JP2014169393A - Vanilla perfume composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel vanilla perfume composition having vanilla aroma that does not exist conventionally, and has good quality and uniqueness; and a method that improves flavor of the vanilla perfume composition.SOLUTION: A vanilla perfume composition such as a vanilla extract and a vanilla flavor is added with β-damascenone, thereby a good quality and unique vanilla aroma which a conventional vanilla perfume composition lacks, and especially a unique dry fruit-like aroma can be imparted.

Description

  The present invention relates to a method for improving the flavor of a vanilla fragrance composition, and more particularly to a vanilla extract, a vanilla flavored fragrance composition containing the vanilla extract, and a method for improving the flavor of vanilla flavor.

  Vanilla is a vine plant belonging to the genus Vanilla. Vanilla is a rare plant in the orchid family that can be up to 60 meters long. The fruit is also shaped like a kidney bean with a length of about 15 to 20 cm.

  This fruit, green vanilla beans, does not have an aroma as it is, but it has a unique sweet fragrance by performing a long-term maturation process on trees and curing repeated fermentation and drying. . The fragrance | flavor extracted from the vanilla beans after this curing process contains many fragrance components (anisaldehyde, 4-hydroxybenzaldehyde, vanillyl ethyl ether etc.) including the main component vanillin, and these It has a unique sweet fragrance intricately intertwined. Therefore, the fragrance extracted from vanilla beans can be used in high-class confectionery, cosmetics, etc. that require fragrance that cannot be obtained with cheap synthetic vanillin produced by chemical synthesis using eugenol, guaiacol, etc., or decomposition of lignin. Widely used.

  As for the fragrance component of vanilla beans, many analyzes have been made so far, and more than 200 components have been identified. For example, Table 1 and Table 2 of Non-Patent Document 1 describe components identified from various vanilla beans in each production area such as Bourbon, Tahiti, Bali, Java, Mexico, Tonga, Costa Rica, and Jamaica. Patent Document 1 describes a fragrance that can be used as a spice flavor. Furthermore, vanilla flavor is illustrated as a spice flavor.

  In addition, as a fragrance compound important for constituting the vanilla fragrance, Table 3 of Non-Patent Document 1 exemplifies a vanilla synthetic fragrance for which a patent application has been made. Further, Patent Document 2 describes that 3-ethoxy-4-isobutyryloxy-benzaldehyde exhibits a natural vanilla fragrance that is closer to a genuine vanilla extract. Furthermore, in Patent Document 3, methyl 4-hydroxy-3-methoxybenzoate, methyl 4-hydroxy-3-ethoxybenzoate, etc. are very interesting strong spice-like or fruit-like, which is completely different from the scent of vanillin itself. It is described to emit a vanilla fragrance.

  As described above, vanilla beans are known to have a large variation in aroma due to the aging process on trees over a long period of time and the curing that repeats fermentation and drying.

  However, the fragrance compound having the above-mentioned vanilla-like fragrance does not give the vanilla fragrance composition the characteristic fragrance of vanilla beans, and also improves the variation in fragrance caused by long-term aging and curing. Was not enough. Therefore, great expectations are placed on the development of a method for imparting a good-quality fragrance to the vanilla fragrance composition by a simple method.

JP 2005-13138 A Japanese Patent No. 3574744 Japanese Patent No. 3934694

Gazette of the Japan Patent Office Known and Conventional Techniques (Fragrance) Part II Food Fragrance p348-366

  An object of the present invention is to solve the above-described problems in the prior art and provide a novel vanilla flavor composition having a good quality and unique vanilla flavor and a method for improving the flavor of the vanilla flavor composition. .

  As a result of intensive research to solve the above problems, the present inventors have added β-damasenone to the vanilla fragrance composition, thereby making it possible to obtain a high quality and uniqueness that is lacking in conventional vanilla fragrance compositions. A method for imparting a unique vanilla fragrance, particularly a unique dried fruit-like fragrance, has been found and the present invention has been completed.

  Thus, the present invention provides a vanilla fragrance composition characterized by containing β-damasenone in an amount of 0.1 ppb to 100 ppb.

  The present invention also provides a vanilla fragrance composition imparted with a dried fruit-like fragrance, characterized in that it contains 0.1 ppb to 100 ppb of β-damasenone.

  Furthermore, this invention provides the flavor improvement method of vanilla-like aroma characterized by adding (beta) -damerone 0.1ppb-100ppb to a vanilla flavor composition.

