CN117413043A - 5-甲基-5-(4-甲基-3-戊烯-1-基)-2(5h)-呋喃酮作为芳香化学品的用途 - Google Patents
5-甲基-5-(4-甲基-3-戊烯-1-基)-2(5h)-呋喃酮作为芳香化学品的用途 Download PDFInfo
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- CN117413043A CN117413043A CN202280039229.9A CN202280039229A CN117413043A CN 117413043 A CN117413043 A CN 117413043A CN 202280039229 A CN202280039229 A CN 202280039229A CN 117413043 A CN117413043 A CN 117413043A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/50—Perfumes
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2093—Esters; Carbonates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2096—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
本发明涉及式(I)的化合物,其用作芳香化学品以赋予组合物甜美、香豆、金合欢、木质印象。本发明进一步涉及式(I)的化合物作为芳香化学品以赋予组合物甜美、香豆、金合欢和/或木质印象以及用于增强和/或改变组合物的芳香的用途。本发明进一步涉及一种组合物,其包含至少一种式(I)的化合物和(i)至少一种不同于式(I)的化合物的芳香化学品或(ii)至少一种非芳香化学载体,或(iii)(i)和(ii)。
Description
发明领域
本发明涉及式(I)的化合物,其用作芳香化学品以赋予组合物甜美、香豆、金合欢、木质印象。本发明进一步涉及式(I)的化合物作为芳香化学品以赋予组合物甜美、香豆、金合欢和/或木质印象以及用于增强和/或改变组合物的芳香的用途。本发明进一步涉及一种组合物,其包含至少一种式(I)的化合物和(i)至少一种不同于式(I)的化合物的芳香化学品或(ii)至少一种非芳香化学载体,或(iii)(i)和(ii)。
发明背景
芳香化学品,尤其是香精很有意义,尤其是在化妆品、清洁和洗衣组合物的领域中。
尽管已存在大量的合成芳香化学品,但始终需要新组分以能够满足极其多样化的应用领域所需的众多性质。这些包括,首先,感官性质,即该化合物应具有有利的嗅觉性质。此外,芳香化学品还应具有另外的正面的附带性质,例如高效制备方法、由于与其它芳香化学品的协同效应而提供更好感官属性的可能性、在某些应用条件下的更高稳定性、更好的更高持久力。
这些性质对如下组合物特别有意义:例如护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物和散香器用的组合物。
特别感兴趣的是可赋予组合物一种或多种不同的感官印象由此有助于该组合物的丰富和有趣的感官属性,尤其是嗅觉属性的芳香化学品。在这方面,可提供甜美、香豆、金合欢和/或木质印象的芳香化学品很有意义。此外,持久性以及顽固性特别有意义,从而在该组合物中以及在用该组合物处理的表面上获得持久的气味印象。
但是,由于即使化学结构的微小变化也会引起感官性质,如气味和/或风味的巨大变化,有针对性地寻找具有特定和独特感官性质,如特定气味的物质是极其困难的。因此在大多数情况下,寻找新的芳香化学品是困难和费力的,不知道是否真的找到具有所需气味和/或风味的物质。
本发明的一个目的是提供可以单独或作为混合物用作组合物中的芳香化学品的物质,特别寻求具有宜人气味的气味强烈的物质。此外,它们应该可与其它芳香化学品组合,以便创造新颖有利的感官属性并且可用于组合物。
本发明的一个目的是提供具有宜人的嗅觉印象;优选选自甜美香调、香豆香调、金合欢香调和木质香调的两种或更多种印象的组合的新型芳香化学品。
本发明的进一步目的在于该芳香化学品应该可由易得的原材料获得,以使它们能够快速和经济地制造。
发明概述:
通过提供本发明的式(I)的化合物实现这些目的。
令人惊讶地发现,本发明的式(I)的化合物宜人的嗅觉印象;优选为选自甜美香调、香豆香调、金合欢香调和木质香调的两种或更多种印象的组合。
本发明的第一个方面涉及式(I)的化合物或其立体异构体用于赋予组合物芳香印象的用途。
本发明的第二个方面涉及式(I)的化合物,其包括以式I(a)和I(b)的化合物为代表的对映体的混合组合物。
本发明的第三个方面涉及一种赋予组合物芳香印象的方法,其至少包括将至少一种式(I)的化合物添加到组合物中的步骤。
本发明的另一个方面涉及至少一种式(I)的化合物用于改变组合物的芳香特征的用途。
本发明的另一个方面涉及一种增进组合物的芳香的方法。所述方法包含将所述至少一种式(I)的化合物与其它成分,例如至少一种不同于式(I)的化合物的其它芳香化学品和/或至少一种非芳香化学载体混合以获得芳香化学组合物的步骤。
本发明的再一个方面涉及一种改变化学组合物的芳香的方法。所述方法包含将至少一种本发明的化合物并入芳香化学组合物中以获得芳香改变的芳香化学组合物的步骤。
此外,式(I)的化合物可以由易得的原材料开始通过简单合成以良好收率和纯度生产。因此,本发明的化合物可以大规模地以简单和具有成本效益的方式生产。
详述
以下详述是示例性的并且无意限制本发明或本发明的应用和用途。此外,无意受到以上技术领域、背景、概述或以下详述中给出的任何理论的束缚。
本文所用的术语“包含”与“包括”或“含有”同义,并且是包容性的或开放性的并且不排除另外的未列举的成员、要素或方法步骤。会认识到,本文所用的术语“包含”包括术语“由...组成”。
