CN112752745B - 作为新型芳香味化合物的2-(5-异丙基-2-甲基环己-2-烯-1-基)乙醛和2-(6-异丙基-3-甲基环己-2-烯-1-基)乙醛 - Google Patents
作为新型芳香味化合物的2-(5-异丙基-2-甲基环己-2-烯-1-基)乙醛和2-(6-异丙基-3-甲基环己-2-烯-1-基)乙醛 Download PDFInfo
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Abstract
本发明涉及式(I)的新化合物和包含或由式(I)的化合物组成的混合物。此外,本发明涉及式(I)的化合物的制备方法和式(I)的化合物作为芳香味化合物的用途,特别是作为铃兰芳香味化合物的用途。本发明最终涉及包含式(I)的至少一种化合物的芳香味化合物制剂和芳香产品或消费品。
Description
技术领域
本发明涉及式(I)的新化合物
以及包含或由式(I)的化合物组成的混合物。此外,本发明涉及式(I)的化合物的制备方法和式(I)的化合物作为芳香味化合物,特别是作为铃兰芳香味化合物的用途。本发明最终涉及包含式(I)的至少一种化合物的芳香味化合物制剂和芳香产品或消费品。
背景技术
具有花香气味的化合物是芳香味化合物工业中以及香水、化妆品、个人护理产品、以及清洗剂、清洁剂和其他消费品制备中不可缺少的成分。尽管已经存在大量的芳香味化合物,但对于香水商店而言,对新的有花香味的、特别是铃兰气味特性的芳香味化合物的需求仍然很大,这使得香水的品类得以扩展。铃兰气味特性是最受欢迎的气味特性之一,经常用于香水和芳香物质混合物。关于铃兰芳香味化合物历史发展的广泛综述文章,可以参见出版物A.Goeke,P.Kraft,D.Lelievre,Perfumer&Flavorist,2018,43(3),24和J.Coulomb,Perfumer&Flavorist,2018,43(4),40。
醛环己烯(Aldehydische Cyclohexene)在文献中被描述为芳香味化合物。EP 1054 053 A1描述了闻起来像铃兰的叔丁基取代的环己烯。化合物(A)闻起来像醛类、花朵、铃兰和油脂,而甲基取代的化合物(B)的特征为,除了具有铃兰气味特性外,还具有白色花香味特性。
EP 2 578 671 A1描述了具有强烈的清新、水性和花香气味特性的芳香味化合物,该芳香味化合物使人联想到铃兰。
WO 2017046071 A1同样描述了具有清新和花香气味特性的环己烯。
所有描述的环己烯(A)至(E)的共同之处在于其含有丙醛取代基。合成是多阶段的,并且在某些情况下以适度的产率进行。此外,通过具有外环双键的环己烯衍生物来合成这些化合物,其在化学上很复杂,因此可以选择性地制备。
对新的芳香味化合物提出了很高的要求:除了其主要特性,即气味特性外,其还应具有额外的积极的次要特性,例如在特定的使用条件下具有更高的稳定性、更高的实质性和/或扩散性或更好的粘附性。此外,其应具有非常好的生物降解性,并且在皮肤病学以及毒理学方面不会令人担心。
以上述积极的次要特性为特征的芳香味化合物能够提高芳香味化合物制剂和芳香产品制备时的有效性。例如通过使用具有更好的感官特性、更高的实质性和/或更好的粘附性的芳香味化合物,可以优化和/或最小化相应配方中芳香味化合物的数量和使用量,这导致在制备芳香产品时可持续地节约资源。
本发明的主要目的是提供具有花香气味特性,特别是铃兰花香气味特性的新化合物,即所述化合物旨在提供在很大程度上符合铃兰花香的自然气味的复杂性的气味印象。此外在其次要特性方面,这些化合物应相当于或优于现有技术中已知的铃兰气味物质。此外,新的芳香味化合物应追溯回可再生和自然界的原料,即可再生有机原料。
本发明的另一目的涉及这种新型化合物的制备。
额外的目的涉及提供具有花香气味特性,特别是铃兰气味特性的新化合物,其用作芳香味化合物或用于制备芳香味化合物制剂,以及包含这些新化合物中的至少一种新化合物的芳香产品或消费品。
根据本发明,所提出的目的通过独立权利要求的主题来解决。本发明的其他方面和优选的设计方案由从属权利要求的语言描述、下述说明书及实施例得出。
发明内容
由于以下事实,使得寻找具有铃兰气味的合适物质变得困难,从而促成本发明:
嗅觉机制不足够已知;而且
一方面特殊嗅觉与另一方面所属芳香味化合物的化学结构之间的联系尚未得到充分研究。
此外,芳香味化合物在结构构造上的微小变化已经导致了感官特性的强烈变化并损害对于人体器官的兼容性。
因此,是否能够成功找到合适的芳香味化合物在很大程度上取决于找寻者的直觉。
本发明的第一个主题涉及通式(I)的新化合物
其中可变基团R1和R2具有如下含义:
R1代表H或-CH2-CHO,和
R2代表H或-CH2-CHO,
条件是R1≠R2;
以及其立体异构体或其混合物。
在本发明的上下文中,术语“式(I)的化合物”应理解为式(I)的单一化合物以及式(I)的化合物以任何所需混合比例的所有混合物。这就是说,以下说明书中关于“式(I)的化合物”的说明既适用于式(I)的单一化合物,也适用于,包括或由将式(I)的化合物以任意混合比例混合而组成的混合物。
根据本发明,式(I)的化合物可优选以各种形式存在,该各种形式对应于可能的异构体,特别是R1和R2的区域异构体和/或式(I)的立体异构体,更确切地说,单一存在以及作为混合物形式存在。
在本发明的一个优选实施例中,区域异构体是式(I)的化合物,其中R1是-CH2-CHO基团且R2是氢原子。
在本发明的另一个优选实施例中,另一区域异构体是式(I)的化合物,其中R1是氢原子且R2是-CH2-CHO基团。
如上定义的根据本发明的式(I)的化合物也可以立体异构体的形式存在。在本发明的上下文中,术语立体异构体包括式(I)的化合物的所有可能的非对映异构体或对映异构体。
此外,式(I)的化合物的定义还包括立体异构体的混合物,特别是外消旋体或对映体富集的混合物,及其对映体纯形式。
令人惊讶地表明,式(I)的化合物提供了非常接近铃兰花自然气味复杂性的气味印象。也就是说,由式(I)的化合物提供的气味印象的特征在于卓越的自然性和复杂性,特别是在铃兰气味方面。
此外,本发明涉及式(I)的化合物,其选自式(II)的化合物和式(III)的化合物:
以及其立体异构体,特别是非对映异构体或对映异构体,或其混合物。
根据本发明的式(II)或式(III)的化合物可称为2-(5-异丙基-2-甲基环己-2-烯-1-基)乙醛或2-(6-异丙基-3-甲基环己-2-烯-1-基)乙醛。
