JP6484877B2 - 香料組成物 - Google Patents
香料組成物 Download PDFInfo
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- JP6484877B2 JP6484877B2 JP2015535543A JP2015535543A JP6484877B2 JP 6484877 B2 JP6484877 B2 JP 6484877B2 JP 2015535543 A JP2015535543 A JP 2015535543A JP 2015535543 A JP2015535543 A JP 2015535543A JP 6484877 B2 JP6484877 B2 JP 6484877B2
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- JP
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- Prior art keywords
- methyl
- composition
- pentanone
- cosmetics
- trimethylcyclopentan
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 40
- 239000002304 perfume Substances 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 41
- 230000003287 optical effect Effects 0.000 claims description 30
- 239000002537 cosmetic Substances 0.000 claims description 27
- 239000003205 fragrance Substances 0.000 claims description 21
- 239000003599 detergent Substances 0.000 claims description 18
- 239000000344 soap Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 7
- 239000000443 aerosol Substances 0.000 claims description 6
- 239000007844 bleaching agent Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000002781 deodorant agent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000003676 hair preparation Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000013040 bath agent Substances 0.000 claims description 4
- 239000000796 flavoring agent Substances 0.000 claims description 4
- 235000019634 flavors Nutrition 0.000 claims description 4
- 239000005871 repellent Substances 0.000 claims description 4
- 230000002940 repellent Effects 0.000 claims description 4
- 239000002979 fabric softener Substances 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- -1 ketone compound Chemical class 0.000 description 15
- 241000402754 Erythranthe moschata Species 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000002453 shampoo Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000001953 sensory effect Effects 0.000 description 6
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- OGCGGWYLHSJRFY-SECBINFHSA-N (R)-alpha-campholenaldehyde Chemical compound CC1=CC[C@H](CC=O)C1(C)C OGCGGWYLHSJRFY-SECBINFHSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 229910003460 diamond Inorganic materials 0.000 description 4
- 239000010432 diamond Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OGCGGWYLHSJRFY-VIFPVBQESA-N 2-[(1s)-2,2,3-trimethylcyclopent-3-en-1-yl]acetaldehyde Chemical compound CC1=CC[C@@H](CC=O)C1(C)C OGCGGWYLHSJRFY-VIFPVBQESA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- RXDABADCDDPISE-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopentyl)pentan-2-one Chemical compound CC(=O)C(C)CCC1CCC(C)C1(C)C RXDABADCDDPISE-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- FEWIGMWODIRUJM-HWKANZROSA-N (E)-4-hexen-3-one Chemical compound CCC(=O)\C=C\C FEWIGMWODIRUJM-HWKANZROSA-N 0.000 description 1