此外,说明书和权利要求书中的术语"(a)"、"(b)"、"(c)"、"(d)"等和类似术语用于区分类似的要素,不一定用于描述先后顺序或时间顺序。要理解的是,如此使用的术语在适当的情形下可互换,并且本文所述的主题的实施方案能够以不同于本文所描述或例示的其它顺序操作。在术语“(A)”、“(B)”和“(C)”或AA)、BB)和CC)或"(a)"、"(b)"、"(c)"、"(d)"、"(i)"、"(ii)"等涉及方法或使用或检测的步骤的情况下,在这些步骤之间没有时间或时间间隔相干性,也就是说,这些步骤可同时进行或在这些步骤之间可能有几秒、几分钟、几小时、几天、几周、几个月或甚至几年的时间间隔,除非在如上下文中阐述的申请中另行指出。
在以下段落中,更详细地定义该主题的不同方面。如此定义的各个方面可与任何其它方面组合,除非清楚地作出相反的指示。特别地,被指为优选或有利的任何特征可与被指为优选或有利的任何其它特征组合。
本说明书通篇提到的“一个实施方案”或“一实施方案”或“优选实施方案”是指联系该实施方案描述的特定要素、结构或特征包括在本发明的至少一个实施方案中。因此,短语“在一个实施方案中”或“在一个优选实施方案中”在本说明书各处的出现不一定都是指同一实施方案,但可能指同一实施方案。此外,要素、结构或特征可以以如本领域技术人员从本公开中显而易见的任何合适的方式组合在一个或多个实施方案中。此外,尽管本文中描述的一些实施方案包括另一些实施方案中所含的一些要素而不包括另一些要素,但如本领域技术人员所理解,不同实施方案的要素的组合意在该主题的范围内并构成不同实施方案。例如,在所附权利要求书中,任何要求保护的实施方案可以以任何组合使用。
此外,本说明书通篇规定的范围也包括端点值,即1至10的范围意味着1和10都包括在该范围内。为避免疑问,申请人应该有权根据适用的法律享有任何等同物。
在本发明中,术语“芳香”是指感官性质并包含气味和/或风味。
术语“芳香化学品”是指用于获得感觉或感官(在本文中可互换使用)印象的物质,并包含其用于获得嗅觉和/或风味印象。术语“嗅觉印象”或“香调(note)”(在此可互换使用)是指没有任何正面或负面判断的气味印象,而本文所用的术语“香气印象”或“香味印象”或“芳香印象”(在本文中可互换使用)与通常感觉宜人的气味印象相关联。因此“香味”或“香气”是指主要引发宜人气味印象的芳香化学品。风味是指引发味觉印象的芳香化学品。
本文所用的术语“芳香组合物”是指引发芳香的组合物。术语芳香组合物包含“气味组合物”和/或“风味组合物”。气味组合物是主要引发气味印象的组合物,风味组合物是主要引发味觉印象的组合物。
术语“芳香属性”是指芳香化学品的整体芳香印象并且由芳香化学品的各个芳香印象组成。
术语气味组合物包含“香味组合物”或“香气组合物”(在本文中可互换使用),它们主要引发通常感觉宜人的气味印象。
一般的表述“有利的感觉性质”或“有利的感官性质”描述了芳香化学品呈现的感官印象的美好性和简明性。“美好性”和“简明性”是本领域技术人员,如调香师熟悉的术语。美好性通常是指自发引起的、带来正面感知的、宜人的感官印象。但是,“美好”不一定与“甜美”同义。“美好”也可以是麝香或檀香的气味。“简明性”通常是指自发引起的感官印象,其对于同一试验评审小组而言,可再现地令人想起相同的具体事物。例如,物质可具有自发令人想起“苹果”的气味:该气味随之简明地是“苹果”。如果这种苹果气味非常宜人,因为该气味令人想起例如香甜的完全成熟的苹果,该气味被称为“美好”。但是,通常酸苹果的气味也是简明的。如果在闻到该物质时同时产生这两种反应,在该实例中因此是美好和简明的苹果气味,则这种物质具有特别有利的感官性质。
术语“的组合”、“与…组合”或“与…结合”在本文中用于表示两种化合物的组合物、方法或用途时,考虑到这两种化合物不需要以所述化合物的物理混合物的形式使用而是可分开使用(例如添加)的事实。如果这些化合物分开使用,它们可以任何顺序相继(即一个接一个)或同时(即基本在相同时间)使用(例如添加)。
术语“增进”在本文中用于描述增强和/或改变芳香化学品或组合物的芳香的效果。术语“增强”包括芳香的美好性和简明性的改进和/或强度的改进。术语“改变”包括芳香属性的改变。术语“美好性”和“简明性”是本领域技术人员,如调香师熟悉的并具有各自的含义。
可通过阈值测定确定该强度。气味的阈值是相关气体空间中的物质浓度,在该浓度下代表性的试验评审小组刚好可感知气味印象,尽管不再必须对其进行定义。
当需要前调特征的应用时,其中要特别迅速和强烈地传递气味,例如在除臭剂、空气清新剂或在味觉领域中在口香糖中,在香味组合物中特别需要增进效果。
术语“本发明涉及”和“本发明针对”在本发明通篇同义使用。
术语“顽固性”描述芳香化学品随时间经过的蒸发行为。可以例如通过将芳香化学品施加到试纸条上和随后嗅觉评价该试纸条的气味印象来测定顽固性。对于具有高顽固性的芳香化学品,评审人员在长时间跨度后仍可识别芳香印象。
术语“持久力”描述芳香化学品与表面,例如皮肤或纺织品的相互作用,尤其是在表面的后续处理,例如洗涤后。可以例如通过用包含芳香化学品的纺织品洗涤剂组合物洗涤纺织品和随后嗅觉评价刚洗涤后的纺织品(湿纺织品)以及评价长时间储存后的干纺织品来测定持久力。
术语“稳定性”描述芳香化学品在与氧气、光和/或其它物质接触时的行为。具有高稳定性的芳香化学品优选在多种多样的组合物中和在各种储存条件下长时间保持其芳香属性。
为了赋予组合物或用组合物处理的表面持久的芳香印象,芳香化学品在组合物中的顽固性、持久力以及稳定性应该优选高。
除非本文中另行规定,本文所述的“化合物(I)”涉及由式(I)定义的化合物或其立体异构体。
术语“立体异构体”是如IUPAC描述的通用术语,其用于单一化合物的仅在其原子的空间取向上不同而非原子的连接性不同的所有异构体。因此,术语立体异构体包括镜像异构体(对映异构体)、几何(顺式/反式或E/Z)异构体和非对映异构体。关于该术语的精确定义,参见IUPAC定义或G.Helmchen:"Vocabulary and Nomenclature of OrganicStereochemistry”.In Houben-Weyl E21a,Stereoselective Synthesis.Helmchen,R.W.Hoffmann,J.Mulzer、E.Schaumann(Hrsg.),1995,1-74。可能的异构体可以作为混合物存在(即外消旋物、顺式/反式混合物或非对映异构体的混合物)。