根据本发明的式(II)或式(III)的化合物可以单一存在,也可以作为上述式(II)或式(III)的化合物的混合物形式存在。
式(II)的化合物的特征在于其特别具有醛类、花香、清新、干燥和铃兰的特性。式(III)的化合物特别是具有让人联想到铃兰的清新、醛类气味和花香的气味特性。
式(II)或式(III)的化合物可以根据式(II)或式(III)的可能的立体异构体,特别是对映异构体或非对映异构体以各种形式存在。
此外,式(II)或式(III)的化合物的定义还包括立体异构体的混合物,还特别是外消旋体或对映体富集的混合物,以及其对映体纯形式。
在根据第一方面的另一个优选的实施例中,本发明涉及如式(IIa)或式(IIb)所示的式(II)的化合物:
及其混合物。
式(IIa)的对映体纯化合物特别具有铃兰、花香和清新的特性。式(IIb)的对映体纯化合物特别具有花香、清新和醛香特性。
在另一个优选实施例中,本发明涉及如式(IIIa)或式(IIIb)所示的式(III)的化合物:
及其混合物。
式(IIIa)的对映体纯化合物特别具有醛类、清新和花香的特性,该特性使人联想到铃兰。
式(IIIb)的对映体纯化合物特别具有清新、花香、醛类和铃兰的特性。
根据本发明的式(IIa)、式(IIb)、式(IIIa)或式(IIIb)的化合物和上述的化合物以外消旋体、对映体富集的混合物或其对映体纯形式存在。
在本文中,术语“式(IIa)的化合物”或“式(IIb)的化合物”或“式(IIIa)的化合物”或“式(IIIb)的化合物”既包括单一化合物,也包括上述化合物以任何所需混合比例的所有混合物。
术语“式(I)的化合物”不仅包括式(II)的化合物、式(III)的化合物、式(IIa)或式(IIb)的化合物和式(IIIa)或式(IIIb)的化合物的单一化合物,还包括其立体异构体,以及前述化合物及其立体异构体以任何所需混合比例的所有混合物。
出人意料地是,根据本发明的化合物主要具有铃兰、花香和清新的特性。
本发明涉及根据本发明的单一化合物本身或根据本发明化合物的混合物。
因此,本发明还涉及混合物,其包含式(I)的化合物,特别是包含(a)如上定义的式(II)的至少一种化合物或其立体异构体,和(b)如上定义的式(III)的至少一种化合物或其立体异构体,或由式(I)的化合物,特别是(a)如上定义的式(II)的至少一种化合物或其立体异构体,和(b)如上定义的式(III)的至少一种化合物或其立体异构体组成。
在包含如上定义的式(II)的化合物和(ii)如上定义的式(III)的化合物或由这两类化合物组成的混合物的情况下,根据本发明以下混合物优选具有
式(II)的化合物与式(III)的化合物的质量比在0.01至99.99范围内,优选在0.1至99.9范围内,更优选在0.5至99.5范围内,更优选在1.0至99.0范围内,更优选在1.5至98.5范围内,最优选在2.0至98.0范围内;
和/或
相对于包含化合物(II)和/或(III)的混合物的总重量计,式(II)和(III)的化合物的总含量大于0.01重量%,优选大于1重量%,优选大于10重量%,更优选大于50重量%,特别优选大于90重量%。
在本发明的另一方面,本发明还包括制备式(I)的化合物、式(II)的化合物和式(III)的化合物的制备方法,其中多种替代的合成途径是可行的。
根据本发明的式(I)或式(II)的化合物可以通过以下更详述的方法合成。
根据本发明的制备式(I)或式(II)的化合物的一种可行性方案在于,已知化合物2-甲基-5-(1-甲基乙基)-2-环己烯-1-醇(IV)与乙烯基醚(R-O)的酸性反应。由此获得的缩醛(V)经酸催化裂解为乙烯基醚(VI),乙烯基醚(VI)直接热转化为所需的醛。乙烯基醚的R基团选自直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基。
另一替代可行性方案在于,已知且市售的天然物质2-甲基-5-(1-甲基乙烯基)-2-环己烯-1-醇(VII)(E.Klein,G.Ohloff,Tetrahedron,1963,19,1091;A.F.Thomas,G.Ohloff,Hel.Chim.Acta 1970,53(5),1145)与乙烯基醚(R-O)的酸性反应。由此获得的缩醛(VIII)经酸催化裂解为乙烯基醚(IX),乙烯基醚(IX)直接热转化为醛(X)。末端双键的氢化能够合成所需的醛(II)。乙烯基醚的R基团选自直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基。
根据本发明的式(I)或式(III)的化合物可以通过以下更详述的方法合成。
制备根据本发明的式(I)或式(III)的化合物的一种可行性方案在于,已知天然物质1-甲基-4-(1-甲基乙基)-2-环己烯-1-醇(XI)(E.Klein,G.Ohloff,Tetrahedron,1963,19,1091;A.F.Thomas,G.Ohloff,Hel.Chim.Acta,1970,53(5),1145。)与乙烯基醚(R-O)的酸性反应。由此获得的缩醛(XII)经酸催化裂解为乙烯基醚(XIII),乙烯基醚(XIII)直接热转化为所需的醛。乙烯基醚的R基团选自直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基。
另一替代可行性方案在于,已知化合物1-甲基-4-(1-甲基乙烯基)-2-环己烯-1-醇(XX)与乙烯基醚的酸性反应。由此获得的缩醛(XXI)在酸性催化下裂解成乙烯基醚(XXII),乙烯基醚(XXII)直接热转化为醛(XXIII)。末端双键的氢化允许合成所需的醛(III)。乙烯基醚的R基团选自直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基。
在上述根据本发明的方法的步骤(i)中,将具有式(IV)、(VII)、(XI)和(XX)的化合物转化为缩醛。为此,优选使用布朗斯台德酸或路易斯酸作为催化剂。
在上述根据本发明方法的步骤(i)中,式(V)、(VIII)、(XII)和(XXI)的化合物的R基团优选定义为链长为C1至C20的直链烷基、链长为C1至C20的支链烷基,环戊基或环己基。
上述根据本发明方法的步骤(ii)和(iii)优选以一锅法进行。在该方法中,进行酸裂解以得到乙烯基醚(VI)、(IX)、(XIII)和(XXII),并且接着在≥150℃的温度下,优选在150至250℃的温度范围下,甚至更优选在160至180℃的温度范围下,进行Claisen重排以得到化合物(II)、(III)、(X)和(XXIII)。优选使用布朗斯台德酸或路易斯酸作为催化剂。
