phase, the petroleum ether-insoluble portion and acetone are mixed to remove the antioxidant acetone-soluble portion from the acetone-insoluble portion containing the antioxidant material. A method of separating the less polar antioxidant portion from the more polar portion of the extract extracted from the Lamiaceae and flavoring plants using an optional edible solvent characterized by separating. The method of claim 10 wherein the petroleum ether is hexane or heptane, and the less polar antioxidant portion is separated from the more polar portion of the extract extracted from the fragrance plant.