用途
本发明的一个实施方案涉及式(I)的化合物或其立体异构体用于赋予组合物芳香印象的用途。
在一个实施方案中,式(I)的化合物包括以式Ia和Ib的化合物为代表的对映体的混合组合物。
在一个实施方案中,式I(a)的化合物和式I(b)的化合物可以单独使用或以任何比例的混合物使用。
在另一实施方案中,式I(a)的化合物和式I(b)的化合物的混合物是其中化合物的比率在1:99至99:1的范围内的混合物。
在另一实施方案中,式I(a)的化合物和式I(b)的化合物的混合物是其中化合物的比率为50:50的比率的混合物。
本领域技术人员可以调节式I(a)的化合物和式I(b)的化合物的比率以达到在0.1:99.9至99.9:0.1的范围内的特定比率,以赋予组合物特定的芳香印象或几种芳香印象。
本发明的一个优选实施方案涉及至少一种式(I)的化合物作为芳香化学品以赋予组合物甜美香调、香豆香调、金合欢香调和/或木质香调的用途。
在进一步实施方案中,本发明涉及式(I)的化合物用于增进组合物的芳香的用途。
在本发明的一个实施方案中,至少一种式(I)的化合物用作香精或香精组合物。
特别地,至少一种式(I)的化合物用于赋予组合物选自甜美香调、香豆香调、金合欢香调和木质香调的香调。
优选地,式(I)的化合物用于赋予组合物选自甜美香调、香豆香调、金合欢香调和木质香调的两种或更多种印象的组合。
优选地,式(I)的化合物是5-甲基-5-(4-甲基-3-戊烯-1-基)-2(5H)-呋喃酮。
如上文所述的合适组合物是例如用于个人护理、家庭护理、工业应用的组合物,以及用于其它应用的组合物,如药物组合物或作物保护组合物。
优选地,根据本发明的式(I)的化合物用于选自香水组合物、身体护理组合物(包括化妆品组合物和口腔牙齿卫生产品)、卫生制品、清洁组合物(包括洗碗组合物)、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物和作物保护组合物的组合物。
在以下段落中描述这些组合物。
组合物
在一个实施方案中,本发明涉及一种组合物,其包含至少一种式(I)的化合物和
(i)至少一种不同于式(I)的化合物的芳香化学品(X),或
(ii)至少一种非芳香化学载体,或
(iii)(i)和(ii)。
优选地,在这一实施方案中,该组合物包含基于组合物的总重量计≥0.01重量%至≤70.0重量%的总量的式(I)的化合物。
优选地,该组合物是芳香组合物,更优选是香精组合物。
不同于式(I)的化合物的芳香化学品
在一个实施方案中,该混合物包含至少一种不同于式(I)的化合物的芳香化学品。不同于式(I)的化合物的芳香化学品也称为芳香化学品(X)。
由于它们的物理性质,式(I)的化合物可很好地与不同于式(I)的化合物的芳香化学品和其它常规成分组合在芳香组合物,特别是香精组合物中。这使得能够例如创造具有新颖有利的感官属性的芳香组合物(优选香精组合物)。尤其如上文已经解释,该化合物可为其它芳香化学品(如香精)提供增进效果。
芳香化学品(X)优选选自:
乙酸香叶酯、α-己基肉桂醛、异丁酸2-苯氧基乙基酯、二氢月桂烯醇、二氢茉莉酮酸甲酯、4,6,6,7,8,8-六甲基-1,3,4,6,7,8-六氢环五[g]苯并吡喃、四氢芳樟醇、乙基芳樟醇、水杨酸苄酯、2-甲基-3-(4-叔丁基苯基)丙醛、肉桂醇、乙酸4,7-亚甲基-3a,4,5,6,7,7a-六氢-5-茚基酯和/或乙酸4,7-亚甲基-3a,4,5,6,7,7a-六氢-6-茚基酯、香茅醇、乙酸香茅酯、四氢香叶醇、香草醛、乙酸芳樟酯、乙酸苏合香酯(styrolyl acetate)、八氢-2,3,8,8-四甲基-2-萘乙酮和/或2-乙酰基-1,2,3,4,6,7,8-八氢-2,3,8,8-四甲基萘、水杨酸己酯、乙酸4-叔丁基环己基酯、乙酸2-叔丁基环己基酯、α-紫罗兰酮、n-α-甲基紫罗兰酮、α-异甲基紫罗兰酮、香豆素、乙酸松油酯、2-苯基乙基醇、4-(4-羟基-4-甲基戊基)-3-环己烯甲醛、α-戊基肉桂醛、巴西酸乙二醇酯、(E)-和/或(Z)-3-甲基环十五-5-烯酮、15-十五-11-烯内酯和/或15-十五-12-烯内酯、15-环十五内酯、1-(5,6,7,8-四氢-3,5,5,6,8,8-六甲基-2-萘基)乙酮、2-异丁基-4-甲基四氢-2H-吡喃-4-醇、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、顺式乙酸-3-己烯酯、反式乙酸-3-己烯酯、反式-2/顺式-6-壬二烯醇、2,4-二甲基-3-环己烯甲醛、2,4,4,7-四甲基辛-6-烯-3-酮、2,6-二甲基-5-庚烯-1-醛、冰片、3-(3-异丙基苯基)丁醛、2-甲基-3-(3,4-亚甲二氧基苯基)丙醛、3-(4-乙基苯基)-2,2-二甲基丙醛、西瓜酮(7-甲基-2H-1,5-苯并二氧杂卓(benzodioxepin)-3(4H)-酮、乙酸3,3,5-三甲基环己基酯、2,5,5-三甲基-1,2,3,4,4a,5,6,7-八氢萘-2-酚、3-(4-叔丁基苯基)-丙醛、2-甲基戊酸乙酯、乙氧基甲氧基环十二烷、2,4-二甲基-4,4a,5,9b-四氢茚并[1,2-d][1,3]二英、乙酸(2-叔丁基环己基)酯和3-[5,5,6-三甲基双环[2.2.1]庚-2-基]环己-1-醇。
在一个优选实施方案中,所述至少一种芳香化学品(i)选自苯甲酸甲酯、乙酸苄酯、乙酸香叶酯、2-异丁基-4-甲基四氢-2H-吡喃-4-醇、芳樟醇、2-异丁基-4-甲基四氢-2H-吡喃-4-醇和苯甲酸甲酯。
在另一优选实施方案中,所述至少一种芳香化学品(i)选自乙基香草醛、香草醛、2,5-二甲基-4-羟基-2H-呋喃-3-酮(furaneol)和3-羟基-2-甲基-4H-吡喃-4-酮(麦芽酚)。