上述根据本发明方法的步骤(iv)在常规条件下将氢气和催化剂(例如钯)施加到载体材料上进行。有利的载体材料包括:活性炭、碳、铝氧化物、金属氧化物、硅胶、沸石、粘土、粘土颗粒、无定形硅酸铝或其他无机载体。优选的载体材料是活性炭。特别优选的催化剂是活性炭上的钯。
此外,本发明还涉及根据本发明的至少一种化合物的用途,特别是上述式(I)、(II)或(III)的化合物或其立体异构体,或上述化合物或其立体异构体的混合物作为芳香味化合物,特别是作为铃兰芳香味化合物,或用于制备芳香味化合物制剂,特别是具有铃兰香味的芳香味化合物制剂的用途。
因此,本发明的另一个主题涉及一种芳香味化合物制剂,其包含如上定义的式(I)、(II)或(III)的至少一种化合物或其立体异构体,优选以感官有效量存在。
在本发明的范围中,芳香味化合物制剂是不同物质的混合物,其根据配方或配方通过规定的方法由相应物质产生。这种制剂是专门为赋予、改变或增强通常被认为是愉快或积极的所需气味印象的目的而制备和使用的。
根据本发明的芳香味化合物制剂,其特别是以香油为形式,优选具有铃兰气味,包含或由根据本发明的式(I)、(II)或(III)的至少一种化合物组成,特别是如上定义的式(I)、(II)或(III)的化合物或其立体异构体,以及一种、两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种不是式(I)、(II)或(III)的化合物的其他芳香味化合物和/或香精组成。
在一个优选实施例中,根据本发明的芳香味化合物制剂包含或由式(II)的化合物和式(III)的化合物或这些化合物的异构体组成。
通过将如上定义的式(I)、(II)或(III)的化合物组合,优选在作为优选给出的实施例之一中,利用一种或多种其他芳香味化合物和/或香精组合,可以制备令人感兴趣的新型芳香味化合物制剂。这样就可以创造出气味特别有趣、天然、新颖、原始的混合物。在上述定义的意义上,针对适合作为其他芳香味化合物和/或香精或用于根据本发明的芳香味化合物制剂中的芳香味化合物,请参见S.Arctander,Perfume and Flavor Materials,Vol.Iund II,Montclair,N.J.1969,Eigenverlag,oder K.Bauer et al.,Common Fragranceand Flavor Materials,4th Edition,Wiley-VCH,Weinheim 2001。
具体而言被提及的为:
天然原料提取物,如精油、冷凝脂(concretes)、净油(absolue)、树脂、树脂类、香脂、酊剂如龙涎香酊;杏仁油;当归籽油;当归根油;茴香油;缬草油;罗勒油;树苔无水物(absolue);海湾油;艾蒿油;苯甲酸酯;佛手柑油;蜂蜡无水物;桦树焦油;苦杏仁油;香料油;紫菜叶油;卡布鲁瓦油;凯德油;菖蒲油;樟脑油;卡南加油;豆蔻油;卡斯卡里拉油;桂皮油;卡西无水物;海狸无水物;雪松叶油;雪松木油;番石榴油;香茅油;柠檬油;卡帕瓦香脂;卡帕瓦油;香菜油;木香根油;孜然油;柏树油;达瓦纳油;萝香草油;莳萝籽油;Eau debrouts无水物;橡树苔无水物;埃莱米油;龙蒿油;柠檬桉油;桉树油;茴香油;云杉针油;高良姜油;白阿魏脂(Galbanum)树脂;天竺葵油;柚子油;愈创木油;古尔峻香脂;古尔均香脂油;蜡菊无水物;蜡菊油;姜油;鸢尾根无水物;鸢尾根油;茉莉花无水物;菖蒲油;蓝色洋甘菊油;罗马洋甘菊油;胡萝卜籽油;卡斯卡里拉油;松针油;留兰香油;香菜籽油;劳丹脂油;劳丹脂无水物;劳丹脂树脂;醒目薰衣草无水物;醒目薰衣草油;薰衣草无水物;薰衣草油;柠檬草油;独活草油;蒸馏石灰油;压榨石灰油;芳樟油;山苍子油;月桂叶油;锤油;马郁兰油;柑油;麻油;含羞草无水物;麝香粮油;麝香酊;麝香鼠尾草油;肉豆蔻油;没药无水物;没药油;桃金娘油;丁香叶油;丁香花油;橙花油;乳香无水物;乳香油;欧拉花油;橙花无水物;橘子油;牛至油;掌叶油;广藿香油;紫苏油;秘鲁香油;欧芹叶油;欧芹籽油;小粮油;薄荷油;胡椒油;全香油;松树油;波利油;玫瑰无水物;紫檀油;玫瑰油;迷迭香油;鼠尾草油;西班牙鼠尾草油;檀香油;芹菜籽油;刺槐油;八角茴香油;苯乙烯油;万寿菊油;杉木针油;茶树油;松节油;百里香油;托鲁香脂;通卡无水物;晚香玉无水物;香草提取物;紫罗兰叶无水物;马鞭草油;香根草油;杜松子油;葡萄酒酵母油;艾草油;冬青油;依兰油;牛膝草油;果子狸无水物;肉桂叶油;肉桂皮油及其馏分或从中分离的成分;
烃类中的单一芳香味化合物,例如3-蒈烯(3-Caren);α-蒎烯;β-蒎烯;α-松油烯;γ-松油烯;对伞花烃;双杂波烯;莰烯;石竹烯;雪松;法尼烯;柠檬烯;长叶烯;月桂烯;罗西美内;瓦伦烯;(E,Z)-1,3,5-十一碳三烯;苯乙烯;二苯基甲烷;
脂肪醇,例如己醇;辛醇;3-辛醇;2,6-二甲基庚醇;2-甲基-2-庚醇;2-甲基-2-辛醇;(E)-2-己烯醇;1-辛烯-3-醇;3,4,5,6,6-五甲基-3/4-庚-2-醇和3,5,6,6-四甲基-4-亚甲基庚-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛-2-醇;9-癸烯醇;10-十一烯醇;4-甲基-3-癸烯-5-醇;
脂族醛及其缩醛,例如己醛;庚醛;辛醛;壬醛;癸醛;十一醛;十二醛;2-甲基辛醛;2-甲基壬醛;(E)-2-己烯醛;(Z)-4-庚烯醛;2,6-二甲基-5-庚烯醛;10-十一烯醛;(E)-4-十烯醛;2-十二烯醛;2,6,10-三甲基-9-十一烯醛;2,6,10-三甲基-5,9-十一碳二烯醛;庚醛二乙缩醛;1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅氧基乙醛(Citronellyloxyacetaldehyd);1-(1-甲氧基丙氧基)-(E/Z)-3-己烯;
脂肪族酮及其肟,例如2-庚酮;2-辛酮;3-辛酮;2-壬酮;5-甲基-3-庚酮;5-甲基-3-庚酮肟;2,4,4,7-四甲基-6-辛烯-3-酮;6-甲基-5-庚烯-2-酮;
脂肪族含硫化合物,例如3-甲硫基己醇;3-甲基硫代己基乙酸酯;3-巯基己醇;3-巯基己基乙酸酯;3-巯基己基丁酸酯;3-乙酰硫代己基乙酸酯;1-薄荷烯-8-硫醇;
脂族腈,例如2-壬酸腈;2-十一碳烯酸腈;2-十三碳烯酸腈;3,12-十三碳二烯酸腈;3,7-二甲基-2,6-辛二烯酸腈;3,7-二甲基-6-辛烯酸腈;