  Furthermore, the present invention provides a method for imparting a dried fruit-like fragrance to a vanilla fragrance composition, comprising adding 0.1 ppb to 100 ppb of β-damasenone to the vanilla fragrance composition.

  By adding the β-damasenone of the present invention to the vanilla flavor composition, a dried fruit-like flavor that is a good and unique vanilla flavor can be imparted.

  Hereinafter, the present invention will be described in more detail.

  Β-Damacenone used in the present invention is a known compound that has been found in Bulgarian rose flower essential oil and has been found as a component of tea, tobacco, raspberry, grape and the like. It is known that β-damasenone itself has a floral fragrance with a rose-like character. However, there is no example used for the vanilla fragrance composition, and neither the description nor the suggestion that β-damerone is added to the vanilla fragrance composition gives a dried fruit-like fragrance.

  β-Damasenone is produced by fermentation and oxidation of carotenoids in plants. As a perfume material, generally chemically synthesized, for example, a method of synthesizing β-damascone using β-cyclocitral as a starting material and dehydrogenating it (Japanese Patent Publication No. 46-43799), or Β-Damasenone can be obtained by a method of synthesizing dehydro-β-damacenol using safranal as a starting material and treating it with palladium (Japanese Patent No. 4304811).

  Examples of the vanilla flavoring composition used in the present invention include vanilla extract, vanilla flavor (vanilla-like food blending flavor), and mixtures thereof.

  Examples of the vanilla extract include a method of obtaining a vanilla extract using vanilla beans as water and / or a water-soluble organic solvent as an extraction solvent. Examples of the water-soluble organic solvent include alcohols such as methanol, ethanol, n-propanol, isopropanol, butanol, 2-butanol, and t-butanol; ketones such as acetone; and ethylene glycol, propylene glycol, glycerin, 1 One or a mixture of plural kinds selected from polyhydric alcohols such as 1,3-butylene glycol and 1,2-butylene glycol can be exemplified. Alternatively, a method of obtaining a vanilla extract by using a supercritical gas such as supercritical carbon dioxide as an extraction solvent can be mentioned.

  Furthermore, the vanilla beans used as an extraction raw material for the vanilla extract may be any one, regardless of the variety, as long as it is generally available on the market. Examples of such vanilla beans include Madagascar (Bourbon) vanilla beans, Mexican vanilla beans, Indonesian vanilla beans, Tahitian vanilla beans, and other hybrid species.

  The synthetic fragrance used in the vanilla flavor is preferably the synthetic fragrance described in Non-Patent Document 1. For example, 2-butyltetrahydrofuran, anis alcohol, anisaldehyde, anisyl acetate, methyl anisate, ethyl anisate, anisole, p-cresol, benzaldehyde, guaiacol, 4-methylguaiacol, 4-ethylquaiacol, 4-vinylguaiacol Eugenol, acetophenone, 1,3-butanediol, diacetyl, acetoin, phenol, maltol, 2-acetylfuran, 3-methyl-2-cyclohexenone, vanillin, ethyl vanillin, vanillic acid, vanillyl alcohol, isovanillin, 2- Phenyl ethyl alcohol, methyl cinnamate, ethyl cinnamate, cinnamic acid, cinnamic aldehyde, vanillyl methyl ether, vanillyl ethyl ether, 4-hydroxybenzyl methyl ether, 4-hydroxyben Aldehyde, 3-methylpentanal, dihydrocoumarin, 2,3-dihydro-2,5-dimethylfuran, 3-methylcyclopentanone, 4-ethylbenzoic acid, phenylacetic acid, 3-phenylpropionic acid, 3,5- Dihydroxy-6-methyl-2,3-dihydro-4H-pyran-4-one, 2,4-hexanedione, 3-methylnonane-2,4-dione, 2,4-decadienal, 2,3-dihydroxybenzofuran, Acetovanillone, 2-methyl-3-pentanone, acetic acid, butyric acid, valeric acid, isovaleric acid, 2-methylbutyric acid, pentadecanoic acid, 5-methyl-2 (3H) -furanone, 5-methyl-2-furfural, furfural, Furfuryl alcohol, valeraldehyde, ethyl butyrate, γ-nonalactone, γ-decalactone, γ-undecalac Or the like can be mentioned down.

