CN115397798A - 有机化合物中或与之相关的改进 - Google Patents
有机化合物中或与之相关的改进 Download PDFInfo
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- CN115397798A CN115397798A CN202180025180.7A CN202180025180A CN115397798A CN 115397798 A CN115397798 A CN 115397798A CN 202180025180 A CN202180025180 A CN 202180025180A CN 115397798 A CN115397798 A CN 115397798A
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- 150000002894 organic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
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- 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
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
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- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
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- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
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Abstract
式(IIa)的化合物及其作为香料的用途,所述化合物是(S,Z)‑3,7‑二甲基壬‑6‑烯‑1‑醇。
Description
本发明涉及新的有机化合物,制备所述化合物的方法及其作为香料成分的用途。本发明还涉及由所述化合物加香的香料组合物和制品,例如精细香料或消费品组合物,或包含所述化合物的香料组合物。
发明背景
香茅醇(二氢香叶醇,3,7-二甲基辛-6-烯-1-醇,式(I)的化合物)作为香料和食品成分被广泛使用。它具有一种花香、玫瑰柑橘气味和味道。虽然它在食品中的使用是安全的,但它在香料中的使用引起了一些担心,因为它可能对一些人造成过敏反应。香茅醇出现在欧盟标明的26种香料过敏原列表中。香料包含香茅醇必须做相应标记。
香茅醇具有一个手性中心,在式(I)的化合物中由星号表示,并且两种对映异构体都存在于自然界中。(+)-香茅醇在香茅油中(例如在亚香茅(Cymbopogon nardus)中)被发现,是一种更常见的异构体。(-)-香茅醇在玫瑰油和天竺葵(Pelargonium geraniums)中被发现。
发明描述
3,7-二甲基壬-6-烯-1-醇(乙基香茅醇,式(II)的化合物)相当于香茅醇形式上延长一个甲基基团。这是具有一个立体中心和一个双键的化合物,并且总共可以产生四个立体异构体。
在式(II)的化合物中,星号表示在C-原子处的立体中心,并且波浪键表示邻接双键的未指明的构型。
3,7-二甲基壬-6-烯-1-醇之前已经被报道过。它通过GC鉴定为覆盆子汁(ShipinKexue 2013,34,199-203)和真菌(Junwu Xuebao 2012,31,92-101)中的一种化合物。它可以从香茅醇开始通过四步合成得到(Biosci.Biotechnol.Biochem.2002,66,582-587)。根据Dragoco(1978 11/12,235)的报道,它也可以从甲基乙基酮开始通过七步合成得到。然而,它的香料性质至今未被报道过。
目前令人惊讶地发现,乙基香茅醇具有花香玫瑰、香茅醇、牡丹、荔枝香气,其气相色谱(GC)阈值为0.22ng。因此在本发明的第一个方面,式(II)的化合物能被用作香料材料,例如作为香茅醇的替代物。它没有出现在欧盟标明的26种香料过敏原列表中。
令人惊讶地进一步发现,式(II)的化合物的香料益处取决于立体化学:四个立体异构体中只有一个是强增香剂,而其他的,如果有的话,仅展现出非常弱的增香剂性质。此外,没有任何一个3,7-二甲基壬-6-烯-1-醇异构体出现在欧盟标明的26种香料过敏原列表中。