脂肪族羧酸的酯,例如(E)-和(Z)-3-己烯基甲酸酯;乙酰乙酸乙酯;乙酸异戊酯;3,5,5-三甲基己基乙酸酯;3-甲基-2-丁烯基乙酸酯;(E)-2-己烯基乙酸酯;(E)-和(Z)-3-己烯基乙酸酯;乙酸辛酯;乙酸-3-辛酯;1-辛烯-3-基乙酸酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)-和(Z)-3-己烯基异丁酸酯;巴豆酸己酯;异戊酸乙酯;2-甲基戊酸乙酯;己酸乙酯;己酸烯丙酯;庚酸乙酯;庚酸烯丙酯;辛酸乙酯;(E,Z)-2,4-癸二烯酸乙酯;2-辛酸甲酯;2-壬酸甲酯;烯丙基-2-异戊氧基乙酸酯;3,7-二甲基-2,6-辛二烯酸甲酯;4-甲基-2-戊基巴豆酸酯;
无环萜烯醇,例如香叶醇;橙花醇;薰衣草醇;橙花叔醇;法尼醇;四氢芳樟醇;四氢香叶醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛烷-2-醇;2-甲基-6-亚甲基-7-辛烯-2-醇;2,6-二甲基-5,7-辛二烯-2-醇;2,6-二甲基-3,5-辛二烯-2-醇;3,7-二甲基-4,6-辛二烯-3-醇;3,7-二甲基-1,5,7-辛三烯-3-醇2,6-二甲基-2,5,7-辛三烯-1-醇;及其甲酸酯,乙酸酯,丙酸酯,异丁酸酯,丁酸酯,异戊酸酯,戊酸酯,己酸酯,巴豆酸酯,角豆酸酯(Tiglinate)和3-甲基-2-丁烯酸酯;
无环萜烯醛和酮,例如香茅醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一烯醛;香叶丙酮;以及香叶醛(Geranial),橙花醛(Neral)的二甲基和二乙基缩醛;
环状萜烯醇,例如薄荷醇;异胡薄荷醇;α-松油醇;4-松油醇;薄荷烷-8-醇;薄荷烷-1-醇;薄荷烷-7-醇;冰片;异冰片;芳樟醇氧化物;诺卜醇;雪松醇;龙涎醇;香根草醇;愈创木醇;及其甲酸酯,乙酸酯,丙酸酯,异丁酸酯,丁酸酯,异戊酸酯,戊酸酯,己酸酯,巴豆酸酯,角豆酸酯和3-甲基-2-丁烯酸酯;
环状萜烯醛和酮,例如薄荷酮;异薄荷酮;8-巯基薄荷烷-3-酮;香芹酮;樟脑;茴香;α-紫罗酮;β-紫罗酮;α-正甲基紫罗酮;β-正甲基紫罗酮;α-异甲基紫罗酮;β-异甲基紫罗酮;α-铁(alpha-Iron);β-大马烯酮;1-(2,4,4-三甲基-2-环己烯-1-基)-2-丁烯-1-酮;1,3,4,6,7,8a-六氢-1,1,5,5-四甲基-2H-2,4a-桥亚甲基萘-8-(5H)-酮;2-甲基-4-(2,6,6-三甲基-1-环己烯-1-基)-2-丁烯醛;诺卡酮;二氢诺卡酮;4,6,8-巨豆三烯-3-酮(4,6,8-Megastigmatrien-3-on);α-甜橙醛(alpha-Sinensal);β-甜橙醛;乙酰化雪松木油(甲基雪松酮);
环醇,例如4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异莰基环己醇;2,6,9-三甲基-Z2,Z5,E9-环十二碳三烯-1-醇;2-异丁基-4-甲基四氢-2H-吡喃-4-醇;
脂环族醇,例如α,3,3-三甲基环己基甲醇;1-(4-异丙基环己基)乙醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基-)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)戊-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊-1-基)-4-戊烯-2-醇;1-(2,2,6-三甲基环己基)戊-3-醇;1-(2,2,6-三甲基环己基)己-3-醇;
环族和脂环族醚,例如桉树脑;雪松基甲醚;环十二烷基甲醚;1,1-二甲氧基环十二烷;(乙氧基甲氧基)环十二烷;α-雪松烯环氧化物;3a,6,6,9a-四甲基十二氢化萘[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基十二氢化萘[2,1b]呋喃;1,5,9-三甲基-13-氧杂双环[10.1.0]十三-4,8-二烯;氧化玫瑰(Rosenoxid);2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二氧六环;
环酮和大环酮,例如4-叔丁基环己酮;2,2,5-三甲基-5-戊基环戊酮;2-庚基环戊酮;2-戊基环戊酮;2-羟基-3-甲基-2-环戊烯-1-酮;3-甲基-顺-2-戊烯-1-基-2-环戊烯-1-酮;3-甲基-2-戊基-2-环戊烯-1-酮;3-甲基-4-环十五碳烯酮;3-甲基-5-环十五碳烯酮;3-甲基环十五烷酮(3-Methylcyclopenta-decanon);4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮;4-叔戊基环己酮;5-环十六烯-1-酮;6,7-二氢-1,1,2,3,3-五甲基-4-(5H)-茚满酮;8-环十六烯-1-酮;9-环十七碳烯-1-酮(9-Cycloheptadecen-1-on);环十五酮;环十六烷酮;
脂环族醛,例如2-甲基-4-(2,2,6-三甲基-环己烯-1-基)-2-丁烯醛;4-(4-羟基-4-甲基戊基)-3-环己烯甲醛;4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛;
脂环族酮,例如1-(3,3-二甲基环己基)-4-戊烯-1-酮;2,2-二甲基-1-(2,4-二甲基-3-环己烯-1-基)-1-丙酮;1-(5,5-二甲基-1-环己烯-1-基-)4-戊烯-1-酮;2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢-2-萘烯基甲基酮(2,3,8,8-Tetramethyl-1,2,3,4,5,6,7,8-octahydro-2-naphtalenylmethylketon);甲基-2,6,10-三甲基-2,5,9-环十二碳三烯酮;叔丁基-(2,4-二甲基-3-环己烯-1-基)酮;
