WO2016167008A1 - Produit contenant du limonène, composition parfumée, et procédé pour supprimer la génération d'odeur de détérioration - Google Patents

Produit contenant du limonène, composition parfumée, et procédé pour supprimer la génération d'odeur de détérioration Download PDF

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Publication number
WO2016167008A1
WO2016167008A1 PCT/JP2016/052873 JP2016052873W WO2016167008A1 WO 2016167008 A1 WO2016167008 A1 WO 2016167008A1 JP 2016052873 W JP2016052873 W JP 2016052873W WO 2016167008 A1 WO2016167008 A1 WO 2016167008A1
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Prior art keywords
limonene
product
ppm
polyphenol
generation
Prior art date
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PCT/JP2016/052873
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English (en)
Japanese (ja)
Inventor
たまみ 鈴木
善久 田中
Original Assignee
アサヒビール株式会社
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Filing date
Publication date
Priority claimed from JP2015174035A external-priority patent/JP6829935B2/ja
Application filed by アサヒビール株式会社 filed Critical アサヒビール株式会社
Publication of WO2016167008A1 publication Critical patent/WO2016167008A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes

Definitions

  • the present invention relates to a limonene-containing product, a fragrance composition, and a method for suppressing the generation of a deteriorated odor.
  • the aroma component contained in such a citrus flavor is converted to other components by heating or storing for a long time.
  • the following techniques are known as examples of countermeasures against such knowledge.
  • Patent Document 1 discloses an extract obtained by solvent extraction from karin, mango, mangosteen, mylobaran, pomegranate or cacao, or epi in order to suppress the production of p-methylacetophenone or the like that occurs when citral is heated.
  • a technique for adding catechin, epicatechin gallate, epigallocatechin gallate, enzyme-treated rutin, quercetin, ferulic acid, caffeic acid, rosmarinic acid, syringic acid or gallic acid is disclosed.
  • Patent Document 2 use of solvent extracts such as Ashitaba, Avocado, Psyllium, etc. to suppress the generation of odors from citral and citral-containing products (see Patent Document 2), and solvent extract from pericarp of periwinkle plants to suppress fragrance degradation A technique used as an agent is known (see Patent Document 3).
  • Patent Document 4 discloses a technique in which eriocitrin or an eriocitrin-containing material is used as an anti-degradation agent for flavor components of citral and limonene.
  • Patent Documents 1 to 3 have been shown to be able to suppress the generation of a deteriorated odor with respect to citral, but can suppress the deterioration with respect to limonene. It was unknown. Moreover, about the technique disclosed by patent document 4, it is shown that the residual rate of a limonene can be raised with the eriocitrin containing material which contains 30% of eriocitrin.
  • an addition amount of 200 ppm (60 ppm as an active ingredient) is required as the addition amount of the eriocitrin-containing material, and there is room for developing a technique capable of effectively suppressing the degradation of limonene even with a small amount.
  • the present inventors diligently studied and found that when a specific polyphenol is allowed to act on a product containing limonene, a very remarkable deterioration odor suppressing effect is exhibited. . Moreover, since the remarkable deterioration odor suppression effect
  • a limonene-containing product comprising limonene and a polyphenol component
  • a limonene-containing product is provided in which the polyphenol component is one or more polyphenol components selected from the group consisting of proanthocyanidins, ellagitannins, and gallotannins.
  • a fragrance composition containing limonene and a polyphenol component there is provided a fragrance composition wherein the polyphenol component is one or more polyphenol components selected from the group consisting of proanthocyanidins, ellagitannins and gallotannins.
  • a method for suppressing the generation of a deteriorated odor in a product containing limonene is to add a polyphenol component to the product, There is provided a method for inhibiting the generation of a deteriorated odor, wherein the polyphenol component is one or more polyphenol components selected from the group consisting of proanthocyanidins, ellagitannins and gallotannins.
  • generation of a degradation odor is suppressed by adding a specific polyphenol component with respect to the product containing limonene.
  • this specific polyphenol component can remarkably suppress the deterioration of limonene as compared with conventional additives, and can sufficiently exhibit the effect even when added in a small amount.
  • a product containing limonene a product in which the generation of the deteriorated odor is sufficiently suppressed can be realized.
  • generation suppression method which concerns on this embodiment is demonstrated.
  • generation suppression method of this embodiment is shown below.
  • the degradation odor production suppressing method is to add a specific polyphenol component to a product containing limonene, and thereby, when heating or long-term storage is performed on limonene.
  • production of the deterioration odor component which arises can be suppressed.
