CN1860212A - 3-异丙基-1-甲基环戊基衍生物及其在芳香用品中的用途 - Google Patents
3-异丙基-1-甲基环戊基衍生物及其在芳香用品中的用途 Download PDFInfo
- Publication number
- CN1860212A CN1860212A CNA2004800281885A CN200480028188A CN1860212A CN 1860212 A CN1860212 A CN 1860212A CN A2004800281885 A CNA2004800281885 A CN A2004800281885A CN 200480028188 A CN200480028188 A CN 200480028188A CN 1860212 A CN1860212 A CN 1860212A
- Authority
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- China
- Prior art keywords
- compound
- methylcyclopentyl
- sec
- propyl
- perfume
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000003205 fragrance Substances 0.000 title claims abstract description 34
- -1 3-isopropyl-1-methylcyclopentyl Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 239000002304 perfume Substances 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000002537 cosmetic Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 235000013599 spices Nutrition 0.000 description 20
- LHXDLQBQYFFVNW-UHFFFAOYSA-N alpha-fenchone Natural products C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 18
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- LHXDLQBQYFFVNW-XCBNKYQSSA-N (+)-fenchone Chemical compound C1C[C@]2(C)C(=O)C(C)(C)[C@H]1C2 LHXDLQBQYFFVNW-XCBNKYQSSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229930006731 (1S,4R)-fenchone Natural products 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LHXDLQBQYFFVNW-OIBJUYFYSA-N (-)-Fenchone Chemical compound C1C[C@@]2(C)C(=O)C(C)(C)[C@@H]1C2 LHXDLQBQYFFVNW-OIBJUYFYSA-N 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 5
- 239000005792 Geraniol Substances 0.000 description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 229940113087 geraniol Drugs 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
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- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RNLHVODSMDJCBR-VURMDHGXSA-N (z)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C/C1CC=C(C)C1(C)C RNLHVODSMDJCBR-VURMDHGXSA-N 0.000 description 2
- 241001647745 Banksia Species 0.000 description 2
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- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- OEYQBKYISMRWQB-UHFFFAOYSA-N Santal Chemical compound C=1C(OC)=CC(O)=C(C2=O)C=1OC=C2C1=CC=C(O)C(O)=C1 OEYQBKYISMRWQB-UHFFFAOYSA-N 0.000 description 2
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- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- ORHSGDMSYGKJJY-SAIIYOCFSA-N (1'r,6's)-2,2,4',7',7'-pentamethylspiro[1,3-dioxane-5,5'-bicyclo[4.1.0]heptane] Chemical compound C12([C@H]3[C@H](C3(C)C)CCC2C)COC(C)(C)OC1 ORHSGDMSYGKJJY-SAIIYOCFSA-N 0.000 description 1