因此在本发明的另一个方面,提供了(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)。
与香茅醇的1.8ng的GC阈值相比,所述化合物具有令人惊讶地低的0.032ng的气相色谱(GC)阈值。这种GC阈值比香茅醇低100倍的高性能分子可以以较低的剂量使用,从而减少对人类和环境的暴露。它具有花香、玫瑰、果香、荔枝香气。它是一种香料材料,可用作香茅醇的替代物。
在本发明的另一个方面中,提供了异构体混合物(在下文中称为异构体混合物),其包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)和至少一种其他化合物,所述其他化合物选自
(R,E)-3,7-二甲基壬-6-烯-1-醇(IIb),
(S,E)-3,7-二甲基壬-6-烯-1-醇(IIc),和
(R,Z)-3,7-二甲基壬-6-烯-1-醇(IId)。
(R,E)-3,7-二甲基壬-6-烯-1-醇(IIb)具有的GC阈值为0.75ng,其仍比香茅醇的值低。它具有尘土、腊样、玫瑰、四氢香叶醇、二氢香叶醇-样、技术性、刺激气味。它与IIa混合得很好,增加浓郁感,补充整体香味印象。
(S,E)-3,7-二甲基壬-6-烯-1-醇(IIc)和(R,Z)-3,7-二甲基壬-6-烯-1-醇(IId)都是弱增香剂,GC阈值分别为2.2ng和3.4ng。它们的气味被描述为多脂的和多脂的花香。它们对异构体混合物的整体香味没有显著贡献。
如果一种化合物存在不同的立体异构体形式,它可以作为混合物使用。或者,它可以拆分为非对映异构体组或纯立体异构体。拆分立体异构体增加了该化合物的生产和纯化的复杂性,因此仅仅出于经济原因,优选使用该化合物的立体异构体的混合物。然而,如果希望制备单独的立体异构体,这可以根据本领域中已知的方法,例如立体选择性合成、制备型HPLC和GC来实现。
在本发明的一个方面,式(IIa)的化合物以高度富集或基本上纯的形式提供,含有少量或基本上不含化合物(IIb)、(IIc)和/或(IId)。这意味着式(IIa)的化合物以至少90重量%,特别地以至少95重量%,更特别地以至少98重量%,甚至更特别地以99重量%或更高存在。
在本发明的另一个方面,提供了异构体混合物,其包含大量的式(IIa)的化合物,以及化合物(IIb)、(IIc)和/或(IId)。这意味着式(IIa)的化合物以至少20重量%,特别地以至少30重量%,更特别地以至少40重量%,甚至更特别地以至少50重量%或更高存在。在该异构体混合物中,式(IIa)的化合物和式(IIb)的化合物的重量比可以在约4:6至约99:1的范围内。
在本发明的另一个方面,以纯或对映异构体-富集形式提供了(S)-异构体(IIa)的(IIc)的混合物。(S)-异构体(IIa)的(IIc)的外消旋混合物具有的GC阈值为0.93ng。
在本发明的另一个方面,提供了式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)和至少一种其他化合物的异构体混合物作为香料的用途,所述其他化合物选自
(R,E)-3,7-二甲基壬-6-烯-1-醇(IIb),
(S,E)-3,7-二甲基壬-6-烯-1-醇(IIc),和
(R,Z)-3,7-二甲基壬-6-烯-1-醇(IId)。
仍然在本发明的另一个方面,提供了一种香料组合物,其包含式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)和至少一种其他化合物的异构体混合物,所述其他化合物选自
(R,E)-3,7-二甲基壬-6-烯-1-醇(IIb),
(S,E)-3,7-二甲基壬-6-烯-1-醇(IIc),和
(R,Z)-3,7-二甲基壬-6-烯-1-醇(IId)。
本发明的化合物或异构体混合物可以单独使用,或可以与已知的增香剂分子联合使用,所述增香剂分子选自广泛范围的天然产物及目前可利用的合成分子,例如精油、醇类、醛类和酮类、醚类和缩醛类、酯类和内酯类、大环类和杂环类、和/或与通常与香料组合物中的增香剂结合使用的一种或多种成分或赋形剂混合使用,所述成分或赋形剂例如为载体材料和本领域中常用的其他助剂。
如本文所用,“载体材料”是指从增香剂的观点来看实际上是中性的材料,即不会显著改变香料感官特性的材料。
