CN117986090A - 具有玫瑰气味的新型香味剂 - Google Patents
具有玫瑰气味的新型香味剂 Download PDFInfo
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- CN117986090A CN117986090A CN202311721363.XA CN202311721363A CN117986090A CN 117986090 A CN117986090 A CN 117986090A CN 202311721363 A CN202311721363 A CN 202311721363A CN 117986090 A CN117986090 A CN 117986090A
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- CN
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- Prior art keywords
- cyclohexane
- methylbutyl
- formula
- fragrances
- fragrance
- 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.)
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- 239000003205 fragrance Substances 0.000 title claims abstract description 313
- 241000220317 Rosa Species 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000000203 mixture Substances 0.000 claims abstract description 127
- -1 3-isopentyl residue Chemical group 0.000 claims abstract description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 15
- 230000002708 enhancing effect Effects 0.000 claims abstract description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 239000003921 oil Substances 0.000 claims description 78
- PIGBSANYUUUPIC-UHFFFAOYSA-N 3-(3-methylbutyl)cyclohexan-1-one Chemical compound CC(C)CCC1CCCC(=O)C1 PIGBSANYUUUPIC-UHFFFAOYSA-N 0.000 claims description 54
- 235000019640 taste Nutrition 0.000 claims description 52
- PKXCDPLNZWFOFM-UHFFFAOYSA-N 3-(3-methylbutyl)cyclohexan-1-ol Chemical compound CC(C)CCC1CCCC(O)C1 PKXCDPLNZWFOFM-UHFFFAOYSA-N 0.000 claims description 49
- 239000002304 perfume Substances 0.000 claims description 40
- BUZQSNSPVVCNMW-UHFFFAOYSA-N 2-(3-methylbutyl)cyclohexan-1-ol Chemical compound CC(C)CCC1CCCCC1O BUZQSNSPVVCNMW-UHFFFAOYSA-N 0.000 claims description 32
- BPUBMURFUMRSSA-UHFFFAOYSA-N 4-(3-methylbutyl)cyclohexan-1-one Chemical compound CC(C)CCC1CCC(=O)CC1 BPUBMURFUMRSSA-UHFFFAOYSA-N 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- QNRGJHPSMHZLCY-UHFFFAOYSA-N 4-(3-methylbutyl)cyclohexan-1-ol Chemical compound CC(C)CCC1CCC(O)CC1 QNRGJHPSMHZLCY-UHFFFAOYSA-N 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 27
- 239000006210 lotion Substances 0.000 claims description 26
- 239000006071 cream Substances 0.000 claims description 25
- NUABBYCKUCDQBN-UHFFFAOYSA-N 2-(3-methylbutyl)cyclohexan-1-one Chemical compound CC(C)CCC1CCCCC1=O NUABBYCKUCDQBN-UHFFFAOYSA-N 0.000 claims description 24
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- 239000000047 product Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
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- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 10
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- TWXUTZNBHUWMKJ-UHFFFAOYSA-N Allyl cyclohexylpropionate Chemical compound C=CCOC(=O)CCC1CCCCC1 TWXUTZNBHUWMKJ-UHFFFAOYSA-N 0.000 claims description 6
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- ZNPGEERBEOWCEF-XVNBXDOJSA-N 1-cyclohexylethyl (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(C)C1CCCCC1 ZNPGEERBEOWCEF-XVNBXDOJSA-N 0.000 claims description 5
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 5
- UEPHOITVJAVVRX-UHFFFAOYSA-N ethyl 2-cyclopent-2-en-1-ylacetate Chemical compound CCOC(=O)CC1CCC=C1 UEPHOITVJAVVRX-UHFFFAOYSA-N 0.000 claims description 5
- 239000000077 insect repellent Substances 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- FMBDBSHYZMEEAU-UHFFFAOYSA-N 1-(methoxymethylidene)-3-(3-methylbutyl)cyclohexane Chemical compound CC(C)CCC1CCCC(=COC)C1 FMBDBSHYZMEEAU-UHFFFAOYSA-N 0.000 claims description 4
- ZSKIYTIKMJYODY-UHFFFAOYSA-N 1-(methoxymethylidene)-4-(3-methylbutyl)cyclohexane Chemical compound CC(C)CCC1CCC(=COC)CC1 ZSKIYTIKMJYODY-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052751 metal Inorganic materials 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 235000019605 sweet taste sensations Nutrition 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001241 acetals Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
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- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000002596 lactones Chemical class 0.000 claims description 3
- 150000002989 phenols Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- KSWGHVZUIAOIOZ-UHFFFAOYSA-N 1-(methoxymethylidene)-2-(3-methylbutyl)cyclohexane Chemical compound CC(C)CCC1CCCCC1=COC KSWGHVZUIAOIOZ-UHFFFAOYSA-N 0.000 claims description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 2
- YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 238000007239 Wittig reaction Methods 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 230000002951 depilatory effect Effects 0.000 claims description 2
- 150000002085 enols Chemical class 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 claims 1
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Abstract
本发明主要涉及下式(I)的化合物的用途,其中X表示氧原子、‑CHO基团、‑OH基团或‑CH2OH基团,在虚线之一的相应位置上分别存在单键或双键,其中当X为OH基团时存在至少一个双键,并且3‑异戊基残基或3‑异戊‑2‑烯基残基在相对于X基团的邻位、间位或对位与环相连,所述化合物用作香味剂和/或芳香剂。本发明另外涉及包含一种或多种此类化合物的香味剂和芳香物质组合物、包含一种或多种此类化合物的有香味或芳香化的制品以及用于赋予、改变和/或增强特定气味味调的相应方法。
Description
本专利申请是申请日为2018年7月23日,发明名称为“具有玫瑰气味的新型香味剂”的中国专利申请201880095963.0的分案申请。
技术领域
本发明主要涉及下式(I)的化合物作为香味剂和/或芳香剂的用途。本发明另外涉及包含一种或多种此类化合物的香味剂和/或芳香剂组合物、包含一种或多种此类化合物的有香味的和芳香化的制品以及用于赋予、改变和/或增强特定气味味调和/或味道味调的对应方法。
背景技术
在US 2010/0130397中,例如描述了4-异戊基环己醇作为芳香剂的用途。
