JP6479980B2 - 有機化合物におけるまたは関連する改善 - Google Patents
有機化合物におけるまたは関連する改善 Download PDFInfo
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- JP6479980B2 JP6479980B2 JP2017525060A JP2017525060A JP6479980B2 JP 6479980 B2 JP6479980 B2 JP 6479980B2 JP 2017525060 A JP2017525060 A JP 2017525060A JP 2017525060 A JP2017525060 A JP 2017525060A JP 6479980 B2 JP6479980 B2 JP 6479980B2
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- methyl
- compound
- perfume
- acid
- fragrance
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- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 97
- 239000000047 product Substances 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 77
- 239000002304 perfume Substances 0.000 claims description 76
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 claims description 60
- -1 4- (tert-butyl) phenyl Chemical group 0.000 claims description 51
- 239000004615 ingredient Substances 0.000 claims description 47
- 239000003205 fragrance Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 150000001299 aldehydes Chemical group 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 241000700159 Rattus Species 0.000 claims description 13
- 210000003494 hepatocyte Anatomy 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical class CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 7
- NRCLUAUOPXATRW-UHFFFAOYSA-N 4-[4-(2-methylpropyl)phenyl]butanal Chemical compound CC(C)CC1=CC=C(CCCC=O)C=C1 NRCLUAUOPXATRW-UHFFFAOYSA-N 0.000 claims description 6
- DKKMZZPXYXGUQH-UHFFFAOYSA-N 4-(4-tert-butylphenyl)butanal Chemical compound CC(C)(C)C1=CC=C(CCCC=O)C=C1 DKKMZZPXYXGUQH-UHFFFAOYSA-N 0.000 claims description 5
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 claims description 4
- 238000012360 testing method Methods 0.000 claims description 4
- RCQMMCWUKHWWDZ-UHFFFAOYSA-N 4-(4-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=C(CCCC=O)C=C1 RCQMMCWUKHWWDZ-UHFFFAOYSA-N 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
- 229940064734 aminobenzoate Drugs 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 3
- 229920000768 polyamine Polymers 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 2
- 229920000333 poly(propyleneimine) Polymers 0.000 claims description 2
- 150000003139 primary aliphatic amines Chemical class 0.000 claims description 2
- 150000005619 secondary aliphatic amines Chemical class 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 claims description 2
- 229940074386 skatole Drugs 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- KNYUABFOOUWDDZ-UHFFFAOYSA-N methyl 2-aminobenzoate;2-(methylamino)benzoic acid Chemical compound CNC1=CC=CC=C1C(O)=O.COC(=O)C1=CC=CC=C1N KNYUABFOOUWDDZ-UHFFFAOYSA-N 0.000 claims 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 claims 1