式(I)的化合物可与其组合以产生根据本发明的组合物的附加芳香化学品可见于例如S.Arctander,Perfume and Flavor Chemicals,第I和II卷,Montclair,N.J.,1969,自行出版或H.Surburg和J.Panten,Common Fragrance and Flavor Materials,第4版,Wiley-VCH,Weinheim 2016。具体地,可以提到:来自天然原材料的提取物,如精油、冷凝脂、净油、树脂、香膏、香脂、酊剂,例如,龙涎香酊;香树油;当归籽油;当归根油;八角茴香油;缬草油;罗勒油;树苔净油;月桂油;艾草油;安息香树脂;香柠檬油;蜂蜡净油;桦焦油;苦杏仁油;香旱芹油;布枯叶油;巴西檀木油;杜松焦油;菖蒲油;樟脑油;依兰油;小豆蔻油;卡藜油;肉桂油;肉桂净油;海狸香净油;雪松叶油;雪松木油;岩蔷薇油;香茅油;柠檬油;古巴香脂;古巴香脂油;芫荽油;木香根油;枯茗油;丝柏油;印蒿油;莳萝叶油;莳萝子油;Eau DeBrouts Absolute;橡苔净油;榄香脂油;龙蒿油;柠檬桉叶油;桉叶油;小茴香油;松针油;白松香油;白松香树脂;老鹳草油;葡萄柚油;愈创木油;古芸香脂;古芸香脂油;蜡菊净油;蜡菊油;姜油;鸢尾根净油;鸢尾根油;茉莉净油;白菖油;蓝春黄菊油;罗马洋甘菊油;胡萝卜籽油;卡藜油;松针油;留兰香油;草贡蒿油;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;圆叶当归油;蒸馏白柠檬油;压榨白柠檬油;芳樟油;山苍子油;月桂叶油;肉豆蔻油;甘牛至油;橘子油;香厚壳桂皮油;含羞草净油;麝香籽油;麝香酊;香紫苏油;肉豆蔻油;没药净油;没药油;桃金娘油;丁香叶油;丁香花油;橙花油;乳香净油;乳香油;红没药油;橙花净油;橙油;牛至油;玫瑰草油;广藿香油;紫苏子油;秘鲁香脂油;欧芹叶油;欧芹子油;苦橙叶油;胡椒薄荷油;胡椒油;众香子油;松树油;胡薄荷油;玫瑰净油;玫瑰木油;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;穗熏衣草油;八角茴香油;苏合香油;万寿菊油;冷杉叶油;茶树油;松节油;百里香油;吐鲁香脂;香豆净油;晚香玉净油;香草提取物;紫罗兰叶净油;马鞭草油;香根草油;杜松子油;酒渣油;苦艾油;冬青油;牛膝草油;麝猫香净油;肉桂叶油;肉桂皮油,及其馏分,或从中分离的成分;
选自烃的个别香精,例如3-蒈烯;α-蒎烯;β-蒎烯;α-萜品烯;γ-萜品烯;p-伞花烃;红没药烯;莰烯;石竹烯;柏木烯;法呢烯;苧烯;长叶烯;月桂烯;罗勒烯;瓦伦烯;(E,Z)-1,3,5-十一碳三烯;苯乙烯;二苯甲烷;
脂族醇,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;(E)-和(Z)-3-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-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;十三醛;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-癸烯醛;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(heptanal diethylacetal);1,1-二甲氧基-2,2,5-三甲基-4-己烯;香茅氧基乙醛;(E/Z)-1-(1-甲氧基丙氧基)-己-3-烯;脂族酮及其肟,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;
脂族含硫化合物,例如3-甲基硫代己醇;3-甲基硫代己醇乙酸酯;3-巯基己醇;3-巯基己醇乙酸酯;3-巯基己醇丁酸酯;3-乙酰硫代己醇乙酸酯;1-薄荷烯-8-硫醇;
脂族腈,例如2-壬烯腈;2-十一碳烯腈;2-十三碳烯腈;3,12-十三碳二烯腈;3,7-二甲基-2,6-辛二烯腈;3,7-二甲基-6-辛烯腈;
脂族羧酸的酯,例如(E)-和(Z)-甲酸3-己烯基酯;乙酰乙酸乙酯;乙酸异戊酯;乙酸己酯;乙酸3,5,5-三甲基己基酯;乙酸3-甲基-2-丁烯基酯;(E)-乙酸2-己烯基酯;(E)-和(Z)-乙酸3-己烯基酯;乙酸辛酯;乙酸3-辛酯;乙酸1-辛烯-3-基酯;丁酸乙酯;丁酸丁酯;丁酸异戊酯;丁酸己酯;(E)-和(Z)-异丁酸3-己烯基酯;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-辛炔酸甲酯(methyl 2-octinate);2-壬炔酸甲酯(methyl2-noninate);2-异戊氧基乙酸烯丙酯;甲基-3,7-二甲基-2,6-辛二烯酸酯;巴豆酸4-甲基-2-戊基酯;
无环萜烯醇,例如香叶醇;橙花醇;芳樟醇;熏衣草醇;橙花叔醇;法呢醇;四氢芳樟醇;2,6-二甲基-7-辛烯-2-醇;2,6-二甲基辛-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;和它们的甲酸酯、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、惕各酸烯酯(tiglinate)和3-甲基-2-丁烯酸酯;