术语“助剂”是指出于与所述组合物的嗅觉性能没有特别关系的原因而可用于香料组合物中的成分。例如,助剂可以为用作加工香料成分或多种成分的助剂的成分,或含有所述成分的组合物,或它可以改善香料成分或含有该成分的组合物的处理或储存。它也可以是提供额外益处(例如赋予颜色或质地)的成分。它也可以为对包含在香料组合物中的一种或多种成分赋予耐光性和化学稳定性的成分。在包含香料的香料组合物中常用的助剂的性质和类型的详细描述不能穷尽,但必须提及的是,所述成分对于本领域技术人员而言是众所周知的。
如本文所用,“香料组合物”是指包含式(IIa)的化合物或异构体混合物以及基础材料的任何组合物,所述基础材料例如为通常与增香剂结合使用的稀释剂,例如邻苯二甲酸二乙酯(DEP)、一缩二丙二醇(DPG)、肉豆蔻酸异丙酯(IPM)、戊-1,2-二醇、柠檬酸三乙酯(TEC)和醇(如乙醇)。任选地,该组合物可包含抗氧化剂助剂。所述抗氧化剂可以选自TT(BASF)、Q(BASF)、生育酚(包括其异构体,CAS 59-02-9;364-49-8;18920-62-2;121854-78-2)、2,6-双(1,1-二甲基乙基)-4-甲基苯酚(BHT,CAS 128-37-0)和相关的酚类、氢醌类(CAS 121-31-9)。
下列清单包括已知增香剂分子的实例,其可与式(IIa)的化合物或其异构体混合物合并:
香料成分的典型的非限制性实例包括:
精油和提取物,例如,海狸,木香根油,橡苔净油,香叶油,树苔净油,罗勒油,果油如香柠檬油和橘子油,香桃木油,玫瑰草油,广藿香油,橙叶油,茉莉油,玫瑰油,檀香油,苦艾油,熏衣草油和/或依兰-依兰油;
醇类,例如肉桂醇((E)-3-苯基丙-2-烯-1-醇);顺式-3-己烯醇((Z)-己-3-烯-1-醇);香茅醇(3,7-二甲基辛-6-烯-1-醇);二氢月桂烯醇(2,6-二甲基辛-7-烯-2-醇);EbanolTM((E)-3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-4-烯-2-醇);丁香酚(4-烯丙基-2-甲氧基苯酚);乙基芳樟醇((E)-3,7-二甲基壬-1,6-二烯-3-醇);金合欢醇((2E,6Z)-3,7,11-三甲基十二碳-2,6,10-三烯-1-醇);香叶醇((E)-3,7-二甲基辛-2,6-二烯-1-醇);Super MuguetTM((E)-6-乙基-3-甲基辛-6-烯-1-醇);芳樟醇(3,7-二甲基辛-1,6-二烯-3-醇);薄荷醇(2-异丙基-5-甲基环己醇);橙花醇(3,7-二甲基-2,6-辛二烯-1-醇);苯乙醇(2-苯乙醇);RhodinolTM(3,7-二甲基辛-6-烯-1-醇);SandaloreTM(3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-2-醇);松油醇(2-(4-甲基环己-3-烯-1-基)丙-2-醇);或TimberolTM(1-(2,2,6-三甲基环己基)己-3-醇);2,4,7-三甲基辛-2,6-二烯-1-醇;和/或[1-甲基-2(5-甲基己-4-烯-2-基)环丙基]-甲醇;
醛类和酮类,例如茴香醛(4-甲氧基苯甲醛);α戊基肉桂醛(2-亚苄基庚醛);GeorgywoodTM(1-(1,2,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);羟基香茅醛(7-羟基-3,7-二甲基辛醛);Iso E(1-(2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);((E)-3-甲基-4-(2,6,6-三甲基环己-2-烯-1-基)丁-3-烯-2-酮);(3-氧代-2-戊基环戊烷乙酸甲酯);3-(4-异丁基-2-甲基苯基)丙醛;麦芽酚;甲基柏木基酮;甲基紫罗兰酮;马鞭草烯酮;和/或香草醛;
醚类和缩醛类,例如(3a,6,6,9a-四甲基-2,4,5,5a,7,8,9,9b-八氢-1H-苯并[e][1]苯并呋喃);香叶基甲基醚((2E)-1-甲氧基-3,7-二甲基辛-2,6-二烯);玫瑰醚(4-甲基-2-(2-甲基丙-1-烯-1-基)四氢-2H-吡喃);和/或(2',2',3,7,7-五甲基螺[二环[4.1.0]庚烷-2,5'-[1,3]二噁烷]);
酯类和内酯类,例如乙酸苄酯;乙酸柏木酯(乙酸(1S,6R,8aR)-1,4,4,6-四甲基八氢-1H-5,8a-亚甲基甘菊环-6-基酯);γ-癸内酯(6-戊基四氢-2H-吡喃-2-酮);(丙酸2-(1-(3,3-二甲基环己基)乙氧基)-2-甲基丙酯);γ-十一烷酸内酯(5-庚基氧杂戊环-2-酮);和/或乙酸岩兰草酯(乙酸(4,8-二甲基-2-丙-2-亚基-3,3a,4,5,6,8a-六氢-1H-甘菊环-6-基)酯);