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- FINOAUDUYKVGDS-UHFFFAOYSA-N (2-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCCCC1C(C)(C)C FINOAUDUYKVGDS-UHFFFAOYSA-N 0.000 description 1
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 description 1
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 1
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- BVDMQAQCEBGIJR-UHFFFAOYSA-N 1-(2,2,6-trimethylcyclohexyl)hexan-3-ol Chemical compound CCCC(O)CCC1C(C)CCCC1(C)C BVDMQAQCEBGIJR-UHFFFAOYSA-N 0.000 description 1
- VPKMGDRERYMTJX-CMDGGOBGSA-N 1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-1-penten-3-one Chemical compound CCC(=O)\C=C\C1C(C)=CCCC1(C)C VPKMGDRERYMTJX-CMDGGOBGSA-N 0.000 description 1
- QUMXDOLUJCHOAY-UHFFFAOYSA-N 1-Phenylethyl acetate Chemical compound CC(=O)OC(C)C1=CC=CC=C1 QUMXDOLUJCHOAY-UHFFFAOYSA-N 0.000 description 1
- YQYKESUTYHZAGG-BZNIZROVSA-N 1-[(1r,2s)-1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone Chemical compound C1([C@H]([C@@](CC2)(C)C(C)=O)C)=C2CCCC1(C)C YQYKESUTYHZAGG-BZNIZROVSA-N 0.000 description 1
- ZALVGSSYVAPZDA-UHFFFAOYSA-N 1-acetyloxynonyl acetate Chemical group CCCCCCCCC(OC(C)=O)OC(C)=O ZALVGSSYVAPZDA-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- FNEWGEWRECZWQM-UHFFFAOYSA-N 2-Ethoxy-4-(methoxymethyl)phenol Chemical compound CCOC1=CC(COC)=CC=C1O FNEWGEWRECZWQM-UHFFFAOYSA-N 0.000 description 1
- GVONPEQEUQYVNH-SNAWJCMRSA-N 2-Methyl-3-(2-pentenyl)-2-cyclopenten-1-one Chemical compound CC\C=C\CC1=C(C)C(=O)CC1 GVONPEQEUQYVNH-SNAWJCMRSA-N 0.000 description 1
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- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 1
- NGYMOTOXXHCHOC-UHFFFAOYSA-N 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol Chemical compound CC(O)C(C)CCC1CC=C(C)C1(C)C NGYMOTOXXHCHOC-UHFFFAOYSA-N 0.000 description 1
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 description 1
- AUBLFWWZTFFBNU-UHFFFAOYSA-N 6-butan-2-ylquinoline Chemical compound N1=CC=CC2=CC(C(C)CC)=CC=C21 AUBLFWWZTFFBNU-UHFFFAOYSA-N 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001090476 Castoreum Species 0.000 description 1
- 241000468081 Citrus bergamia Species 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
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- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- XRHCAGNSDHCHFJ-UHFFFAOYSA-N Ethylene brassylate Chemical compound O=C1CCCCCCCCCCCC(=O)OCCO1 XRHCAGNSDHCHFJ-UHFFFAOYSA-N 0.000 description 1
- 238000006996 Haller-Bauer cleavage reaction Methods 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 239000006071 cream Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 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