无环萜烯醛和酮,例如香叶醛;橙花醛;香茅醛;7-羟基-3,7-二甲基辛醛;7-甲氧基-3,7-二甲基辛醛;2,6,10-三甲基-9-十一烯醛;香叶基丙酮;以及香叶醛、橙花醛、7-羟基-3,7-二甲基辛醛的二甲基-和二乙基缩醛;环萜烯醇,例如薄荷醇;异蒲勒醇;α-萜品醇;萜品-4-醇;薄荷-8-醇;薄荷-1-醇;薄荷-7-醇;冰片;异冰片;氧化芳樟醇;诺卜醇;雪松醇;龙涎醇(ambrinol);岩兰草醇;愈创木醇;和它们的甲酸酯、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、惕各酸烯酯(tiglinate)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-3-酮;香芹酮;樟脑;小茴香酮;α-紫罗兰酮;β-紫罗兰酮;α-n-甲基紫罗兰酮;β-n-甲基紫罗兰酮;α-异甲基紫罗兰酮;β-异甲基紫罗兰酮;α-鸢尾酮;α-二氢大马酮;β-二氢大马酮;β-大马酮;δ-二氢大马酮;γ-二氢大马酮;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-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;圆柚酮;二氢圆柚酮;4,6,8-巨豆三烯-3-酮;α-甜橙醛;β-甜橙醛;乙酰化柏木油(甲基柏木酮);
环醇,例如4-叔丁基环己醇;3,3,5-三甲基环己醇;3-异龙脑基环己醇;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;
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;2-乙基-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;
环状和脂环族醚,例如桉油醇;柏木甲基醚;环十二烷基甲基醚;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[2,1-b]呋喃;3a-乙基-6,6,9a-三甲基十二氢萘并[2,1-b]呋喃;1,5,9-三甲基-13-氧杂双环-[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)-1,3-二氧杂环己烷;
环状和大环酮,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;7-环十六烯-1-酮;(7/8)-环十六烯-1-酮;9-环十七烯-1-酮;环十五酮;环十六酮;
脂环族醛,例如2,4-二甲基-3-环己烯甲醛;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;
环醇的酯,例如乙酸2-叔丁基环己基酯;乙酸4-叔丁基环己基酯;乙酸2-叔戊基环己基酯;乙酸4-叔戊基环己基酯;乙酸3,3,5-三甲基环己基酯;乙酸十氢-2-萘基酯;巴豆酸2-环戊基环戊基酯;乙酸3-戊基四氢-2H-吡喃-4-基酯;乙酸十氢-2,5,5,8a-四甲基-2-萘基酯;乙酸4,7-亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;丙酸4,7-亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;异丁酸4,7-亚甲基-3a,4,5,6,7,7a-六氢-5或6-茚基酯;乙酸4,7-亚甲基八氢-5或6-茚基酯;
脂环族醇的酯,例如巴豆酸1-环己基乙酯;
脂环族羧酸的酯,例如3-环己基丙酸烯丙酯;环己氧基乙酸烯丙酯;顺式-和反式-二氢茉莉酮酸甲酯;顺式-和反式-茉莉酮酸甲酯;2-己基-3-氧代环戊烷甲酸甲酯;2-乙基-6,6-二甲基-2-环己烯甲酸乙酯;2,3,6,6-四甲基-2-环己烯甲酸乙酯;2-甲基-1,3-二氧戊环-2-乙酸乙酯;
芳脂族醇,例如苄醇;1-苯乙醇、2-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-甲氧基苄基醇;1-(4-异丙基苯基)乙醇;
芳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;乙酸2-苯乙酯;丙酸2-苯乙酯;异丁酸2-苯乙酯;异戊酸2-苯乙酯;乙酸1-苯乙酯;乙酸α-三氯甲基苄酯;乙酸α,α-二甲基苯基乙酯;丁酸α,α-二甲基苯基乙酯;乙酸肉桂酯;异丁酸2-苯氧基乙酯;乙酸4-甲氧基苄酯;
芳脂族醚,例如2-苯乙基甲基醚;2-苯乙基异戊基醚;2-苯乙基1-乙氧基乙基醚;苯乙醛二甲缩醛;苯乙醛二乙缩醛;氢化阿托醛二甲基缩醛(hydratropaaldehydedimethyl acetal);苯乙醛甘油缩醛;2,4,6-三甲基-4-苯基-1,3-二氧杂环己烷;4,4a,5,9b-四氢茚并[1,2-d]-m-二英(dioxine);4,4a,5,9b-四氢-2,4-二甲基茚并[1,2-d]-m-二英;
芳族和芳脂族醛,例如苯甲醛;苯基乙醛;3-苯基丙醛;氢化阿托醛(hydratropaaldehyde);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-叔丁基苯基)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-戊基肉桂醛;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-亚甲二氧基苯基)丙醛;
芳族和芳脂族酮,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-羟苯基)-2-丁酮;1-(2-萘基)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;苯乙酸乙酯;苯乙酸香叶酯;苯乙酸苯乙酯;肉桂酸甲酯;肉桂酸乙酯;肉桂酸苄酯;肉桂酸苯乙酯;肉桂酸肉桂酯;苯氧基乙酸烯丙酯;水杨酸甲酯;水杨酸异戊酯;水杨酸己酯;水杨酸环己酯;顺式-水杨酸-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-苯基缩水甘油酸乙酯;3-甲基-3-苯基缩水甘油酸乙酯;