- 229920001308 poly(aminoacid) Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 241000234269 Liliales Species 0.000 description 36
- 235000019645 odor Nutrition 0.000 description 33
- 239000002253 acid Substances 0.000 description 21
- 239000000126 substance Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 238000004140 cleaning Methods 0.000 description 11
- 239000002671 adjuvant Substances 0.000 description 10
- 239000007844 bleaching agent Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000000178 monomer Substances 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 239000003599 detergent Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical class OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229940088598 enzyme Drugs 0.000 description 8
- 239000004753 textile Substances 0.000 description 8
- 239000002386 air freshener Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000002537 cosmetic Substances 0.000 description 7
- ZDFKSZDMHJHQHS-UHFFFAOYSA-N 2-tert-butylbenzoic acid Chemical compound CC(C)(C)C1=CC=CC=C1C(O)=O ZDFKSZDMHJHQHS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000012190 activator Substances 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002736 nonionic surfactant Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 5
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 5
- 150000001447 alkali salts Chemical class 0.000 description 5
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- 239000000796 flavoring agent Substances 0.000 description 5
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- 238000009472 formulation Methods 0.000 description 5
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- 235000019198 oils Nutrition 0.000 description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
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- 239000002689 soil Substances 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- KHWTYGFHPHRQMP-UHFFFAOYSA-N (4-propan-2-ylcyclohexyl)methanol Chemical compound CC(C)C1CCC(CO)CC1 KHWTYGFHPHRQMP-UHFFFAOYSA-N 0.000 description 4
- NEHPIUGJDUWSRR-UHFFFAOYSA-N 1-(4-propan-2-ylcyclohexyl)ethanol Chemical compound CC(C)C1CCC(C(C)O)CC1 NEHPIUGJDUWSRR-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- OHRBQTOZYGEWCJ-UHFFFAOYSA-N 3-(3-propan-2-ylphenyl)butanal Chemical compound CC(C)C1=CC=CC(C(C)CC=O)=C1 OHRBQTOZYGEWCJ-UHFFFAOYSA-N 0.000 description 4
- RRNBIGHISSKZEB-UHFFFAOYSA-N 4-[2-methyl-4-(2-methylpropyl)phenyl]butanal Chemical compound C(C(C)C)C1=CC(=C(C=C1)CCCC=O)C RRNBIGHISSKZEB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
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- 229910052910 alkali metal silicate Inorganic materials 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
