JPH08231979A - Deterioration preventive for perfumary - Google Patents

Abstract

PURPOSE: To obtain a deterioration preventive containing an extract of leaves of Nandina domestica as an essential component and efficiently preventing the deterioration of perfumary caused with light and heat, etc. CONSTITUTION: The objective preventive contains an extract of leaves of Nandina domestica. The extract is preferably extracted with water and/or a polar organic solvent and obtained by, e.g. adding water or water-containing alcohol in an amount of 5-20wt. times to pulverized leaves of Nandina domestica, extracting with stirring at 30-80 deg.C for 1-20hr, purifying and condensing the resultant extracted solution in turn. Using amount of the extract of leaves of Nandina domestica is usually 0.01-1wt.% to perfumary.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a perfume deterioration-preventing agent, and more particularly to a perfume deterioration-preventing agent containing an extract of Nanten leaf as an active ingredient.

[0002]

BACKGROUND OF THE INVENTION Perfumes are mainly used for cosmetics or foods and drinks. For example, perfumes for cosmetics or foods and drinks include natural flavors, essential oils, synthetic flavors,
It consists of oleoresin, extracts derived from animals and plants as raw materials, fragrances recovered from natural products, and multi-components that are appropriately blended with materials such as essences that are processed into water-soluble substances, during storage of fragrances or addition of fragrances. It is unavoidable that the fragrance deteriorates during the manufacturing process of cosmetics or foods and drinks.
Research on deterioration prevention has been conducted conventionally.

For example, there has been proposed a method of adding ionol, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), and phenols such as diisoeugenol to flavors to prevent their deterioration (Soviet Patent. (See Japanese Patent No. 22471). However, these synthetic deterioration inhibitors tend to be shunned in terms of their effects on the human body, and development of flavor deterioration inhibitors using natural products instead of these synthetic materials as raw materials has been underway. For example, it has been proposed that an extract of bayberry, a plant of the family Prunusceae, is useful for stabilizing flavors added to foods and drinks, cosmetics, etc. (see JP-A-6-108087). Further, “a method for preventing flavor deterioration of foods and drinks” (see JP-A-4-27374) was previously proposed,
This proposal proposes at least one selected from the group consisting of chlorogenic acid, caffeic acid, and ferulic acid, which are known to be contained in coffee beans, etc., and vitamin C, rutin,
By including at least one selected from the group consisting of quercetin in foods and drinks, it is possible to prevent deterioration and so-called flavors such as reduction and change of aroma and flavor during the processing and storage of foods and drinks, occurrence of off-taste and off-flavor, or It can be suppressed. Also, the leaves of the southern sky are crushed and dried, and the non-polar substances in the southern sky are removed with a non-polar organic solvent,
Then, the polar substance is extracted with a polar organic solvent, dried under reduced pressure, and
After adjusting the pH to 3 and extracting the chloroform-soluble part and removing it, adjusting the water-soluble part to pH 12 and extracting the chloroform-soluble part again, and again after drying under reduced pressure to dryness, preparative thin layer chromatography It has been proposed that a natural antioxidant substance obtained by the method described above can be produced, and that this antioxidant substance can be used for foods, cosmetics, and pharmaceuticals (see Japanese Patent Laid-Open No. 271654). However, this proposal makes no mention of the ability of preventing the deterioration of a mixed fragrance composition for cosmetics or foods and drinks, which is composed of a collection of multi-components as well as fragrances.

[0004]

The cause of deterioration of the aroma and flavor of a fragrance, a mixed fragrance composition for cosmetics or foods and drinks is caused by light during storage or during processing.
Many reactions such as oxidation, reduction, dehydrogenation, polymerization, ring closure, ring opening, esterification, decarboxylation, and transfer of double bonds are involved by the action of heat, air, enzymes and the like. Therefore,
Not all known antioxidants are necessarily effective in preventing the deterioration of fragrances. For example, the antioxidants fragrances and cosmetics produced and collected from Nanten leaves through multiple steps have been proposed so far. Deterioration-preventing ability for a mixed flavor composition for foods or foods and drinks has some effect, but is not always satisfactory. Further, the "method for preventing flavor deterioration of food and drink" has a drawback that chlorogenic acid and the like must be used in combination with vitamin C and the like.