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;肉桂腈;3-甲基-5-苯基-2-戊腈;3-甲基-5-苯基戊腈;邻氨基苯甲酸甲酯;N-甲基邻氨基苯甲酸甲酯;邻氨基苯甲酸甲酯与7-羟基-3,7-二甲基辛醛的席夫碱、2-甲基-3-(4-叔丁基苯基)丙醛或2,4-二甲基-3-环己烯甲醛;6-异丙基喹啉;6-异丁基喹啉;6-仲丁基喹啉;2-(3-苯基丙基)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、苯基醚和苯基酯,例如草蒿脑;茴香脑;丁子香酚;丁子香基甲基醚;异丁子香酚;异丁子香基甲基醚;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;乙酸丁香酚酯;2-甲氧基-4-甲基酚;2-乙氧基-5-(1-丙烯基)酚;苯乙酸对甲酚酯;
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(octanolide);3-甲基-1,4-辛内酯;1,4-壬内酯;1,4-癸内酯;8-癸-1,4-内酯;1,4-十一内酯;1,4-十二内酯;1,5-癸内酯;1,5-十二内酯;4-甲基-1,4-癸内酯;1,15-十五内酯;顺式-和反式-11-十五烯-1,15-内酯;顺式-和反式-12-十五烯-1,15-内酯;1,16-十六内酯;9-十六烯-1,16-内酯;10-氧杂-1,16-十六内酯;11-氧杂-1,16-十六内酯;12-氧杂-1,16-十六内酯;1,12-十二烷二酸乙二醇酯;1,13-十三烷二酸乙二醇酯;香豆素;2,3-二氢香豆素;八氢香豆素。
该组合物中所用的芳香化学品(X)获自已知商业来源并从德国采购。
在一个优选实施方案中,该组合物包含至少一种式(I)的化合物和至少一种芳香化学品(X)。
非芳香化学载体:
本发明的组合物中的非芳香化学载体优选选自表面活性剂、油组分、抗氧化剂、除臭活性剂和溶剂。
优选地,所述至少一种非芳香化学载体是没有感官性质或没有明显感官性质的化合物、化合物混合物或其它添加剂。非芳香化学载体可用于稀释和/或固定式(I)的化合物和-任选地,如上文定义的所述至少一种芳香化学品(X)(如果包含在该组合物中)。
本发明的组合物中的非芳香化学载体优选选自表面活性剂、油组分、溶剂或上述两种或更多种的任何混合物。
溶剂
在本发明中,“溶剂”用于稀释根据本发明使用的式(I)的化合物而没有自己的香气。
根据组合物选择溶剂的量。
优选地,溶剂以基于组合物的总重量计0.01重量%至99.0重量%的总量,更优选0.05重量%至95.0重量%的总量,再更优选0.1重量%至80.0重量%的总量,最优选0.1重量%至70.0重量%,特别是0.1重量%至60.0重量%的总量存在于该组合物中。
在一个优选实施方案中,该组合物包含基于组合物的总重量计0.05重量%至10重量%,更优选0.1重量%至5重量%,再更优选0.2重量%至3重量%的总溶剂。在本发明的再一个优选实施方案中,该组合物包含基于组合物的总重量计20重量%至70重量%,更优选25重量%至50重量%的总溶剂。
优选的溶剂选自乙醇、异丙醇、二乙二醇单乙基醚、甘油、丙二醇、1,2-丁二醇、二丙二醇、柠檬酸三乙酯、肉豆蔻酸异丙酯和上述两种或更多种的任何混合物。
在一个优选实施方案中,该组合物包含至少一种式(I)的化合物和至少一种溶剂和任选至少一种芳香化学品(X)。
油组分
优选地,总油组分以基于组合物的总重量计0.1至80重量%,更优选0.5至70重量%,再更优选1至60重量%,再更优选1至50重量%,特别是1至40重量%,更特别是5至25重量%,尤其是5至15重量%的量存在。
优选地,油组分选自基于含有6至18个,优选8至10个碳原子的脂肪醇的格尔伯特醇,以及其它另外的酯,如肉豆蔻酸肉豆蔻醇酯、棕榈酸肉豆蔻醇酯、硬脂酸肉豆蔻醇酯、异硬脂酸肉豆蔻醇酯、油酸肉豆蔻醇酯、山嵛酸肉豆蔻醇酯、芥酸肉豆蔻醇酯、肉豆蔻酸鲸蜡醇酯、棕榈酸鲸蜡醇酯、硬脂酸鲸蜡醇酯、异硬脂酸鲸蜡醇酯、油酸鲸蜡醇酯、山嵛酸鲸蜡醇酯、芥酸鲸蜡醇酯、肉豆蔻酸十八烷醇酯、棕榈酸十八烷醇酯、硬脂酸十八醇酯、异硬脂酸十八烷醇酯、油酸十八烷醇酯、山嵛酸十八烷醇酯、芥酸十八烷醇酯、异硬脂醇肉豆蔻酸酯、异硬脂醇棕榈酸酯、异硬脂醇硬脂酸酯、异硬脂醇异硬脂酸酯、异硬脂醇油酸酯、异硬脂醇山嵛酸酯、异硬脂醇油酸酯、肉豆蔻酸油醇酯、棕榈酸油醇酯、硬脂酸油醇酯、异硬脂酸油醇酯、油酸油醇酯、山嵛酸油醇酯、芥酸油醇酯、肉豆蔻酸二十二烷醇酯、棕榈酸二十二烷醇酯、硬脂酸二十二烷醇酯、异硬脂酸二十二烷醇酯、油酸二十二烷醇酯、山嵛酸二十二烷醇酯、芥酸二十二烷醇酯、瓢儿菜醇肉豆蔻酸酯、瓢儿菜醇棕榈酸酯、瓢儿菜醇硬脂酸酯、瓢儿菜醇异硬脂酸酯、瓢儿菜醇油酸酯、瓢儿菜醇山嵛酸酯和瓢儿菜醇芥酸酯。也合适的是C18-C38烷基-羟基羧酸与直链或支链C6-C22脂肪醇的酯,更尤其是苹果酸二辛酯、直链和/或支链脂肪酸与多元醇(例如丙二醇、二聚二醇或三聚三醇)的酯、基于C6-C10脂肪酸的甘油三酯、基于C6-C18脂肪酸的液体单-、二-和三甘油酯混合物、C6-C22脂肪醇和/或格尔伯特醇与芳族羧酸,更特别是苯甲酸的酯、二羧酸与含有2至10个碳原子和2至6个羟基的多元醇的酯、植物油、支链伯醇、取代环己烷、直链和支链C6-C22脂肪醇碳酸酯,例如碳酸二辛酯(CC)、基于含有6至18,优选8至10个碳原子的脂肪醇的Guerbet碳酸酯、苯甲酸与直链和/或支链C6至C22醇的酯(例如TN)、每烷基含有6至22个碳原子的直链或支链、对称或不对称二烷基醚,例如二辛基醚(OE)、环氧化脂肪酸酯与多元醇和烃的开环产物,或其混合物。
在一个优选实施方案中,该组合物包含至少一种式(I)的化合物和至少一种油组分和任选至少一种芳香化学品(X)。
抗氧化剂
要理解的是,抗氧化剂能够抑制或防止由氧效应和其它氧化过程造成的受保护的组合物的不合意的变化。抗氧化剂的作用在大多数情况下在于它们充当在自氧化过程中产生的自由基的自由基清除剂。
在一个优选实施方案中,抗氧化剂选自
·氨基酸(例如甘氨酸、丙氨酸、精氨酸、丝氨酸、苏氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物,
·咪唑(例如尿刊酸)及其衍生物,
·肽,如D,L-肌肽、D-肌肽、L-肌肽(=β-丙氨酰-L-组氨酸)及其衍生物,