杂环类,例如异丁基喹啉(2-异丁基喹啉)。
仍然在本发明的另一个方面,提供一种香料制品,例如精细香料或个人或家居护理产品,其用式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物加香。
式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物可被用于广泛范围的加香制品,例如任何精细或功能香料领域,例如香料、空气护理产品、家居产品、洗衣产品、身体护理产品和化妆品。取决于具体制品和其他增香剂成分的性质和用量,该化合物可以以广泛不同的用量使用。比例通常为制品的0.0001至5重量%。在一个实施方案中,本发明的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物可用于织物软化剂,用量为0.001至0.3重量%(例如0.01至0.1(包括0.05)重量%)。在另一个实施方案中,式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物不仅可用于精细香料,也可用于消费品如洗发香波、织物软化剂或织物洗涤剂,用量为0.001至30重量%(例如至多约10%或至多20重量%),更优选地为0.01至5重量%。然而,这些值仅作为示例给出,因为经验丰富的调香师也可能以更低或更高的浓度实现效果或可以创造出新颖的谐香。
在一个实施方案中,提供了一种加香制品,其包含可接受量的式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物。例如,所述加香制品基于制品总量可以包含0.000001重量%至90重量%(包括0.00001重量%、0.0001重量%、0.001重量%、0.01重量%、0.05重量%、0.1重量%、0.5重量%、1重量%、5重量%、8重量%、10重量%、15重量%、20重量%、25重量%、30重量%、50重量%、60重量%、65重量%)的该化合物或其异构体混合物。
式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物也可用于消费品基料,简单地通过将本发明化合物或包含式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物的香料组合物或其混合物与消费品基料直接混合来进行,或者可以在较早的步骤中将其用捕获材料捕获,然后与消费品基料混合,所述捕获材料例如为聚合物、胶囊、微胶囊和纳米胶囊、脂质体、膜形成剂、吸收剂例如碳或沸石、环状低聚糖及其混合物。
因此,本发明另外提供了生产加香制品的方法,所述方法包括掺入作为香料成分的式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物,使用常规技术和方法,通过直接将该化合物和消费品基料混合来进行,或者通过将包含式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物的香料组合物混合,然后将其与消费品基料混合来进行。通过加入嗅觉可接受量的如上所述的本发明化合物,消费品基料的气味香型将被改善、增强或改变。
因此,本发明进一步提供了一种赋予、增强、改善或改变香料组合物或消费品的令人快乐的性质的方法,所述方法包括向所述香料组合物或消费品中添加式(IIa)的化合物或包含(S,Z)-3,7-二甲基壬-6-烯-1-醇(IIa)的异构体混合物。
如本文所用,“消费品基料”是指用作消费品以满足特定作用例如清洁、软化和护理等的组合物。这类产品的实例包括精细香料,例如香料和淡香水(eau de toilette);织物护理产品、家居产品和个人护理产品,例如化妆品、洗衣护理洗涤剂、漂洗调理剂、个人清洁组合物、洗碗机用洗涤剂、表面清洁剂;洗衣产品,例如软化剂、漂白剂、洗涤剂;身体护理产品,例如洗发香波、沐浴露;空气护理产品(包括优选包含挥发性且通常具有令人愉悦气味的化合物的产品,这些化合物即使非常少量也能有利地掩盖令人不愉快的气味)。用于生活区的空气清新剂特别包括天然和合成精油类,例如松针油、柑橘油、桉树油、薰衣草油等,其用量例如为至多50重量%。作为气雾剂它们往往包含较少量的此类精油,例如少于5%或少于2%重量,但额外地包括化合物,例如乙醛(特别地,<0.5%重量)、异丙醇(特别地,<5%重量)、矿物油(特别地,<5%重量)和推进剂。
化妆品包括:
美容护肤化妆品,尤其是沐浴产品、皮肤洗涤和清洁产品、护肤品、眼妆、唇部护理产品、指甲护理产品、私密护理产品、足部护理产品;
具有特定功效的化妆品,尤其是防晒霜、美黑产品、脱色产品、除臭剂、止汗剂、脱毛剂和剃须产品;
美容牙科护理产品,尤其是牙科和口腔护理产品、牙齿护理产品、假牙清洁剂、假牙黏合剂;和
化妆护发产品,特别是洗发香波、护发产品、头发定型产品、头发造型产品和染发产品。
乙基香茅醇(II)能通过不同方法制备,如在以下实施例1中解释的从乙基芳樟醇(III)开始的两步方法。或者,它能从香茅醇开始通过四步反应得到(Biosci.Biotechnol.Biochem.2002,66,582-587),或者根据Dragoco(1978 11/12,235)报道的从甲基乙基酮开始通过七步合成得到。
在一个实施方案中,用于制备乙基香茅醇(II)的方法的起始材料是从可再生资源得到的。使用这种起始材料,终产品也是从可再生资源可获得的。
现通过以下非限制性实施例进一步描述本发明。
实施例:
实施例1.3,7-二甲基壬-6-烯-1-醇(II)的制备
乙基香茅醇(II)从乙基芳樟醇(III)开始,经过乙基香叶醇/乙基橙花醇(IV),通过两步反应制备:
a)3,7-二甲基壬-2,6-二烯-1-醇(IV)
在N2下,向装有冷凝器的1000mL的3颈圆底烧瓶中加入乙基芳樟醇(III,637.8g,3.79mol),VO(OSiPh3)3(20.1g,0.022mol)和PhMe(139g),并将溶液回流(加热板设定在110℃)。反应进程通过GC跟踪,直到观察到70:30的乙基芳樟醇:乙基香叶醇/乙基橙花醇(3,7-二甲基壬-2,6-二烯-1-醇)的平衡混合物。总共反应3h后,将反应混合物冷却至室温。除去PhMe,得到粗浅棕色液体(667g)。将该反应混合物通过刮膜式蒸发器(长度=16cm,OD5.5cm,80℃,0.04mbar),得到回收的VO(OSiPh3)3(17g)和粗物质(乙基芳樟醇+乙基香叶醇/乙基橙花醇混合物)(562.8g)。该粗物质经过滤、分馏(苏尔寿(Sulzer)填充柱(长度=50cm,ID 30mm))得到乙基芳樟醇(250.1g),然后得到乙基香叶醇/乙基橙花醇(IV,92g,100%纯度,48%分离收率),为四种异构体的混合物,比例为1:3.36:3.51:5.59。
E/E,E/Z,Z/E和Z/Z异构体的混合物:
1H-NMR(CDCl3,400MHz):δ=5.47-5.37(m,4x1H),5.14-5.03(m,4x1H),4.14(d,J=6.8Hz,2x2H),4.11-4.07(m,2x2H),2.16-1.94(m,4x6H),1.89(br s,4x1H),1.75(m,2x3H),1.67(m,4x3H),1.60(s,2x3H),1.00-0.94(m,4x3H)ppm。
13C-NMR(CDCl3,100MHz):δ=139.6(s),139.5(s),139.34(s),139.28(s),137.9(s),137.7(s),137.3(s),137.1(s),124.43(d),124.37(d),123.42(d),123.35(d),122.3(d),122.1(d),59.1(t),58.78(t),58.76(t),39.8(t),39.5(t),32.22(t),32.19(t),31.9(t),26.3(t),26.2(t),26.1(t),25.9(t),24.7(t),24.6(t),23.3(q),22.72(q),22.68(q),16.1(q),15.8(q),12.73(q),12.69(q),12.67(q),12.6(q)ppm。
主要的E/E异构体:
13C-NMR(CDCl3,100MHz):δ=139.3(s),137.1(s),123.4(d),122.3(d),59.1(t),39.5(t),32.2(t),26.2(t),16.1(q),15.8(q),12.7(q)ppm。
峰1.MS(EI,Rt 6.43min.,70eV):168(1,[M]+·),121(9),93(17),84(14),83(33),67(15),55(100),53(10),41(39),39(15),29(11)。
峰2.MS(EI,Rt 6.51min.,70eV):168(1,[M]+·),121(9),93(18),84(14),83(35),67(15),55(100),53(10),41(38),39(14),29(10)。