- WINCSBAYCULVDU-UHFFFAOYSA-N 1,1,2-trimethylcyclopentane Chemical compound CC1CCCC1(C)C WINCSBAYCULVDU-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- YFVHFDOLNGHBLQ-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-1-ol Chemical compound OCCC(C)CCC1CC=C(C)C1(C)C YFVHFDOLNGHBLQ-UHFFFAOYSA-N 0.000 description 1
- LDCGUZAOEXJZJJ-UHFFFAOYSA-N CC1(C(=CCC1C)CCCC(C)=O)C Chemical compound CC1(C(=CCC1C)CCCC(C)=O)C LDCGUZAOEXJZJJ-UHFFFAOYSA-N 0.000 description 1
- XPNWVVLSHXADMG-UHFFFAOYSA-N CC1(C(CCC1C)CC(CCC)=O)C Chemical group CC1(C(CCC1C)CC(CCC)=O)C XPNWVVLSHXADMG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 1
- 240000000513 Santalum album Species 0.000 description 1
- 235000008632 Santalum album Nutrition 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- OGCGGWYLHSJRFY-UHFFFAOYSA-N alpha-campholenaldehyde Chemical compound CC1=CCC(CC=O)C1(C)C OGCGGWYLHSJRFY-UHFFFAOYSA-N 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003788 bath preparation Substances 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000008294 cold cream Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- FEWIGMWODIRUJM-UHFFFAOYSA-N hex-4-en-3-one Natural products CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 239000007934 lip balm Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004667 medium chain fatty acids Chemical class 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229940098458 powder spray Drugs 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JXHZRQHZVYDRGX-UHFFFAOYSA-M sodium;hydrogen sulfate;hydrate Chemical compound [OH-].[Na+].OS(O)(=O)=O JXHZRQHZVYDRGX-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/105—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings
- C07C49/11—Saturated compounds containing keto groups bound to acyclic carbon atoms containing rings monocyclic
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2072—Aldehydes-ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
(1)下記一般式(A)で表される化合物。
(式(A)中、1’位は光学活性であり、R1及びR2は、一方がメチル基を表し、他方はエチル基を表すか、又はR1とR2が共にメチル基を表す。)
(2)1’位の立体の光学純度が20%e.e.〜99%e.e.の範囲であり、R1及びR2がメチル基である、前記1に記載の化合物。
(3)R1及びR2の一方がメチル基であり、他方がエチル基である前記1に記載の化合物。
(4)式(A)の1’位の光学活性に関してR体が過剰である、前記1〜3のいずれか1項に記載の化合物。
(5)1’位の立体の光学純度が20%e.e.〜99%e.e.の範囲である光学活性な(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン。
(6)(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン。
(7)前記1〜6のいずれか1項に記載の化合物を含有することを特徴
(8)前記1〜6のいずれか1項に記載の化合物を0.01〜60重量%含有することを特徴とする前記6に記載の香料組成物。
(9)化合物の化学純度が80%以上であることを特徴とする前記7又は8に記載の香料組成物。
(10)前記7〜9のいずれか1項に記載の香料組成物によって香気付けした製品。
(11)製品がフレグランス製品、香粧品、基礎化粧品、仕上げ化粧品、頭髪化粧品、日焼け化粧品、薬用化粧品、ヘアケア製品、石鹸、身体洗浄剤、浴用剤、衣料用洗剤、衣料用柔軟仕上げ剤、洗浄剤、台所用洗剤、漂白剤、エアゾール剤、消臭・芳香剤、忌避剤又は雑貨から選ばれる1種である前記10に記載の香気付けした製品。