[0005]

Means for Solving the Problems As a result of intensive studies conducted by the inventors of the present invention, the extract of water and / or polar organic solvent of the leaves of the present invention was found to be:
Surprisingly, in the process of processing cosmetics or foods and drinks to which the compounded fragrance composition is added, as well as preventing the deterioration of the fragrance, compared with the above-mentioned conventionally proposed anti-oxidant substance of Nanten leaf (see JP-A-5-131413). Further, they have found that it is possible to remarkably suppress deterioration of so-called perfume such as reduction or change of perfume due to heating and light during storage period, generation of off-taste and off-flavor, and completed the present invention. Although the mechanism of this effect is unknown, compared with the antioxidant substances purified and collected from the conventionally proposed Nanten leaf through multiple steps, the extract of Nanten leaf extract of the present invention consisting of a less-purified multi-component It is considered that, in particular, it contributes broadly to the prevention of the deterioration of the aroma and flavor of the compounded fragrance composition for cosmetics or foods and drinks, which is composed of a multi-component assembly.

Accordingly, the present invention provides a deterioration preventive agent for a fragrance, a fragrance composition for cosmetics, or a mixed fragrance composition for foods and drinks, which contains an extract of leaves of Nanten as an active ingredient.
Further, the present invention is a deterioration preventing agent for a fragrance, a fragrance composition for cosmetics, or a mixed fragrance composition for foods and drinks, which contains, as an active ingredient, a nanten extract obtained by extracting Nantian leaves with water and / or a polar organic solvent.

The extract of Nanten leaf, which is the active ingredient of the product of the present invention, is, for example, a supercritical carbon dioxide extraction method or the above-mentioned conventionally proposed method (Japanese Patent Laid-Open No. 5-131).
For example, an extract obtained by using water and / or a polar organic solvent is preferable.

Nandina domestic (Nandina domestic) used in the present invention
a Thunb) is wild or planted as a garden tree in the warm rural mountains of our country, and its leaves are used as a side dish and fruits are used as crude drugs (antitussives).
It is easily available. The Nanten used in the present invention can be used in raw leaves or dried leaves, and it is preferable to use these leaves after crushing them in order to improve extraction efficiency. The method for producing an extract from Nanten leaf is not particularly limited, but an extraction method with water and / or a polar organic solvent that gives an extract highly effective in preventing deterioration of perfume will be described in detail below. .

The method of extracting the crushed Nanten leaves is not particularly limited, and may be a conventionally known extraction method such as polar or non-polar organic solvent extraction, water extraction or supercritical extraction. Preferable examples include polar organic solvent extraction, water extraction, and extraction with a water-containing polar organic solvent in which water and a polar organic solvent are mixed. Here, there is no limitation on the mixing ratio of water and the polar organic solvent, and the range of 0 to 100% by weight of the solvent can be exemplified.
Further, examples of the type of polar organic solvent include methanol, ethanol, acetone, ethyl acetate and the like.

According to one preferred embodiment of extraction, for example, about 5 to 20 times by weight of water or alcohols such as methanol and ethanol or hydroalcohols are added to ground southern leaves, for example, about 30 times. ℃ ~ 80 ℃,
Stir and extract while heating for about 1 to 20 hours. At the time of extraction, it is preferable to perform treatment in the presence of an adsorbent such as activated carbon for the purpose of adsorbing and removing pigment components such as chlorophyll that elute from the leaves of Nanten. After the completion of the extraction treatment, the extract is cooled, insoluble solids are separated and removed, and the mixture is filtered with filter paper, and the filtrate is concentrated to obtain a concentrated liquid. The concentrated solution thus obtained can be used as the active ingredient of the present invention, but it is preferable to further purify the concentrated solution before use.
As a purification means, a commonly used method may be used, for example, a resin adsorption purification method in which a porous resin such as SepaBeads SP-207 [trade name of Mitsubishi Chemical Co., Ltd.] or Duolite XAD-7 is brought into contact with a concentrated liquid. Can be adopted. When the resin adsorption purification method is adopted, the active ingredient adsorbed on the resin is eluted with ethanol or the like, and the eluate is concentrated to obtain the southern leaf extract used in the present invention.

The fragrances to which the product of the present invention can be applied include, for example, conventionally known synthetic fragrances, natural fragrances, natural essential oils, oleoresin, extracts derived from animals and plants, recovered fragrances from natural products, and water-soluble fragrances thereof. Examples include processed essences and blended fragrance compositions prepared by appropriately blending these.