尽管已经存在许多香味剂和芳香剂,在香水和芳香物质工业中总体上仍然需要新的香味剂和芳香剂。例如,对如下香味剂或芳香剂存在需要:所述香味剂或芳香剂能够(在香味剂或芳香剂组合物中)产生除了主气味味调或味道味调之外的其他感兴趣的味调并且用其新颖的或原创的嗅觉特性来扩展香水制造者的可能性。尤其感兴趣的是具有能够与花香和/或果香香味剂和/或芳香剂进行和谐组合的气味味调的香味剂和/或芳香剂。在此优选应将不同气味方面和味调叠加,以便由此产生总体上复杂的气味印象。
为了创造新型组合物,总是需要具有特殊感受特性的香味剂和/或芳香剂,它们适合用作具有复杂感受特征的新型香水组合物的基础。除了某一种味调之外,所寻找的优选的香味剂和/或芳香剂应具有为其赋予特征和复杂性的其他味调和方面。
寻找适合的玫瑰类物质(这产生了本发明)由于以下状况而变得困难:
i)气味感受的机理不是充分已知的;
ii)一方面的特殊的气味感受与另一方面的相关联的香味剂和/或芳香剂的化学结构之间的关系没有得到足够的研究;
iii)通常而言,对已知香味剂和/或芳香剂的结构性构造的甚至很小变化就造成感受特性的强烈变化并且影响人类器官的耐受性。
因此,寻找适合的香味剂和/或芳香剂成功与否很大程度上依赖于寻找者的直觉。
现在的主要目的在于找到具有感兴趣的、优选复杂的且原创的感受特征并且适合作为在香水制造中使用的香味剂或芳香剂的香味剂和/或芳香剂。
在本发明的范围内尤其寻找如下物质:所述物质可以具有或赋予、改变和/或增强以下味调中的一种、多种或所有:青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味。尤其应找到具有如下味调的物质:所述味调可以优选具有花香和/或果香味调中的至少一种并且可以优选另外闻起来有玫瑰味或可以赋予玫瑰味调。
所寻找的物质应能够实现制备具有特殊的气味味调和方面的新型香味剂和/或芳香剂组合物。在此有利的可能是使用尤其适合用于与具有木材味调和/或花香味调和/或果香味调的其他香味剂和/或芳香剂组合的那些物质。
此外,实现这个主要目的的香味剂和/或芳香剂应优选地具备除了其主要的、即嗅觉上的特性之外还具备另外有利的次要特性,例如在某些应用条件下的高稳定性、高扩散度、良好的附着能力、高亲和性气味增强特性(所谓的提升或加强效果)和/或在与另外的香味剂和/或芳香剂组合时对其自然性、清新性、填充性、(散发)力度和/或传播性进行补充,从而可以实现显著的感官效果。
本发明的另一个目的涉及此类新型香味剂和/或芳香剂的制备,所述香味剂和/或芳香剂呈其异构体及异构体混合物的任何形式。
另一个目的涉及提供新型的化合物以用作香味剂和芳香剂,优选提供混合物,以及提供包含这些混合物的消费品及其制备。
这些目的通过在主权利要求中限定的特征组合来实现。优选的实施方式是从属权利要求的主题。
发明内容
在第一方面,本发明涉及式(I)的化合物用作香味剂和/或芳香剂的用途,
其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在虚线之一的相应位置上分别存在单键或双键,当X为OH基团时存在至少一个双键,并且其中3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位中与环相连,其前提条件是,当在环中存在双键时,则3-异戊基残基或3-异戊-2-烯基残基作为邻位或间位取代基直接结合到这个双键上。
在此处和下文中,一种特别优选的替代方案是式(Ia)的化合物用作香味剂和/或芳香剂的用途,
其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在虚线之一的相应位置上分别存在单键或双键,并且当X为OH基团时,存在至少一个双键。
在此处和下文中,另一种特别优选的替代方案是式(Ib)的化合物用作香味剂和/或芳香剂的用途,
其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在虚线之一的相应位置上分别存在单键或双键,并且当X为OH基团时,存在至少一个双键。
在此处和下文中,一种替代的特别优选的替代方案是式(Ic)的化合物用作香味剂和/或芳香剂的用途,
其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在虚线之一的相应位置上分别存在单键或双键,并且当X为OH基团时,存在至少一个双键。
在此处以及在下文中,式(I)、式(Ia)、式(Ib)和/或式(Ic)的特别优选的替代方案是所述双键为“C=C”双键。
另外,以下分子变体作为香味剂和/或芳香剂的用途也是优选的:
这些分子变体分别被展示为具有间位取代基,但是这些取代基还可以分别优选地结合在邻位或对位,例如在以下情况下:4-异戊基环己-2-烯-1-醇、2-异戊基环己-2-烯-1-醇、4-异戊基环己-2-烯-1-酮或2-异戊基环己-2-烯-1-酮。因此,上文所示的所有示例化学式在具有邻位或对位取代基时也是优选的。
式(I)、式(Ia)、式(Ib)和/或式(Ic)的化合物具备完全独立的嗅觉特性,这些嗅觉特性与已知的香味剂和/或芳香剂明显不同并且还超越那些已知的香味剂和/或芳香剂。式(I)、式(Ia)、式(Ib)和/或式(Ic)的化合物适合于用作香味剂和/或芳香剂是此前未知的。因此特别出人意料的是,能够发现这些具有感兴趣且复杂的嗅觉特性的有价值的香味剂和/或芳香剂。
特别优选将根据本发明的化合物用作玫瑰香味剂和/或芳香剂的用途。
本发明的一个优选变体涉及式(I)、式(Ia)、式(Ib)和/或式(Ic)的化合物用作香味剂和/或芳香剂的用途,其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,并且在虚线之一的相应位置上存在至少一个双键。
将以下分子变体作为香味剂和/或芳香剂的用途是特别优选的:
这些分子变体分别被展示为特别优选地具有间位取代基,这些取代基还可以分别优选结合在邻位或对位,例如在以下情况下:4-异戊基环己-2-烯-1-醇、2-异戊基环己-2-烯-1-醇、4-异戊基环己-2-烯-1-酮或2-异戊基环己-2-烯-1-酮。因此,所有上文所示的示例化学式在具有邻位或对位取代基时也是优选的。
这些化合物是特别优选的,因为它们具有向玫瑰味和果香味方向增强的气味特征。另外它们具有有利的次要特征,例如在某些应用条件下的高稳定性。
本发明的一个替代性优选变体涉及用作香味剂和/或芳香剂的式(I)、式(Ia)、式(Ib)和/或式(Ic)的化合物,其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在环中和异丁基侧链中的虚线之一的相应位置上分别存在双键。
本发明的另一个优选实施方式涉及用作香味剂和/或芳香剂的式(I)、式(Ia)、式(Ib)和/或式(Ic)的化合物,其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在虚线之一的位置上分别存在单键或双键,并且其中所述化合物不是2-(3-甲基丁基)环己烷-1-醇、2-(3-甲基丁基)环己烷-1-酮、3-(3-甲基丁基)环己烷-1-醇、3-(3-甲基丁基)环己烷-1-酮、4-(3-甲基丁基)环己烷-1-醇或4-(3-甲基丁基)环己烷-1-酮。
将以下分子变体作为香味剂和/或芳香剂的用途是特别优选的。:
这些分子变体被优选地展示为具有间位取代基,这些取代基还可以分别结合在邻位或对位,例如在以下情况下:4-异戊基环己-2-烯-1-醇、2-异戊基环己-2-烯-1-醇、4-异戊基环己-2-烯-1-酮或2-异戊基环己-2-烯-1-酮。因此,所有上文所示的示例化学式在具有邻位或对位取代基时也是优选的。
本发明的一个替代性优选实施方式涉及用作香味剂和/或芳香剂的式(I)、式(Ia)、式(Ib)和/或式(Ic)的化合物,其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,在环中或者在异丁基侧链中的虚线之一的相应位置上存在双键。
这些化合物是特别优选的,因为它们可以特别良好地改变和/或增强果香、花香和木材的味调。
在第二方面,本发明涉及式(II)的化合物,
其中X表示-CHO基团或-CH2OH基团,在虚线之一的位置上存在单键或双键,并且其中3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位中与环相连,其前提条件是,当在环中存在双键时,则3-异戊基残基或3-异戊-2-烯基残基作为邻位或间位取代基直接结合到所述双键上。
本发明的第一方面的优选实施方式和结构变体分别还适用于第二方面并且还可以与根据式II的基础结构合理地组合。
在此背景下,本发明的另一个优选设计方案涉及以下分子变体:
式(II)的化合物在环与杂原子之间具有附加的“碳”原子,使得这些化合物特别适合用作香味剂。此外,根据本发明的化合物由于异常出色的附着能力(长期持久性)和高亲和性而证明了自己。
本发明的一个替代的优选设计方案涉及式(II)的化合物,其中X表示-CHO基团或-CH2OH基团,在虚线的位置上分别存在单键并且3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位中与环相连,其前提条件是,当在环中存在双键时,则3-异戊基残基或3-异戊-2-烯基残基作为邻位或间位取代基直接结合到这个双键上。
本发明的一个优选的设计方案涉及用作香味剂和/或芳香剂的式(II)的化合物的用途,
其中X表示-CHO基团或-CH2OH基团,在虚线的位置上分别存在单键或双键,并且3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位中与环相连,其前提条件是,当在环中存在双键时,则3-异戊基残基或3-异戊-2-烯基残基作为邻位或间位取代基直接结合到这个双键上。
将以下分子变体作为香味剂和/或芳香剂的用途是特别优选的:
这些分子变体被优选地展示为具有间位取代基,这些取代基还可以结合在邻位或对位,例如在以下情况下:2-异戊基环己-2-烯-1-甲醛、4-异戊基环己-2-烯-1-甲醛、2-(3-甲基丁-2-烯基)环己基甲醛、4-(3-甲基丁-2-烯基)环己基甲醛、[2-(3-甲基丁-2-烯基)环己基]甲醇、[4-(3-甲基丁-2-烯基)环己基]甲醇、(2-异戊基环己-2-烯-1-基)甲醇或(4-异戊基环己-2-烯-1-基)甲醇。因此,所有上文所示的示例化学式在具有邻位或对位取代基时也是优选的。
式(II)的化合物具有包括玫瑰香和花香味调的突出且独一无二的气味特征。此外,根据本发明的化合物由于异常出色的附着能力(长期持久性)和高亲和性而证明了自己。
本发明的一个替代的优选设计方案涉及用作香味剂和/或芳香剂的式(II)的化合物,其中X表示-CHO基团或-CH2OH基团,在虚线的位置上存在单键并且3-异戊基残基或3-异戊烯基残基在相对于X基团的邻位、间位或对位与环相连。
将以下分子变体作为香味剂和/或芳香剂的用途是特别优选的:2-异戊基环己基甲醛、(2-异戊基环己基)甲醇、3-异戊基环己基甲醛、(3-异戊基环己基)甲醇、4-异戊基环己基甲醛和(4-异戊基环己基)甲醇。
这些化合物是特别优选的,因为它们具有气味增强的特性(所谓的提升或加强效果)和/或在与另外的香味剂和/或芳香剂组合时对其自然性、清新性、填充性、(散发)力度和/或传播性进行补充。
本发明的另一个替代的优选设计方案涉及用作香味剂和/或芳香剂的式(II)的化合物的用途,其中X表示-CHO基团或-CH2OH基团,在虚线之一的位置上存在至少一个双键并且3-异戊基残基或3-异戊烯基残基在相对于X基团的邻位、间位或对位与环相连。
将以下分子变体作为香味剂和/或芳香剂的用途是特别优选的:
这些分子变体被优选地展示为具有间位取代基,这些取代基还可以结合在邻位或对位,例如在以下情况下:2-异戊基环己-2-烯-1-甲醛、4-异戊基环己-2-烯-1-甲醛、2-(3-甲基丁-2-烯基)环己基甲醛、4-(3-甲基丁-2-烯基)环己基甲醛、[2-(3-甲基丁-2-烯基)环己基]甲醇、[4-(3-甲基丁-2-烯基)环己基]甲醇、(2-异戊基环己-2-烯-1-基)甲醇或(4-异戊基环己-2-烯-1-基)甲醇。因此,所有上文所示的示例化学式在具有邻位或对位取代基时也是优选的。
根据本发明的或根据本发明待使用的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物可以以任意的光学活性形式,以及以立体异构体的任意混合物存在,例如作为非对映异构体混合物或者作为外消旋体存在。
