Classifications

• • 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
  • C11B9/0007—Aliphatic compounds
  • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
• • 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
• • 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
  • A23L2/52—Adding ingredients
  • A23L2/56—Flavouring or bittering agents
• • 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
  • A23L2/70—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter
  • A23L2/72—Clarifying or fining of non-alcoholic beverages; Removing unwanted matter by filtration
• • 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
  • A23L27/20—Synthetic spices, flavouring agents or condiments
• • 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
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/202—Aliphatic compounds
  • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
• • 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
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/202—Aliphatic compounds
  • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
  • A23L27/2026—Hydroxy 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/35—Ketones, e.g. benzophenone
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/37—Esters of carboxylic acids
• • 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
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/50—Perfumes

Definitions

• the present invention relates to a fragrance composition that can be used as a food fragrance, a cosmetic fragrance and the like, and more specifically, 4,8-dimethyl-3,7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadiene-
• the present invention relates to a fragrance composition characterized by mixing three compounds of 2-yl coconut acetate and 4,8-dimethyl-3,7-nonadien-2-one at a specific ratio.
• Non-patent Document 1 citral in citral-containing products decreases at each stage during production, distribution, and storage, and its structure changes due to reactions such as oxidation, cyclization, hydration, and isomerization. The feeling of sensation and the generation of a very strong deodorizing odor will occur, leading to a significant reduction in product quality.
• Non-Patent Document 2 discloses various antioxidant odor-causing substances produced from citral, such as isoascorbic acid and other antioxidants for the purpose of preventing their occurrence.
• Patent Document 1 By adding a mixture of 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-one so far, it has excellent olfactory properties, And providing a fragrance composition having high color stability (Patent Document 1), and providing a fragrance composition having a natural, fresh and strong lemon-like fragrance (Patent Document 2), 4,8-dimethyl-3, A combination of two kinds of 7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate and alcohols derived from terpene compounds, a fresh and strong lemon-like taste and It is disclosed to provide a fragrance composition that can impart flavor and has high temporal stability in an acidic beverage (Patent Document 3).
• the above references include the addition of a mixture of 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-one or 4,8-dimethyl-3,7 -It has a citral-like aroma characteristic by combining two kinds of nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate with alcohols derived from terpene compounds, and the like. It is disclosed that a perfume composition having high stability over time can be produced.
• An object of the present invention is to provide a natural taste and a highly flavorful fragrance that matches the consumer's natural orientation, in particular, a fragrance pronounced of a lemon sensation, and has a high stability and generation of a strange odor over time.
• the object is to provide a reduced fragrance composition, and a food / beverage product and a cosmetic product containing the fragrance compound.
• the present inventors have conducted extensive studies, and as a result, surprisingly, three kinds of related substances having different functional groups, namely alcohol (4,8-dimethyl-3,7-nonadiene-2) -Ol), ester (4,8-dimethyl-3,7-nonadien-2-yl acetate) and ketone (4,8-dimethyl-3,7-nonadien-3-one) It has been found that the feeling of lemon is remarkably improved. Surprisingly, a specific ratio is important for the ratio of the three kinds, and the ratio was also intensively studied.
• the present invention relates to 4,8-dimethyl-3,7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadien-2-yl acetate, 4,8-dimethyl-3,7- Three compounds of nonadien-2-one are one in 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate is reduced to 0.
• a perfume composition comprising a mixture of 02 to 0.4,4,8-dimethyl-3,7-nonadien-2-one in a ratio of 0.04 to 0.8.
• this invention is food / beverage products or cosmetics characterized by mix
• the fragrance composition of the present invention can be added to foods and beverages and cosmetics to give a natural and natural citral-like lemon feeling and fresh feeling, and citral having similar aroma characteristics. Compared with the fragrance
• the present invention has the formula (1) (In the formula, the wavy bond indicates cis type or trans type or a mixture of cis type and trans type in any ratio) 4,8-dimethyl-3,7-nonadien-2-ol represented by the formula (2) (In the formula, the wavy bond represents cis-type or trans-type or a mixture of cis-type and trans-type in any proportion, and Ac represents an acetyl group) 4,8-dimethyl-3,7-nonadien-2-yl acetate represented by the formula (3) (Wherein the wavy bond represents cis-type or trans-type, or a mixture of cis-type and trans-type in any proportion), and three types of 4,8-dimethyl-3,7-nonadien-2-one It is a fragrance
• 4,8-dimethyl-3,7-nonadien-2-ol can be obtained by subjecting citral to Grignard reaction with methylmagnesium chloride (MeMgCl) as shown in the following reaction formula (Agarwal et al .; Indian Perfum ., 27, 112-118 (1983)).
• MeMgCl methylmagnesium chloride
• 4,8-dimethyl-3,7-nonadien-2-yl acetate is obtained by converting 4,8-dimethyl-3,7-nonadien-2-ol to acetic anhydride (Ac 2 O) as shown in the following reaction formula.
• acetic anhydride Ac 2 O
• pyridine Pyr.