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- 229910017052 cobalt Inorganic materials 0.000 description 4
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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
-
- 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
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- 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
-
- 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
- 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
- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
-
- 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
- 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
-
- 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
- C11D3/502—Protected perfumes
- C11D3/507—Compounds releasing perfumes by thermal or chemical activation
Description
同じく、WO2009027957は、香料パレットからの、既知の香料成分の組み合わせの調合物に帰する解決策を提案する。
R5は、分岐または直鎖の、飽和または不飽和C2−C7アルキルまたはアルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物であって、
前記化合物は、4−(4−(tert−ブチル)フェニル)ブタナール、4−(4−イソプロピルフェニル)ブタナール、4−(4−イソブチルフェニル)ブタナール、4−(4−(tert−ブチル)フェニル)−3−メチルブタナールではない、前記化合物を提供する。
4−(4−イソブチルフェニル)ブタナールは、DE3933781から、医薬品のための中間体として知られている。公報は、この化合物の匂いおよび香料成分としてのその使用についてはサイレントである。
さらに、本発明の化合物は、特に、実質的で、長続きするミュゲの匂い特性を生成することができる。
Lilial(商標)を取り巻く規制問題は、それがラットおよびイヌにおいて、in vitroでグルコース合成および脂肪酸合成を阻害することが知られているtert−ブチル安息香酸(t−BBA)に酵素的に分解されるという事実から生じている(McCune et al, Arch Biochem Biophys (1982) 214 (1): 124-133)。
tert-ブチル安息香酸は、雄性ラットにおいて精巣への影響を引き起すことが知られている(Hunter et al. Food Cosmet. Toxicol. 1965, 3: 289-298; Cagen et al. J. Am. Coll. Toxicol. 1989, 8 (5): 1027-1038)。
したがって、本発明は、その別の側面において、香料成分としての上記に定義される化合物の使用を提供する。
本発明のさらに別の側面において、上記で定義された化合物を含む香料組成物を提供する。
本発明のさらに別の側面において、上記で定義された化合物を含むミュゲの匂い特性を保有する香料組成物を提供する。
本発明による香料組成物は、一種以上の本発明の化合物により完全に作製することができる。しかしながら、香料組成物はまた、一種以上の本発明の化合物に加えて、一種以上の追加の香料成分を含有してもよい。
好ましくは、香料組成物に採用されてもよい少なくとも一種の追加の香料成分は、3−(4−イソブチル−2−メチルフェニル)プロパナールのような、ミュゲの匂い特性を保有する。
R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキル、アルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物との反応生成物であることが好ましい。
R5は、H、Meまたは分岐または直鎖の、飽和または不飽和C2−C7アルキルまたはアルケニル、シクロアルキルまたはシクロアルケニル残基である;
好ましくは、式中、R1〜R4は、独立して、Hまたはメチルから選択され;およびR5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキル、アルケニル、シクロアルキルまたはシクロアルケニル残基であり、ここでR5はtert−ブチルまたはイソプロピル残基ではないことを条件とする;
の化合物を放出するのに好適である。
の化合物を放出するのに好適であることは、特に好ましい。
式
R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキルまたはアルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物により香りづけされる、ファインフレグランスまたはパーソナルケアもしくは家庭用ケア組成物などの消費者製品を提供する。
便器洗浄剤または化粧室洗浄剤、すなわち水洗便器および男性用小便器を洗浄するための製品であり、これらの製品は好ましくは、粉末、ブロック、錠剤または液体、好ましくはゲルの形態で供給される。界面活性剤などの他の典型的な成分に加えて、これらは一般的に、有機酸(例えば、クエン酸および/または乳酸)あるいは、水あかもしくは尿スケール(urine scale)を除去するための硫酸水素ナトリウム、アミド硫酸またはリン酸を含む;