The fragrance deterioration preventive agent of the present invention may contain only the extract of Nanten leaf obtained as described above, or a composition of the extract and a suitable diluent or carrier. It may be in the form of. Examples of such diluents or carriers include solid diluents or carriers such as gum arabic, dextrin, glucose and sucrose, or liquid diluents or carriers such as water, ethanol, propylene glycol, glycerin and surfactants. can do. The deterioration preventive agent for perfume of the present invention may be used in any dosage form, for example, powder, granule, liquid, emulsion, paste or any other suitable dosage form. For example, gum arabic, dextrin, etc. may be added and used in the form of powder, granules, etc.,
Further, for example, it can be dissolved in ethanol, propylene glycol, glycerin, or a mixture thereof to be used as a liquid dosage form. Further, it may be used in the form of a mixture containing the deterioration inhibitor for perfume of the present invention and another known deterioration inhibitor for perfume such as L-ascorbic acid, rutin, quercetin, chlorogenic acid, caffeic acid and ferulic acid. Good.

The deterioration preventive agent for perfumes containing the extract of Nanten leaf of the present invention as an active ingredient is a synthetic perfume, natural perfume, natural essential oil, oleoresin, extracts derived from animals and plants, and perfume recovered from natural products. And deterioration of the fragrance can be prevented by directly adding and mixing the essence obtained by processing them into a water-soluble essence and the prepared fragrance composition prepared by appropriately mixing them, or to a product flavored with the fragrance. By adding and blending, the deterioration of the scent of the product can be effectively prevented. Examples of such products include food / drinks / favorites, feed / feeds, health / medicines, and cosmetics. These are beverages such as fruit juice-free beverages, beverages containing fruit juice, lactic acid bacteria beverages, powdered beverages, frozen desserts such as ice cream, sherbet, and frozen desserts; desserts such as pudding, jellies, bavarois, yogurt; other drops, candy, chocolate, Foods and drinks / favourites such as bean jam, processed meat products, grilled meat sauce, pickles, etc .; health / medical products such as tablets, liquid oral medicines, powdered oral medicines, poultices, etc .; soaps, detergents,
It is useful as a deterioration preventive agent for perfumes such as shampoos, rinses, fragrances, and cosmetics such as cosmetics.

The amount of the extract of Nanten leaf, which is the active ingredient of the product of the present invention, may be appropriately selected according to the kind of the fragrances mentioned above, but generally about 0.00 is added to the above fragrances.
A range of about 1 to 1% by weight is often adopted.

[0015]

EXAMPLES The deterioration preventive agent for perfume of the present invention will be described in more detail with reference to the following examples.

(Manufacturing Example 1 of Extract of Nanten Leaf Extract) 750 g of water and activated carbon 1.
5 g was added, and the mixture was extracted at 70 ° C. with stirring for 1 hour. After cooling, filtration with filter paper is performed to remove insoluble solids, and the extract 680
g was obtained. Next, this extract was added to porous resin SP-20.
7 (trade name of Mitsubishi Chemical Co., Ltd.) was gradually poured into a column packed with 100 ml. Next, the resin was thoroughly washed with water, and then 150 g of a 50% aqueous ethanol solution was flowed to elute the substance adsorbed on the resin. The resulting solution was concentrated under reduced pressure and then dried to obtain 13.3 g of southern leaf extract. (Abbreviated as Nanten leaf extract 1)

(Production Example 2 of extract of Nanten leaf) 50 g of 50% ethanol aqueous solution was added to 50 g of dried ground leaf of Nanten leaf.
00 g and 1.5 g of activated carbon were added, and the mixture was extracted with stirring at 70 ° C. for 1 hour. After cooling, the insoluble solid content was removed by filtration with filter paper to obtain 402 g of an extract. The extract thus obtained was concentrated under reduced pressure and then dried to obtain 13.4 g of a southern leaf extract. (Abbreviated as Nanten Leaf Extract 2)

