CN100371307C - 4-甲基癸-4-烯-3-醇和芳香组合物 - Google Patents
4-甲基癸-4-烯-3-醇和芳香组合物 Download PDFInfo
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- CN100371307C CN100371307C CNB2004800261805A CN200480026180A CN100371307C CN 100371307 C CN100371307 C CN 100371307C CN B2004800261805 A CNB2004800261805 A CN B2004800261805A CN 200480026180 A CN200480026180 A CN 200480026180A CN 100371307 C CN100371307 C CN 100371307C
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- 239000004615 ingredient Substances 0.000 claims abstract description 3
- 238000004519 manufacturing process Methods 0.000 claims 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
- 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
-
- 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
- C07C33/03—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond in beta-position, e.g. allyl alcohol, methallyl alcohol
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- 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
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及4-甲基癸-4-烯-3-醇及其作为芳香成分的用途。
Description
本发明涉及4-甲基癸-4-烯-3-醇，本发明还涉及它的生产方法及含有它的芳香组合物。
在芳香剂工业中，总是需求能够增强或改进气味香调或者能够赋予新的香气的化合物。
由于回归古典的自然香韵是大势所趋，因此能够增强花香、水果香、青香香气的化合物是人们特别感兴趣的。意想不到地，我们发现了4-甲基癸-4-烯-3-醇能够满足这种要求。
由此，本发明的一个方面涉及4-甲基癸-4-烯-3-醇作为芳香剂的用途。
4-甲基癸-4-烯-3-醇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掺混使用，所述成分或赋形剂例如载体物质，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应用中使用，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、酶等等时，基底能够释放4-甲基癸-4-烯-3-醇，然后与用品混合。
因此，本发明还提供一种制造芳香用品的方法，包括掺加4-甲基癸-4-烯-3-醇作为芳香成分，通过将其直接掺混至用品中，或者通过掺混含有4-甲基癸-4-烯-3-醇的芳香组合物，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、粉底霜，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。
4-甲基癸-4-烯-3-醇可以按照实施例1所述的过程，通过例如将2-甲基辛-2-烯醛在乙基溴化镁的存在下烷基化来制备。
实施例1：4-甲基癸-4-烯-3-醇
于氮气环境下，将2-甲基辛-2-烯醛(2.7g，19mmol)于二乙醚(10ml)中的溶液缓慢添加至乙基溴化镁于二乙醚(7.0ml，21mmol)中的3M溶液中，其中在0-5℃下，在氮气环境下将所述乙基溴化镁的溶液用相同溶剂(10ml)稀释。将反应混合物在室温下搅拌24h，倾在冰冷却的2N HCl溶液并且用MTBE(100ml)萃取。将合并的有机层用盐水洗涤(2×100ml)，干燥(MgSO4)并且真空浓缩。将粗产物(1.8g，55％产率)通过闪蒸色谱(硅胶；正己烷/MTBE 4∶1)纯化，得到嗅觉上纯的样品。B.p.99℃/10毫巴。
1H-NMR(400MHz，in CDCl3)：δ0.82(t，J＝7.5，3H)，0.89(t，J＝7.0，3H)，1.22-1.42(m，6H)，1.53(m，2H)，1.56(s，3H)，2.01(q，J＝7.2，2H)，2.73(s，1H)，3.85(t，J＝6.8，1H)，5.34(t，J＝7.2，1H).13C NMR(100MHz，in CDCl3)：δ9.9(q)，10.7(q)，13.8(q)，22.4(t)，27.3(t)，27.4(t)，29.1(t)，31.4(t)，79.2(d)，126.6(d)，136.7(s).IR(neat)：λmax 3356，2959，2929，2873，2858，1458，1335，1099，1002，963cm-1.