·类胡萝卜素、胡萝卜素(例如α-胡萝卜素、β-胡萝卜素、番茄红素、叶黄素)或其衍生物,
·绿原酸及其衍生物,
·硫辛酸及其衍生物(例如二氢硫辛酸),
·金硫葡糖、丙基硫尿嘧啶和其它硫醇(例如硫氧还蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺和它们的糖基、N-乙酰基、甲基、乙基、丙基、戊基、丁基和十二烷基、棕榈酰基、油酰基、γ-亚油酰基、胆甾醇基和甘油基酯)以及它们的盐,
·硫代二丙酸二月桂酯、硫代二丙酸二硬脂醇酯、硫代二丙酸及其衍生物(酯、醚、肽、脂质、核苷酸、核苷和盐),
·亚砜亚胺化合物(例如丁硫氨酸亚砜亚胺、高半胱氨酸亚砜亚胺、丁硫氨酸砜、五-、六-、七-硫堇亚砜亚胺),
·(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、植酸、乳铁蛋白),
·α-羟基酸(例如柠檬酸、乳酸、苹果酸),
·腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素、boldin(=来自植物波尔多树(Peumus boldus)的生物碱,boldo提取物),
·EDTA、EGTA及其衍生物,
·不饱和脂肪酸及其衍生物(例如γ-亚麻酸、亚油酸、油酸),
·叶酸及其衍生物,
·泛醌和泛醇及其衍生物,
·维生素C和衍生物(例如抗坏血酸棕榈酸酯、抗坏血酸磷酸镁、抗坏血酸乙酸酯),
·生育酚和衍生物(例如维生素E乙酸酯),
·维生素A和衍生物(维生素A棕榈酸酯),
·安息香树胶的苯甲酸松柏醇酯、芸香酸(rutic acid)及其衍生物、α-糖基芸香苷、阿魏酸、亚糠基葡萄糖醇,
·丁基羟基甲苯(BHT)、丁基羟基苯甲醚(BHA),
·去甲二氢愈创木脂酸、去甲二氢愈创木酸、三羟基苯丁酮、尿酸及其衍生物、甘露糖及其衍生物,
·超氧化物岐化酶,
·锌及其衍生物(例如ZnO、ZnSO4),
·硒及其衍生物(例如蛋氨酸硒)和
·均二苯乙烯及其衍生物(例如均二苯乙烯氧化物、反式-均二苯乙烯氧化物),
·和上述两种或更多种的混合物。
在一个优选实施方案中,抗氧化剂选自季戊四醇、羟基氢化肉桂酸四-二-叔丁酯、去甲二氢愈创木酸、阿魏酸、白藜芦醇、没食子酸丙酯、丁基羟基甲苯(BHT)、丁基羟基苯甲醚(BHA)、抗坏血酸棕榈酸酯、生育酚和上述两种或更多种的混合物。
优选地,根据本发明的组合物包含基于组合物的总重量计0.001至25重量%,优选0.005至10重量%,更优选0.01至8重量%,再更优选0.025至7重量%,再更优选0.05至5重量%的总量的抗氧化剂。
在一个优选实施方案中,该组合物包含至少一种式(I)的化合物和至少一种抗氧化剂和任选至少一种芳香化学品(X)。
除臭活性剂
除臭组合物(除臭剂和止汗剂)对抗、遮蔽或消除体臭。通过皮肤细菌作用于顶质分泌汗液以致形成气味令人不快的降解产物而形成体臭。
除臭活性剂优选选自止汗剂、酯酶抑制剂、抗菌剂和上述两种或更多种的混合物。
合适的止汗剂选自铝、锆或锌的盐。实例是氯化铝、水合氯化铝、二氯化羟铝、倍半氯化羟铝,和它们例如与1,2-丙二醇的络合物,尿囊素羟铝(aluminumhydroxyallantoinate)、氯化酒石酸铝、三氯羟铝锆、四氯羟铝锆、五氯羟铝锆,和它们例如与氨基酸,如甘氨酸的络合物。优选使用水合氯化铝、四氯羟铝锆、五氯羟铝锆及其络合物。
优选地,止汗剂选自氯化铝、水合氯化铝(aluminum chlorohydrate)、二氯化羟铝(aluminum dichlorohydrate)、倍半氯化羟铝(aluminum sesquichlorohydrate)、尿囊素羟铝(aluminum hydroxyallantoinate)、氯化酒石酸铝、三氯羟铝锆、四氯羟铝锆、五氯羟铝锆和上述两种或更多种的混合物。
在腋窝区出汗的情况下,由细菌形成细胞外酶-酯酶,主要是蛋白酶和/或脂酶,并裂解汗中存在的酯,在该过程中释放气味。合适的酯酶抑制剂是例如柠檬酸三烷基酯、如柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯,特别是柠檬酸三乙酯。酯酶抑制剂抑制酶活性并由此减轻臭味形成。可能通过柠檬酸酯的裂解释放游离酸并降低皮肤的pH值至通过酰化使酶失活的程度。另一些酯酶抑制剂是甾醇硫酸酯或磷酸酯,例如羊毛甾醇、胆固醇、菜油甾醇、豆甾醇和谷甾醇的硫酸酯或磷酸酯,二羧酸及其酯,例如戊二酸、戊二酸单乙酯、戊二酸二乙酯、己二酸、己二酸单乙酯、己二酸二乙酯、丙二酸和丙二酸二乙酯,羟基羧酸及其酯,例如柠檬酸、苹果酸、酒石酸或酒石酸二乙酯、甘氨酸锌和上述两种或更多种的混合物。
优选地,酯酶抑制剂选自柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯、柠檬酸三乙酯、羊毛甾醇、胆固醇、菜油甾醇、豆甾醇、谷甾醇硫酸酯、谷甾醇磷酸酯、戊二酸、戊二酸单乙酯、戊二酸二乙酯、己二酸、己二酸单乙酯、己二酸二乙酯、丙二酸、丙二酸二乙酯、柠檬酸、苹果酸、酒石酸、酒石酸二乙酯、甘氨酸锌和上述两种或更多种的混合物。
优选地,根据本发明的组合物包含基于组合物的总重量计0.01至20重量%,优选0.1至10重量%,更特别是0.5至5重量%的总量的酯酶抑制剂。
本文所用的术语“抗菌剂”包含具有杀菌和/或抑菌性质的物质。这些物质通常对抗革兰氏阳性菌,例如4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N'-(3,4-二氯苯基)-脲、2,4,4'-三氯-2'-羟基二苯醚(三氯生)、4-氯-3,5-二甲基酚、2,2'-亚甲基-双-(6-溴-4-氯酚)、3-甲基-4-(1-甲基乙基)-酚、2-苄基-4-氯酚、3-(4-氯苯氧基)-丙-1,2-二醇、丁基氨基甲酸3-碘-2-丙炔酯、洗必泰、3,4,4'-三氯碳酰苯胺(TTC)、苯氧基乙醇、单癸酸甘油酯、单辛酸甘油酯、单月桂酸甘油酯(GML)、单癸酸双甘油酯(DMC)、水杨酸-N-烷基酰胺,例如水杨酸-正辛基酰胺或水杨酸-正癸基酰胺。