特殊目的のための洗浄製品、例は、ガラスセラミック製のホブ用のもの、ならびにまたカーペット洗浄剤およびシミ抜き剤である。
塗料保存剤、塗料艶出し剤、塗料洗浄剤、洗浄保存剤、洗車用シャンプー、自動車洗浄およびワックス製品、トリム金属用艶出し剤、トリム金属用保護フィルム、プラスチック洗浄剤、タール除去剤、スクリーン洗浄剤、エンジン洗浄剤など。
(a)化粧用スキンケア製品、特に風呂用製品、肌洗浄およびクレンジング製品、スキンケア製品、アイメイク、リップケア製品、ネイルケア製品、デリケートゾーンケア製品、フットケア製品;
(b)特定の効果を有する化粧品、特に日焼け止め剤、日焼け製品、脱色素製品、デオドラント、制汗剤、脱毛剤、シェービング製品、香水;
(c)化粧用デンタルケア製品、特にデンタルおよびオーラルケア製品、トゥースケア製品、義歯用洗浄剤、義歯用接着剤;ならびに
(d)化粧用ヘアケア製品、特にヘアシャンプー、ヘアケア製品、ヘアセッティング製品、整髪製品およびヘアカラー製品。
例えば液体もしくは固体形態いずれかの、洗剤または繊維用仕上げ剤。
エアフレッシュナーおよび部屋用芳香剤は以下を含む:
好ましくは揮発性で通常心地よい香りの化合物を含有し、有利には非常に少量であっても、不快な臭いをマスクすることができる製品。居住エリアのエアフレッシュナーは、特に、天然および合成の精油、例えば松葉油、柑橘油、ユーカリ油、ラベンダー油などを、例えば50重量%までの量で含有する。エアロゾルとしては、それらは、かかる精油より少量の、一例として5重量%未満または2重量%未満を含有する傾向があるが、さらに、例えばアセトアルデヒド(特に、<0.5重量%)、イソプロピルアルコール(特に、<5重量%)、鉱油(特に、<5重量%)、および噴射剤などの化合物を含む。その他の提供形態としては、スティックおよびブロックが含まれる。それらは典型的には、精油を含むゲル濃縮物を用いて生産される。ホルムアルデヒド(保存用)およびクロロフィル(好ましくは<5重量%)、およびさらなる成分を添加することも可能である。しかし、エアフレッシュナーは居住空間に限定されず、自動車、食器棚、食器洗浄機、冷蔵庫または靴用に意図されてもよく、掃除機での使用も可能である。家庭においては(例えば食器棚において)、例えば、臭気改良剤に加えて殺菌剤も使用され、これらは、好ましくはリン酸カルシウム、タルク、ステアリン、および精油などの化合物を含有し、これらの製品は例えば小袋の形態をとる。
ビルダー物質、界面活性剤、酵素、好ましくは有機および/または無機の過酸素化合物、過酸素活性剤などの漂白剤、水混和性有機溶媒、金属イオン封鎖剤、電解質、pH調整剤、増粘剤、ならびに汚れ放出(soil release)活性物質、光学的増白剤、灰色化阻害剤、色移り防止剤、発泡調節剤、および染料などのさらなる補助剤。
界面活性剤は、本発明の消費者製品中に5重量%〜50重量%の量で使用することができる。
水溶性無機ビルダー材料には、アルカリケイ酸塩およびポリリン酸塩、例えば三リン酸ナトリウムが含まれる。結晶性または非晶質アルカリアルミノシリケート、例えば結晶性アルミノケイ酸ナトリウムもまた、水不溶性、水分散性無機ビルダー材料として、例えば50重量%までの量で、用いることができる。アルミノシリケートは典型的には、30μm未満の粒径を有する粒子を含む。
ビルダー物質は、本発明の消費者製品組成物に、60重量%までのレベルで含有させてもよい。
本発明をさらに例証するために役立つ一連の例が以下に続く。
この化合物を含む混合物は、NL7502553に記載されており、香料に有用な、心地よく鋭い、刺激性の匂いを有する。
材料は、例1に従って調製され、出発材料として3−(4−(イソブチル)フェニルプロパナールを用いた。
3−(4−イソブチル−2−メチルフェニル)プロパナールを例1に記載される手順に従って変換し、無色オイルとして4−(4−イソブチル−2−メチルフェニル)ブタナールを得た。
雄性ラット(Sprague Dawley; Lifetechnologies)からの凍結保存された肝細胞を解凍し、Cyropreserved Hepatocytes Recovery Medium(CHRM;Lifetechnologies)中で洗浄し、Williams E Medium(WEM;Lifetechnologies)中で懸濁した。Lilial(商標)または本発明の化合物(最終濃度:100μM)を細胞(1x106生細胞/ml)に添加し、懸濁液をデュプリケート(duplicate)にてシェーカー上において37℃で4時間までインキュベートした。テストステロンの代謝を陽性対照として観察した。試験化合物の減少および対応する安息香酸誘導体の形成を、メタノール中でのトリメチルシリルジアゾメタン(Sigma-Aldrich)による誘導体化後に形成されるメチルエステルのGC−MS分析により決定した。試験化合物は、ジアゾメタンと反応し、Lilial(商標)および式(I)の化合物の定量のために用いられるメチルケトンを生ずる。代謝を氷冷した1M HClで停止し、サンプルをtert−ブチルメチルエーテル(MTBE)で抽出し、GC−MSにより分析した。対照としてテストステロンを含有するインキュベーションも、氷冷した1M HClで停止し、遠心分離して細胞を分離し、濾過し、テストステロンの減少をLC−MSにより分析した。試験物質の減少および安息香酸代謝物の形成を定量するために、参照材料であるLilial(商標)および本発明の化合物、tert−ブチル安息香酸(Fluka)の較正曲線を肝細胞インキュベーション培地中に調製し、肝細胞サンプルと同様に分析した。
表1に表されるデータから、本発明の化合物のベンゼン環におけるオルト置換基および/またはブタナールであるアルデヒド官能基は、in vitroにおいて対応する安息香酸誘導体の形成に影響を与えることが明らかである。Lilial(商標)からのtert−ブチル安息香酸などの安息香酸誘導体は、雄性ラットにおける生殖毒性を引き起すので、雄性ラットにおけるこれらの毒性効果は、本発明の化合物のオルト置換基により防がれ、アルデヒド官能基がブタナールであることにより減少する。