  The dried fruit-like aroma of the present invention includes elements such as a ripe fruit-like aroma, a fruity ester-like aroma, and a sweet honey aroma. Specifically, the raisin-like, dried fig-like, and prunes are included. May be expressed as a dry apricot-like scent.

  To the vanilla flavor composition, β-damasenone is added to the vanilla flavor composition used in the present invention in an amount of 0.1 ppb to 100 ppb, preferably 0.1 ppb to 10 ppb, and more preferably 0.5 ppb to 10 ppb. A dried fruit-like aroma can be imparted to improve the aroma.

  If the amount of β-damerone added to the vanilla flavor composition is less than 0.1 ppb, the aroma of the vanilla flavor composition cannot be improved. In addition, when the amount of β-damasenone added to the vanilla flavor composition exceeds 100 ppb, the rose-like flavor of the β-damacenone itself is imparted, which is originally different from the flavor of the vanilla flavor composition. End up.

  The vanilla fragrance composition obtained in the present invention can be used as it is by adding it to foods and beverages, cosmetics, health / hygiene / pharmaceuticals, but if desired, an emulsifier such as lecithin, glycerin. Fatty acid ester and sucrose fatty acid ester are added and homogenized to obtain an emulsified state, and further mixed with powdering aids such as gum arabic, starch, dextrin, xanthan gum and cyclodextrin, and spray dried and vacuum dried. It can use as an emulsified form or a powder form by drying using drying means, such as.

  The vanilla fragrance composition obtained by the present invention can impart a high-quality and characteristic vanilla fragrance to foods and drinks, cosmetics, health / hygiene / pharmaceuticals and the like.

  For example, beverages such as fruit juices, fruit liquors, milk beverages, carbonated beverages; frozen confections such as ice creams, sherbets, ice candy; Japanese and Western confectionery, jams, chewing gums, breads, coffee, The vanilla fragrance composition of the present invention can be used for taste products such as cocoa, tea, tea, tobacco, soups such as Japanese-style soups, Western-style soups, flavor seasonings, various instant beverages / foods, various snack foods, etc. By adding an appropriate amount, it is possible to provide foods and drinks to which a high-quality aroma is imparted.

  In addition, for example, shampoos, hair rinses, hair conditioners, hair packs, hair sprays, styling agents, hair creams, pomades, other hair cosmetic bases; osiroy, lipstick, other cosmetics By adding an appropriate amount of the vanilla fragrance composition of the present invention to a base, a cosmetic detergent base, or the like, it is possible to provide cosmetics imparted with a high-quality fragrance.

  In addition, laundry detergents, disinfectants, indoor air fresheners and other health and hygiene materials; providing health, hygiene and medicines such as flavoring and flavoring agents to facilitate the use of pharmaceuticals Can do.

  Hereinafter, the present invention will be described more specifically with reference to examples. The present invention is not limited to these.

Reference Example 1: Method for Producing Vanilla Extract A 2 L 4-necked flask was charged with 200 g of Madagascar carbilla beans, 580 g of 95% ethanol, 40 g of 5% aqueous sodium hydroxide and 380 g of water, and the temperature in the flask. Extract with stirring at 60-65 ° C. for 4 hours. After completion of extraction, the mixture is cooled to 25 ° C. and left overnight. By carrying out decant separation with a smooth cloth, 756 g of vanilla extract was obtained (reference product 1).

Example 1: Effect of β-Damasenone Addition to Vanilla Extract Reference Product 1 was subdivided into 20 g portions, and 0.1 μ% solution of β-Damasenone diluted with ethanol was added to 1 μg (addition concentration of β-Damasenone of 0. 05 ppb: comparative product 1), 2 μg (addition concentration of β-damasenone 0.1 ppb: product 1 of the present invention), 10 μg (addition concentration of β-damagenone 0.5 ppb: product 2 of the present invention), 20 μg (addition of β-damasenone) Concentration 1 ppb: product 3 of the present invention, 200 μg (addition concentration of β-damagenone 10 ppb: product 4 of the present invention), 1 mg (addition concentration of β-damasenone 50 ppb: product 5 of the present invention), 2 mg (addition concentration of β-damagenone 100 ppb) : Inventive product 6), 6 mg (addition concentration of β-damerone 300 ppb: Comparative product 2) are mixed to obtain comparative products 1 and 2 and inventive products 1 to 6 A vanilla fragrance composition was prepared.