环状醇的酯,例如2-叔丁基环己基乙酸酯;4-叔丁基环己基乙酸酯;2-叔戊基环己基乙酸酯;4-叔戊基环己基乙酸酯;3,3,5-三甲基环己基乙酸酯;十氢-2-萘基乙酸酯;2-环戊基环戊基巴豆酸酯;3-戊基四氢-2H-吡喃-4-基乙酸酯;十氢-2,5,5,8a-四甲基-2-萘乙酸酯;4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基乙酸酯;4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基丙酸酯;4,7-桥亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基异丁酸酯;4,7-桥亚甲基八氢-5或6-茚基乙酸酯;
脂环族醇的酯,例如1-环己基乙基巴豆酸酯;
脂环族羧酸的酯,例如烯丙基-3-环己基丙酸酯;烯丙基环己氧基乙酸酯;顺式和反式甲基二氢茉莉酸酯;顺式和反式茉莉酸甲酯;2-己基-3-氧代环戊烷羧酸甲酯;2-乙基-6,6-二甲基-2-环己烯羧酸乙酯;2,3,6,6-四甲基-2-环己烯羧酸乙酯;2-甲基-1,3-二氧戊环-2-乙酸乙酯;
脂族醇,例如苯甲醇;1-苯乙醇;3-苯基丙醇;2-苯基丙醇;2-苯氧基乙醇;2,2-二甲基-3-苯基丙醇;2,2-二甲基-3-(3-甲基苯基)丙醇;1,1-二甲基-2-苯乙醇;1,1-二甲基-3-苯基丙醇;1-乙基-1-甲基-3-苯基丙醇;2-甲基-5-苯基戊醇;3-甲基-5-苯基戊醇;3-苯基-2-丙烯-1-醇;4-甲氧基苄醇;1-(4-异丙基苯基)乙醇;
脂族醇和脂族羧酸的酯,例如乙酸苄酯;丙酸苄酯;异丁酸苄酯;异戊酸苄酯;2-苯乙基乙酸酯;2-苯乙基丙酸酯;2-苯乙基异丁酸酯;2-苯乙基异戊酸酯;1-苯乙基乙酸酯;α-三氯甲基苄基乙酸酯;α,α-二甲基苯乙基乙酸酯;α,α-二甲基苯乙基丁酸酯;乙酸肉桂酯;2-苯氧乙基异丁酸酯;4-甲氧基苄基乙酸酯;
脂族醚,例如2-苯乙基甲醚;2-苯乙基异戊基醚;2-苯乙基-1-乙氧基乙醚;苯乙醛二甲基缩醛;苯乙醛二乙基缩醛;水合丙醛二甲基缩醛(Hydratropaaldehyd dimethylacetal);苯乙醛甘油缩醛;2,4,6-三甲基-4-苯基-1,3-二氧六环;4,4a,5,9b-四氢茚并[1,2-d]-m-二噁英;4,4a,5,9b-四氢-2,4-二甲基茚并[1,2-d]-m-二噁英;
芳族和脂族醛,例如苯甲醛;苯乙醛;3-苯丙醛;水合丙醛(Hydratropaaldehyd);4-甲基苯甲醛;4-甲基苯乙醛;3-(4-乙基苯基)-2,2-二甲基丙醛;2-甲基-3-(4-异丙基苯基)丙醛;2-甲基-3-(4-异丁基苯基)丙醛;3-(4-叔丁基苯基)丙醛;肉桂醛;α-丁基肉桂醛(alpha-Butylzimtaldehyd);α-己基肉桂醛(alpha-Hexylzimtaldehyd);3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧基苯甲醛;3,4-二甲氧基苯甲醛;2-甲基-3-(4-甲氧基苯基)丙醛;2-甲基-3-(4-亚甲基二氧基苯基)丙醛;
芳香族和脂肪族酮,例如苯乙酮;4-甲基苯乙酮;4-甲氧基苯乙酮;4-叔丁基-2,6-二甲基苯乙酮;4-苯基-2-丁酮;4-(4-羟基苯基)-2-丁酮;1-(2-萘基)乙醇;2-苯并呋喃基乙酮;(3-甲基-2-苯并呋喃基)乙酮;二苯甲酮;1,1,2,3,3,6-六甲基-5-茚满基甲基酮;6-叔丁基-1,1-二甲基-4-茚满基甲基酮;1-[2,3-二氢-1,1,2,6-四甲基-3-(1-甲基乙基)-1H-5-茚基]乙酮;5’,6’,7’,8’-四氢-3’,5’,5’,6’,8’,8’-六甲基-2-萘乙酮;
芳族和脂族羧酸及其酯,例如苯甲酸;苯乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄酯;苯乙酸甲酯(Methylphenylacetat);苯乙酸乙酯;香叶基苯乙酸酯;苯乙酸苯乙酯;肉桂酸甲酯(Methylcinnmat);肉桂酸乙酯;肉桂酸苄酯;肉桂酸苯乙酯;肉桂酸肉桂酯(Cinnamylcinnamat);苯氧乙酸烯丙基酯;水杨酸甲酯;水杨酸己酯;水杨酸环己酯;水杨酸顺-3-己烯酯;水杨酸苄酯;水杨酸苯乙酯;2,4-二羟基-3,6-二甲基苯甲酸甲酯;3-苯基甘油酸乙酯;3-甲基-3-苯基甘油酸乙酯;
含氮芳族化合物,例如2,4,6-三硝基-1,3-二甲基-5-叔丁基苯;3,5-二硝基-2,6-二甲基-4-叔丁基苯乙酮;肉桂酸腈;3-甲基-5-苯基-2-戊烯酸腈;3-甲基-5-苯基戊酸腈;氨基苯甲酸甲酯(Methylanthranilat);甲基-N-氨基苯甲酸甲酯;氨基苯甲酸甲酯与7-羟基-3,7-二甲基辛醛,2-甲基-3-(4-叔丁基苯基)丙醛或2,4-二甲基-3-环己烯甲醛的席夫碱;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;2-(3-苯丙基)吡啶;吲哚;粪臭素;2-甲氧基-3-异丙基吡嗪;2-异丁基-3-甲氧基吡嗪;
酚类,苯醚类和苯酯类,例如甲基胡椒酚(Estragole);茴香醚;丁香基甲醚;异丁香酚;异丁香基甲醚;百里香酚;香芹酚;二苯醚;β-萘甲醚;β-萘乙醚;β-萘异丁基醚;1,4-二甲氧基苯;异乙酸丁子香氛酯(Eugenyl acetat);2-甲氧基-4-甲基苯酚;2-乙氧基-5-(1-丙烯基)苯酚;对甲苯基苯基乙酸酯;
杂环化合物,例如2,5-二甲基-4-羟基-2H-呋喃-3-酮;2-乙基-4-羟基-5-甲基-2H-呋喃-3-酮;3-羟基-2-甲基-4H-吡喃-4-酮;2-乙基-3-羟基-4H-吡喃-4-酮;
内酯,例如1,4-辛内酯;3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸烯-1,4-内酯;1,4-十一烷内酯;1,4-十二烷内酯;1,5-癸内酯;1,5-十二烷内酯;4-甲基-1,4-癸内酯;1,15-十五烷内酯;1,16-十六烷内酯;9-十六烯-1,16-内酯;10-氧杂-1,16-十六烷内酯;11-氧杂-1,16-十六烷内酯;12-氧杂-1,16-十六烷内酯;乙烯-1,12-十二烷二酸酯(Ethylen-1,12-dodecandioat);乙烯-1,13-十三烷二酸酯;2,3-二氢香豆素;八氢香豆素。
在一个优选实施例中,根据本发明的芳香味化合物制剂,特别是香油形式的芳香味化合物制剂,包含根据本发明的具有铃兰气味的式(I)、(II)或(III)的一种、两种或多种芳香味化合物,以及可选择性地包含具有花香、甜香、水性、粉状气味的一种或多种其他芳香味化合物。
