CN102093174B - [(4e,4z)-5-甲氧基-3-甲基-4-戊烯基]-苯及其在香料组合物中的应用 - Google Patents
[(4e,4z)-5-甲氧基-3-甲基-4-戊烯基]-苯及其在香料组合物中的应用 Download PDFInfo
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Abstract
本发明涉及新型化合物[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯以及通过加入嗅觉上可接受量的所述新型化合物来改善、提升或改变芳香制剂的方法。
Description
技术领域
本发明涉及新型化学实体,以及将该新型化学实体掺入芳香材料中和作为芳香材料的应用。
背景技术
香料工业一直需要提供新型化学物质来供给香料商和其它相关人员,以赋予香料、古龙水(colognes)和个人护理产品新的香味。本领域技术人员明白,化学结构中的小差异将如何导致分子气味、性质和特征中出乎意料且显著的差异。这些变异使得香料商和其他人员采用新的化合物来产生新香味。例如,取代基稍有不同的苯化合物具有完全不同的气味特征[Ishikawa,等,International Journal of Quantum Chemistry 79:101-108(2000)]。对于叔丁基环己烷,据称气味取决于化合物的构型,因此采用相同构型的类似物具有类似的气味。因此,许多反式化合物显示共有明显的尿-汗-型气味,而相应的顺式化合物无臭或至多具有弱的不确定的花香或木香。然而,一些其他的反式和顺式-叔丁基环己烷显示具有相反的感觉活性[Ohloff,等,HelveticaChimica Acta 66,Fasc.5:1343-1354(1983)]。因此,本领域技术人员难以预测给定的结构在感觉活性方面是否有效。鉴定理想的芳香化学物质仍然存在困难。
发明内容
本发明提供了新型化合物以及该新型化合物在提升、改善或改变香料、古龙水、花露水(toilet waters)、个人产品等产品的香味中意想不到的有益使用。
更具体说,本发明涉及具有意想不到的强烈而独特的芳香效果的新型[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯化合物以及通过加入嗅觉上可接受量 的下式I所代表的[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯来改善、提升或改变芳香制剂的方法:
式I。
通过阅读下面的说明书将明白本发明的这些和其它实施方式。
具体实施方式
本发明的化合物可由3-甲基-5-苯基-戊醛(从探索国际(Quest International)购得)。反应步骤可由以下所示的方案表述:
本领域技术人员将理解,本发明化合物可具有许多手性中心,从而提供本发明化合物的异构体。在本文中,所述化合物包括:这些化合物的同分异构混合物,以及可采用本领域技术人员已知的技术进行分离的那些异构体。合适的分离技术包括色谱法如高效液相色谱(称为HPLC),具体是凝胶色谱法和固相显微提取法(称为SPME)。
意外地发现本发明的化合物具有强烈而意想不到的芳香效果,例如独特的香茅、中性葡萄柚(pamplemousse)样和大黄(rhubarb)样气味。
本发明的化合物可以广泛地应用于目前的香料产品,包括香水和古龙水的制备,为个人护理产品、织物护理产品、空气清新剂以及化妆用配制品 加香,所述个人护理产品包括例如肥皂、淋浴凝胶和护发产品。这些化合物还可用于对清洗剂加香,所述清洗剂包括但不限于去污剂、洗碗物质、刷洗组合物、窗户清洁剂等。在这些制剂中,本发明的化合物可单独使用或与其它加香组合物、溶剂、辅助试剂等联用。可采用的其它成分的性质和种类是本领域技术人员已知的。
本发明中可采用许多香味类型,唯一的限制是要与采用的其它成分相容。合适的香味包括但不限于:水果,例如杏仁、苹果、樱桃、葡萄、梨、菠萝、橙、草莓、覆盆子味道;麝香,花香,例如熏衣草样、玫瑰样、鸢尾样、康乃馨样味道。其它令人愉快的气味包括:草药和来自松树、云杉的森林气味以及其它森林气味。香味也可来自各种油,例如精油,或来自植物原料如薄荷、留兰香等。合适的香味的列表参见美国专利4,534,891,其内容全文结合于此作为参考。合适香味的其它来源参见《香水、化妆品与香皂》(Perfumes,Cosmetics and Soaps),第二版,W.A.Poucher编,1959年。该论文中提及的香味有:刺槐、金合欢、素心兰(chypre)、仙客来、蕨、栀子、山楂、天芥菜、忍冬、风信子、茉莉、丁香、百合、木兰、羞草、水仙花、新割甘草、橙花、兰花、木犀草、香豌豆、三叶草(trefle)、晚香玉、香草、紫罗兰、壁花等。
术语“芳香制剂”、“芳香组合物”和“香料组合物”应理解为表示相同含义,指用于为香料、古龙水、花露水、个人产品、织物护理产品等提供芳香特征的制剂。本发明的芳香制剂是包含本发明化合物的组合物。
嗅觉上可接受的量应理解为表示芳香制剂中的化合物含量,其中该化合物提供其独特的嗅觉特性。然而,芳香制剂的嗅觉效果是各香料或芳香成分的效果总和。因此,可利用本发明化合物,或者通过改变制剂中其它成分的嗅觉反应来改善或提升芳香制剂的芳香特性。所述嗅觉上可接受的量可根据许多因素变化,这些因素包括其它成分、它们的相对含量和所需的嗅觉效果。