(12)前記1〜6に記載の化合物を添加することを特徴とする香料組成物の香気を増強又は変調する方法。
また、S体が過剰である本発明の化合物は、対応するR体の化合物と混合して所望の光学純度とし、それにより優れた香気・香料組成物を得るために使用することができる。
本発明は、下記一般式(A)で表される化合物である。
上記式(A)において、1’位の立体の光学純度が20%e.e.〜99%e.e.の範囲であることが好ましく、また、1’位の光学活性に関してR体が過剰であることが好ましい。
(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン、
(1’S)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン、
(1’R)−3−エチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン、
(1’S)−3−エチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン、
(1’R)−4−メチル−6−(2,2,3−トリメチルシクロペンタン−1−イル)−3−ヘキサノン。
(1’S)−4−メチル−6−(2,2,3−トリメチルシクロペンタン−1−イル)−3−ヘキサノン。
また、上記の化合物(1)の化学純度は80%以上であればよく、好ましくは90%以上である。
(スキーム1)
NMR測定装置(1H−NMR、13C−NMR):AVANCEIII 500型(500MHz;ブルカーバイオスピン社製)
内部標準物質:CDCl3
ガスクロマトグラフ質量分析計(GC/MS):GCMS−QP2010Ultra(島津製作所社製)
使用カラム:BC−WAX(長さ50m×内径0.25mm、液相膜厚0.15μm、ジーエルサイエンス社製)
ガスクロマトグラフィー(GC、化学純度):GC−4000(ジーエルサイエンス社製)
使用カラム:InertCap 1(長さ30m×内径0.25mm、液相膜厚0.25μm、ジーエルサイエンス社製)
ガスクロマトグラフィー(GC、光学純度及び異性体比率):GC−2010(島津製作所社製)
使用カラム:β−DEX325(長さ30m×内径0.25mm、液相膜厚0.25μm、SUPELCO社製)
旋光度計:P−1020(日本分光社製)
赤外吸収スペクトル測定装置:NICOLET iS10(Thermo Scientific社製)
(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンの合成
1H NMR(CDCl3,500MHz)δ 0.48(d,3H,J=5.4Hz),0.82(dd,3H,J=6.8,1.2Hz),0.84(s,3H),0.92−1.02(m,1H),1.08(t,3H,J=7.0Hz),1.12−1.17(m,1H),1.18−1.27(m,1H),1.29−1.33(m,1H),1.34−1.43(m,1H),1.49−1.51(m,1H),1.52−1.58(m,1H),1.66−1.76(m,2H),1.77−1.85(m,1H),2.13(d,3H,J=3.8Hz),2.50(m,1H);
13C NMR(CDCl3,500MHz)δ 212.86,212.82,50.98,50.73,47.63,47.42,45.17,42.26,32.36,32.02,30.06,28.17,28.13,27.91,27.88,27.86,25.61,25.60,16.44,15.88,14.32,13.79;
比旋光度 [α]20 +24.7(neat);
IR(ATR,ダイヤモンドセル使用,cm-1):2953,2868,1715,1458,1386,1365,1162.
香気:強いムスク,透明感があり温かみのある香気.
(1’S)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンの合成
1H NMR(CDCl3,500MHz)δ 0.48(d,3H,J=5.4Hz),0.82(dd,3H,J=6.8,1.2Hz),0.84(s,3H),0.92−1.02(m,1H),1.08(t,3H,J=7.0Hz),1.12−1.17(m,1H),1.18−1.27(m,1H),1.29−1.33(m,1H),1.34−1.43(m,1H),1.49−1.51(m,1H),1.52−1.58(m,1H),1.66−1.76(m,2H),1.77−1.85(m,1H),2.13(d,3H,J=3.9Hz),2.50(m,1H);
13C NMR(CDCl3,500MHz)δ 212.93,212.89,50.98,50.73,47.65,47.43,45.17,42.27,32.37,32.02,30.06,28.17,28.14,27.91,27.90,27.87,25.62,25.61,16.45,15.88,14.33,13.81;
比旋光度 [α]20 −17.0(neat);
IR(ATR,ダイヤモンドセル使用,cm-1):2950,2867,1713,1458,1364,1162.
香気:ウッディ,フルーティ,微かにメタリック.
(1’R)−3−エチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンの合成
1H NMR(CDCl3,500MHz)δ 0.47(d,3H,J=5.7Hz),0.82(d,3H,J=6.8Hz),0.84(s,3H),0.84−0.88(m,3H),0.90−1.01(m,1H),1.06−1.21(m,2H),1.27−1.37(m,3H),1.43−1.54(m,3H),1.56−1.65(m,1H),1.69−1.83(m,2H),2.11(d,3H,J=4.9Hz),2.33−2.40(m,1H);
13C NMR(CDCl3,500MHz)δ 213.10,213.02,55.21,50.99,50.90,45.18,42.29,42.26,30.61,30.47,30.07,28.67,28.57,28.23,28.22,28.19,28.11,25.62,24.83,24.30,14.34,13.82,11.83,11.73;
比旋光度 [α]20 +22.7(neat);
IR(ATR,ダイヤモンドセル使用,cm-1):2951,2867,1712,1457,1365,1351,1160.
香気:ムスク,パウダリー,ミルキーで甘さのある香気.