• the active ingredients of the present invention are 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7-
• the mixing ratio of these three compounds is 4,8-dimethyl-3, with respect to 1 of 4,8-dimethyl-3,7-nonadien-2-ol.
• 7-nonadien-2-yl acetate is 0.02 to 0.4
• 4,8-dimethyl-3,7-nonadien-2-one is 0.04 to 0.8, preferably 4,8-dimethyl 4,8-dimethyl-3,7-nonadien-2-yl acetate is 0.04 to 0.2,4,8-dimethyl-3,7- to 1,3,7-nonadien-2-ol
• Nonadien-2-one is 0.08 to 0.4.
• the total addition amount of the three compounds varies depending on the purpose or the type of the fragrance composition, but is generally from 0.000000001 mass% (10 ppt) to 10 mass%, preferably 0.00%, based on the total amount of the fragrance composition. A range of 000001 mass% (10 ppb) to 5 mass% can be exemplified.
• the other components blended in the fragrance composition of the present invention are not particularly limited, and various fragrance materials that have been used conventionally can be used depending on the application and purpose. Specifically, aldehydes And conventionally known fragrance materials such as alcohols and esters. Moreover, there is no restriction
• the fragrance composition of the present invention includes shampoos, hair creams, pomades, other hair cosmetics, white powder, lipstick, other cosmetics, laundry detergents, disinfectants, indoor air fresheners, and various other health care products. -It can be widely used for hygiene materials, pharmaceuticals and other general cosmetics.
• the amount of the fragrance composition of the present invention added to a food or drink or cosmetic varies depending on the kind of the food or drink or cosmetic, but is generally 4,8-dimethyl-3,7 in the food or drink or cosmetic. -The total concentration of the three compounds nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate and 4,8-dimethyl-3,7-nonadien-2-one is 0. When it is added so that the amount becomes 000000000001% by mass (0.01 ppt) to 0.05% by mass, a natural and natural citral-like aroma flavor can be imparted to foods and drinks and cosmetics.
• the heptane layer was washed with saturated aqueous sodium hydrogen carbonate and brine and then dried over anhydrous sodium sulfate, and heptane was distilled off with a rotary evaporator to obtain 53 g of a crude oil.
• the crude oil was subjected to simple distillation to obtain 45 g of 4,8-dimethyl-3,7-nonadien-2-ol having a GC purity of 99.0%. (Boiling point: 59-63 ° C / 70 Pa)
• the heptane layer was washed with water and a 5% soda ash aqueous solution and then dried over anhydrous sodium sulfate, and heptane was distilled off with a rotary evaporator to obtain 31 g of crude oil.
• the crude oil was subjected to simple distillation to obtain 30 g of 4,8-dimethyl-3,7-nonadien-2-yl acetate having a GC purity of 99.1%. (Boiling point: 71 ° C./80 Pa)
• the heptane layer was washed with a 3% aqueous hydrochloric acid solution and brine and then dried over anhydrous sodium sulfate, and heptane was distilled off with a rotary evaporator to obtain 2.1 g of a crude oil.
• Example 1 and Comparative Examples 1 to 4 (Lemon flavor) According to the following prescription, the fragrance composition No. 1 of the present invention was obtained by a conventional method. As Comparative Examples 1 to 4, 4,8-dimethyl-3,7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadien-2-yl acetate, 4,8-dimethyl-3,7 -Perfume compositions Nos. 2 to 5 having different blending ratios of nonadien-2-one were obtained.
• the perfume composition No. 1 is 4,8-dimethyl-3,7-nonadien-2-ol and 4,8-dimethyl-3,7-nonadien-2-yl acetate and 4,8- The mixing ratio of dimethyl-3,7-nonadien-2-one is 4,8-dimethyl-3,7-nonadiene-2-ol with respect to 1 of 4,8-dimethyl-3,7-nonadien-2-ol.
• perfume composition No. 2 is a perfume composition having a lower blending ratio of 4,8-dimethyl-3,7-nonadien-2-yl acetate than the blending ratio of the present invention.
• This is a fragrance composition having a higher proportion of 4,8-dimethyl-3,7-nonadien-2-yl acetate than the proportion of the invention, and fragrance composition No. 4 is 4,8-dimethyl from the proportion of the present invention.
• -3,7-nonadien-2-one is a fragrance composition having a low blending ratio
• fragrance composition No. 5 has 4,8-dimethyl-3,7-nonadien-2-one from the blending ratio of the present invention. It is a fragrance composition with a high blending ratio.
• Perfume composition No. 6 (Comparative Example 5) was converted into 4,8-dimethyl-3,7-nonadiene of Example 1 according to the invention of Patent Document 3 by the formulation shown below according to the inventions of Patent Documents 1 and 2.
• Perfume composition No. 7 (Comparative Example 6) was prepared by mixing 2,4,8-trimethyl-7-nonen-2-ol instead of -2-one, and 4,8-dimethyl-3 of Example 1 was used. , 7-nonadien-2-ol, 4,8-dimethyl-3,7-nonadien-2-yl acetate, citral instead of 4,8-dimethyl-3,7-nonadien-2-one Composition No.
• Table 4 shows the average values of the results of the fragrance compositions obtained in Example 1 and Comparative Examples 1 to 8 (Nos. 1 to 9) based on the following evaluation criteria by 10 expert panelists.
• Table 5 shows the comments obtained at the time.
• the lemon beverage 1 of the present invention had a fresh scent with a lemon feeling and a natural feeling even after being stored at 50 ° C. for 10 days, and the way of feeling a strange odor was reduced compared to the lemon beverages 2 to 4.
• perfume composition No. 10 of the present invention was obtained by a conventional method.
• Example 4 Comparative Example 13
• the grapefruit drink 1 of this invention and the grapefruit drink 2 which is a comparison object were obtained by the conventional method.
• perfume composition No. 12 of the present invention was obtained by a conventional method.
• Example 6 Comparative Example 15
• an orange beverage 1 of the present invention and an orange beverage 2 as a comparison target were obtained by a conventional method.
• perfume composition No. 14 of the present invention was prepared by a conventional method.

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• 2011
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  • 2012-01-27 WO PCT/JP2012/051759 patent/WO2012105430A1/ja active Application Filing
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