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940093468 ethylene brassylate Drugs 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 230000014860 sensory perception of taste Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
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- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
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- 239000003981 vehicle Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/297—Saturated compounds containing keto groups bound to rings to a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/13—Monohydroxylic alcohols containing saturated rings
- C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
- C07C31/135—Monohydroxylic alcohols containing saturated rings monocyclic with a five or six-membered rings; Naphthenic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- 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
- 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
- Chemical & Material Sciences (AREA)
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Abstract
本发明涉及式(1a)和(1b)的-3-异丙基-1-甲基环戊基衍生物,其中R1、R2和R3在权利要求中有所定义,本发明还涉及它们在芳香用品中的用途。
Description
本发明涉及3-异丙基-1-甲基环戊基衍生物,即(3-异丙基-1-甲基环戊基)乙醇、(3-异丙基-1-甲基环戊基)乙酮和(3-异丙基-1-甲基环戊基)甲醇,以及它们作为芳香剂的用途。本发明还涉及它们的生产方法及含有它们的芳香组合物。
在芳香剂领域中,总是需求可增强或改进气味味感或者能够赋予新的香气的化合物。
目前发现,某些3-异丙基-1-甲基环戊基衍生物具有广受欢迎的花香、水果香和木香香气,并且它们制备起来相对简单和容易,其制备用的起始原料是天然存在的(1S)-(+)-和(1R)-(-)-葑酮。
因此,本发明的一个方面涉及下式1a的化合物和其对映异构体即(1R,3S)-对映异构体作为芳香剂的用途:
其中R1是氢或甲基;
R2是氢;并且
R3是羟基;或者
R2和R3与跟它们相连的碳原子一起形成羰基。
据发现,式1a的某些化合物的气味阈值平均两倍低于对应的对映异构体。因此,富含式1a的(1R,3S)对映异构体的下式I的化合物是优选的。
本文中使用术语“富含”是指对于所选对映异构体而言对映异构体纯度大于1∶1的化合物。具有约1∶3或更大纯度,例如约1∶4的化合物是优选的。特别优选的是具有1∶9或更大对映异构体纯度的化合物,如5∶95或1∶99。
特别优选的本发明的化合物是[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇、1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙酮和1~[(1R,3S)-3-异丙基-1-甲基环戊基]乙醇。
本发明的化合物可以单独使用或与基本物料联合使用。本文中,“基本物料”包括所有已知的香气分子,选自目前可获得的广泛的天然产品和合成分子,例如精油类,醇类,醛类和酮类,醚类和缩醛类,酯类和内酯类,大环和杂环类,和/或与一种或多种常规在芳香组合物中与增香剂结合使用的成分或赋形剂例如载体物质掺混使用,及其它本领域常用的辅剂。
下面所列的物质包括可以与本发明化合物结合使用的已知香气分子的实例:
-醚制油和萃取物,例如树苔净油,罗勒油,海狸香油,广木香根油,桃金娘油,橡苔净油,老鹳草油,茉莉净油,广藿香油,玫瑰油,檀香油,苦艾油,熏衣草油或衣兰油;
-醇类,例如香茅醇,EbanolTM,丁子香酚,金合欢醇,香叶醇,Super MuguetTM,芳樟醇,苯乙醇,SandaloreTM,萜品醇或TimberolTM;
-醛类和酮类,例如α-戊基肉桂醛,GeorgywoodTM,羟基香茅醛,Iso E Super,Isoraldeine,Hedione,麦芽酚,甲基柏木基酮,甲基紫罗酮或香草醛;
-醚和缩醛类,例如AmbroxTM,香叶基甲基醚,氧化玫瑰或SpirambreneTM;
-酯类和内酯类,例如乙酸苄酯,乙酸柏木酯,γ-癸内酯,Helvetolide,γ-十一内酯或乙酸岩兰草酯。
-大环化合物类,例如黄葵内酯,巴西酸亚乙酯或Exaltolide。
-杂环化合物类,例如异丁基喹啉。
本发明的化合物可以在广泛的芳香用品中使用,例如在精细香料和功能性香料的任何领域中,例如香水、家用产品、洗衣产品、身体护理用产品和美容品。化合物可以是以宽泛变化范围的量使用,这取决于具体的应用和其它增香成分的性质和数量。使用比例一般是用品的约0.001至约20wt%。在一个实施方案中,本发明的化合物可以在织物柔软剂中以约0.001-0.05wt%的量使用。在另一个实施方案中,本发明的化合物可以在精细香料中以约0.1-20wt%、更优选约0.1-5wt%的量使用。然而,这些数值仅仅是以实例的方式给出的,因为富有经验的香料调配者使用较低或较高的浓度也可以达到效果或可能产生新的谐香。