在根据本发明的芳香味化合物制剂,特别是香油中,相对于芳香味化合物制剂的总重量计,如上定义的式(I)、(II)或(III)的至少一种化合物或其异构体的量为0.0001至40重量%,优选0.001至25重量%。除了作为溶液或乳液中的液体使用外,本发明的化合物或包含其的芳香味化合物制剂,例如香油,还可以吸附在固体上或(微)封装在载体中使用。这些呈现方式可以确保,气味物质在产品中细密地分布以及在使用过程中可控制地释放。这种固体可以是多孔无机材料,例如轻质硫酸盐、硅胶、沸石、石膏、粘土、粘土颗粒、气体混凝土(Gasbeton)等,或有机材料,例如木材、纤维素基材料、糖或塑料,例如PVC、聚醋酸乙烯酯或聚氨酯。
封装产品例如可以通过喷射干化,作为包合物或作为挤出产品存在。例如,可以通过所谓的凝聚方法借助于胶囊材料来实现香油的微封装化,胶囊材料例如由聚氨酯类材料或软明胶制成。被喷射干化过的香油例如可以通过喷射干化包含香油的乳液或分散体来制备,其中可以使用改性淀粉、蛋白质、糊精和植物胶作为载体。包合物可以例如通过将香油和环糊精或尿素衍生物的分散体引入合适的溶剂(例如水)来制备。
挤出产品可以通过将香油与合适的蜡质物质融合并通过挤出随后固化,需要时在合适的溶剂中,例如异丙醇中进行。
在更有针对性地进行香味释放方面,吸附物和包封产物可以通过采用合适材料涂覆以进一步优化,为此可以优选使用蜡质塑料,例如聚乙烯醇。
在本发明的一个优选实施例中,在吸附在载体上使用的香油组合物中,相对于香油组合物的总重量计,如上定义的根据本发明的式(I)、(II)或(III)的化合物或其异构体的用量为0.00001至5重量%,优选0.00001至1重量%,更优选0.0005至0.01重量%。
如上定义的用作芳香味化合物的本发明的化合物及其混合物以及如上定义的本发明的芳香味化合物制剂特别用于制备芳香产品。
因此,本发明还涉及芳香产品或消费品,包括其初产品和中间产品,其包含根据本发明的芳香味化合物或芳香味化合物制剂。根据本发明的芳香产品或消费品优选以感官有效量包含如上定义的根据本发明的化合物。在此,根据本发明的化合物或者单独使用,或者是根据本发明的混合物或芳香味化合物制剂的组分使用。
芳香产品或消费品通常含有多种不同的化合物。使用根据本发明的化合物是特别有利的,因为其反应活性低,使得根据本发明的化合物和消费品的成分都不会发生不利的变化。此外,根据本发明的化合物在实现所需香气作用所需的浓度下不会对消费品的物理或物理化学性质(例如粘度或pH)产生不利影响。
芳香产品或消费品中包含的物质通常是防腐剂、研磨剂(Abrasiva)、抗痤疮剂、抗衰老剂、抗菌剂(antibakterielle Mittel)、抗脂肪团剂、抗头皮屑剂、抗炎剂、抗刺激剂、刺激抑制剂、微生物抑制剂、抗氧化剂、收敛剂、抗汗剂、抗菌剂(antiseptische Mittel)、抗静电剂、粘合剂、缓冲剂、载体材料、螯合剂、细胞兴奋剂、清洁剂、护理剂、脱毛剂、表面活性物质、除臭剂、止汗剂、润肤剂、乳化剂、酶、精油、纤维、成膜剂、固定剂、发泡剂、泡沫稳定剂、防起泡剂、泡沫增强剂、杀菌剂、胶凝剂、凝胶化剂、护发剂、头发定型剂、头发拉直剂、保湿剂、滋润物质、保湿物质、漂白剂、增强剂、去污剂、光学增白剂、浸渍剂(Mittel)、防污剂、减摩剂、润滑剂、保湿剂、软膏、遮光剂、增塑剂、覆盖剂、抛光剂、光泽剂、聚合物、粉末、蛋白质、再脂化剂、研磨剂(abschleifende Mittel)、有机硅、皮肤舒缓剂、皮肤清洁剂、皮肤护理剂、皮肤愈合剂、皮肤增白剂、皮肤保护剂、皮肤柔软剂、凉爽剂、皮肤凉爽剂、增温剂、皮肤增温剂、稳定剂、紫外线吸收剂、紫外线过滤剂、清洗剂、织物柔软剂、悬浮剂、皮肤晒黑剂、增稠剂、维生素、油、蜡、脂肪、磷脂、饱和脂肪酸、单不饱和脂肪酸或多不饱和脂肪酸、a-羟基酸、多羟基脂肪酸、液化剂、着色剂、护色剂、颜料、防腐剂、香精、调味剂、芳香味化合物、多元醇、表面活性剂、电解质、有机溶剂或有机硅衍生物。根据本发明的化合物在混合物中与这些物质具有高兼容性。
在芳香产品或消费品中,根据本发明的芳香味化合物的量比重,即如上定义的根据本发明的式(I)、(II)或(III)的化合物或其同分异构体,或根据本发明的芳香味化合物制剂的量比重,计为0.0001至5重量%,优选0.001至2重量%,特别优选0.001至1重量%。
在本发明的含义中,芳香产品或消费品是清洗剂和清洁剂,卫生或护理产品,特别是来自身体和头发护理,化妆品,家用领域的产品,精细香料(香水),空气护理和空气清新剂,特别是织物柔软剂,漂白剂,消毒剂,香味释放系统,皮肤防晒剂,头发护理产品和除臭剂。特别地,消费品是酸性,碱性和中性清洗剂,例如地板清洁剂,窗玻璃清洁剂,餐具清洗剂,浴室和卫生清洁剂,擦洗乳,固体和液体厕所清洁剂,粉末和泡沫地毯清洁剂,液体清洗剂,粉末清洗剂,衣物预处理剂如漂白剂,浸泡剂和污渍去除剂,衣物织物柔软剂,清洗肥皂,清洗片剂,消毒剂,表面消毒剂及液体形式,凝胶状形式或涂覆在固体载体上的空气改善剂,包括用于厕所香味的气雾剂喷雾剂,蜡和抛光剂如家具抛光剂,地板蜡,鞋油和身体护理产品,例如固体和液体肥皂,沐浴露,洗发水,剃须香皂,剃须泡沫,沐浴油,水包油型油包水型/>和水包油包水型/>的化妆品乳液,例如,护肤霜和乳液,面霜和乳液,防晒霜和乳液,晒后霜和乳液,护手霜和乳液,足部霜和乳液,脱毛霜和乳液,须后霜,须后霜和乳液,须前霜,晒黑霜和乳液,护发产品,如喷发剂,发胶,护发剂,护发素,永久和半永久染发剂,定型剂(如冷浪和直发剂),洗发剂,发乳和乳液,清爽湿巾,除臭剂和止汗剂,例如腋下喷雾剂,滚装剂,除臭棒,除臭剂和装饰性化妆品例如彩妆(Make-Up)。
最后,本发明还涉及一种用于芳香产品或消费品的加香方法,其包括将根据本发明的至少一种化合物或根据本发明的芳香味化合物制剂添加到待加香产品或消费品中。根据本发明的化合物或根据本发明的芳香味化合物制剂在该方法中的优点在于其能够易于掺入消费品中。
如上所述的本发明化合物的特征在于,其提供了在很大程度上符合铃兰花的自然气味的复杂性的气味印象。此外,其可以由可再生和天然的原料,即可再生资源制成。根据本发明化合物的另一个优点是其易于获得:其合成基于内环环己烯而进行,而非以复杂方式制备的外环己烯。
具体实施方式
下面借助实施例更详细地阐述了本发明。
实施例1:2-((5-异丙基-2-甲基-环己-2-烯-1-基)乙醛的制备
将100g 5-异丙基-2-甲基环己-2-烯-1-醇(0.65mol)和0.4g 85%磷酸加入具有顶部搅拌棒、恒温器连接部、冷却器和氮气环境的1升双壁容器中。然后,在35℃下在1至2小时内滴加98g丁基乙烯基醚(0.98mol)。针对后续反应,将混合物在35℃下再搅拌6小时。在室温下,将混合物用5%苏打溶液洗涤,然后用5%氯化钠溶液洗涤,然后蒸发。粗产量为165g。