ベータ酸化は、対応する安息香酸ではなく、4−置換フェニル酢酸誘導体をもたらすはずである。実際、安息香酸の形成は、Lilial(商標)と比較して、低いレベルまで減少する。
Claims (7)
- ミュゲの匂い特性を付与するための、香料成分としての、式I
R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキル、アルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物の使用。 - 式I
R 4 は、メチルであり;および
R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキルまたはアルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物であって、
前記化合物は、4−(4−(tert−ブチル)フェニル)ブタナール、4−(4−イソプロピルフェニル)ブタナール、4−(4−イソブチルフェニル)ブタナール、4−(4−(tert−ブチル)フェニル)−3−メチルブタナールではない、前記化合物。 - 式I
R 4 は、メチルであり;
および R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキル、アルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物を放出するのに好適である、プロ香料であって、
前記プロ香料は、前記化合物とアミン化合物の反応生成物であり、
前記アミン化合物は、芳香族アミン、一級または二級脂肪族アミン、エーテルアミン、エチレン−およびプロピレン−アミン、アミノ酸、ポリアミン、一級および二級ポリエーテルアミン、ポリエチレンイミン、ポリプロピレンイミン、ポリアミドアミン、ポリアミノ酸、ポリビニルアミン、ポリ(エチレングリコール)ビス(アミン)、アミノ置換ポリビニルアルコール;N−(3−アミノプロピル)イミダゾール、ニペコタミド、スカトールおよびメチルオルト−アミノベンゾアート(アントラニル酸メチル)、メチルメタ−アミノベンゾアート、メチルパラ−アミノベンゾアートならびにインドールからなる群から選択される、前記プロ香料。 - 式I
R 4 は、メチルであり;および
R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキル、アルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表される化合物を含む、
および/または請求項3に記載のプロ香料を含む、ミュゲの匂い特性を付与するための、香料組成物。 - アルデヒド官能基を有する置換基に対してアリール環上のオルト位が非置換である、および/またはアルデヒド官能基としてブタナールを有しない、任意のアリール置換プロパナール着臭剤を含まない、請求項4に記載の香料組成物。
- 1種以上の追加のフレグランス成分を含む、請求項4または5に記載の香料組成物。
- ミュゲの匂い特性をファインフレグランスまたは消費者製品に付与する方法であって、それに式I
R 4 は、メチルであり;および
R5は、分岐または直鎖の、飽和または不飽和C3〜C7アルキル、アルケニル、シクロアルキルまたはシクロアルケニル残基である;
により表されるアリール置換ブタナール化合物、
および/または請求項3に記載のプロ香料を添加するステップを含み、
前記化合物は、試験条件下で、それらが、3−(4−tert−ブチルフェニル)−2−メチルプロパナールよりもはるかに少ない程度にその安息香酸誘導体に分解するという基準において添加に好適であり、
前記化合物は、ラットから単離された肝細胞とインキュベートした場合に、その安息香酸誘導体への酵素的に媒介される分解を受ける、非常に減少した感受性を有する、前記方法。
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US11225655B2 (en) * | 2010-04-16 | 2022-01-18 | Nuevolution A/S | Bi-functional complexes and methods for making and using such complexes |
WO2013045301A1 (en) * | 2011-09-30 | 2013-04-04 | Firmenich Sa | Floral perfuming compositions as substitutes for lilial® |
DE102012201422A1 (de) * | 2012-02-01 | 2013-08-01 | Henkel Ag & Co. Kgaa | Kombination aus Aminoalkohol, Duftstoff und Kieselsäureester und ihre Verwendung als Duftstoffvorläufer |
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2014
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CO2017005642A2 (es) | 2017-08-31 |
JP2017534732A (ja) | 2017-11-24 |
WO2016074697A1 (en) | 2016-05-19 |
CN107074712B (zh) | 2021-06-29 |
BR112017007005B1 (pt) | 2021-11-09 |
RU2669029C1 (ru) | 2018-10-05 |
BR112017007005A2 (pt) | 2017-12-12 |
EP3218459A1 (en) | 2017-09-20 |
SG11201702973RA (en) | 2017-05-30 |
US20180230399A1 (en) | 2018-08-16 |
MX2017004871A (es) | 2017-07-04 |
CN107074712A (zh) | 2017-08-18 |
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