  • generation suppression method of this embodiment shows a very high degradation odor production suppression effect.
  • polyphenols are generally known to exhibit astringency. For example, when a small amount of polyphenol is added to limonene-containing products such as beverages and foods, a good aftertaste can be imparted. That is, since this polyphenol component exhibits a sufficient deterioration odor generation suppressing effect even with a limited addition amount, for example, it has a good aftertaste derived from the polyphenol component for limonene-containing products such as beverages and foods. While imparting, the deterioration of limonene can be suppressed.
  • the product containing limonene according to this embodiment can be appropriately selected from products that can contain limonene (hereinafter referred to as “limonene-containing product” or simply “ Also referred to as “product”). More specifically, examples of the product containing limonene include beverages and foods containing limonene, and cosmetics. In this embodiment, the product by which the production
  • Beverages include beverages such as soft drinks, alcoholic beverages, lactic acid bacteria beverages, fruitless beverages, beverages containing fruit juices, tea, green tea, and energy drinks, and foods include confectionery such as ice cream, strawberries, and gums, and dressings And other seasonings.
  • the cosmetics include perfumes, cosmetics, bathing agents, fragrances, detergents, mouthwashes, and the like.
  • generation suppression method of this embodiment is preferably used especially when a product is a drink.
  • the limonene-containing product is a beverage will be exemplified and the description will be continued.
  • the beverage according to this embodiment may be an alcoholic beverage or a non-alcoholic beverage.
  • the lower limit of the alcohol concentration as an alcoholic beverage is 1% or more, for example, Preferably it is 2% or more, More preferably, it is 3% or more.
  • the upper limit of the alcohol concentration as an alcoholic beverage is 25% or less, for example, Preferably it is 20% or less, More preferably, it is 18% or less.
  • the unit of alcohol concentration is volume (v / v)%.
  • the pH of the beverage when a drink is acidic, ie, when the pH of a drink is less than 7, the effect becomes remarkable.
  • the pH of the beverage can be less than 6, or the pH can be less than 5.
  • the pH of the beverage can be measured according to a known method. For example, it can be measured using a pH meter HM-30R manufactured by Toa DKK Corporation.
  • a pH adjuster can also be suitably added with respect to a drink.
  • the pH adjuster may be appropriately selected according to the product to be designed, and examples thereof include carboxylic acids such as citric acid and carboxylates such as sodium citrate. Moreover, what is necessary is just to adjust the addition amount of this pH adjuster, monitoring the pH of a product sequentially.
  • generation suppression method of this embodiment it suppresses producing
  • generation of p-cymene generated from limonene during heating or storage is suppressed.
  • the present inventors have found that the smell like kerosene derived from p-cymene causes the limonene aroma to be damaged.
  • the generation of this p-cymene can be effectively suppressed by the method for suppressing the generation of deteriorated odor of the present embodiment, it has been found that the aroma of limonene can be effectively maintained as a result.
  • the content of limonene in the entire product can be appropriately set according to the product to be designed.
  • the lower limit of the content of limonene is, for example, 0.05 ppm or more, preferably 0.1 ppm or more, more preferably 0.5 ppm or more, based on the entire product.
  • the upper limit of the content of limonene is, for example, 3,000 ppm or less, preferably 2,000 ppm or less, more preferably 1,000 ppm or less, based on the entire product.
  • ppm is a mass ratio.
  • generation suppression method of this embodiment can add combining various flavors other than said limonene according to the use etc. of a product.
  • the polyphenol component used in the degradation odor production suppressing method of the present embodiment is one or more polyphenol components selected from the group consisting of proanthocyanidins, ellagitannins, and gallotannins.
  • Proanthocyanidins are polyphenols having a structure in which a plurality of epicatechins, catechins, epigallocatechins, and gallocatechins are polymerized. Specific examples thereof include procyanidin A1 (Procyanidin A1), procyanidin A2 (Procyanidin A2), and procyanidin B1 (Procyanidin). B1), procyanidin B2 (Procyanidin B2), procyanidin B3 (Procyanidin B3), procyanidin C1 (Procyanidin C1), procyanidin C2 (Procyanidin C2), prodelphinidin B1 (Prodelphindin B1), Prodeldindin B1 idinB3) and the like.
  • the polymerization mode of catechin in the proanthocyanidins of the present embodiment is not limited to the above-described compound groups, and includes positional isomers thereof.
  • Some proanthocyanidins are galloylated and glycosylated, and these are considered to exhibit the same effect.
  • a derivative obtained by performing a specific chemical conversion on proanthocyanidins for the purpose of improving the effect of suppressing the generation of deteriorated odor can also be applied to the method for suppressing the generation of deteriorated odor.