峰3.MS(EI,Rt 6.62min.,70eV):168(0,[M]+·),137(9),93(9),84(8),83(37),67(13),55(100),53(9),41(36),39(12),29(10)。
峰4.MS(EI,Rt 6.67min.,70eV):168(1,[M]+·),93(9),84(8),83(39),67(13),55(100),53(9),43(8),41(35),39(12),29(9)。
b)3,7-二甲基壬-6-烯-1-醇(II)
在空气氛围下,将3,7-二甲基壬-6-烯-1-醇(IV,92g,0.547mol,100%纯度)和MeOH(108g)加入至500mL高压釜容器中,再加入雷尼镍(0.92g,以颗粒形式一次性加入),然后密封该容器。在搅拌(600rmp)下,将该高压釜用N2(1.8bar)冲洗三次,然后用H2(2.0bar)冲洗三次。在调节氢气压力至10bar后,将高压釜加热至50℃,同时搅拌增加至1500rmp。反应进程通过取样跟踪。在t=6h 39min时,停止高压釜的加热和H2流。一旦冷却,释放出压力,将反应釜用N2(1.8bar)冲洗三次。过滤反应混合物,除去多相催化剂,并除去甲醇,得到3,7-二甲基壬-6-烯-1-醇(II,78.6g,86.9%纯度,79.8%收率),为无色液体,其含有两个双键异构体,比例为2:1。
1H-NMR(CDCl3,400MHz):δ=5.14-5.03(m,2x1H,E+Z),3.74-3.60(m,2x2H,E+Z),2.09-1.89(m,2x4H,E+Z),1.67(q,J=1.2Hz,3H,Z),1.60(sb,3H,E),1.66-1.13(m,2x5H,E+Z),0.98(t,J=7.5Hz,3H,E),0.96(t,J=7.5Hz,3H,Z),0.91(d,J=6.7Hz,3H,E),0.91(d,J=6.6Hz,3H,Z)ppm。
13C-NMR(CDCl3,100MHz):δ=137.0(s,Z),136.7(s,E),124.3(d,Z),123.1(d,E),61.1(2t,E+Z),39.8(2t,E+Z),37.5(t,Z),37.2(t,E),32.3(t,E),29.2(2d,E+Z),25.3(t,E),25.0(t,Z),24.7(t,Z),22.8(q,Z),19.5(2q,E+Z),15.8(q,E),12.8(q,Z),12.7(q,E)ppm。
峰1.MS(EI,Rt=6.43min.,70eV):170(3,[M]+·),123(39),95(18),83(18),81(42),71(18),70(19),69(21),67(26),55(100),41(45)。
峰2.MS(EI,Rt=6.43min.,70eV):170(3,[M]+·),123(39),95(18),83(19),81(41),71(18),70(18),69(21),67(26),55(100),41(45)。
实施例2.立体异构体分离
3,7-二甲基壬-6-烯-1-醇(II)转化为相应的4-硝基苯甲酸3,7-二甲基壬-6-烯-1-基酯(V),以通过SFC(超临界流体色谱法)分离单独的异构体,随后经酯水解得到单独的化合物(IIa)、(IIb)、(IIc)和(IId)。
a)4-硝基苯甲酸3,7-二甲基壬-6-烯-1-基酯(V)
在0℃下,向搅拌的化合物1(5g,29mmol,1equiv)的DCM(100mL)溶液中加入对硝基苯甲酸(2)(7.35g,44mmol,1.5equiv),DCC(11.3g,55mmol,1.9equiv)和DMAP(1.41g,11.6mmol,0.4equiv)。在rt下搅拌16h。过滤反应混合物,并将过滤的固体用DCM(50mL)洗涤。将滤液用水(200mL)洗涤,用硫酸钠干燥,并减压浓缩。将粗产物(V)通过HPLC纯化,得到3(6g,64%),为无色液体。
b)SFC分离:
对化合物(V)(6g)进行SFC纯化(15%共溶剂:甲醇中的0.5%异丙胺,柱:Lux A1(250×30mm,5μ),流速:3ml/min),得到四个级分(Vc)、(Va)、(Vb)和(Vd)。
c)酯水解:
在rt下,向搅拌的化合物Va的THF-MeOH-H2O(7:2:1vol)溶液中加入LiOH.H2O(2equiv)。在rt下搅拌2h。将反应混合物减压浓缩,用水稀释,并用EtOAc萃取。将合并的有机层用硫酸钠干燥,并减压浓缩。将粗产物通过快速柱色谱法纯化,使用在石油醚中的6-7%EtOAc作为洗脱剂,得到IIa,为无色液体。