本发明的一个优选变体涉及式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物,这些化合物呈其在2、3或4位的顺式或反式异构体(E/Z异构体)以及其混合物的所有形式。
在第三方面,本发明涉及根据本发明变体的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物作为玫瑰味调香味剂的用途。
在第四方面,本发明涉及式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物的用途,用于赋予、改变和/或增强选自由以下味调组成的组的一种或多种气味味调:青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味,优选为青草味和/或果香味的味调中的至少一种。
本发明的一个优选设计方案涉及根据本发明变体的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物用途,用于赋予选自由以下味调组成的组的一种、两种或多种气味味调:青草味、清新味、果香味和木材味。
本发明优选地涉及根据本发明变体的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物作为香味剂和/或芳香剂的用途,
i)具有玫瑰味调
和/或
ii)用于赋予、改变和/或增强选自由以下味调组成的组的一种或多种气味味调:青草味、药草味、清新味、果香味、木材味、甜味、泥土味、油脂味、金属味和香胶味,其中优选赋予、改变和/或增强青草味和/或果香味的味调中的至少一种。
在第五方面,本发明涉及一种香味剂和/或芳香剂,其包含根据本发明变体的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的至少一种化合物。
式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物由于其嗅觉特性而优异地适合用于香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物中。式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的一种或多种化合物可以与许多其他的香味剂和/或芳香剂组合并且用在大量不同的产品和制品中。式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物可以特别有利地按各种不同的量比率与另外的香味剂和/或芳香剂组合成根据本发明的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物。
在另一个变体中,本发明涉及一种香味剂和/或芳香剂混合物,其具有至少一种根据第五方面的香味剂和/或芳香剂和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮,另外包含一种或多种额外的香味剂和/或芳香剂,其中所述额外的香味剂和/或芳香剂或者一种、多种或全部的香味剂和/或芳香剂选自由以下项组成的组:天然原料提取物,优选精油、冷凝酯、净油、树脂、类树脂、香胶、酊剂和/或单独香味剂,优选地选自下组:(1)烃;(2)脂肪族醇;(3)脂肪族醛及其缩醛;(4)脂肪族酮及其肟;(5)脂肪族含硫化合物;(6)脂肪族腈;(7)脂肪族羧酸的酯;(8)非环状萜醇;(9)非环状萜醛和萜酮;(10)环状萜醇;(11)环状萜醛和萜酮;(12)环状醇;(13)环脂肪族醇;(14)环状和环脂肪族醚;(15)环状和大环状酮;(16)环脂肪族醛;(17)环脂肪族酮;(18)环状醇的酯;(19)环脂肪族醇的酯;(20)环脂肪族羧酸的酯;(21)芳香脂肪族醇;(22)芳香脂肪族醇与脂肪族羧酸的酯;(23)芳香脂肪族醚;(24)芳香族和芳香脂肪族醛;(25)芳香族和芳香脂肪族酮;(26)芳香族和芳香脂肪族羧酸及其酯;(27)含氮的芳香族化合物;(28)酚、苯基醚和苯基酯;(29)杂环化合物;(30)内酯;及其混合物。
在第六方面,本发明涉及一种香味剂和/或芳香剂组合物,其包含:至少一种式(III)的化合物,以及至少一种另外的香味剂。所述式(III)的化合物,
其中
X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,
在虚线之一的相应位置上分别存在单键或双键,并且其中3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位与环相连。
根据本发明的或根据本发明待使用的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物在本发明应用的范围内通常以有效感受量来使用,即以使它们展现出感受作用的总量来使用。
优选地,本发明或式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮与其他的香味剂一起使用。
此类香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物可以以常见方式制备,例如通过将成分简单地共混或均匀化。这些另外的香味剂和/或芳香剂可以为任意的其他的香味剂和/或芳香剂。
在根据本发明的优选的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物中,式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物(优选在前文作为优选给出的设计方案中)的总量与其他香味剂和/或芳香剂的总量的重量比优选在1:1000至1:0.5的范围内。
尤其通过将根据本发明的变体中上述各式且尤其式(I)和式(III)的化合物(优选以作为优选给出的设计方案之一中)与一种或多种另外的香味剂和/或芳香剂(优选具有木材、果香和/或花香的气味或味道)组合,可以制备感兴趣的新型香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物。以此方式可以创造具有特别感兴趣的、天然的、新的且原创的味调的混合物。如上所述,适合作为根据本发明香味剂和/或芳香剂组合物的组分(b)的香味剂和/或芳香剂,例如可以在S.Arctander,Perfume and Flavor Materials,Vol.Iund II,Montclair,N.J.1969,Eigenverlagoder K.Bauer et al.,Common Fragrance andFlavor Materials,4th Edition,Wiley-VCH,Weinheim 2001中找到。
具体地可以提及:天然原料提取物,如精油、浸膏、净油、树脂、类树脂、香胶、酊剂,例如龙涎香酊;香树油;当归种子油;当归根油;大茴香油;缬草油;罗勒油;树苔净油;月桂叶油;艾草油;安息香树脂;佛手柑油;蜂蜡净油;桦焦油;苦杏仁油;香薄荷油;布枯叶油;香脂豆木油;杜松油;菖蒲油;樟脑油;依兰依兰油;豆蔻油;苦香树皮油;黑醋栗油;黑醋栗净油;海狸香净油;柏叶油;柏木油;岩蔷薇油;香茅油;柠檬油;苦配巴香膏;苦配巴香膏油;香菜油;闭鞘姜根油;孜然油;奠柏油;茚蒿油;莳萝草油;莳萝籽油;苦橙花叶水净油;橡树苔净油;榄香脂油;龙蒿油;柠檬桉油;桉树油;小茴香油;云杉针油;白松香油;白松香树脂;天竺葵油;葡萄柚油;愈创木油;古云香膏;古云香膏油;永久花净油;永久花油;姜油;鸢尾根净油;鸢尾根油;茉莉净油;菖蒲油;洋甘菊油,蓝色;罗马洋甘菊油;胡萝卜种子油;苦香树皮油;松针油;留兰香油;葛缕子油;赖百当油;赖百当净油;赖百当树脂;醒目薰衣草净油;醒目薰衣草油;薰衣草净油;薰衣草油;柠檬草油;独活草油;蒸馏酸橙油;压榨酸橙油;芳樟油;山苍子油;月桂叶油;肉豆蔻油墨角兰油;橘子油;马尾松油;含羞草净油;麝香颗粒油;麝香酊剂;香紫苏油;肉豆蔻油没药净油;没药油;桃金娘油;康乃馨叶油;康乃馨花油;橙花油;乳香净油;乳香油;金合欢油;橙花净油;橙子油;牛至油;玫瑰草油;广藿香油;紫苏油;秘鲁香膏油;欧芹叶油;欧芹籽油;苦橙叶油;薄荷油;胡椒油;甘椒油;松油;波莱油玫瑰净油;玫瑰木油;玫瑰油;迷迭香油;鼠尾草油,达尔马提亚;鼠尾草油,西班牙;檀木油;芹菜籽油;穗华薰衣草油;八角茴香油;安息香油;万寿菊油;冷杉针油;茶树油;松脂油;百里香油;妥卢香膏;零陵香净油;晚香玉净油;香草提取物;紫罗兰叶净油;马鞭草油;香根草油;杜松浆果油;葡萄酒酵母油;苦艾油;冬青油;依兰油;牛膝花油;麝猫净油;肉桂叶油;肉桂皮油及其级分,或由其中分离出的内含物质;
来自烃类的组的单独香味剂,例如3-蒈烯;α-蒎烯;β-蒎烯;α-萜烯;γ-萜烯;对伞花烃;红没药醇;莰烯;石竹烯;雪松烯;金合欢烯;柠檬烯;长叶烯;月桂烯;罗勒烯;巴伦西亚桔烯;(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-庚烯-2-醇和3,5,6,6-四甲基-4-亚甲基庚烷-2-醇的混合物;(E,Z)-2,6-壬二烯醇;3,7-二甲基-7-甲氧基辛烷-2-醇;9-癸烯醇;10-十一碳烯醇;4-甲基-3-癸烯-5-醇;
脂肪醛及其缩醛,例如己醛;庚醛;辛醛;壬醛;癸醛;十一碳醛;十二碳醛;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;10-十一碳烯醛;(E)-4-癸烯醛;2-十二碳烯醛;2,6,10-三甲基-9-十一碳烯醛;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;香茅基氧基乙醛;1-(1-甲氧基-丙氧基)-(Z)-3-己烯;1-(1-甲氧基-丙氧基)-(E)-3-己烯;
脂肪酮及其酮肟,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-甲基硫代己醇;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-乙酰基硫代己基乙酸酯;1-薄荷烯-8-硫醇;
脂肪族腈,例如2-壬烯酸腈;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)-3-己烯基甲酸酯和(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)-3-己烯基乙酸酯和(Z)-3-己烯基乙酸酯;乙酸辛酯;3-辛基乙酸酯;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)-3-己烯基异丁酸酯和(Z)-3-己烯基异丁酸酯;巴豆酸己酯;异戊酸乙酯;乙基-2-甲基戊酸酯;己酸乙酯;己酸烯丙基酯;庚酸乙酯;庚酸烯丙基酯;辛酸乙酯;(E,Z)-2,4-癸二烯酸乙酯;2-辛炔酸甲酯;2-壬炔酸甲酯;2-异戊氧基乙酸烯丙基酯;3,7-二甲基-2,6-辛二烯酸甲酯;4-甲基-2-戊基-巴豆酸酯;
非环状萜醇,例如香叶醇;橙花醇;薰衣草醇;橙花叔醇;金合欢醇;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、惕各酸酯和3-甲基-2-丁烯酸酯;
非环状萜醛和萜酮,例如香茅醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一碳烯醛;香叶基丙酮;以及香叶醛、橙花醛的二甲基缩醛和二乙基缩醛,
环状萜醇,例如薄荷醇;异胡薄荷醇;α-萜品醇;萜品醇-4;薄荷烷-8-醇;薄荷烷-1-醇;薄荷烷-7-醇;冰片醇;异冰片醇;芳樟醇氧化物;诺普醇;雪松醇;龙涎醇;香根草醇;愈创醇;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、惕各酸酯和3-甲基-2-丁烯酸酯;
环状萜醛和萜酮,例如薄荷酮;异薄荷酮;8-巯基薄荷烷-3-酮;香芹酮;樟脑;葑酮;α-紫罗兰酮;β-紫罗兰酮;α-正甲基紫罗兰酮;β-正甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-铁(α-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-甲桥萘-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;α-甜橙醛;β-甜橙醛;酰基化的柏木油(甲基柏木基酮);