首先将粗产物与165g二苄基醚和6.5g己酸一起加入具有磁力搅拌器、20cmVigreux塔(Vigreuxkolonne)和蒸馏桥(Destillations brücke)的500ml三颈烧瓶中,并在90mbar下加热。在160-175℃下,将形成的低沸物在5个小时内,在塔顶温度达到约80℃的情况下蒸馏出。随后对粗产物进行蒸馏(底部温度:125-170℃,塔顶温度:70-110℃,真空:1mbar)。蒸馏出72g。根据DB-1-GC或GCMS,60%的产物作为顺式/反式异构体形成。在蒸馏塔(Fischer500AC)上对两种异构体进行分离。1mbar下的沸点:2-(5-异丙基-2-甲基环己-2-烯-1-基)乙醛:71℃,2-(5-异丙基-2-甲基环己-2-烯-1-基)乙醛:73℃。
2-(5-异丙基-2-甲基-环己-2-烯-1-基)乙醛:m/z:43(11),55(14),67(16),81(28),93(100),109(6),119(10),136(45),147(1),180(5)
气味描述:醛类气味,铃兰花香,清新。
2-(5-异丙基-2-甲基-环己-2-烯-1-基)乙醛:m/z:43(13),55(17),67(21),81(33),93(100),109(9),119(13),136(55),147(2),180(4)
气味描述:清新,铃兰花香,醛类气味。
实施例2:2-(6-异丙基-3-甲基-环己-2-烯-1-基)乙醛的制备
在2升搅拌器中加入122g(0.8mol)薄荷酮(Piperiton)和700ml甲醇。在0-5℃下,缓慢加入80g 25%(0.5mol)氢氧化钠溶液。温度上升到大约20℃。在轻微冷却下,在28-33℃下在1小时内滴加181g 30%(1.6mol)过氧化氢。然后将混合物在28℃下再搅拌6小时。然后将混合物倒入1000mL水中并每次用300mL MTBE萃取两次。将MTBE相合并并依次用水,10%碘化钾溶液和水洗涤而不含过氧化物,然后蒸发。得到130g粗产物。根据GC/GCMS,反式薄荷酮环氧化物(trans-Piperitonepoxid)和顺式薄荷酮环氧化物以1:3.5的比例存在。
首先将粗产物与500ml甲醇一起装入2升搅拌器中,并在0-5℃下加入50g(1mol)一水合肼。温度上升到17-20℃。在冷却和氮气释放的情况下,在20-25℃下在30分钟内滴加60g(1mol)乙酸。将混合物再搅拌2小时。将混合物倒入1500ml水中,然后每次用500ml MTBE萃取两次。将MTBE相合并并依次用水和饱和碳酸氢钠洗涤,然后蒸发。得到99g粗产物。根据GC/GCMS,反式-4-异丙基-1-甲基环己-2-烯-1-醇和顺式-4-异丙基-1-甲基环己-2-烯-1-醇以1:3.5的比例存在。在14mbar下,在85-102℃的沸点下,在30cm填料塔上蒸馏得到26g馏分,其通过GC/GCMS包含19%的反式-4-异丙基-1-甲基环己-2-烯-1-醇和67%的顺式-4-异丙基-1-甲基环己-2-烯-1-醇。
首先将馏出物(26g)与0.1g 85%磷酸一起装入具有磁力搅拌器、恒温器连接部、冷却器和氮气环境的0.1升双壁容器中。然后在35℃下在1至2小时内滴加22g(0.22mol)丁基乙烯基醚。针对后续反应,将混合物在35℃下再搅拌2小时。在室温下,将混合物用5%苏打溶液洗涤,然后用5%氯化钠溶液洗涤,然后在60℃和700至5mbar下在旋转蒸发器上蒸发。产率为31.3g。
首先将30g粗产物与30g二苄基醚和1.5g己酸一起装入具有磁力搅拌器、20cmVigreux塔和蒸馏桥的250ml三颈烧瓶中,并在90mbar下加热。在160-175℃下,在3个小时内在塔顶温度达到约80℃的情况下,将形成的低沸物蒸馏出。随后蒸馏粗产物(底部温度125-170℃,塔顶温度65-90℃,真空1mbar)。蒸馏出10g。
根据DB-1-GC或GCMS,产生60%的产物(顺式/反式异构体)。
m/z:43(17),55(23),67(36),81(100),93(77),110(19),119(18),136(47),165(13),180(14)
气味描述:醛类气味,清新,铃兰花香。
m/z:43(19),55(27),67(40),81(100),93(95),110(24),119(21),136(51),165(15),180(13)
气味描述:清新,醛类气味,铃兰花香。
实施例3:香油A
香油A1或A2的组成:
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当计量加入6重量%的香油A1或A2时,得到以下结果,与香油A1相比,在香油A2中添加2-(5-异丙基-2-甲基-环己-2-烯-1-基)乙醛增强了花香方面的特性。
实施例4:香油B
香油B1或B2的组成:
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当计量加入0.5重量%的香油B1或B2时,得到以下结果:由于2-(6-异丙基-3-甲基环己-2-烯-1-基)乙醛的比例,香油B2具有比不含2-(6-异丙基-3-甲基环己-2-烯-1-基)乙醛的香油B1更强的花香特性。此外,香油B2显示出比香油B1更清新的高等特性。
Claims (22)
1.式(I)的化合物
其中
R1代表H或-CH2-CHO,和
R2代表H或-CH2-CHO,
条件是R1≠R2;
以及其立体异构体或其混合物;
所述化合物具有铃兰气味。
2.根据权利要求1所述的化合物,其特征在于,式(I)的化合物由以下式(II)或式(III)表示:
以及其立体异构体,特别是非对映异构体或对映异构体,或其混合物。
3.根据权利要求2所述的化合物,其特征在于,式(II)的化合物由以下式(IIa)或式(IIb)表示:
或其混合物。
4.根据权利要求2所述的化合物,其特征在于,式(III)的化合物由以下式(IIIa)或式(IIIb)表示:
或其混合物。
5.一种混合物,其包含根据权利要求2至4中任一项所述的式(II)的至少一种化合物或其立体异构体,和式(III)的至少一种化合物或其立体异构体,或其由根据权利要求2至4中任一项所述的式(II)的至少一种化合物或其立体异构体,和式(III)的至少一种化合物或其立体异构体组成。
6.一种根据权利要求1、2或3所述的式(I)或式(II)的化合物的制备方法,包括以下步骤:
(i)化合物2-甲基-5-(1-甲基乙基-)2-环己烯-1-醇(IV)与至少一种乙烯基醚的酸性反应,以获得缩醛(V);(ii)通过酸催化将步骤(i)中获得的缩醛(V)裂解为乙烯基醚(VI);和
(iii)将步骤(ii)中获得的乙烯基醚(VI)热转化为醛(II);
根据以下反应流程图:
其中,R基团选自由直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基组成的组。
7.一种根据权利要求1、2或3所述的式(I)或式(II)的化合物的制备方法,包括以下步骤:
(i)化合物2-甲基-5-(1-甲基乙烯基)-2-环己烯-1-醇(VII)与至少一种乙烯基醚的酸性反应,以获得缩醛(VIII);
(ii)通过酸催化将步骤(iv)中获得的缩醛(VIII)裂解为乙烯基醚(IX);
(iii)将步骤(v)中获得的乙烯基醚(IX)热转化为醛(X);和
(iv)氢化末端双键以获得醛(II);
根据以下反应流程图:
其中,R基团选自由直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基组成的组。
8.一种根据权利要求1、2或4所述的式(I)或式(III)的化合物的制备方法,包括以下步骤:
(i)化合物1-甲基-4-(1-甲基乙基-)-2-环己烯-1-醇(XI)与至少一种乙烯基醚的酸性反应,以获得缩醛(XII);
(ii)通过酸催化将步骤(vii)中获得的缩醛(XII)裂解为乙烯基醚(XIII);和
(iii)将步骤(viii)中获得的乙烯基醚(XIII)热转化为醛(III);
根据以下反应流程图:
其中,R基团选自由直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基组成的组。
9.一种根据权利要求1、2或4所述的式(I)或式(III)的化合物的制备方法,包括以下步骤:
(i)化合物1-甲基-4-(1-甲基乙烯基)-2-环己烯-1-醇(XX)与至少一种乙烯基醚的酸性反应,以获得缩醛(XXI);
(ii)通过酸催化将步骤(vii)中获得的缩醛(XXI)裂解为乙烯基醚(XXII);
(iii)将步骤(viii)中获得的乙烯基醚(XXII)热转化为醛(XXIII);和
(iv)氢化末端双键以获得醛(III);
根据以下反应流程图:
其中,R基团选自由直链C1至C20烷基、支链C1至C20烷基、环戊基和环己基组成的组。
10.根据权利要求1-5中任一项所述的式(I)、(II)或(III)的至少一种化合物或其立体异构体、或式(I)、(II)或(III)的化合物的混合物或其立体异构体的混合物作为芳香味化合物或用于制备芳香味化合物制剂的用途。
11.一种芳香味化合物或芳香味化合物制剂,其包含根据权利要求1-4中任一项所述的式(I)、(II)或(III)的至少一种化合物或其立体异构体。
12.根据权利要求11所述的芳香味化合物或芳香味化合物制剂,其特征在于,所述化合物或其立体异构体以感官有效量存在。
13.根据权利要求11所述的芳香味化合物制剂,还包含一种或多种附加的芳香味化合物和/或芳香族化合物,其特征在于,所述一种或多种附加的芳香味化合物和/或芳香族化合物选自:由天然原料的提取物和/或单味剂组成的组。
14.根据权利要求13所述的芳香味化合物制剂,其特征在于,所述天然原料的提取物为精油、冷凝脂、净油、树脂、类树脂、香脂或酊剂。
15.根据权利要求13所述的芳香味化合物制剂,其特征在于,所述单味剂选自烃、脂族醇、脂族醛及其缩醛、脂族酮及其肟、脂族含硫化合物、脂族腈、脂族羧酸的酯、无环萜醇、无环萜醛和酮、环状萜醇、环状萜醛和酮、环状醇、环脂醇、环状和环脂醚、环状和大环酮、环脂醛、环脂酮、环状醇的酯、环脂醇的酯、脂族醇、脂族醇和脂族羧酸的酯、脂族醚、芳族和脂族醛、芳族和脂族酮、芳族和脂族羧酸及其酯、含氮芳族化合物、酚、苯基醚和苯基酯、杂环化合物、内酯。
16.根据权利要求11-15中任一项所述的芳香味化合物制剂,其特征在于,相对于所述芳香味化合物制剂的总重量计,根据权利要求1-4中任一项所述的式(I)、(II)或(III)的化合物的总量为0.00001至5重量%。
17.根据权利要求16所述的芳香味化合物制剂,其特征在于,相对于所述芳香味化合物制剂的总重量计,根据权利要求1-4中任一项所述的式(I)、(II)或(III)的化合物的总量为0.00001至1重量%。
18.根据权利要求17所述的芳香味化合物制剂,其特征在于,相对于所述芳香味化合物制剂的总重量计,根据权利要求1-4中任一项所述的式(I)、(II)或(III)的化合物的总量为0.0005至0.01重量%。
19.芳香产品,其包含:根据权利要求11至18中任一项所述的芳香味化合物或芳香味化合物制剂,以及可选择地补充剂。
20.根据权利要求19所述的芳香产品,其特征在于,所述补充剂为载体。
21.根据权利要求19所述的芳香产品,还包含一种或多种添加剂,所述一种或多种添加剂选自:由防腐剂、研磨剂、抗痤疮剂、抗衰老剂、抗菌剂、抗脂肪团剂、抗头皮屑剂、抗炎剂、抗刺激剂、刺激抑制剂、微生物抑制剂、抗氧化剂、收敛剂、抗汗剂、抗菌剂、抗静电剂、粘合剂、缓冲剂、载体材料、螯合剂、细胞兴奋剂、清洁剂、护理剂、脱毛剂、表面活性物质、除臭剂、止汗剂、润肤剂、乳化剂、酶、精油、纤维、成膜剂、固定剂、发泡剂、泡沫稳定剂、防起泡剂、泡沫增强剂、杀菌剂、胶凝剂、凝胶化剂、护发剂、头发定型剂、头发拉直剂、湿润剂、滋润物质、保湿物质、漂白剂、增强剂、去污剂、光学增白剂、浸渍剂、防污剂、减摩剂、润滑剂、保湿剂、软膏、遮光剂、增塑剂、覆盖剂、抛光剂、光泽剂、聚合物、粉末、蛋白质、再脂化剂、研磨剂、有机硅、皮肤舒缓剂、皮肤清洁剂、皮肤护理剂、皮肤愈合剂、皮肤增白剂、皮肤保护剂、皮肤柔软剂、凉爽剂、皮肤凉爽剂、增温剂、皮肤增温剂、稳定剂、紫外线吸收剂、紫外线过滤剂、清洗剂、织物柔软剂、悬浮剂、皮肤晒黑剂、增稠剂、维生素、油、蜡、脂肪、磷脂、饱和脂肪酸、单不饱和脂肪酸或多不饱和脂肪酸、a-羟基酸、多羟基脂肪酸、液化剂、着色剂、护色剂、颜料、防腐剂、香精、调味剂、芳香味化合物、多元醇、表面活性剂、电解质、有机溶剂或有机硅衍生物组成的组。
22.根据权利要求19-21中任一项所述的芳香产品,所述芳香产品选自:清洗剂和清洁剂、卫生或护理产品,特别是在家用的身体和头发护理、化妆品领域,精细香料或香水、空气护理和空气清新剂。
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