  • procyanidin B2, procyanidin B1, and procyanidin C1 are particularly preferably used.
  • Examples of ellagitannins include compounds having a hexahydroxydiphenyl group, a sangisoruboyl group, and a galloyl group that give ellagic acid by hydrolysis. Specifically, punicalagin, punicalin, castalazine, vescalazine, eugeniiin, sanguiin H-1, sanguiin H-4 (Sanguin H-4) ), 2,3-hexahydroxydiphenoylglucose (2,3-hexahydroxydiphenoylglucose), 4,6-hexahydroxydiphenoylglucose (4,6-hexahydroxydiphenoylglucose), chebulagic acid, geraniin (Geraniin) Granatin A (Granatin A), Granatin B (Granatin B) Elaeocarpusin, Corilagin, Cornusinin A, Cornusinin B, Agrimoninin, Emburicanin (Emblicanin
  • punicalazine, punicalin, castalazine, bescalazine, eugeniin, telimaglandin I, and telimagrandin II are preferably used in the method for suppressing the generation of degraded odor of this embodiment.
  • punicalagin, eugeniin, and terimalangin I are particularly preferably used.
  • gallotannins examples include tannic acid, hamamelitannin, monogalloylglucose, digalloyllucose, trigalloylglucose, galloylglucose, galloyllucose, galloylglucose Ylglucose, hexagalloylglucose, heptagalloylglucose, octagalloylglucose, nonagalloylglucose Loylglucose), decagalloylglucose, undecagalloylglucose, dodecagalloylglucose and the like.
  • tannic acid and hamamelitannin are particularly preferably used among the gallotannins.
  • generation suppression method of this embodiment it achieves by adding said polyphenol component with respect to a limonene containing product.
  • the addition amount can be appropriately set according to the type of product to be applied, etc., but is, for example, 0.01 ppm or more, preferably 0.1 ppm or more, more preferably 0.5 ppm, with respect to the entire limonene-containing product. More preferably, it is 1 ppm or more.
  • the upper limit of the addition amount of a polyphenol component is not specifically limited, For example, it is 30,000 ppm or less with respect to the whole limonene containing product.
  • the upper limit of the amount of the polyphenol component added can be 3,000 ppm or less, more preferably 1,000 ppm or less, from the viewpoint of imparting a good aftertaste. More preferably 500 ppm or less.
  • the upper limit of the amount of polyphenol component added is 100 ppm or less, preferably 50 ppm or less, more preferably 10 ppm or less, More preferably, it can be 5 ppm or less.
  • Such a fragrance composition contains, for example, 0.001 part by mass or more of the above polyphenol component, more preferably 0.01 part by mass or more, and more preferably 100 parts by mass of limonene. It contains 0.1 parts by mass or more, particularly preferably 1 part by mass or more, and particularly preferably 10 parts by mass or more.
  • flavor composition which concerns on this embodiment does not necessarily need to be uniform as a whole, and the polyphenol component may be mixed with solid form.
  • the upper limit of the polyphenol component contained in the fragrance composition according to the present embodiment is, for example, 60,000,000 parts by mass or less, preferably 6,000,000 parts by mass with respect to 100 parts by mass of limonene. It is as follows.
  • limonene tends to be denatured when heated, stored for a long period of time, or in an environment having a low pH.
  • flavor composition of this embodiment deterioration of limonene can fully be suppressed by adding a polyphenol component.
  • the amount of the components contained in the beverage is quantified using gas chromatography (GC) analysis.
  • GC gas chromatography
  • the procedure for this analysis is as follows. (Sample preparation method) Weigh 50.0 g of the sample, add 100 ⁇ L of 2-octanol as an internal standard, and dilute with 50 mL of water. Separately, a solid phase (Oasis HLB 200 mg / 6 cc manufactured by Waters) that was sequentially conditioned with dichloromethane (5 mL), ethanol (5 mL), and water (20 mL) was prepared and included in the diluted sample obtained above. Adsorb all organic components.
  • Example 1 As a model solution, a beverage containing an alcohol concentration of 5.0% and limonene of 10 ppm was prepared, and the pH of this beverage was adjusted using citric acid and trisodium citrate so that the pH was 3.0. Here, the pH was measured using a pH meter HM-30R manufactured by Toa DKK Corporation. To this beverage, procyanidin B2, which is a polyphenol belonging to proanthocyanidins, was added so as to be 0.1 ppm of the whole beverage, and after sealing, it was allowed to stand at a temperature of 37 ° C. for 7 days. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 1 as a ratio to the content in Comparative Example 1 described later.
  • Example 2 In the method of Example 1, the sample was allowed to stand in the same manner as in Example 1 except that the amount of procyanidin B2 was adjusted to 1.0 ppm, and the amount of p-cymene contained in the beverage was quantified. The results are shown in Table 1.
  • Example 3 To the beverage prepared in the same manner as in Example 1, punicalagin, a polyphenol belonging to ellagitannin, was added so as to be 0.1 ppm of the whole beverage, and sealed, and then at a temperature of 37 ° C. for 7 days. Left to stand. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 1 as a ratio to the content in Comparative Example 1 described later.