环状醇,例如4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异樟脑基环己醇;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;
环脂肪族醇,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-环戊烯-1-基)丁醇;2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇;3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-戊-2-醇;3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇;3,3-二甲基-5-(2,2,3-三甲基-3-环戊烯-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;
环状和环脂肪族醚,例如桉叶素;柏木基甲基醚;环十二碳基甲基醚;1,1-二甲氧基环十二烷;(乙氧基甲氧基)环十二烷;α-环氧柏木烷;3a,6,6,9a-四甲基十二氢萘并[2,1b]呋喃;3a-乙基-6,6,9a-三甲基十二氢萘并[2,1b]呋喃;1,5,9-三甲基-13-氧杂二环[10.1.0]十三碳-4,8-二烯;玫瑰醚;2-(2,4-二甲基-3-环己烯-1-基)-5-甲基-5-(1-甲基丙基)-1,3-二噁烷;
环状的和大环状的酮,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-顺式-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-环十五烯酮;3-甲基-5-环十五烯酮;3-甲基环十五酮;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)-茚酮;8-环十六烯-1-酮;9-环十七烯-1-酮;环十五碳酮;环十六碳酮;
环脂肪醛,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;
环脂肪族酮,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;甲基-2,6,10-三甲基-2,5,9-环十二碳三烯基酮;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-萘基乙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5或6-茚基乙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5或6茚基丙酸酯;4,7-甲桥-3a,4,5,6,7,7a-六氢-5或6茚基异丁酸酯;4,7-甲桥八氢-5或6-茚基乙酸酯;
环脂肪族醇的酯,例如1-环己基乙基巴豆酸酯;
环脂肪族羧酸的酯,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酮酸酯;顺式和反式甲基茉莉酮酸酯;甲基-2-己基-3-氧代环戊烷羧酸酯;乙基-2-乙基-6,6-二甲基-2-环己烯羧酸酯;乙基-2,3,6,6-四甲基-2-环己烯羧酸酯;乙基-2-甲基-1,3-二氧戊环-2-乙酸酯;
芳香脂肪族醇,例如苄醇;1-苯基乙基醇;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-苯基乙基醇;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-甲氧基苄基醇;1-(4-异丙基苯基)乙醇;
芳香脂肪族醇与脂肪族羧酸的酯,例如乙酸苄基酯;丙酸苄基酯;异丁酸苄基酯;异戊酸苄基酯;2-苯基乙基乙酸酯;2-苯基乙基丙酸酯;2-苯基乙基异丁酸酯;2-苯基乙基异戊酸酯;1-苯基乙基乙酸酯;α-三氯甲基苄基乙酸酯;α,α-二甲基苯基乙基乙酸酯;α,α-二甲基苯基乙基丁酸酯;乙酸肉桂基酯;2-苯氧基乙基异丁酸酯;4-甲氧基苄基乙酸酯;
芳香脂肪族醚,例如2-苯基乙基甲基醚;2-苯基乙基异戊基醚;2-苯基乙基-1-乙氧基乙基醚;苯基乙醛二甲基缩醛;苯基乙醛二乙基缩醛;氢化阿托醛二甲基缩醛;苯基乙醛甘油缩醛;2,4,6-三甲基-4-苯基-1,3-二噁烷;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;
芳香族和芳香脂肪族醛,例如苯甲醛;苯基乙醛;3-苯基丙醛;氢化阿托醛;4-甲基苯甲醛;4-甲基苯基乙醛;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;α-己基肉桂醛;3-甲基-5-苯基戊醛;4-甲氧基苯甲醛;4-羟基-3-甲氧基苯甲醛;4-羟基-3-乙氧基苯甲醛;3,4-亚甲基二氧苯甲醛;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-亚甲基二氧苯基)丙醛;
芳香族和芳香脂肪族酮,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-萘烯基)乙酮;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;
芳香族和芳香脂肪族羧酸及其酯,例如苯甲酸;苯基乙酸;苯甲酸甲酯;苯甲酸乙酯;苯甲酸己酯;苯甲酸苄基酯;甲基苯基乙酸酯;乙基苯基乙酸酯;香叶基苯基乙酸酯;苯基乙基苯基乙酸酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄基酯;苯基乙基肉桂酸酯;肉桂酸肉桂基酯;烯丙基苯氧基乙酸酯;水杨酸甲酯;水杨酸己酯;水杨酸环己基酯;顺式-3-己烯基水杨酸酯;水杨酸苄基酯;苯基乙基水杨酸酯;甲基-2,4-二羟基-3,6-二甲基苯甲酸酯;乙基-3-苯基甘油酸酯;乙基-3-甲基-3-苯基甘油酸酯;
含氮的芳香族化合物,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;N-甲基氨基苯甲酸甲酯;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-苯基丙基)嘧啶;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、苯基醚和苯基酯,例如草蒿脑;茴香脑;丁香酚基甲基醚;异丁香油酚;异丁香酚基甲基醚;百里香酚;香芹酚;二苯基醚;β-萘基甲基醚;β-萘基乙基醚;β-萘基异丁基醚;1,4-二甲氧基苯;乙酸丁香酚基酯;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;1,4-十一碳内酯;1,4-十二碳内酯;1,5-癸内酯;1,5-十二碳内酯;4-甲基-1,4-癸内酯;1,15-十五碳内酯;1,16-十六碳内酯;9-十六碳烯-1,16-内酯;10-氧杂-1,16-十六碳内酯;11-氧杂-1,16-十六碳内酯;12-氧杂-1,16-十六碳内酯;1,12-十二碳二酸亚乙基酯(ethylene 1,12-dodecanedioate);1,13-十三碳二酸亚乙基酯(ethylene1,13-tridecanedioate);2,3-二氢香豆素;八氢香豆素。
在第七方面,本发明涉及一种香味剂和/或芳香剂组合物,其包含:
(a)组分:在根据本发明变体中的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的一种或多种化合物,和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮,以及
(b)组分:一种或多种,优选两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种其他的香味剂和/或芳香剂。
因此,在另一个变体中,本发明涉及一种香味剂和/或芳香剂组合物,其包含:
a)根据权利要求1至3所述的式(I)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮以及
b)一种或多种、优选两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种其他的香味剂和/或芳香剂;
(i)所述其他的香味剂和/或芳香剂赋予木材、果香和/或花香气味和/或味道,或者
(ii)其中所述其他的香味剂和/或芳香剂赋予不同的气味。
在本发明的香味剂和/或芳香剂组合物的一个优选变体中,将本发明的化合物或根据本发明式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)待使用的本发明的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮优选地与一种或多种其他的花香和/或果香香味剂和/或芳香剂组合,特别优选地与两种、三种、四种、五种或更多种其他的花香和/或果香香味剂和/或芳香剂组合。
在另一个优选变体中,本发明涉及香味剂和/或芳香剂组合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮,所述香味剂和/或芳香剂组合物包含一种、两种、三种、四种、五种或更多种赋予花香和/或果香气味味调的香味剂和/或芳香剂。
在此,本发明的或本发明使用的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮有利地(至少部分地)实现了对花香香味剂和/或芳香剂的气味增强。
可以与本发明的或本发明使用的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮(尤其在根据本发明的香味剂和/或芳香剂组合物中)有利地组合的花香香味剂和/或芳香剂优选地选自由以下项组成的组:
羟基香茅醛、甲氧基香茅醛、兔耳草醛[2-甲基-3-(4-异丙基苯基)丙醛]、1-(4-异丙基-环己基)乙醇4-叔丁基-α-甲基二氢肉桂醛顺式六氢枯醇3-[4-(1,1-二甲基乙基)苯基]丙醛2,2-二甲基-3-(3-甲基苯基)丙醇3-甲基-3-(3-甲基苄基)-丁烷-2-醇、2-异丁基-4-甲基四氢-2H-吡喃-4-醇2-甲基-3-(3,4-亚甲基二氧基苯基)丙醛4-(4-羟基-4-甲基戊基)-3-环己烯甲醛4-(八氢-4,7-甲桥-5H-亚茚-5-叉-丁醛鲜草醛、4-(4-甲基-3-戊烯-1-基)-3-环己烯甲醛八氢-5-(4-甲氧基亚丁基)-4,7-甲桥-1H-茚2,6-二甲基-2-庚醇1-乙基-1-甲基-3-苯基丙醇2,2-二甲基-3-苯基-1-丙醇(玲兰醇)、普法尼醇(Profarnesol)、二氢法尼醇、法尼醇、橙花叔醇、羟基香茅醛二甲基乙缩醛、己基苯甲酸、香叶醇、橙花醇、芳樟醇、四氢香叶醇、四氢芳樟醇、乙基芳樟醇、惕各酸香叶醇酯、苯乙醇(2-苯基乙基醇)、香茅醇、玫瑰醚、2-甲基-5-苯基戊醇(Rosaphen)、3-甲基-5-苯基戊醇(Phenoxanol)、甲基二氢茉莉酮酸酯(高顺式)、2-庚基环戊酮(Projasmon P)、顺式茉莉酮、二氢茉莉酮、肉桂醇(3-苯基-2-丙烯-1-醇)、二氢肉桂醇(3-苯基丙醇)、2-甲基-4-苯基-1,3-二氧戊环和二氢月桂烯醇(2,6-二甲基-7-辛烯-2-醇)。
在第八方面,本发明涉及一种香味剂和/或芳香剂组合物,其中所述其他的一种或多种香味剂和/或芳香剂选自由以下项组成的组:2-环戊-2-烯-1-基乙酸乙酯、(E)-丁-2-烯酸-1-环己基乙酯、(E)-丁-2-烯酸-2-环戊基环戊酯、3-环己基丙酸烯丙酯、己酸烯丙酯、(E)-丁-2-烯酸-1,3-二甲基丁酯、2-甲基丙酸-1,3-二甲基丁-3-烯基酯和/或(E)-1-(2,6,6-三甲基环己-2-烯-1-基)丁-2-烯-1-酮。
在本发明的香味剂和/或芳香剂组合物的一个优选变体中,将本发明的或根据本发明待使用的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮优选地与一种或多种其他的香味剂和/或芳香剂组合,特别优选与两种、三种、四种、五种或更多种其他的香味剂和/或芳香剂组合,其中所述香味剂和/或芳香剂选自下组:2-环戊-2-烯-1-基乙酸乙酯、(E)-丁-2-烯酸-1-环己基乙酯、(E)-丁-2-烯酸-2-环戊基环戊酯、3-环己基丙酸烯丙酯、己酸烯丙酯、(E)-丁-2-烯酸-1,3-二甲基丁酯、2-甲基丙酸-1,3-二甲基丁-3-烯基酯、(E)-1-(2,6,6-三甲基环己-2-烯-1-基)丁-2-烯-1-酮。