气味描述：花香，玫瑰香，脂肪香，清新香气，金属香，青香。
实施例2：肥皂用芳香组合物
成分 重量份
Agrumex 15
乙酸4-叔丁基环己酯 50
卡必醇 302
对-甲酚 12
大马烯酮(1％于DPG中) 15
δ二氢大马酮(1％于DPG中) 20
乙基麦芽酚 2
苹果酯(Fructone) 10
天芥菜精 10
羟基香茅醛 20
4-(对-羟基苯基)-2-丁酮 5
β紫罗酮 300
Iso E Super 50
新铃兰醛 20
芳樟醇 40
甲基紫罗酮 500
壬烯酸甲酯(Neofolione) 10
壬二烯醛(10％于TEC中) 2
檀香醇(Sandela) 50
乙酸萜烯酯 20
对-甲苯醛(p-Tolulaldehyde) 2
香草醛 5
乙酸三环癸烯酯(Verdyl acetate) 20
4-甲基癸-4-烯-3-醇 20
1500
4-甲基癸-4-烯-3-醇使得该组合物闻起来更圆润、丰满、更多奶油香和水果香，赋予其青香的天然感觉。
Claims (4)
1.4-甲基癸-4-烯-3-醇。
2.4-甲基癸-4-烯-3-醇作为芳香成分的用途。
3.含有4-甲基癸-4-烯-3-醇的芳香组合物。
4.一种制造芳香用品的方法，包括掺加4-甲基癸-4-烯-3-醇的步骤。
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| GB0321313.9 | 2003-09-12 | ||
| GBGB0321313.9A GB0321313D0 (en) | 2003-09-12 | 2003-09-12 | Organic compound |
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| EP (1) | EP1663925A1 (zh) |
| JP (1) | JP2007505049A (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0045453A1 (de) * | 1980-07-31 | 1982-02-10 | L. GIVAUDAN & CIE Société Anonyme | Neue Alkenole (I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe sowie Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) |
| EP0086945A1 (de) * | 1982-01-27 | 1983-08-31 | L. GIVAUDAN & CIE Société Anonyme | Neue Alkenole(I), Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe und Riechstoffkompositionen mit einem Gehalt an (I) |
| US5116813A (en) * | 1989-03-15 | 1992-05-26 | Kao Corporation | Perfume composition |
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| FR2119580A5 (zh) * | 1970-12-22 | 1972-08-04 | Firmenich & Cie | |
| FR2318130A1 (fr) * | 1975-07-18 | 1977-02-11 | Rhone Poulenc Ind | Procede de preparation d'aldehydes a, b-ethyleniques |
| DE3360094D1 (en) * | 1982-01-27 | 1985-05-15 | Givaudan & Cie Sa | Unsaturated ethers, process for their preparation, use of these ethers as fragrances, and flavouring compositions containing these ethers |
| US6126953A (en) * | 1996-08-19 | 2000-10-03 | The Procter & Gamble Company | Fragrance delivery systems for personal care articles |
| US6180121B1 (en) * | 1998-03-05 | 2001-01-30 | Colgate-Palmolive Company | Fragrance enhancing compositions for cosmetic products |
| DE10152992A1 (de) * | 2001-10-26 | 2003-05-08 | Haarmann & Reimer Gmbh | Gemische zur Verwendung als Moschusriechstoff |
| DE10333379A1 (de) * | 2003-07-23 | 2005-02-10 | Symrise Gmbh & Co. Kg | Acetale, ihre Verwendung als Reichstoffe und Verfahren zu ihrer Herstellung |
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2003
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- 2004-09-10 WO PCT/CH2004/000570 patent/WO2005026092A1/en active Application Filing
- 2004-09-10 BR BRPI0414248-9A patent/BRPI0414248A/pt not_active IP Right Cessation
- 2004-09-10 MX MXPA06002669A patent/MXPA06002669A/es unknown
- 2004-09-10 CN CNB2004800261805A patent/CN100371307C/zh not_active Expired - Fee Related
- 2004-09-10 JP JP2006525601A patent/JP2007505049A/ja not_active Ceased
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0045453A1 (de) * | 1980-07-31 | 1982-02-10 | L. GIVAUDAN & CIE Société Anonyme | Neue Alkenole (I) und Verfahren zu deren Herstellung, Verwendung von (I) als Riech- und/oder Geschmackstoffe sowie Riech- und/oder Geschmackstoffkompositionen mit einem Gehalt an (I) |
| EP0086945A1 (de) * | 1982-01-27 | 1983-08-31 | L. GIVAUDAN & CIE Société Anonyme | Neue Alkenole(I), Verfahren zu deren Herstellung, Verwendung von (I) als Riechstoffe und Riechstoffkompositionen mit einem Gehalt an (I) |
| US5116813A (en) * | 1989-03-15 | 1992-05-26 | Kao Corporation | Perfume composition |
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| EP1663925A1 (en) | 2006-06-07 |
| WO2005026092A1 (en) | 2005-03-24 |
| CN1849286A (zh) | 2006-10-18 |
| GB0321313D0 (en) | 2003-10-15 |
| BRPI0414248A (pt) | 2006-11-21 |
| US20070027062A1 (en) | 2007-02-01 |
| MXPA06002669A (es) | 2006-06-06 |
| JP2007505049A (ja) | 2007-03-08 |
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