(1’R)−4−メチル−6−(2,2,3−トリメチルシクロペンタン−1−イル)−3−ヘキサノンの合成
1H NMR(CDCl3,500MHz)δ 0.48(d,3H,J=6.5Hz),0.82(dd,3H,J=6.9,1.4Hz),0.84(s,3H),0.88−1.02(m,1H),1.05(dd,3H,J=7.3,1.2Hz),1.07(t,3H,J=6.5Hz),1.10−1.25(m,3H),1.27−1.41(m,2H),1.43−1.57(m,2H),1.66−1.85(m,2H),2.41−2.48(m,2H),2.49−2.55(m,1H);
13C NMR(CDCl3,500MHz)δ 215.55,215.53,51.01,50.75,46.55,46.40,45.20,42.28,34.19,34.09,32.55,32.25,30.08,28.24,28.18,28.16,28.04,25.65,25.63,16.77,16.18,14.35,13.83,7.85,7.80;
IR(ATR,ダイヤモンドセル使用,cm-1):2937,2868,1713,1459,1376,1365,1104,973.
香気:パウダリー,ムスク,ウッディ、シトラス.
実施例1で合成した化合物に関して、それぞれ官能評価を行った。5年以上経験した10人の専門パネリストにより、香気の質の検討を行った。結果を下記表1に示す。この化合物は拡散性に優れ、透明感のある強いムスク香気を有しており、有用な化合物であることが示された。
下記表2の処方に従い、上記実施例1で合成した化合物を用いて香水用香料組成物を調製した。
下記表3の処方に従い、上記実施例6の香料組成物を0.5%賦香した液体洗剤(100g)を作製した。このものの官能評価は、5年以上経験した4人の専門パネリストが行い、明るく温かみのあるフルーティ−フローラル調がはっきりと認識でき、嗜好性が高く、香質に優れていると4人全員が判断した。
下記表4の処方に従い、上記実施例6の香料組成物を1.0%賦香したシャンプー(100g)を作製した。このものの官能評価は、5年以上経験した4人の専門パネリストが行い、嗜好性が高く、香質に優れていると4人全員が判断した。
下記表5の処方に従い、上記実施例6の香料組成物を0.95%賦香したボディーシャンプー(100g)を作製した。このものの官能評価は、5年以上経験した4人の専門パネリストが行い、明るいフルーティ−フローラル調がはっきり認められ、嗜好性が高く、香質に優れていると4人全員が判断した。
光学活性な(1’R)又は(1’S)の3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンを様々な比率で混合することにより得られた光学活性体に関して、それぞれ官能評価を行い、香気質の差異について比較を行った。評価は5年以上経験した10人の専門パネリストが行った。結果を下記表6に示す。1’位の立体において(1’R)体の光学純度が高いものほど、より透明感のある良好な強いムスク香気を示すと評価された。
◎:強くハッキリとしたムスク香を有する
○:ハッキリとしたムスク香を有する
△:微かなムスク香を有する
×:ムスク香を有さない
Claims (10)
- 1’位の立体の光学純度が20%e.e.〜99%e.e.の範囲であり、R1及びR2がメチル基である、請求項1に記載の組成物。
- R1及びR2の一方がメチル基であり、他方がエチル基である請求項1に記載の組成物。
- (1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノン。
- 請求項1〜3のいずれか1項に記載の組成物又は(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンを含有することを特徴とする香料組成物。
- 式(A)の化合物又は(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンを0.01〜60重量%含有することを特徴とする請求項5に記載の香料組成物。
- 化合物の化学純度が80%以上であることを特徴とする請求項5又は6に記載の香料組成物。
- 請求項5〜7のいずれか1項に記載の香料組成物によって香気付けした製品。
- 製品がフレグランス製品、香粧品、基礎化粧品、仕上げ化粧品、頭髪化粧品、日焼け化粧品、薬用化粧品、ヘアケア製品、石鹸、身体洗浄剤、浴用剤、衣料用洗剤、衣料用柔軟仕上げ剤、洗浄剤、台所用洗剤、漂白剤、エアゾール剤、消臭・芳香剤、忌避剤又は雑貨から選ばれる1種である請求項8に記載の香気付けした製品。
- 請求項1〜3のいずれか1項に記載の組成物又は(1’R)−3−メチル−5−(2,2,3−トリメチルシクロペンタン−1−イル)−2−ペンタノンを添加することを特徴とする香料組成物の香気を増強又は変調する方法。
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