JP6476474B2 - 香味香気配合物(iv) - Google Patents
香味香気配合物(iv) Download PDFInfo
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- JP6476474B2 JP6476474B2 JP2015535046A JP2015535046A JP6476474B2 JP 6476474 B2 JP6476474 B2 JP 6476474B2 JP 2015535046 A JP2015535046 A JP 2015535046A JP 2015535046 A JP2015535046 A JP 2015535046A JP 6476474 B2 JP6476474 B2 JP 6476474B2
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- flavor
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- 239000000796 flavoring agent Substances 0.000 title claims description 46
- 235000019634 flavors Nutrition 0.000 title claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 52
- 239000003205 fragrance Substances 0.000 claims description 51
- 238000009472 formulation Methods 0.000 claims description 31
- 239000002304 perfume Substances 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 238000004140 cleaning Methods 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 239000000047 product Substances 0.000 description 23
- 239000000049 pigment Substances 0.000 description 14
- 239000012467 final product Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002671 adjuvant Substances 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000004606 Fillers/Extenders Substances 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 239000000945 filler Substances 0.000 description 7
- 239000006254 rheological additive Substances 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000001069 triethyl citrate Substances 0.000 description 4
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 4
- 235000013769 triethyl citrate Nutrition 0.000 description 4
- CGPASQCYOZAETB-UHFFFAOYSA-N 3,7-dimethyldec-6-en-1-yn-3-yl acetate Chemical compound CCCC(C)=CCCC(C)(OC(C)=O)C#C CGPASQCYOZAETB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- ZNPHSSQNHJVPGE-UHFFFAOYSA-N 3,7-dimethyldec-6-en-1-yn-3-ol Chemical compound CC(C#C)(CCC=C(CCC)C)O ZNPHSSQNHJVPGE-UHFFFAOYSA-N 0.000 description 2
- KSJHIVXGLQFMNU-UHFFFAOYSA-N 6-methylnon-5-en-2-one Chemical compound CCCC(C)=CCCC(C)=O KSJHIVXGLQFMNU-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- PDHFSBXFZGYBIP-UHFFFAOYSA-N 2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethanol Chemical compound OCCSCCSCCO PDHFSBXFZGYBIP-UHFFFAOYSA-N 0.000 description 1
- WCMNDAINCFBGOF-UHFFFAOYSA-N 3,7-dimethyldeca-1,6-dien-3-yl acetate Chemical compound CCCC(C)=CCCC(C)(OC(C)=O)C=C WCMNDAINCFBGOF-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 240000008384 Capsicum annuum var. annuum Species 0.000 description 1
- 235000002568 Capsicum frutescens Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- -1 cyclic oligosaccharide Chemical class 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000011981 lindlar catalyst Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 150000002678 macrocyclic compounds Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008328 tiger balm Substances 0.000 description 1
- 229940096662 tiger balm Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
-
- 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