  Aroma evaluation was performed by 10 panelists who were well trained in each vanilla fragrance composition. For evaluation of the fragrance, the above-mentioned vanilla fragrance composition was prepared in a 30 ml sample bottle, and the fragrance of the bottle mouth and its solution were applied to odor paper for the reference product 1 for evaluation. The fragrance score is -1: the fragrance is degraded, 0: no significant difference, 1: slightly good vanilla-like fragrance, 2: good vanilla-like fragrance, 3: remarkably good vanilla Scoring as scent. Table 1 shows the average scores and average aroma evaluation results of the 10 panelists.

  As is clear from the results in Table 1, the addition effect of β-damerenone was not observed for Comparative Product 1, and the products 1 to 6 of the present invention were particularly emphasized by the aroma of dried fruit due to the addition of β-damerenone. A good vanilla aroma was obtained. On the other hand, in the comparative product 2, a good quality vanilla fragrance was impaired, and a rose-like odor was felt.

Example 2 Effect of β-Damasenone Addition to Vanilla Flavor A vanilla basic blended fragrance composition composed of the components shown in Table 2 was prepared as a vanilla flavor, and this was designated as Reference Product 2.

  Using 1000 g of the reference product 2, 50 μg of a 0.1% by weight solution obtained by diluting β-damasenone with ethanol (addition concentration of β-damasenone 0.05 ppb: comparative product 3), 100 μg (addition of β-damasenone) Concentration 0.1 ppb: Product 7 of the present invention, 500 μg (Additional concentration of β-damasenone 0.5 ppb: Product 8 of the present invention), 1 mg (Addition concentration of β-Damasenone 1 ppb: Product 9 of the present invention), 10 mg (β-Damasenone) Addition concentration of 10 ppb: product of the present invention 10), 50 mg (addition concentration of β-damasenone 50 ppb: product of the present invention 11), 100 mg (addition concentration of β-damagenone 100 ppb: product of the present invention 12), 300 mg (addition of β-damagenone) Concentration 300 ppb: Comparative products 4) were mixed to prepare novel vanilla fragrance compositions of comparative products 3 and 4 and inventive products 7-12. .

  Aroma evaluation was performed by 10 panelists who were well trained in each vanilla fragrance composition. The evaluation of fragrance was carried out by preparing the vanilla fragrance composition in a 30 ml sample bottle and applying the fragrance of the bottle mouth and the solution thereof to odor paper for the reference product 2. The fragrance score is -1: the fragrance is degraded, 0: no significant difference, 1: slightly good vanilla-like fragrance, 2: good vanilla-like fragrance, 3: remarkably good vanilla Scoring as scent. Table 3 shows the average scores and average aroma evaluation results of the 10 panelists.

  As is apparent from the results in Table 3, the addition effect of β-damerenone was not observed for the comparative product 3, and the products 7 to 12 of the present invention were particularly enhanced by the addition of β-damerenone, and the aroma of dried fruit was emphasized. A good vanilla aroma was obtained. On the other hand, in the comparative product 4, a good-quality vanilla aroma was impaired and a rose-like odor was felt.

Example 3: Effect of addition of vanilla flavor composition to sweetened milk Vanilla flavored sweetened milk was prepared according to the formulation shown in Table 4 below.

  The above-mentioned sweetened milk is blended with the reference product 1, comparative product 1 and the present invention product 4 as a vanilla flavor composition, and the sweetened milk added with the reference product 1 is blended with the comparative product 1 and the present product 4 Aroma evaluation was conducted by 10 panelists who were well trained on the sweetened milk. As a result, all 10 panelists were not significantly different from the sweetened milk blended with the comparative product 1 as the vanilla flavor composition, but the sweetened milk blended with the present product 4 was a reference product. It was evaluated that the vanilla aroma was remarkably improved compared to the sweetened milk blended with No. 1, and a dried fruit-like aroma was particularly imparted.

Claims (4)

  The vanilla fragrance | flavor composition characterized by containing (beta) -damercenone 0.1ppb-100ppb.   The vanilla fragrance | flavor composition to which dry fruit-like fragrance | flavor was provided characterized by containing (beta) -damercenone 0.1ppb-100ppb.   A method for improving the flavor of vanilla-like fragrance, comprising adding 0.1 ppb to 100 ppb of β-damasenone to the vanilla fragrance composition.   A method for imparting a dried fruit-like fragrance to a vanilla fragrance composition, comprising adding 0.1 ppb to 100 ppb of β-damasenone to the vanilla fragrance composition.