本发明的化合物可以用于芳香用品,简单地通过将芳香组合物直接与芳香用品混合,或者,可以将它们在在先的步骤中用截留材料截留,所述截留材料例如聚合物、胶囊、微胶囊和毫微胶囊、脂质体、成膜剂、吸收剂如碳或沸石、环状低聚糖及其混合物,或者可以将它们与基底化学键合,使得当施加外部刺激,如光、酶等时,基底能够释放芳香分子,然后与用品混合。
因此,本发明附加地提供一种制备芳香用品的方法,包括掺加富含其对映异构体之一的式I化合物作为芳香成分,所述掺加通过将化合物直接掺混至用品中,或者通过掺混含有富含其对映异构体之一的式I化合物的芳香组合物,然后使用常规的技术和方法将其混合至芳香用品中。
本文中,“芳香用品”是指任何产品,如精细香料,例如香水和化妆水(Eau de Toilette);家用产品,例如洗碗机用的洗涤剂、表面清洁剂;洗衣产品,例如柔软剂、漂白剂、去污剂;身体护理用产品,例如洗发液、浴用凝胶;及美容品,例如除臭剂、雪花膏,包括增香剂。所列的这些产品是以举例说明方式给出的并且不以任何方式限制本发明。
相比本领域的具有花香香气特征的大部分香气分子,例如羟基香茅醛、香叶醇、芳樟醇和4-(4-羟基-4-甲基戊基)环己-3-烯-1-甲醛,本发明其中R3是羟基的式1a化合物无论在碱性条件下还是在酸性条件下都是格外稳定的,因此使得它们特别适用于很多各种类型的芳香用品。
式1a化合物及其对映异构体的制备可以是例如通过(1R)-(-)-葑酮/(1S)-(+)-葑酮(1,3,3-三甲基-2-降冰片烷酮)的Haller-Bauer重排,然后在碱性条件下,例如在NaOH或KOH的碱的存在下水解成3-异丙基-1-甲基环戊烷羧酸。然后,将所得酸与甲基锂反应,得到其中R2和R3与跟它们相连的碳原子一起形成羰基的式I化合物。为得到本发明的其它化合物,可以通过用例如NaBH4还原,将所得的酮转变成仲醇。
(3-异丙基-1-甲基环戊基)甲醇可以通过将3-异丙基-1-甲基环戊烷羧酸(A)(其通过葑酮的重排制得)在LAH的存在下还原成相应的醇来制备,如下述反应路径所示:
反应路径1:
光学纯的式1a和1b化合物及富含对映异构体之一的式I化合物(即,式1a或1b的化合物)的对映异构体混合物,可以由光学纯的葑酮或由富含(1R)-(-)-葑酮或(1S)-(+)-葑酮的对映异构体混合物作为起始原料来合成。
下面将参考以下非限定性实施例来描述本发明。
以下实施例1-6中所述所有最终产品均为无色油。它们由(1R)-(-)-和(1S)-(+)-葑酮起始来获得,其中所述(1R)-(-)-和(1S)-(+)-葑酮分别含有8%和2%的另一种对映异构体。所汇报的NMR数据在以下的共同条件下测定:1H于400下并且13C于100MHz下;在CDCl3中;化学位移(δ)以TMS的低磁场ppm计;偶合常数J以Hz计。
实施例1:[(1R,3S)-3一异丙基-1-甲基环戊基]甲醇
将(1R,3S)-3-异丙基-1-甲基环戊烷羧酸(70.0g,0.41mol,其由(1R)-(-)-葑酮获得(V.Braun,J.;Jacob,A.Chem.Ber.1933,66,1461))于二***(100ml)中的溶液,在氮气条件下缓慢添加至氢化铝锂(13.3g,0.35mol)于相同溶剂(500ml)中的悬浮液中。加热回流3h之后,将反应混合物冷却至10℃,仔细添加2N NaOH溶液(70ml)并且继续搅拌0.5h。滤掉白色固体,将滤液用盐水洗涤(2×500ml),干燥(MgSO4)并且真空浓缩。使用10cm Vigreux柱(0.9-1.1毫巴,96-98℃),将粗产物(79.0g)蒸馏纯化,得到[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇(57.0g,90%产率)。
1H-NMR:δ0.87(d,J=6.7,3H),0.88(d,J=6.7,3H),1.01(s,3H),1.08(dd,J=12.3,11.0,1H),1.16-1.38(m,3H),1.48(ddd,J=12.4,6.9,0.8,1H),1.53-1.72(m,3H),1.74-1.87(m,1H),3.35(d,JAB=10.4,1H),3.39(d,JAB=10.4,1H).13C-NMR:δ21.5(2q),25.0(q),30.4(t),33.8(d),35.6(t),41.5(t)43.8(s),46.9(d),72.1(t).[α]D 22-12.0(c1.0,EtOH).
气味描述:花香,青香,茉莉香,铃兰香,清新香气,新鲜。
实施例2:[(1S,3R)-3-异丙基-1-甲基环戊基]甲醇
按照实施例1的实验过程,由(1S)-(+)-葑酮作为起始原料制备。
[α]D 22+13.5(c1.0,EtOH)。
气味描述:花香,水果香,青香,玫瑰香,橙皮香(圆柚香)。
实施例3:1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙酮
0℃下,用25分钟的时间,将甲基锂于二***(200ml,0.32mol)中的1.6M溶液滴加至(1R,3S)-3-异丙基-1-甲基环戊烷羧酸(25.5g,0.15mol)于THF(250ml)中的溶液中。在0℃下搅拌3h之后,边冷却边加入氯三甲基硅烷(151ml,1.2mol)并且允许反应混合物温热至室温,倾倒在冰冷却的水中(200ml),搅拌0.5h并且用MTBE萃取(2×250ml)。将合并的有机相用水(200ml)、2M NaOH(150ml)和盐水(3×200ml)洗涤,干燥(MgSO4)并且真空浓缩,得到粗产物1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙酮(27.6g),将其的样品(1.5g)通过球对球蒸馏来纯化(0.93g,68%产率)。
1H-NMR:δ0.89(2d,J=6.6,6H),1.19(s,3H),1.24(dq,J=12.4,9.1,1H),1.34-1.43(m,2H),1.56-1.77(m,3H),1.81-1.90(m,1H),2.09(ddd,J=13.1,9.1,4.0,1H),2.15(s,3H).13C-NMR:δ21.3(q),21.4(q),25.0(q),25.3(q),30.2(t),33.3(d),35.6(t),41.0(t),46.6(d),55.3(s),213.0(s).[α]D 22-1.0(c 1.1,EtOH).