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
-
- 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
- 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
- A23L27/2028—Carboxy 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
- A61K8/37—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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
-
- 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
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
- C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
(式中、
R1は、−H(水素)または−CH3(メチル)を表し、
R2は:
の部分を表すかまたは
R2は、メチル(=「−CH3」)を表し、
R3は、−OH(ヒドロキシ)または−O(CO)CH3(アセチルオキシ)を表す)の香気香味材料としての使用に関する。
(i)少なくとも1種の式(I)の化合物:
(式中、R1は、−Hまたは−CH3を表し、
R2は:
の部分を表すかまたは
R2は−CH3を表し、R3は、−OHまたは−O(CO)CH3を表す)を含む香味香気配合物にも関する。
(i)少なくとも1種の式(I)の化合物を、香味香気配合物の総重量に対し0.0001〜10wt%(好ましくは0.01〜5wt%)含む、液体香味香気配合物に関する。
(i)式(Ia)〜(Ig)の化合物からなる群から選択される少なくとも1種の化合物を、香味香気配合物の総重量に対し0.0001〜10wt%(好ましくは0.01〜5wt%)含む、好ましい液体香味香気配合物に関する。
(i)式(II)〜(VII)の化合物からなる群から選択される少なくとも1種の化合物(特に好ましくは式(II)、(V)、(VI)および(VII)の化合物)を、香味香気配合物の総重量に対し0.0001〜10wt%(好ましくは0.01〜5wt%)含む、より好ましい液体香味香気配合物に関する。
(i)少なくとも1種の式(I)の化合物と、
(ii)ジプロピレングリコール、ミリスチン酸イソプロピル、クエン酸トリエチルおよびアルコール(エタノール等)からなる群から選択される少なくとも1種の希釈剤と、
任意選択で、
(iii)付香化合物溶剤、補佐剤、増粘剤、界面活性剤、顔料、体質顔料、レオロジー調整剤、染料、酸化防止剤およびフィラーからなる群から選択される少なくとも1種の助剤化合物と
を含む、液体香味香気配合物に関する。
(i)式(Ia)〜(Ig)の化合物からなる群から選択される少なくとも1種の化合物と、
(ii)ジプロピレングリコール、ミリスチン酸イソプロピル、クエン酸トリエチルおよびアルコール(エタノール等)からなる群から選択される少なくとも1種の希釈剤と、
任意選択で、
(iii)付香化合物溶剤、補佐剤、増粘剤、界面活性剤、顔料、体質顔料、レオロジー調整剤、染料、酸化防止剤およびフィラーからなる群から選択される少なくとも1種の助剤化合物と
を含む、好ましい液体香味香気配合物に関する。
(i)式(II)〜(VII)の化合物(特に好ましくは式(II)、(V)、(VI)および(VII)の化合物)からなる群から選択される少なくとも1種の化合物と、
(ii)ジプロピレングリコール、ミリスチン酸イソプロピル、クエン酸トリエチルおよびアルコール(エタノール等)からなる群から選択される少なくとも1種の希釈剤と、
任意選択で、
(iii)付香化合物溶剤、補佐剤、増粘剤、界面活性剤、顔料、体質顔料、レオロジー調整剤、染料、酸化防止剤およびフィラーからなる群から選択される少なくとも1種の助剤化合物と
を含む、より好ましい液体香味香気配合物に関する。
(i)少なくとも1種の式(I)の化合物と、
(ii)付香化合物溶剤、補佐剤、増粘剤、界面活性剤、顔料、体質顔料、レオロジー調整剤、染料、酸化防止剤およびフィラーからなる群から選択される少なくとも1種の助剤化合物と
を含む、固体香味香気配合物に関する。
(i)式(Ia)〜(Ig)の化合物からなる群から選択される少なくとも1種の化合物と、
(ii)付香化合物溶剤、補佐剤、増粘剤、界面活性剤、顔料、体質顔料、レオロジー調整剤、染料、酸化防止剤およびフィラーからなる群から選択される少なくとも1種の助剤化合物と、
を含む、好ましい固体香味香気配合物に関する。
(i)式(II)〜(VII)の化合物(特に好ましくは式(II)、(V)、(VI)および(VII)の化合物)からなる群から選択される少なくとも1種の化合物と、
(ii)付香化合物溶剤、補佐剤、増粘剤、界面活性剤、顔料、体質顔料、レオロジー調整剤、染料、酸化防止剤およびフィラーからなる群から選択される少なくとも1種の助剤化合物と
を含む、より好ましい固体香味香気配合物に関する。
全ての化合物の香りの強さを1から10までの尺度(1=非常に弱い;10=非常に強い)を用いて4人のパネルに評価させた。さらに、この4人には化合物の香りについても記述させた。1人に3、6、8、24、48、72および96時間後の持続性を評価させた。このような評価は、単体の液体化合物のそれぞれの原液に紙片を浸して行った。
香りの記述:医薬品;摘みたてのハーブ;青葉;快い
強さ:4.5
持続性:3〜6時間
香りの記述:グリーン;ハーブ;花様;フレッシュ;土
強さ:6
持続性:6〜8時間
香りの記述:フルーティ;トロピカルフルーツ;甘い;キャンディ
強さ:3.5
持続性:8〜24時間
[a)6−メチル−5−ノネン−2−オンのエチニル化による3,7−ジメチル−6−デセン−1−イン−3−オールの製造]
6−メチル−5−ノネン−2−オンを1360.0gを、窒素雰囲気下でオートクレーブに装入し、冷却して温度を15℃にする。アンモニア(NH3)2548.0gを加える。反応混合物を再び冷却して15℃にする。次いでアセチレン(C2H2)を加える。反応混合物を再び冷却して15℃にする。次いで40重量%の水酸化カリウム(KOH)水溶液26.4gを連続して加える。反応終了後、反応混合物を酢酸で中和し、水で抽出して、溶媒を除去する。次いで、得られた未精製物を蒸留することにより3,7−ジメチル−6−デセン−1−イン−3−オールを得る。
3,7−ジメチル−6−デセン−1−イン−3−オールを609.0gおよびp−トルエンスルホン酸を0.54gを水中で混合し、40℃の温度に加熱する。無水酢酸414.1gを2時間以内に加える。約20時間後、反応混合物を冷却し、蒸留することにより、酢酸3,7−ジメチル−6−デセン−1−イン−3−イルを得る。