  • Example 4 In the method of Example 3, the mixture was left standing in the same manner as in Example 3 except that the amount of punicaladine was adjusted to 1.0 ppm, and the amount of p-cymene contained in the beverage was quantified. The results are shown in Table 1.
  • Tannic acid which is a polyphenol belonging to gallotannin, was added to the beverage prepared in the same manner as in Example 1 so that the total amount of the beverage was 0.1 ppm, and the bottle was sealed and sealed at a temperature of 37 ° C. Let stand for days. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 1 as a ratio to the content in Comparative Example 1 described later.
  • Example 6 In the method of Example 5, except that the amount of tannic acid added was adjusted to 1.0 ppm, the mixture was allowed to stand in the same manner as in Example 5 to quantify the amount of p-cymene contained in the beverage. The results are shown in Table 1.
  • Example 7 To the beverage prepared in the same manner as in Example 1, procyanidin B1, which is a polyphenol belonging to proanthocyanidins, was added so as to be 0.1 ppm of the whole beverage, and the cap was sealed, and at a temperature of 37 ° C. for 7 days. Left to stand. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 2 as a ratio to the content in Comparative Example 1 described later.
  • Example 8 In the method of Example 7, the sample was allowed to stand in the same manner as in Example 7 except that the amount of procyanidin B1 added was adjusted to 1.0 ppm, and the amount of p-cymene contained in the beverage was quantified. The results are shown in Table 2.
  • Example 9 To the beverage prepared in the same manner as in Example 1, procyanidin C1, which is a polyphenol belonging to proanthocyanidins, was added so as to be 0.1 ppm of the whole beverage, and sealed at a temperature of 37 ° C. Let stand for 7 days. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 2 as a ratio to the content in Comparative Example 1 described later.
  • Example 10 In the method of Example 9, the sample was allowed to stand in the same manner as in Example 9 except that the amount of procyanidin C1 added was adjusted to 1.0 ppm, and the amount of p-cymene contained in the beverage was quantified. The results are shown in Table 2.
  • Example 12 In the method of Example 11, the amount of p-cymene contained in the beverage was quantified by standing in the same manner as in Example 11 except that the amount of eugenin was adjusted to 1.0 ppm. The results are shown in Table 2.
  • Example 13 To the beverage prepared in the same manner as in Example 1, terimaglandin I, which is a polyphenol belonging to ellagitannin, was added so as to be 0.1 ppm of the whole beverage, sealed and then brought to a temperature of 37 ° C. Left for 7 days. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 2 as a ratio to the content in Comparative Example 1 described later.
  • Example 14 In the method of Example 13, the sample was allowed to stand in the same manner as in Example 13 except that the amount of added terimaglandin I was adjusted to 1.0 ppm, and the amount of p-cymene contained in the beverage was quantified. . The results are shown in Table 2.
  • Example 15 Hamamelitannin, a polyphenol belonging to gallotannin, was added to the beverage prepared in the same manner as in Example 1 so that it would be 0.1 ppm of the whole beverage, and sealed at a temperature of 37 ° C. Let stand for 7 days. After standing, the amount of p-cymene contained in the beverage was quantified. The p-cymene content is shown in Table 2 as a ratio to the content in Comparative Example 1 described later.
  • Example 16 In the method of Example 15, the mixture was left standing in the same manner as in Example 15 except that the amount of hamamelitannin added was adjusted to 1.0 ppm, and the amount of p-cymene contained in the beverage was quantified. The results are shown in Table 2.
  • Comparative Example 1 The beverage prepared by the same method as in Example 1 was left standing by the same method as in Example 1 without adding anything, and the amount of each component contained in the beverage was quantified. The results of Comparative Example 1 are shown in Tables 1 and 2 as a control (100%).
  • generation suppression method of this invention can keep the aroma of limonene effectively. This method is useful for the development of various products such as foods and beverages containing limonene and cosmetics.
  • the limonene product of the present invention is sufficiently suppressed in the generation of a deteriorated odor, and can effectively bring a pleasant aroma to those who use it.

Abstract

Ce produit contenant du limonène comprend du limonène et un composant de polyphénol, le polyphénol étant un ou plusieurs composants choisi(s) dans le groupe constitué de proanthocyanidines, d'ellagitannins et de gallotannins.
PCT/JP2016/052873 2015-04-13 2016-02-01 Produit contenant du limonène, composition parfumée, et procédé pour supprimer la génération d'odeur de détérioration WO2016167008A1 (fr)

Applications Claiming Priority (4)

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JP2015-081560 2015-04-13
JP2015081560 2015-04-13
JP2015-174035 2015-09-03
JP2015174035A JP6829935B2 (ja) 2015-04-13 2015-09-03 アルコール飲料

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