另外,本发明的或根据本发明式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的待使用的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮有利地适合用于尤其对果香香味剂和/或芳香剂在其气味方面进行增强。
可以与本发明的化合物或根据本发明式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的待使用的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮有利组合的果香香味剂和/或芳香剂,并且因此为根据本发明香味剂和/或芳香剂组合物的特别优选的(其他的)香味剂的果香香味剂和/或芳香剂,优选地选自由以下项组成的组:
2-甲基-丁酸乙酯、4-(对羟基苯基)-2-丁酮、乙基-3-甲基-3-苯基甘油酸酯、丁酸异戊酯、乙酸异戊酯、乙酸正丁酯、丁酸乙酯、3-甲基丁酸乙酯、正己酸乙酯、正己酸烯丙酯、乙基-2-反式-4-顺式癸二烯酸酯、1,1-二甲氧基-2,2,5-三甲基-4-己烷、2,6-二甲基-5-庚烯-1-醛、γ-十一烷酸内酯、γ-壬烷酸内酯、己醛、3Z-己醛、正癸醛、正十二碳醛、柠檬醛、香草醛、乙基香草醛、麦芽酚、乙基麦芽酚及其混合物。
在另一个变体中,在香味剂和/或芳香剂组合物中式(I)的化合物或先前提及的香气物质(Erstriechstoff)的总量与其他香味剂和/或芳香剂的总量的重量比,优选在1:1000至1:0.5的范围内。
在本发明的优选的香味剂和/或芳香剂混合物和/或组合物中,式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮的总量,分别基于所述香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物的总质量,在0.0001至99.9重量%的范围内,优选在0.001至99.5重量%的范围内,特别优选在0.01至99重量%的范围内。
在本发明的优选的其他的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物中,式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮的总量,分别基于所述香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物的总质量,在0.01至90重量%的范围内,优选在0.05至80重量%的范围内,更优选在0.1至70重量%的范围内,特别优选在0.25至50重量%的范围内,尤其优选在0.5至40重量%的范围内,最优选在0.75至25重量%的范围内。
在根据本发明的优选的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物中,在根据本发明变体中式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物所使用的的总量足以将其他香味剂和/或芳香剂的气味向青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味的方向,优选向青草味和/或果香味方向,优选向玫瑰味方向,改变或增强和/或赋予一种或多种上述味调。
如果一种或多种式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮主要用于赋予香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物更多的清新性、(传播)散发性、补充性、和谐性和/或自然性和/或增强某些(其他的香味剂和/或芳香剂已经存在的)味调,则组分(a)的总量基于所述香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物的总量,优选相对较低并且特别优选在0.01至5重量%范围内,优选在0.1至2重量%范围内。如果在优选的浓度范围内选择相对较低的浓度,则在有些情况下尚不足以赋予上述独有气味味调,这取决于相应组合物的其他组分。
上文针对根据本发明的用途描述的本发明优选的实施方式,还将对应地适用于本发明的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物以及根据本发明的有香味的制品,尤其关于优选重量比的数值。
根据本发明的或根据本发明待使用的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物,尤其在本发明范围内标示为优选或特别优选的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物,具备非常复杂和多样的气味印象。否则,该印象只能通过多种组分的混合(例如精油或者香料混合物)来实现。
式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物除了其主要的(即气味方面的)特性之外还具有有利的次要特性,尤其与具有类似嗅觉特性的香味剂和/或芳香剂相比的良好的附着能力和高亲和性,以及在特定介质和制剂中的高稳定性和高扩散度。
在第八方面,本发明涉及一种用于以果香和/或木材味调中一种、多种或全部来改变和/或增强(提升)气味的方法,并且所述方法包括以下步骤:
(a)提供根据以上权利要求1至3之一所述的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或一种/多种本发明的香味剂混合物和/或香味剂组合物;
(b)将有效感受量的这种物质或这些物质与具有一种或多种果香和/或木材味调的一种或多种香味剂和/或芳香剂的混合物共混,
这足以在成品制剂中引起、在感受上改变和/或增强果香和/或木材气味味调。
本发明的或根据本发明待使用的式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮也可以增强根据本发明的香味剂和/或芳香剂混合物的强度,以及补充所述混合物的总体气味表现,并且可以用于赋予香味剂和/或芳香剂组合物更多的充实性、清新性、(散发)力度、传播性、光亮性、补充性、和谐性和/或自然性。
一种或多种式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮,尤其可以用于赋予香味剂和/或芳香剂组合物清新性、(传播)散发性、补充性、和谐性和/或自然性和/或增强已有气味味调。
在第九方面,本发明涉及式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮的用途,用于向头发和/或皮肤或者纺织纤维赋予气味(关于优选的气味味调,请参照上文的说明),其中式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮优选地与表面活性剂或表面活性剂混合物组合使用。
在第九方面,本发明涉及式(I)、式(Ia)、式(Ib)、式(Ic)、式(II)和/或式(III)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮,香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物的用途,用作提高香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物的亲和性和/或保留度(Retention)的试剂和/或用作固定剂(介体)。
式(I)的化合物的感受特性及其作为香味剂和/或芳香剂的适用性此前没有描述并且出人意料地显示出多个优点,尤其还有提高的亲和性。
下表1包含根据本发明的或根据本发明待使用的式(I)的一些化合物的感受描述、尤其气味描述。
重要的总是所展示的式(I)的化合物的结构式。
表1
另外特别优选香味剂组合或香味剂组合物。在此尤其通过与其他的次要香味剂的组合实现了对若干香味剂的果香味调的异常提高。以下表2包含对具有次要或组合香味剂的4-(3-甲基丁基)环己-1-醇(Symrose)的感受描述,尤其气味描述。
表2
在一个优选的变体中,本发明涉及香味剂组合物和香味剂组合,包含(comprehensive):有效感受量的根据本发明变体的式(I)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和至少一种香味剂和/或芳香剂混合物,其中一种或多种所述香味剂和/或芳香剂混合物选自下组:2-环戊-2-烯-1-基乙酸乙酯、(E)-丁-2-烯酸-1-环己基乙酯、(E)-丁-2-烯酸-2-环戊基环戊酯、3-环己基丙酸烯丙酯、己酸烯丙酯、(E)-丁-2-烯酸-1,3-二甲基丁酯、2-甲基丙酸-1,3-二甲基丁-3-烯基酯和/或(E)-1-(2,6,6-三甲基环己-2-烯-1-基)丁-2-烯-1-酮。
通过将4-(3-甲基丁基)环己烷-1-醇(Symrose)与另外的第二香味剂组合,增强了香味剂的气味印象。它们通常变得更有果香味和更自然,并且因此获得了更轻微改变的特征。不再感受到如金属味调的异味。
优选地,将Symrose或在本发明中提及的另外的化合物与以下次要香味剂组合:Sultanene、Aprifloren、Datilat、Buccoxime、Vertacetal Coeur、TEC中50%的Oxanthia、Cassiffix、Amarocit、Fragolane、Pyroprunat、Cassix 150、烯丙基环己基丙酸酯、己酸烯丙基酯、Frutinat、异戊酸酯、大马酮α。
化合物3-(3-甲基丁基)环己烷-1-酮(2)或3-(3-甲基丁基)环己烷-1-醇(3)的以下变体和基础香味剂与表2中列出的次要香味剂或组合香味剂一起给出了增强协同的果香气味,所述气味部分地已经来自基础香味剂但是通过组合而得以特别增强。
在第十方面,本发明涉及有香味的或芳香化的制品,包含:
i)有效感受量的根据本发明变体的式(I)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物,
ii)一种、两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种其他的香味剂或芳香剂,其中优选所述其他的香味剂中的一种、多种或全部赋予果香和/木材气味,
iii)一种或多种其他的添加物质、辅助物质和/或活性物质,优选两种、三种、四种、五种或更多种添加物质、辅助物质和/或活性物质。在此应理解,所述其他的添加物质、辅助物质和/或活性物质不是香味剂和调味剂。
在一个优选的实施方式中,本发明涉及有香味的或芳香化的制品,包含:有效感受量的根据本发明变体的式(I)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和至少一种香味剂和/或芳香剂混合物,其中一种或多种所述香味剂和/或芳香剂混合物选自下组:2-环戊-2-烯-1-基乙酸乙酯、(E)-丁-2-烯酸-1-环己基乙酯、(E)-丁-2-烯酸-2-环戊基环戊酯、3-环己基丙酸烯丙酯、己酸烯丙酯、(E)-丁-2-烯酸-1,3-二甲基丁酯、2-甲基丙酸-1,3-二甲基丁-3-烯基酯和/或(E)-1-(2,6,6-三甲基环己-2-烯-1-基)丁-2-烯-1-酮。
除了式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或根据本发明的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物(如下文所定义的)之外,根据本发明的有香味的或芳香化的制品还可以包含的添加物质、辅助物质和/或活性物质优选地选自由以下项组成的组:
防腐剂,优选在US2006/0089413中所述的那些,磨料、抗粉刺剂和用于皮脂减少的试剂,优选在WO 2008/046791中所述的那些,抗皮肤老化剂,优选在WO 2005/123101中所述的那些,抗菌剂、抗蜂窝炎剂、去屑剂,优选在WO 2008/046795中所述的消炎剂、刺激抑制剂、抗刺激剂(抗炎症的、抑制刺激的和防止刺激的试剂),优选在WO 2007/042472和US2006/0089413中所述的那些,抗微生物剂,优选在WO 2005/123101中所述的那些,抗氧化剂,优选在WO 2005/123101中所述的那些,收敛剂、汗液抑制剂、抗静电剂、粘合剂、缓冲剂、载体材料,优选在WO 2005/123101中所述的那些,螯合剂,优选在WO 2005/123101中所述的那些,细胞兴奋剂、清洁剂、护理剂、脱毛剂、表面活性物质、除臭剂和止汗剂,优选在WO2005/123101中所述的那些,增塑剂、乳化剂,优选在WO 2005/123101中所述的那些,酶、精油,优选在US2008/0070825中所述的那些,驱虫剂,优选在WO 2005/123101中所述的那些,纤维、成膜剂、(其他)固定剂、发泡剂、泡沫稳定剂、消泡物质、增泡剂、杀真菌剂、凝胶化剂、凝胶形成剂,优选在WO 2005/123101中所述的那些,毛发护理剂、毛发变形剂、直发剂、湿度调节剂(助湿物质、润湿物质和/或保湿物质),优选在WO 2005/123101中所述的那些,渗透质,优选在WO 2005/123101中所述的那些,相容性溶质,优选在WO 01/76572和WO 02/15686中所述的那些,漂白剂、增强剂、去污剂、光亮剂、浸泡剂、防污剂、减摩擦剂、增滑剂、保湿霜、膏剂、遮光剂、塑化剂、遮盖剂、抛光剂、增亮剂、聚合物,优选在WO 2008/046676中所述的那些,粉末、蛋白质和蛋白水解液,优选在WO 2005/123101和WO 2008/046676中所述的那些,补油剂、打磨剂、皮肤舒缓剂、皮肤清洁剂、皮肤护理剂、皮肤治愈剂(皮肤修复剂),优选包含胆甾醇和/或脂肪酸和/或神经酰胺和/或伪神经酰胺,在此优选在WO 2006/053912中所述的那些,皮肤提亮剂,优选在WO 2007/110415中所述的那些,护肤剂、皮肤软化剂、皮肤冷却剂,优选在WO 2005/123101中所述的那些,皮肤加热剂,优选在WO 2005/123101中所述的那些,稳定剂、UV吸收剂和UV过滤剂,优选在WO 2005/123101中所述的那些,亚苄基-β-二羰基化合物,优选在WO 2005/107692中所述的那些,α-苯甲酰肉桂酸腈,优选在WO 2006/015954中所述的那些,AhR受体对抗药,优选在WO 2007/128723和WO 2007/060256中所述的那些,清洗剂、织物软化剂、悬浮剂、皮肤美黑剂,优选在WO 2006/045760中所述的那些,增稠剂、维生素,优选在WO 2005/123101中所述的那些,脂肪油、蜡和脂肪,优选在WO 2005/123101中所述的那些,磷脂,优选在WO 2005/123101中所述的那些,脂肪酸(饱和脂肪酸,单或多不饱和脂肪酸,α-羟基酸,多羟基脂肪酸),优选在WO 2005/123101所述的那些,着色剂、颜色保护剂以及颜料,优选在WO 2005/123101中所述的那些,抗腐蚀剂、醇和多元醇,优选在WO 2005/123101中所述的那些,表面活性剂,优选在WO 2005/123101中所述的那些,动物提取物、酵母提取物、藻类或微藻类提取物、电解质、塑化剂、有机溶剂,优选在WO 2005/123101中所述的那些,头发生长调节剂(头发生长促进剂或头发生长抑制剂),优选在EP2168570和EP 2193785中所述的那些,或者硅酮和硅酮衍生物,优选在WO 2008/046676中所述的那些。
本发明的一个优选的实施方式涉及有香味的或芳香化的制品,包含:
有效感受量的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物,优选地以上文作为优选给出的形式之一,所述有效感受量足以赋予、改变和/或增强,优选赋予和/或增强青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味的气味味调中的一种或多种。
一种、两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种其他的香味剂和/或芳香剂,其中优选所述其他的香味剂和/或芳香剂中的一种、两种、三种或更多种赋予木材、果香和/或花香气味,
两种、三种、四种、五种或更多种添加物质、辅助物质和/或活性物质,其中优选选自由以下项组成的组的一种、两种、三种或更多种添加物质、辅助物质和/或活性物质:防腐剂、无机盐、螯合剂、表面活性剂、护肤剂和/或护发剂、酶、乳化剂、脂肪、脂肪油、蜡、脂肪醇、硅酮、硅酮衍生物和水。
本发明的另一个优选的实施方式涉及根据本发明的有香味的或芳香化的制品,所述制品选自由以下项组成的组:洗涤剂和清洗剂,卫生产品或护理产品,尤其在身体护理和头发护理、化妆品和日用品领域内。
因为根据本发明的香味剂和/或芳香剂组合物适合用于将制品香味化或芳香化,所以在另一个优选的实施方式中本发明涉及一种有香味的或芳香化的制品,包含:
根据本发明的香味剂组合物,优选地以被标示为优选的形式之一,优选地以有效感受量,以及
一种或多种其他的添加物质、辅助物质和/或活性物质,优选两种、三种、四种、五种或更多种添加物质、辅助物质和/或活性物质,优选两种、三种、四种、五种或更多种上文给出的添加物质、辅助物质和/或活性物质作为优选。
本发明的一个替代性的、根据本发明优选的变体涉及有香味的或芳香化的制品,所述制品选自由以下项组成的组:香水净油、香水、淡香水、须后水、古龙水、须前产品、喷洒古龙水、有香味的清新纸巾、酸性、碱性或中性清洁剂、纺织品清新剂、熨烫助剂、液态洗涤剂、粉末状洗涤剂、洗涤物预处理剂、织物软化剂、清洗皂、清洗片剂、消毒剂、表面消毒剂、空气清新剂、气溶胶喷雾、蜡和抛光剂、身体护理剂、手霜和乳液、足霜和乳液、脱毛霜和乳液、须后霜和乳液、美黑霜和乳液、护发产品、除臭剂、止汗剂、装饰性化妆产品、蜡烛、灯油、卫生香、杀虫剂、驱虫剂、燃料。
本发明的另一个优选的变体涉及有香味的或芳香化的制品,其中分别相对于所述有香味的或芳香化的制品的总质量,式(I)、式(Ia)、式(Ib)、式(Ic)、和/或式(II)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或根据本发明的香味剂和/或芳香剂混合物和/或香味剂和/或芳香剂组合物(优选在上文作为优选给出的设计方案中)的总量在0.00001至10重量%的范围内,优选在0.0001至5重量%的范围内,更优选在0.001至2重量%的范围内,最优选在0.005至1重量%的范围内。
在第十一方面,本发明涉及本发明的香味剂和/或芳香剂组合物,优选地以作为优选给出的形式之一的用途,
(A)用作香味剂和/或芳香剂组合物
(a)(i)具有玫瑰味调,和/或
(ii)用于赋予、改变和/或增强选自由以下味调组成的组的一种或多种气味味调:青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味,优选为青草味和/或果香味的味调中的至少一种,
和/或
(b)(i)具有果香和/或花香味调,和/或
(ii)用于赋予、改变和/或增强选自由以下味调组成的组的一种或多种气味味调和/或味道味调:木材味、果香味和/或花香味,和/或
(c)具有花香、果香、玫瑰味调
和/或
(B)用作有香味的或芳香化的制品的成分。
包含式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮的根据本发明香味剂和/或芳香剂组合物可以以液态、未稀释或用溶剂稀释的方式用于香味化。优选的溶剂为乙醇、异丙醇、二乙二醇单乙醚、甘油、丙二醇、1,2-丁二醇、二丙二醇、苯二甲酸二乙酯、柠檬酸三乙酯、豆蔻酸异丙酯、三醋酸甘油酯和二醋酸甘油酯。
此外,包含式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮的根据本发明香味剂和/或芳香剂组合物可以吸附在载体上,所述载体不仅用于使香味剂和/或芳香剂分布在产品中而且还用于在应用时进行受控释放。此类载体可以为多孔无机材料,如轻质硫酸盐、二氧化硅凝胶、沸石、石膏、粘土、粘土颗粒、充气混凝土等,或有机材料,如木材、基于纤维素的材料、糖类、糊精(例如麦芽糊精)或塑料,如PVC、聚乙酸乙烯酯或聚氨酯。本发明组合物与载体材料的组合代表了示例性的本发明制品。
包含根据本发明化合物的香味剂和/或芳香剂组合物还可以作为包合物或作为喷出(挤出)产品(即根据本发明的制品),被微胶囊化、被喷雾干燥,并且以这种形式添加例如至待香味化的产品中。
在某些情况下,如此改性的组合物的特性可以通过用适当材料进行所谓的“涂覆”而在针对性的香味释放方面得以进一步优化,为此优选使用蜡状塑料例如聚乙烯醇。所获得的产品进而代表根据本发明的制品。
将根据本发明香味剂和/或芳香剂组合物的微胶囊做成根据本发明的制品,可以例如使用封装材料(例如由聚氨酯类物质或软明胶形成)通过所谓的凝聚方法来实现。经喷雾干燥的香味剂和/或芳香剂组合物可以例如通过将包含香味剂和/或芳香剂组合物的乳液或分散体喷雾干燥来制备,其中作为载体可以使用改性的淀粉、蛋白质、糊精和植物胶。包合物可以例如通过向适合的溶剂(例如水)中添加香味剂和/或芳香剂组合物和环糊精或脲衍生物的分散体来制备。挤出产品可以通过将香味剂和/或芳香剂组合物与适合的蜡状物质熔融并且通过挤出以及后续的硬化(在适当时在适合的溶剂例如异丙醇中)来获得。
式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物以及包含一种或多种式(I)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮的根据本发明香味剂组合物可以以浓缩形式,在溶液中使用,或以上述的改性形式使用,以便制备本发明的有香味的或芳香化的制品,例如香水净油、香水、淡香水、须后水、古龙水、须前产品、喷洒古龙水和有香味的清新纸巾以及酸性、碱性和中性清洁剂的香水化产品,例如地板清洁剂、窗玻璃清洁剂、餐具清洗剂、浴室和卫生间清洁剂、清洗乳、固态和液态的厕所清洁剂、粉末和泡沫状的地毯清洁剂、纺织品清新剂、熨烫助剂、液态洗涤剂、粉末状洗涤剂、洗涤预处理剂如漂白剂、柔顺剂和去污剂、织物软化剂、清洗皂、清洗片剂、消毒剂、表面消毒剂以及呈液态、凝胶状或施加在固态载体上的形式的空气清新剂、气溶胶喷雾剂、蜡和抛光剂如家具抛光剂、地板蜡、鞋油以及身体护理剂例如固态和液态的皂、沐浴露、洗发水、剃须皂、剃须泡沫、浴油、水包油,油包水和水包油包水类型的化妆乳液例如皮肤霜和乳液、面霜和乳液、防晒霜和乳液、晒后霜和乳液、手霜和乳液、足霜和乳液、脱毛霜和乳液、须后霜和乳液、美黑霜和乳液、护发产品例如发胶、啫喱、固定用发乳液、护发素、永久和半永久的染发剂、毛发变形剂如冷烫剂和直发剂、发根营养液,、发霜和乳液、除臭剂和止汗剂例如腋窝喷雾、滚擦剂(Roll-ons)、除臭棒、除臭霜或装饰性化妆产品例如眼影、指甲油、化妆品、口红、睫毛膏以及蜡烛、灯油、卫生香、杀虫剂、驱虫剂和燃料。
根据本发明的经喷雾干燥的固体制剂(作为对应于本发明制品的例子)作为半成品特别适合用于制备根据本发明的其他制剂。根据本发明的经喷雾干燥的固体制剂优选包含50至95重量%的载体物质,尤其麦芽糊精和/或淀粉,5至40重量%的辅助物质,优选天然或人造的多糖和/或植物胶如改性的淀粉或阿拉伯胶。
在第十二方面,本发明涉及一种方法,用于赋予、改变和/或增强选自由以下味调组成的组的一种或多种气味味调:青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味,优选为青草味和/或果香味的味调中的至少一种,优选玫瑰味调,所述方法包括以下步骤:
提供如上定义的式(I)的一种或多种化合物(优选在上文作为优选给出的形式之一中)或者如上定义的香味剂和/或芳香剂组合物(优选在上文作为优选给出的形式之一中),提供制品,
将所述制品与有效感受量的如上定义的所述式(I)的化合物或所述香味剂和/或芳香剂组合物进行接触。
根据本发明的对应的优选的方法为如下方法,其中在进行接触之后(i)获得有香味的或芳香化的制品或者(ii)从此时存在的选自由以下项组成的组的制品来制备:
香水净油、香水、淡香水、须后水、古龙水、须前产品、喷洒古龙水、有香味的清新纸巾、酸性,碱性或中性清洁剂、纺织品清新剂、熨烫助剂、液态洗涤剂、粉末状洗涤剂、洗涤物预处理剂、织物软化剂、清洗皂、清洗片剂、消毒剂、表面消毒剂、空气清新剂、气溶胶喷雾剂、蜡和抛光剂、身体护理剂、手霜和乳液、足霜和乳液、脱毛霜和乳液、须后霜和乳液、美黑霜和乳液、护发产品、除臭剂、止汗剂、装饰性化妆产品、蜡烛、灯油、卫生香、杀虫剂、驱虫剂、燃料。
在第十三方面,本发明涉及一种方法,用于制备根据本发明的或根据本发明待使用的式(I)、式(Ia)、式(Ib)、式(Ic)和/或式(II)的化合物。合成可以借助于本身已知的反应和方法来进行。例如可以借助于1,4-格氏反应,由可购买的化合物2-环己-3-烯(化合物1)来制备酮(2)。随后酮(2)的还原产生了醇(3)(参见下文方案1)。