酢酸3,7−ジメチル−6−デセン−1−イン−3−イルを314.0g、リンドラー触媒(CaCO3上5%Pd+3.5%Pb)を3.0g、エチレンジチオジエタノールを0.01gおよび酢酸亜鉛を0.14gをオートクレーブに装入し、窒素雰囲気下で40℃の温度に加熱する。窒素を水素(H2)に交換し、反応混合物を絶対圧が2barになるまで装入する。理論量の水素が消費されたら、反応混合物を濾過して蒸留(2mbar、140℃)することにより酢酸3,7−ジメチル−1,6−デカジエン−3−イル(=式Vの化合物)を得る。
強さ:5
持続性:8〜24時間
香りの記述:タイガーバーム;樟脳;古い地下室;田舎の地下室
強さ:9
持続性:3〜6時間
香りの記述:フレッシュさ;樟脳様;メントール;針葉樹林;菊;ハエ防除剤(poison for flys)
強さ:6.5
持続性:3〜6時間
Claims (7)
- 式(II)、(V)、(VI)および(VII)の化合物からなる群から選択される少なくとも1種の化合物が使用される、請求項1に記載の使用。
- 式(II)〜(VII)の少なくとも1種の化合物を、前記香味香気配合物の総重量に対し0.0001〜10wt%含む、請求項3に記載の香味香気配合物。
- 固体、ゲル様または液体である、請求項3または4に記載の香味香気配合物。
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EP12187649 | 2012-10-08 | ||
EP12187649.4 | 2012-10-08 | ||
PCT/EP2013/070832 WO2014056849A1 (en) | 2012-10-08 | 2013-10-07 | Flavor and fragrance formulation (iv) |
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JP2015537064A JP2015537064A (ja) | 2015-12-24 |
JP6476474B2 true JP6476474B2 (ja) | 2019-03-06 |
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US (1) | US20150208701A1 (ja) |
EP (1) | EP2904077B1 (ja) |
JP (1) | JP6476474B2 (ja) |
CN (1) | CN104704097B (ja) |
ES (1) | ES2699240T3 (ja) |
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US2838576A (en) * | 1958-06-10 | Tertiary alcohols | ||
US2589275A (en) * | 1948-02-04 | 1952-03-18 | Givaudan Corp | Preparation of 3-methyl-citrals |
US2740817A (en) * | 1948-02-04 | 1956-04-03 | Givaudan Corp | Methyl-6-ionones, methyl-irones, and the like and process for preparing the same |
CH284407A (fr) * | 1949-10-05 | 1952-07-31 | Givaudan & Cie Sa | Procédé de fabrication d'un mélange de méthyl-3-citrals cis et trans. |
GB786349A (en) * | 1954-09-13 | 1957-11-13 | Hoffmann La Roche | Novel unsaturated alcohols and a process for the manufacture thereof |
GB777515A (en) * | 1955-04-13 | 1957-06-26 | Rhone Poulenc Sa | Improvements in or relating to tertiary alcohols |
FR1332794A (fr) * | 1962-07-04 | 1963-07-19 | Int Flavors & Fragrances Inc | Nouveaux alcools acycliques primaires utilisables en parfumerie |
US3453317A (en) * | 1962-07-11 | 1969-07-01 | Hoffmann La Roche | Unsaturated carbonyl compounds and processes |
WO1999043639A1 (en) * | 1998-02-24 | 1999-09-02 | The Procter & Gamble Company | Tertiary alcohol fragrance raw material delivery system |
JP2000319684A (ja) * | 1999-05-10 | 2000-11-21 | Kuraray Co Ltd | 香料組成物 |
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2013
- 2013-10-07 CN CN201380052195.8A patent/CN104704097B/zh active Active
- 2013-10-07 ES ES13773267T patent/ES2699240T3/es active Active
- 2013-10-07 IN IN2646DEN2015 patent/IN2015DN02646A/en unknown
- 2013-10-07 EP EP13773267.3A patent/EP2904077B1/en active Active
- 2013-10-07 US US14/430,251 patent/US20150208701A1/en not_active Abandoned
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MX2015004316A (es) | 2015-10-29 |
EP2904077B1 (en) | 2018-08-22 |
CN104704097A (zh) | 2015-06-10 |
ES2699240T3 (es) | 2019-02-08 |
WO2014056849A1 (en) | 2014-04-17 |
IN2015DN02646A (ja) | 2015-09-18 |
MX360017B (es) | 2018-10-10 |
JP2015537064A (ja) | 2015-12-24 |
EP2904077A1 (en) | 2015-08-12 |
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