(Example 1) (Deterioration-preventing effect test of mixed fragrance for detergent) A mixed fragrance composition for detergent was prepared according to the following formulation. (Unit is g) Geraniol 30 Phenylethyl alcohol 15 Linalool 5 Geranyl acetate 3 Phenylethyl acetate 4 Geranium oil 15 Cinnamic alcohol 3 Diphenyl oxide 3 Patchouli oil 2 Linalyl acetate 5 α-Ionone 2 Phenylacetic acid 2 Geranyl 1 Guayakwood oil 6 Rosephenon 4 total 100 To the above composition, 0.03 g of Nanten Leaf Extract Extract 1 was added,
The mixture and the composition alone were exposed to sunlight for 1 week, and the deterioration of the fragrance of these compositions was confirmed by 10
A sensory test was conducted by a human expert panel. as a result,
All of the inspectors had no abnormality in the composition to which the extract of leaf extract of Nanten was added, but the composition to which the extract of leaf extract of Southern was not added had an unbalanced aroma balance of the original fragrance and further felt an offensive odor. It was judged.

Example 2 (Test for Deterioration-Preventing Effect of Cheese-Prepared Flavor) A cheese-prepared flavor composition was prepared according to the following formulation. (Unit is g) Acetic acid 8 Isobutyric acid 3 n-Caproic acid 336 n-Valeric acid 4 Caprylic acid 112 Capric acid 84 Methyl n-amyl ketone 3 Methyl n-heptyl ketone 3 Methyl n-nonyl ketone 3 δ- Decalactone 1 δ-dodecalactone 1 dimethylsulfide 0.4 Methional 0.1 Vegetable oil 441.5 Total 1000.0 To the above composition, 0.3 g of Nanten Leaf Extract 2 was added and mixed. The above composition alone and the one obtained by adding Nanten leaf extract to the composition were exposed to sunlight for 1 week, and a sensory test was conducted by 10 expert panelists for deterioration of the fragrance of these compositions. As a result, all the inspectors, the composition to which the southern sky leaf extract was added was not abnormal, but the composition to which the southern sky leaf extract was not added, the flavor balance of the original mixed flavor for cheese was lost, Furthermore, it was judged that a strange taste or smell was felt.

Example 3 (Test for Deterioration Preventing Effect of Citral in Juice) (1) Formulation for Juice Preparation (Unit: g) Fructose, Glucose Liquid Sugar 133.0 g Citric Acid 1.5 g Sodium Citrate 0 0.17 g 1% citral / ethanol solution 0.5 g To this, dechlorinated water was added to make 1000 ml. To the syrup solution prepared with this formulation, the following deterioration inhibitors were added and mixed to prepare 3 types of juice including the control, and 2
Hot-pack (95 ° C) into a transparent juice bottle of 00 ml
Then cooled. 1. Control-2. Nanten extract 0.333 3. α-G Rutin 0.250 Addition amount (g / l)

(2) Test method The above juice was exposed to sunlight for 2 days. The amount of light is Eihiro Seiki's precision solar radiation (300 nm to 3000 n for sunlight).
m). (3) Quantification of citral HPLC analysis was performed under the following conditions to quantify citral and calculate the rate of change. Instrument: WATERS 600E SYSTEM CONTROLLER Column: PURERS 5 μC 18 120 Å 4.6 × 150 nm (MILLIPORE) Eluent: A ・ ・ ・ H ₂ O 900 B ・ ・ ・ MeOH 1000 MeOH 100 H ₃ PO ₄ 2 30min linear gradient from 30% B in A to 100% B Flow rate: 0.7 ml / min Detector: SIC CHROMATOCORDER 12 Test results are shown in (Table 1).

[0022]

[Table 1]

The numerical value in the upper row of the table shows the peak area of the HPLC analysis, the numerical value in the parentheses shows the residual rate of citral (% by weight), and the numerical value in the lower row shows the citral concentration. From (Table 1), it was confirmed that the extract extracted from the leaves of Nanten showed a deterioration preventing effect equivalent to that of α-G rutin.

[0024]

EFFECTS OF THE INVENTION According to the fragrance deterioration-preventing agent of the present invention, which contains the extract of Nanten leaf as an active ingredient, it is possible to effectively prevent fragrance deterioration caused by light, heat or the like.

Claims (2)

[Claims] 1. A deterioration preventive agent for a fragrance, which comprises an extract of Nanten leaf as an active ingredient. 2. The deterioration preventive agent for perfumes according to claim 1, which is obtained by extracting the leaves of Nanten with water and / or a polar organic solvent.