方案1
在第十四方面,本发明涉及一种用于制备化合物(I)的方法,该方法至少包括步骤(i)、(ii)和(iii),其特征在于,从2-异戊基环己酮或3-异戊基环己酮或4-异戊基环己酮出发
i)通过维蒂希反应获得1-异戊基-2-(甲氧基亚甲基)环己烷(化合物4a)、1-异戊基-3-(甲氧基亚甲基)环己烷(化合物4b)或1-异戊基-4-(甲氧基亚甲基)环己烷(化合物4c),
ii)通过随后的烯醇裂解产生醛(化合物5a,b,c),
iii)并且通过任选的随后的还原获得醇(化合物6a,b,c)(参见以下方案2)。
方案2
下面借助实施例详细阐释本发明。除非另外表明,所有数值都是关于重量。
在表示小数点时,与德国正字法相反,使用点号代替逗号。
所使用的缩写:DPG:二丙二醇,TEC:柠檬酸三乙酯,MTBE:甲基叔丁基醚,THF:四氢呋喃,LAH:氢化锂铝,RT:室温。
具体实施方式
下面将借助于实施方式说明本发明。如下文详细阐释的,以下文中所描述的方式可以合成根据本发明的式(I)的化合物。另外要注意的是,IUPAC命名法可能与此前使用的日常名称有差异。
实施例1:3-异戊基环己酮(2)
格氏试剂的制备:将镁屑(16.5g,0.687mol)在研钵中轻轻碾碎并放置在烧瓶中的300ml THF中,加入一勺尖的碘,在回流下加热(溶液必须褪色),然后才可以滴加1/10的3-甲基丁基溴(93.8g,0.621mol),在开始形成格氏试剂之后,滴加150ml THF中的剩余的3-甲基丁基溴,使混合物回流1小时,随后使混合物冷却。
格氏溶液经由导管被转移到搅拌良好、被冷却到-5℃的300ml THF中的碘化铜悬浮液(8.0g,0.042mol)中。在碘化铜溶解之后冷却到-20℃并且滴加环己-2-烯-1-酮(34g,0.354mol)且在-20℃下继续搅拌4小时,然后解冻到室温(RT)并继续搅拌过夜。处理:将混合物加入到600ml冰冷的饱和氯化铵溶液中,加入300ml MTBE。相分离,用100ml MTBE萃取三次,并且用200ml饱和NaCl溶液洗涤合并的有机相2次,干燥并浓缩。在15cm的韦式分馏柱中在真空下分馏粗产物(60.0g)。
产量:52.0g(87%)
1H-NMR(400MHz,CDCl3)δ2.42(ddt,J=13.8,4.0,1.9Hz,1H),2.35(dddt,J=14.1,5.0,3.6,1.5Hz,1H),2.25(dddd,J=14.1,12.2,6.1,1.2Hz,1H),2.04(dddd,J=13.8,8.0,6.3,3.9Hz,1H),2.00(ddt,J=13.7,11.6,1.1Hz,1H),1.96-1.84(m,1H),1.79-1.70(m,1H),1.70-1.58(m,1H),1.50(dp,J=13.2,6.6Hz,1H),1.40-1.24(m,3H),1.23-1.14(m,2H),0.87(d,J=6.6Hz,6H);
13C-NMR(101MHz,CDCl3)δ212.16(C=O),48.31(CH2-环),41.55(CH2-环),39.38(CH-环),35.91(CH2),34.35(CH2),31.35(CH2-环),28.08(CH-(CH3)2,25.32(CH2-环),22.58(CH-(CH3)2,22.57(CH-(CH3)2。
实施例2:3-异戊基环己醇(3)
在RT下,将LAH(2.48g,0.065mol)放置在200ml THF中。在0-10℃下小心滴加在70ml THF中的化合物2(10.0g)。在RT下,搅拌30分钟。
处理:将混合物加入到300ml冰水中(放热,生成H2)。加入150ml MTBE,然后加入150ml的25%的硫酸,直至沉淀(Al(OH)3)缓慢溶解,相分离,每次用50ml MTBE萃取水相2次,用100ml苏打溶液洗涤经合并的有机相1次并用100ml饱和NaCl溶液洗涤经合并的有机相1次,用Na2SO4干燥并浓缩。使用韦氏分馏柱在真空中在(60℃/500-10mbar)下,分馏粗产物(10.0g)。
产量:9.5g(94%)
反式异构体NMR:1H-NMR(400MHz,CDCl3)δ4.09-4.01(m,1H),1.78-1.57(m,5H),1.56-1.45(m,3H),1.25(ddd,J=13.3,10.5,2.9Hz,1H),1.21-1.15(m,4H),1.04-0.92(m,1H),0.86(d,J=6.6Hz,6H)
13C-NMR(101MHz,CDCl3)δ67.08(CH),39.97(CH2),36.41(CH2),34.26(CH2),33.61(CH2),32.35(CH2),31.97(CH),28.36(CH),22.81(CH3),22.81(CH3),20.21(CH2)。
顺式异构体NMR:1H-NMR(400MHz,CDCl3)δ3.55(tt,J=10.8,4.2Hz,1H),2.03-1.93(m,2H),1.76(dp,J=12.9,3.2Hz,1H),1.69-1.61(m,1H),1.55-1.42(m,J=6.5Hz,1H),1.33-1.17(m,6H),1.16-1.07(m,1H),0.93-0.83(m,1H),0.87(d,J=6.6Hz,6H),0.77(tdd,J=12.6,10.9,3.5Hz,1H)
13C-NMR(101MHz,CDCl3)δ71.14(CH),42.93(CH2),36.90(CH),36.35(CH2),36.06(CH2),34.91(CH2),32.35(CH2),28.36(CH),24.33(CH2),22.83(CH3)22.81(CH3)。
实施例3:(3E/Z)-1-异戊基-3-(甲氧基亚甲基)环己烷(4)
将甲氧基甲基三苯基氯化鏻(84.2g,0.246mol)放置在500ml THF中并且冷却到0℃,在0至5℃下分批加入叔丁酸钾(112g,0.40mol)。继续搅拌30分钟,随后将100ml THF中的3-异戊基环己酮(27.5g,0.164mol)缓慢滴入反应溶液中,此时将温度保持在低于10℃。在<10℃下继续搅拌30分钟,然后在22小时的过程中缓慢升温到RT。
处理:用H2O使混合物骤冷,用1000ml乙酸乙酯萃取3次,用200ml饱和NaCl溶液洗涤合并的有机相,干燥并且浓缩(60℃/500-10mbar)。在球形管上蒸馏粗产物(96.2g)。(150℃,0.8mbar)。
产量:36.2g(定量(quantitative))
1H-NMR(400MHz,CDCl3)δ5.75(d,J=1.7Hz,1H),5.74(t,J=2.0Hz,1H),3.53(s,6H),2.75-2.67(m,1H),2.66-2.59(m,1H),2.06(dt,J=13.0,2.3Hz,1H),2.02-1.91(m,1H),1.91-1.80(m,1H),1.80-1.69(m,4H),1.70-1.55(m,1H),1.49(dddd,J=12.8,10.4,6.3,2.6Hz,2H),1.43(s,2H),1.40-1.11(m,13H),1.10-0.94(m,2H),0.94-0.81(m,12H)。
13C-NMR(101MHz,CDCl3)δ138.95,138.94异构体,117.98,117.93异构体,59.28,59.28异构体,39.44异构体,38.21异构体,37.14,37.43,37.14异构体,36.27,36.24异构体,34.68,34.51异构体,33.19,31.38,28.32,28.30异构体,28.25,28.23异构体,26.93异构体,22.70,22.67异构体,22.65,22.63异构体。
实施例4:3-异戊基环己基甲醛(5)
在1l的搅拌器中加入置于THF(400ml)中的化合物4(35.0g,0.178mol)和10%的HCl溶液(96ml),然后将反应物(educt)依次加入并将混合物加热到沸腾温度,在回流下加热1小时。
处理:用水将混合物骤冷并且用MTBE萃取3次。用H2O洗涤合并的有机相一次,干燥并蒸发(60℃/500-10mbar)。在韦式分馏柱中在真空下分馏粗产物(31.0g)。
产量:31.0g(95%)
反式异构体NMR:1H-NMR(400MHz,CDCl3)δ9.60(d,J=1.57Hz,1H),2.23(ttd,J=12.17,3.52,1.62Hz,1H),1.98(mc,3H),1.75(tq,J=14.30,3.34,1.72Hz,1H),1.71(mc,1H),1.64(mc,3H),1.20(mc,5H),1.14(J=3.70Hz,1H),0.86(d,J=6.73Hz,6H)。
13C-NMR(101MHz,CDCl3)δ204.83,50.64,37.13,36.31,36.05,35.05,33.58,28.22,26.12,25.44,22.63,22.63。
实施例5:(3-异戊基环己基)甲醇(6)
在氮气(将设备完全冲刷)下,将LAH(3.2g,0.085mol)在RT下放置在200ml THF中。在0-10℃下小心滴加在70ml THF中的3-异戊基环己基甲醛(14.0g,0.077mol)。在RT下搅拌30分钟。
处理:将混合物加到300ml冰水中(放热,生成H2)。将150ml MTBE加入混合物,然后加入150ml的25%的硫酸,直至沉淀(Al(OH)3)缓慢溶解,相分离,每次用50ml MTBE萃取水相2次,用100ml苏打溶液洗涤合并的有机相1次并用100ml饱和NaCl溶液洗涤1次,用Na2SO4干燥,蒸发(60℃/500-10mbar)。在球形管蒸馏器上蒸馏粗产物(13.3g)。(90℃,1.0mbar)。
产量:12.7g(90%)
1H-NMR(600MHz,CDCl3)δ3.46(dd,J=10.5,6.3Hz,1H),3.44(dd,J=10.6,6.3Hz,1H),1.82-1.71(m,3H),1.56-1.45(m,2H),1.45-1.36(m,2H),1.31-1.21(m,2H),1.21-1.12(m,3H),0.88(d,J=6.8Hz,1H),0.86(d,J=6.6Hz,6H),0.85-0.77(m,2H),0.57(q,J=11.9Hz,1H);
13C-NMR(151MHz,CDCl3)δ68.93,40.60,37.50,36.18,35.46,33.41,32.77,29.59,28.54,25.82,22.71,22.68。
实施例6:1-异戊基环己基甲醛(7)
类似于化合物3来制备化合物7。
1H-NMR(400MHz,CDCl3)δ9.81(d,J=1.3Hz,1H),9.55(d,J=4.0Hz,1H),2.45(dtd,J=6.8,3.9,1.9Hz,1H),2.01(ddt,J=10.0,10.1,3.9Hz,1H),1.93-1.81(m,4H),1.80-1.66(m,3H),1.65-1.59(m,4H),1.59–1.51(m,3H),1.51–1.43(m,2H),1.42-1.30(m,5H),1.29-1.20(m,4H),1.19–1.08(m,3H),0.92(d,J=6.6Hz,3H),0.87(d,J=6.6Hz,3H),0.86(d,J=6.5Hz,3H),0.84(d,J=6.5Hz,3H)。
13C-NMR(101MHz,CDCl3)δ206.13,205.71,70.63,61.38,55.81,52.19,51.07,42.00,41.96,41.75,37.26,36.94,36.72,36.44,35.70,32.44,30.34,29.32,28.73,28.19,28.14,27.03,26.52,26.11,25.27,25.01,24.77,24.70,24.21,23.80,23.69,22.87,22.71,22.68,22.62,22.52,22.28,22.13。
实施例7:(1-异戊基环己基)甲醇(8)
类似于化合物4,由化合物7来备化合物8
产率:>90%
1H-NMR(400MHz,CDCl3)δ3.71(dd,J=10.8,3.1Hz,1H),3.67-3.58(m,3H),1.871.64(m,9H),1.64–1.44(m,5H),1.04–1.29(m,18H),0.84–0.89(12H)。