化合物(Vb)、(Vc)和(Vd)相应地水解,分别得到化合物(IIb)、(IIc)和(IId)。单独的异构体的构型通过手性GC和NMR分析确定。
实施例3.香料实施例
在如下谐香中,比较了化合物(IIa)、(S)-异构体(IIa)和(IIc)的混合物和香茅醇。这种沐浴露应该以1至1.5%应用在最终使用基料中。
整体谐香给出了一种新鲜多汁果香柑橘谐香,具有主要是新鲜柑橘柠檬头香,结合有玫瑰覆盆子荔枝中段香。
香茅醇(用于谐香A)在使用中通常在纯净和盛放时支持玫瑰新鲜度。
(S)-乙基香茅醇(IIa+IIc,用于谐香B)在纯净时和使用中给谐香带来额外的令人快乐的新鲜度和自然度。此外,在淋浴体验期间它带来了明显改善的盛放和扩散的显著益处。
(S,Z)-乙基香茅醇(IIa,用于谐香C)为组合物提供强烈的花香玫瑰香质和令人愉悦的多汁果香荔枝感,其与香茅醇比较在使用中提供了更优的纯净强度、更好的盛放和空间填充,甚至在减少5倍用量时仍有明显的令人快乐的益处。相比外消旋的(S)-乙基香茅醇,这个特定的异构体提供盛放和令人愉悦的快乐特征,且没有(S,E)-异构体的技术性和和粗糙方面。
实施例4.GC阈值的比较
在如下表格中,比较了香茅醇、芳樟醇和香叶醇-橙花醇混合物与相应的所谓乙基类似物的GC阈值,乙基类似物即在形式上延长一个甲基基团。
化合物 | GC阈值ng |
香茅醇 | 1.8 |
乙基香茅醇 | 0.22 |
芳樟醇 | 4 |
乙基芳樟醇 | 8.7 |
香叶醇/橙花醇混合物 | 2.9 |
乙基-香叶醇/-橙花醇混合物 | 1.6 |
芳樟醇:3,7-二甲基-1,6-辛二烯-3-醇;乙基芳樟醇:3,7-二甲基壬-1,6-二烯-3-醇;香叶醇/橙花醇:E/Z-3,7-二甲基-2,6-辛二烯-1-醇;乙基-香叶醇/-橙花醇:E/Z-3,7-二甲基壬-2,6-二烯-1-醇。
可以看到,典型地,用乙基基团替换甲基基团不会明显改变与化合物影响力或性能相关的GC阈值。而令人惊讶的是,在乙基香茅醇的情况中,该化合物具有明显高于甲基类似物香茅醇的性能。
Claims (8)
4.权利要求1所定义的式IIa的化合物或权利要求2所定义的异构体混合物作为香料的用途。
5.改善、增强或改变消费品基料的方法,通过向其中添加嗅觉可接受量的权利要求3所定义的式II的化合物、权利要求1所定义的式IIa的化合物或权利要求2所定义的异构体混合物来进行。
6.香料用品,包含作为增香剂的权利要求1所定义的式IIa的化合物或权利要求2所定义的异构体混合物和消费品基料。
7.根据权利要求6的香料用品,其中所述消费品基料选自精细香料、家居产品、洗衣产品、身体护理产品、化妆品和空气护理产品。
8.香料组合物,包含权利要求1所定义的式IIa的化合物或权利要求2所定义的异构体混合物和基础材料。
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GB1225134A (zh) * | 1967-11-17 | 1971-03-17 | ||
EP1705171A1 (en) * | 2001-12-19 | 2006-09-27 | Flexitral, Inc. | Improved aromachemicals |
CN101107211A (zh) * | 2005-01-19 | 2008-01-16 | 玛奈·菲尔萨公司 | 新颖的香味化合物、其合成方法、及其用途 |
US20100152083A1 (en) * | 2008-12-16 | 2010-06-17 | Jose Maria Velazquez | Perfume Systems |
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GB1225134A (zh) * | 1967-11-17 | 1971-03-17 | ||
EP1705171A1 (en) * | 2001-12-19 | 2006-09-27 | Flexitral, Inc. | Improved aromachemicals |
CN101107211A (zh) * | 2005-01-19 | 2008-01-16 | 玛奈·菲尔萨公司 | 新颖的香味化合物、其合成方法、及其用途 |
US20100152083A1 (en) * | 2008-12-16 | 2010-06-17 | Jose Maria Velazquez | Perfume Systems |
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