芳香制剂中使用的本发明化合物的含量约为0.005-70重量%,优选约0.005-10重量%,最优选约0.5-8重量%,甚至更优选约1-7重量%。本领域技术人员能采用所需含量的本发明化合物来提供所需的香味效果和强度。除本 发明化合物之外,其它材料也可与芳香制剂联用。在不背离本发明的范围的前提下,也可采用公知物质如表面活性剂、乳化剂、包封芳香成分的聚合物。
用于芳香制剂时,本发明的化合物提供意想不到的强烈的清新、花香、玫瑰香、香茅、中性葡萄柚样和大黄样特征,使得芳香制剂更加理想且引人注意。本发明化合物的气味品质有助于美化和提升最终的和谐程度并改善芳香制剂中其他材料的性能。
下面提供的是本发明的具体实施方式。本发明的其它改进是本领域技术人员容易明白的。这些改进应理解为在本发明的范围内。除非另有说明,本文中所用的所有百分比都是重量百分比,ppm应理解为表示百万分之一,L应理解为升,g应理解为克,mmHg应理解为毫米汞柱。实施例中使用的IFF应理解为表示国际香料和香精公司(International Flavors & FragranceInc.,纽约,纽约州,美国)。
实施例I
制备(5,5-二甲氧基-3-甲基戊基)-苯:3L的反应烧瓶配备有机械搅拌器、温度计适配器、温度计、回流冷凝器和氮气进口。将反应烧瓶置于干冰-IPA浴上。搅拌的同时,在烧瓶中加入3-甲基-5-苯基-戊醛(704g,从探索国际购得)、原甲酸三甲酯(CH(OCH3)3(424g,从西格玛-奥德里奇公司(Sigma-Aldrich Corp)购得)和甲醇(CH3OH,640g)。然后反应罐温度冷却至-20℃,加入HCl(3g)。发生放热反应,反应罐温度为30-40℃。去除干冰-IPA浴,反应物质加热至40℃。反应完全之后,一次性加入甲醇钠(25%在CH3OH中,16g)。将粗产物浓缩并经硅藻土(celite)滤床过滤,得到3-甲基-5-苯基-戊醛(927g)。
H1 NMR:0.98ppm(d,3H);1.4-1.78ppm(2m,5H);2.55-2.7ppm(m,2H);3.3ppm(s,6H);4.6ppm(d,1H);5.9ppm(d,1H);7.15-7.3ppm(m,5H)。
实施例II
制备[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯:1L的反应烧瓶配备有机械搅拌器、2英寸的防溅柱(splash column)、垂直取下的蒸馏头、带有接收容器的馏分分割器、恒温井、热电偶、氮气进口和加料漏斗。联合使用电子温度控制器和加热套进行加热。干冰阱连接馏分分割器,然后连接至真空。矿物油鼓泡器连接至氮气进口以监测进口流量。缓慢搅拌的同时,在反应罐中加入吡啶(4g,从西格玛-奥德里奇公司购得)和磷酸(H3PO4,2g)。将反应物质搅拌5分钟,充分混合。将反应罐加热至超过190℃,加入3-甲基-5-苯基-戊醛(927g,根据实施例I制备)。反应完全之后,蒸馏粗产物得到[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯,其中4E∶4Z异构体比率为55∶45(???g)。产物在1.2mmHg压力下的沸点为89℃。
H1 NMR:1.0ppm(d,3H);1.5-1.5ppm(m,2H);2.1-2.7ppm(m,4H);3.55ppm(s,3H);4.2ppm(d,1H);5.9ppm(d,1H);7.15-7.3ppm(m,H)。
[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯具有强烈的清新、花香、玫瑰香、香茅、中性葡萄柚样和大黄样气味。
实施例III
以下所示芳香配方表明,[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯能够赋予麝香芳香制剂以清新、花香、玫瑰香、香茅、中性葡萄柚样和大黄样气味。
*“+”表示含[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯的配方;和
“-”表示不含[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯的配方。
Claims (9)
1.一种化合物,[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯。
2.一种通过加入嗅觉上可接受量的[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯来改善、提升或改变芳香制剂的方法。
3.如权利要求2所述的方法,其特征在于,所述芳香制剂被掺入选自下组的产品:香料、化妆品、个人护理产品、织物护理产品、清洁产品和空气清新剂。
4.如权利要求2所述的方法,其特征在于,所述芳香制剂被掺入选自下组的产品:古龙水、花露水。
5.如权利要求3所述的方法,其特征在于,所述清洁产品选自:去污剂、洗碗组合物、刷洗组合物和窗户清洁剂。
6.如权利要求2所述的方法,其特征在于,所述嗅觉上可接受量占所述芳香制剂0.005-10重量%。
7.如权利要求2所述的方法,其特征在于,所述嗅觉上可接受量占所述芳香制剂0.5-8重量%。
8.如权利要求2所述的方法,其特征在于,所述嗅觉上可接受量占所述芳香制剂1-7重量%。