气味描述:土香/苔香,青香,木香。
实施例4:1-[(1S,3R)-3-异丙基-1-甲基环戊基]乙酮
按照实施例3的实验过程,由(1S)-(+)-葑酮作为起始原料制备。
[α]D 22+1.0(c 1.1,EtOH)。
气味描述:花香,乡土味,水果香,青香。
实施例5:1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙醇
将实施例3的1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙酮(3.0g,18mmol)于乙醇(8ml)中的溶液添加至硼氢化钠(0.42g,10.7mmol)于相同溶剂(17ml)中的冷(冰浴)溶液中。在室温下搅拌1.5h之后,将反应混合物倾倒在冰冷却的2M HCl(100ml)上并且用MTBE萃取(2×100ml)。将合并的有机相用盐水洗涤(2×50ml),干燥(MgSO4)并且真空浓缩。将粗产物(2.8g)通过球对球蒸馏来纯化(2.34g,77%产率,非对映异构体比~1∶1)。
1H-NMR:δ0.87(d,J=6.6,3H),0.875(d,J=6.6,3H),0.88(2d,J=6.6,6H),0.92(s,3H),0.93(s,3H),1.05(t,J=11.7,1H),1.12(d,J=6.4,3H),1.125(d,J=6.4,3H),1.14(t,J=11.8,1H),1.17-1.74(m,12H),1.47(2s,2H),1.78-1.88(m,2H),3.53(q,J=6.3,1H),3.55(q,J=6.3,1H).13C-NMR:δ18.5(2q),21.3(2q),21.4(3q),21.5(q),29.8(t),30.0(t),33.7(2d),35.8(t),35.9(t),41.9(2t),46.3(2d),46.8(s),46.9(s),75.4(d),75.7(d).[α]D 22-7.0(c 1.0,EtOH).
气味描述:花香,土香/苔香,微微的松油醇味/土香。
实施例6:1-[(1S,3R)-3-异丙基-1-甲基环戊基]乙醇
按照实施例5的实验过程,由(1S)-(+)-葑酮作为起始原料制备。
[α]D 22+8.0(c 1.0,EtOH)。
气味描述:橙皮香/柑橘香,水果香,青香,清新香气(圆柚香,大黄香)。
实施例7:女性用高级香水
成分* 重量份
香茅醇 50
仙客来醛 15
丙二酸二乙酯 5
双丙二醇(DPG) 149
花青醛(Florhydral) 12
Gardenol 10
香叶醇 50
二氢茉莉酮酸甲酯(Hedione) 25
α-己基肉桂醛 200
羟基香茅醛 35
异环柠檬醛(1%于DPG中) 15
异茉莉酮 2
乙酸苄酯 40
茉莉酯 20
柠檬油 10
新铃兰醛 25
芳樟醇 65
乙酸芳樟酯 50
Methyldiantilis 2
巴拉圭香柠檬油 5
苯乙醇 65
Silvial 100
[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇 50
总计1000
*化学名称参见Flavor and Fragrance Materials-2003,AlluredPublishing Corp.Carol Stream III.,U.S.A.。
存在5%的[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇给该配方带来奶油香、铃兰香特征。
实施例8:肥皂用花香组会物
成分* 重量份
Agrumex 100
二苯甲酮 60
乙酸苄酯 55
香柠檬基料 80
乙酸4-叔丁基环己酯 150
苯醚 20
双丙二醇(DPG) 78
Ebanol 20
羟基香茅醛 200
茉莉基料 80
苯乙酸甲酯 2
Nerol 20
苯丙醇 40
玫瑰基料 100
玫瑰醇 65
Sandela 30
Silvial 100
[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇 50
总计1250
*化学名称参见Flavor and Fragrance Materials-2003,AlluredPublishing Corp.Carol Stream III.,U.S.A.。
[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇使得这种铃兰香的芳香柔和且丰满。
Claims (3)
1、下式1a化合物及其对映异构体作为芳香剂的用途:
其中R1是氢或甲基;
R2是氢;和
R3是羟基;或者
R2和R3与跟它们相连的碳原子一起形成羰基。
2、权利要求1的化合物作为芳香剂的用途,其中所述化合物选自:[(1R,3S)-3-异丙基-1-甲基环戊基]甲醇,[(1S,3R)-3-异丙基-1-甲基环戊基]甲醇,1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙酮,1-[(1S,3R)-3-异丙基-1-甲基环戊基]乙酮,1-[(1R,3S)-3-异丙基-1-甲基环戊基]乙醇和1-[(1S,3R)-3-异丙基-1-甲基环戊基]乙醇。
3、下式I的化合物作为芳香剂的用途:
其中所述式I化合物富含具有下式1a的对映异构体:
其中R1、R2和R3具有如权利要求1所给出的相同含义。
下式I的化合物作为芳香剂的用途:
其中所述式I化合物富含具有下式1b的对映异构体:
其中R1、R2和R3具有如权利要求1所给出的相同含义。
前述权利要求之一所定义的化合物在芳香用品中的用途。
含有前述权利要求1-4任一项所定义的化合物的芳香用品。
权利要求6的芳香用品,其中芳香用品是香水、家用产品、洗衣产品、身体护理用产品或美容产品。
一种芳香用品的生产方法,包括掺入权利要求1、2、3和4中所定义的式Ia化合物或其对映异构体的步骤。
下式1a的化合物:
其中
R1是氢和甲基;
R2是氢;和
R3是羟基;或者
R2和R3与跟它们相连的碳原子一起形成羰基。
下式1b的化合物:
其中
R1是氢和甲基;
R2是氢;和
R3是羟基;或者
R2和R3与跟它们相连的碳原子一起形成羰基。