13C-NMR(101MHz,CDCl3)δ65.83,63.35,44.10,42.09,38.29,37.08,37.01,35.57,35.46,31.57,30.96,29.59,29.59,28.83,28.44,28.30,26.21,25.97,25.77,23.01,22.87,22.87,22.53,22.37。
实施例8:4-异戊基环己基甲醛(9)
类似于化合物3来制备化合物9。
1H-NMR(400MHz,CDCl3)δ9.38(s,1H),9.34–9.32(m,1H),1.90–1.78(m,3H),1.73–1.61(m,3H),1.61–1.52(m,2H),1.48–1.33(m,4H),1.26–1.15(m,2H),1.10–0.92(m,12H),0.88(d,J=6.6Hz,7H),0.86(d,J=6.6Hz,7H),0.68–0.53(m,2H)。
13C-NMR(101MHz,CDCl3)δ203.68,202.89,50.52,47.39,37.61,36.95,36.57,36.48,35.20,34.12,32.20,32.20,29.84,29.84,28.59,28.54,26.17,26.17,24.31,24.31,22.83,22.83,22.83,22.83。
实施例9:(4-异戊基环己基)甲醇(10)
类似于化合物4,由化合物9来制备化合物10
产率:>90%
1H-NMR(400MHz,CDCl3)δ3.44(d,J=6.3Hz,2H),1.78(d,J=9.1Hz,4H),1.48(ddt,J=11.4,7.5,4.5Hz,1H),1.41(dd,J=10.8,5.3Hz,1H),1.17(d,J=3.1Hz,4H),1.15(d,J=3.5Hz,1H),0.98–0.88(m,5H),0.86(d,J=6.6Hz,6H)。
13C-NMR(101MHz,CDCl3)δ122.66,68.83,67.44,66.47,40.17,38.44,38.12,36.7736.32,35.43,35.11,34.18,33.82,32.74,31.83,29.52,28.97,28.86,28.28,28.24,25.76,25.38,22.70,22.68。
实施例10:洗发水
将实施例1的化合物以0.5重量%的剂量合并到具有以下组成的洗发水基本成分中:月桂基醚硫酸钠12%
(例如Texapon NSO,Cognis Deutschland GmbH公司)
椰油酰胺基丙基甜菜碱2%
(例如Dehyton K,Cognis Deutschland GmbH公司)
氯化钠 1.4%
柠檬酸 1.3%
苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸乙酯、对羟基苯甲酸丁酯和对羟基苯甲酸丙酯 0.5%
水 82.8%
洗发水基本成分的pH值为约6。由此制备了100ml的20重量%的洗发水水溶液。将2缕发丝一起在这种洗发水溶液中洗涤2分钟,随后在手温下的流动水下冲洗20秒。一缕发丝湿着包装在铝箔中,而第二缕发丝用吹风机吹干。由一个小组在气味方面评估这两缕发丝。这两缕发丝的气味描述为:强烈发散的,类似玫瑰的,果香味的。
实施例11:织物软化剂
将实施例2的香水组合物(在添加6重量%的实施例1的酮之后)以0.5重量%的剂量合并到具有以下组成的织物软化剂基本成分中:
甲基硫酸季铵(Esterquat,酯季铵盐),约90%5.5%(例如Rewoquat WE 18,WitcoSurfactants GmbH公司)
烷基二甲基苄基氯化铵,约50%0.2%
(例如Preventol R50,BayerAG公司)
约1%的着色溶液, 0.3%
水 94.0%
织物软化剂基本成分的pH值在2至3的范围内。用370g的1%的织物软化剂水溶液(基于所述织物软化剂基本成分,包含0.5重量%的实施例2的香水组合物)在线测试机(Linetest machine)中以织物软化程序在20℃下将两块织物布料冲洗30分钟。将布料拧干然后甩干20秒。将一块布料湿着用收缩塑料膜包裹,并且另一块悬挂至干燥。接着由一个小组在气味方面评估这两块布料。
对这两块布料的气味描述:花香的,清新的,发散的,以及在木材味方面带有轻微水果味和甜味底调;完整且和谐的气味印象。
实施例12:洗涤粉末
将实施例3的香水油组合物(在1重量%的添加之后)以0.4重量%的剂量并入到具有以下配方的洗涤粉末基本成分:
用370g的1%的水性洗涤粉末碱液(基于包含0.4重量%的实施例3的香水油组合物的洗涤粉末基本成分(洗涤粉末碱液的pH值明显处于碱性范围内))在线测试机中以主洗涤过程在60℃下将两块布料洗涤45分钟。首先用冷水冲洗布料5分钟、拧干、然后甩干20秒。将一块布料湿着用收缩塑料膜包裹,另一块悬挂至干燥。接着由一个小组在气味方面评估这两块布料。
气味描述分别为:强烈的,发散的,具有天然味调和果香底调的类似玫瑰味;完整且和谐的气味印象。
实施例13:香水1
实施例14:香水2
实施例15:香水3
实施例16:香水4
实施例17:香水5
实施例18:香水6
实施例19:香水7
实施例20:香水8
所有香水实施例显示出果香型混合气味。香水实施例5至8的特征在于特别增强的果香味调。
Claims (15)
1.式(I)的化合物的用途,
其中
X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,
在虚线之一的相应位置上分别存在单键或双键,其中当X=OH基团时存在至少一个双键,并且其中3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位与环相连,
所述化合物用作香味剂和/或芳香剂。
2.根据权利要求1所述的式(I)的化合物的用途,其中X表示氧原子、-CHO基团、-OH基团或-CH2OH基团,并且在虚线之一的相应位置上存在至少一个双键,所述化合物用作香味剂和/或芳香剂。
3.根据权利要求1所述的式(I)的化合物的用途,其中X表示-CHO基团或-CH2OH基团,并且在虚线之一的相应位置上存在单键或双键,所述化合物用作香味剂和/或芳香剂。
4.根据权利要求1至3所述的式(I)的化合物的用途,用作玫瑰味调的芳香剂。
5.根据权利要求1至3所述的式(I)的化合物的用途,用于赋予、改变和/或增强选自由以下味调组成的组的一种、两种或多种气味味调:青草味、药草味、清新味、果香味、花香味、木材味、甜味、泥土味、油脂味、金属味和香胶味,优选为青草味和/或果香味的味调中的至少一种。
6.一种香味剂和/或芳香剂,包含式(I)的至少一种化合物。
7.一种香味剂和/或芳香剂混合物,具有根据权利要求6所述的至少一种香味剂和/或芳香剂,
所述香味剂和/或芳香剂混合物另外包含一种或多种附加的香味剂和/或芳香剂,其中所述附加的香味剂和/或芳香剂或者一种、多种或全部的香味剂和/或芳香剂选自由以下项组成的组:天然原料提取物,优选精油、冷凝酯、净油、树脂、类树脂、香胶、酊剂和/或单独香味剂,优选地选自下组:(1)烃;(2)脂肪族醇;(3)脂肪族醛及其缩醛;(4)脂肪族酮及其肟;(5)脂肪族含硫化合物;(6)脂肪族腈;(7)脂肪族羧酸的酯;(8)非环状萜醇;(9)非环状萜醛和萜酮;(10)环状萜醇;(11)环状萜醛和萜酮;(12)环状醇;(13)环脂肪族醇;(14)环状和环脂肪族醚;(15)环状和大环状酮;(16)环脂肪族醛;(17)环脂肪族酮;(18)环状醇的酯;(19)环脂肪族醇的酯;(20)环脂肪族羧酸的酯;(21)芳香脂肪族醇;(22)芳香脂肪族醇与脂肪族羧酸的酯;(23)芳香脂肪族醚;(24)芳香族和芳香脂肪族醛;(25)芳香族和芳香脂肪族酮;(26)芳香族和芳香脂肪族羧酸及其酯;(27)含氮的芳香族化合物;(28)酚、苯基醚和苯基酯;(29)杂环化合物;(30)内酯;以及
其混合物。
8.一种香味剂和/或芳香剂组合物,包含:
a)根据权利要求1至3所述的式(I)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮以及
b)一种或多种、优选两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种其他的香味剂和/或芳香剂。
9.根据权利要求8所述的香味剂和/或芳香剂组合物,
其中所述一种或多种其他的香味剂和/或芳香剂选自由以下项组成的组:2-环戊-2-烯-1-基乙酸乙酯,(E)-丁-2-烯酸-1-环己基乙酯,(E)-丁-2-烯酸-2-环戊基环戊酯,3-环己基丙酸烯丙酯,己酸烯丙酯,(E)-丁-2-烯酸-1,3-二甲基丁酯,2-甲基丙酸-1,3-二甲基丁-3-烯基酯和/或(E)-1-(2,6,6-三甲基环己-2-烯-1-基)丁-2-烯-1-酮。
10.一种有香味的或芳香化的制品,包含
有效感受量的根据权利要求1至3所述的式(I)的一种或多种化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或根据权利要求7所述的香味剂和/或芳香剂混合物和/或根据权利要求8或9所述的香味剂和/或芳香剂组合物,
一种、两种、三种、四种、五种、六种、七种、八种、九种、十种或更多种其他的香味剂和/或芳香剂,其中优选所述其他的香味剂和/或芳香剂中的一种、多种或全部赋予果香和/或木材气味,
一种或多种其他的添加物质、辅助物质和/或活性物质,优选两种、三种、四种、五种或更多种添加物质、辅助物质和/或活性物质。
11.根据权利要求10所述的有香味或芳香化的制品,其中所述有香味或芳香化的制品选自由以下项组成的组:
香水净油、香水、淡香水、须后水、古龙水、须前产品、喷洒古龙水、有香味的清新纸巾、酸性、碱性或中性清洁剂、纺织品清新剂、熨烫助剂、液态洗涤剂、粉末状洗涤剂、洗涤物预处理剂、织物软化剂、清洗皂、清洗片剂、消毒剂、表面消毒剂、空气清新剂、气溶胶喷雾剂、蜡和抛光剂、身体护理剂、手霜和乳液、足霜和乳液、脱毛霜和乳液、须后霜和乳液、美黑霜和乳液、护发产品、除臭剂、止汗剂、装饰性化妆产品、蜡烛、灯油、卫生香、杀虫剂、驱虫剂、燃料。
12.根据权利要求10或11所述的有香味或芳香化的制品,其中分别基于所述制品的总质量,式(I)的化合物和/或2-(3-甲基丁基)环己烷-1-醇和/或2-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮和/或4-(3-甲基丁基)环己烷-1-醇和/或4-(3-甲基丁基)环己烷-1-酮和/或3-(3-甲基丁基)环己烷-1-醇和/或3-(3-甲基丁基)环己烷-1-酮的总量在0.00001至10重量%的范围内,优选在0.0001至5重量%的范围内,特别优选在0.001至2重量%的范围内,最优选在0.005至1重量%的范围内。
13.式(II)的化合物
其中X表示-CHO基团或-CH2OH基团;并且在虚线任何之一的位置上分别存在单键或双键,并且其中3-异戊基残基或3-异戊-2-烯基残基在相对于X基团的邻位、间位或对位中与环相连,其前提条件是,当在环中存在双键时,则3-异戊基残基或3-异戊-2-烯基残基作为邻位或间位取代基直接结合到这个双键上。
14.根据权利要求1至3所述的式(I)的化合物或者根据权利要求13所述的式(II)的化合物,其中所述化合物以在2、3或4位处以顺式:反式异构体混合物的形式存在,其中主要为反式构型。
15.一种用于制备根据权利要求13或14所述的化合物(II)的方法,至少包括步骤(i)和(ii),其特征在于,从2-环己-3-烯出发:
(i)通过维蒂希反应获得1-异戊基-2-(甲氧基亚甲基)环己烷(化合物4a)、1-异戊基-3-(甲氧基亚甲基)环己烷(化合物4b)或1-异戊基-4-(甲氧基亚甲基)环己烷(化合物4c),
(ii)通过随后的烯醇裂解产生醛(化合物5a,b,c),
(iii)并且通过任选的随后的还原获得醇(化合物6a,b,c)。
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US20210324300A1 (en) | 2021-10-21 |
JP2021532230A (ja) | 2021-11-25 |
US11634659B2 (en) | 2023-04-25 |
JP7201788B2 (ja) | 2023-01-10 |
EP3826986A1 (de) | 2021-06-02 |
CN112469685A (zh) | 2021-03-09 |
CN112469685B (zh) | 2024-01-02 |
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