9.一种芳香制剂,其包含嗅觉上可接受量的[(4E,4Z)-5-甲氧基-3-甲基-4-戊烯基]-苯。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US12/637,827 US8168163B2 (en) | 2009-12-15 | 2009-12-15 | [(4E, 4Z)-5-methoxy-3-methyl-4-pentenyl]-benzene and its use in perfume compositions |
US12/637,827 | 2009-12-15 |
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CN102093174A CN102093174A (zh) | 2011-06-15 |
CN102093174B true CN102093174B (zh) | 2015-09-30 |
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US (1) | US8168163B2 (zh) |
EP (1) | EP2338868B1 (zh) |
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Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3943943A (en) * | 1974-07-09 | 1976-03-16 | Liggett & Myers Incorporated | Cinnamic derivatives as tobacco additives |
CN1113388A (zh) * | 1993-08-09 | 1995-12-13 | 弗门尼舍有限公司 | 纺织物的加香方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US4534891A (en) | 1982-11-12 | 1985-08-13 | International Flavors & Fragrances Inc. | Branched C13 -alk-1-en-5-ones and use thereof in perfumery |
DE10348062A1 (de) * | 2003-10-16 | 2005-05-19 | Symrise Gmbh & Co. Kg | Kurzkettige Enolester als Riechstoff-Prekursoren |
US8071530B2 (en) * | 2006-08-14 | 2011-12-06 | International Flavors & Fragrances Inc. | Organoleptic compounds and their use in perfume compositions |
US7632792B2 (en) * | 2007-11-16 | 2009-12-15 | International Flavors & Fragrances Inc. | Methyl cyclohexane carboxylates and their use in perfume compositions |
-
2009
- 2009-12-15 US US12/637,827 patent/US8168163B2/en not_active Expired - Fee Related
-
2010
- 2010-11-16 EP EP10191450.5A patent/EP2338868B1/en not_active Not-in-force
- 2010-11-16 ES ES10191450.5T patent/ES2439041T3/es active Active
- 2010-12-13 CN CN201010602206.3A patent/CN102093174B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3943943A (en) * | 1974-07-09 | 1976-03-16 | Liggett & Myers Incorporated | Cinnamic derivatives as tobacco additives |
CN1113388A (zh) * | 1993-08-09 | 1995-12-13 | 弗门尼舍有限公司 | 纺织物的加香方法 |
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US20110142783A1 (en) | 2011-06-16 |
US8168163B2 (en) | 2012-05-01 |
CN102093174A (zh) | 2011-06-15 |
EP2338868B1 (en) | 2013-10-16 |
EP2338868A1 (en) | 2011-06-29 |
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