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WO2005030915A1 (en) * | 2003-09-30 | 2005-04-07 | Givaudan Sa | 3-isopropyl-1-methylcyclopentyl derivatives and their use in fragrance applications |
MX343109B (es) * | 2004-04-09 | 2016-10-25 | Wyeth * | Atenuacion sinergistica del virus de la estomatitis vesicular, vectores de los mismos y composiciones inmunogenicas de los mismos. |
JP4102412B2 (ja) * | 2006-06-26 | 2008-06-18 | 花王株式会社 | アルコール系化合物 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2946823A (en) * | 1958-04-28 | 1960-07-26 | Givaudan Corp | Process for making methyl-(4-isopropyl-1-cyclopentyl)-ketone and intermediate obtained thereby |
US3609193A (en) * | 1969-04-30 | 1971-09-28 | Reynolds Tobacco Co R | Process of coupling aldehydes and ketones |
US4234463A (en) * | 1978-10-20 | 1980-11-18 | International Flavors & Fragrances Inc. | Cyclohexene methanol derivatives in perfume |
US4533492A (en) * | 1983-04-07 | 1985-08-06 | International Flavors & Fragrances Inc. | Acetyl dimethylbutylcyclohexene and organoleptic uses thereof |
JPH0791554B2 (ja) * | 1989-06-21 | 1995-10-04 | 高砂香料工業株式会社 | 香料組成物 |
WO2005030915A1 (en) * | 2003-09-30 | 2005-04-07 | Givaudan Sa | 3-isopropyl-1-methylcyclopentyl derivatives and their use in fragrance applications |
-
2003
- 2003-09-30 GB GBGB0322750.1A patent/GB0322750D0/en not_active Ceased
-
2004
- 2004-09-29 EP EP04761944A patent/EP1668102B1/en not_active Not-in-force
- 2004-09-29 MX MXPA06003263A patent/MXPA06003263A/es active IP Right Grant
- 2004-09-29 WO PCT/CH2004/000604 patent/WO2005030914A1/en active IP Right Grant
- 2004-09-29 BR BRPI0414884-3A patent/BRPI0414884A/pt not_active IP Right Cessation
- 2004-09-29 AT AT04761944T patent/ATE377066T1/de not_active IP Right Cessation
- 2004-09-29 DE DE602004009814T patent/DE602004009814T2/de active Active
- 2004-09-29 CN CNB2004800281885A patent/CN100552010C/zh not_active Expired - Fee Related
- 2004-09-29 US US10/572,804 patent/US20070054836A1/en not_active Abandoned
- 2004-09-29 JP JP2006529545A patent/JP2007507434A/ja active Pending
- 2004-09-29 ES ES04761944T patent/ES2295900T3/es active Active
Also Published As
Publication number | Publication date |
---|---|
BRPI0414884A (pt) | 2006-12-12 |
DE602004009814D1 (de) | 2007-12-13 |
EP1668102A1 (en) | 2006-06-14 |
ES2295900T3 (es) | 2008-04-16 |
ATE377066T1 (de) | 2007-11-15 |
DE602004009814T2 (de) | 2008-09-04 |
US20070054836A1 (en) | 2007-03-08 |
JP2007507434A (ja) | 2007-03-29 |
GB0322750D0 (en) | 2003-10-29 |
EP1668102B1 (en) | 2007-10-31 |
WO2005030914A1 (en) | 2005-04-07 |
MXPA06003263A (es) | 2006-06-08 |
CN100552010C (zh) | 2009-10-21 |
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