优选地,抗菌剂选自壳聚糖、苯氧基乙醇、5-氯-2-(2,4-二氯苯氧基)-酚、4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N'-(3,4-二氯苯基)-脲、2,4,4'-三氯-2'-羟基二苯醚(三氯生)、4-氯-3,5-二甲基酚、2,2'-亚甲基-双-(6-溴-4-氯酚)、3-甲基-4-(1-甲基乙基)-酚、2-苄基-4-氯酚、3-(4-氯苯氧基)-丙-1,2-二醇、丁基氨基甲酸3-碘-2-丙炔酯、洗必泰、3,4,4'-三氯碳酰苯胺(TTC)、苯氧基乙醇、单癸酸甘油酯、单辛酸甘油酯、单月桂酸甘油酯(GML)、单癸酸双甘油酯(DMC)、水杨酸-N-烷基酰胺和上述两种或更多种的混合物。
优选地,根据本发明的组合物包含基于组合物的总重量计0.01至5重量%,优选0.1至2重量%的总量的抗菌剂。
在一个优选实施方案中,该组合物包含至少一种式(I)的化合物和至少一种除臭活性剂和任选至少一种芳香化学品(X)。
表面活性剂
优选地,表面活性剂选自阴离子型、非离子型、阳离子型、两性、两性离子型表面活性剂和上述两种或更多种的混合物。更优选地,表面活性剂是阴离子型表面活性剂。
优选地,根据本发明的组合物含有基于组合物的总重量计0至40重量%,更优选0至20重量%,更优选0.1至15重量%,特别是0.1至10重量%的总量的表面活性剂。
优选的非离子表面活性剂是脂肪醇聚二醇醚、烷基酚聚二醇醚、脂肪酸聚二醇酯、脂肪酸酰胺聚二醇醚、脂肪胺聚二醇醚、烷氧基化甘油三酯、混合醚和混合甲缩醛、任选部分氧化的烷基(烯基)寡糖苷或葡糖醛酸衍生物、脂肪酸-N-烷基葡糖酰胺、蛋白水解产物(特别是小麦基植物产品)、多元醇脂肪酸酯、糖酯、山梨糖醇酐酯、聚山梨醇酯和胺氧化物。如果非离子型表面活性剂含有聚二醇醚链,它们可具有常规同系物分布,尽管它们优选具有窄范围的同系物分布。
两性离子表面活性剂是在分子中含有至少一个季铵基团和至少一个COO(-)或SO3 (-)基团的表面活性化合物。
特别合适的两性离子表面活性剂是所谓的甜菜碱,如N-烷基-N,N-二甲基甘氨酸铵,例如椰油烷基二甲基甘氨酸铵,N-酰氨基丙基-N,N-二甲基甘氨酸铵,例如椰油酰氨基丙基二甲基甘氨酸铵,和在烷基或酰基中含有8至18个碳原子的2-烷基-3-羧甲基-3-羟乙基咪唑啉,和椰油酰氨基乙基羟乙基羧甲基甘氨酸盐。以CTFA名称椰油酰胺丙基甜菜碱(Cocamidopropyl Betaine)为人所知的脂肪酸酰胺衍生物特别优选。
两性表面活性剂也合适,特别是作为助表面活性剂。两性表面活性剂是在分子中除C8至C18烷基或酰基外还含有至少一个游离氨基和至少一个-COOH或-SO3H基团并能够形成内盐的表面活性化合物。合适的两性表面活性剂的实例是N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸,在烷基中含有大约8至18个碳原子。特别优选的两性表面活性剂是丙酸N-椰油烷基氨基酯(N-cocoalkylaminopropionate)、氨基丙酸椰油酰氨基乙基酯(cocoacylaminoethyl aminopropionate)和酰基肌氨酸。
阴离子型表面活性剂以水溶性阴离子基团,例如羧酸根、硫酸根、磺酸根或磷酸根,和亲脂基团为特征。从业人员从相关教科书中大量获知皮肤安全的阴离子型表面活性剂并可购得。它们特别是烷基硫酸盐(以它们的碱金属、铵或链烷醇铵盐的形式)、烷基醚硫酸盐、烷基醚羧酸盐、酰基羟乙基磺酸盐、酰基肌氨酸盐、含有直链C12-C18烷基或酰基的酰基牛磺酸,以及磺基琥珀酸盐和酰基谷氨酸盐(以它们的碱金属或铵盐的形式)。
特别合适的阳离子型表面活性剂是季铵化合物,优选卤化铵,更尤其是氯化和溴化铵,如烷基三甲基氯化铵、二烷基二甲基氯化铵和三烷基甲基氯化铵,例如鲸蜡基三甲基氯化铵、硬脂基三甲基氯化铵、二硬脂基二甲基氯化铵、月桂基二甲基氯化铵、月桂基二甲基苄基氯化铵和三鲸蜡基甲基氯化铵。此外,易生物降解的季铵酯化合物,例如以Stepantexe为名出售的二烷基甲硫酸铵和甲基羟烷基二烷氧基烷基甲硫酸铵,以及系列的相应产品可用作阳离子型表面活性剂。“酯基季铵盐(Esterquats)”通常被理解为是季铵化脂肪酸三乙醇胺酯盐。它们可为该组合物提供特别的柔软感。它们是通过有机化学的相关方法制成的已知物质。适合根据本发明使用的另一些阳离子型表面活性剂是季铵化蛋白水解产物。
由于式(I)的化合物的特征感官性质及其持久力、顽固性以及稳定性,其尤其可用于为含表面活性剂的组合物,例如清洁剂(特别是洗衣护理产品和通用清洁剂)提供气味,优选香味印象。其可优选用于赋予含表面活性剂的组合物持久的甜美香调、香豆香调、金合欢香调和/或木质香调。
在一个优选实施方案中,该组合物包含至少一种式(I)的化合物和至少一种表面活性剂和任选至少一种芳香化学品(X)。
合适的组合物是例如香水组合物、身体护理组合物(包括化妆品组合物和口腔牙齿卫生产品)、卫生制品、清洁组合物(包括洗碗组合物)、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物和作物保护组合物。
香水组合物可选自精细香氛产品、液体形式、凝胶形式或施加到固体载体上的形式的空气清新剂、气溶胶喷雾、加香清洁剂、香精蜡烛和油,如灯油或按摩油。
精细香氛产品的实例是香精提取物、Eau de Parfums、Eau de Toilettes、Eau deColognes、Eau de Solide和Extrait Parfum。
身体护理组合物包括化妆品组合物和口腔牙齿卫生产品,并可选自须后产品、须前产品、古龙水(splash cologne)、固体和液体皂、沐浴凝胶、洗发水、剃须皂、剃须泡沫、浴油、水包油型、油包水型和水包油包水型化妆品乳液,例如护肤霜和护肤水、面霜和面部水、防晒霜和防晒水、晒后霜和晒后水、护手霜和护手水、护足霜和护足水、脱毛霜和脱毛水、须后霜和须后水、美黑霜和美黑水,护发产品,例如头发喷雾剂、发胶、头发定型水、护发素、洗发水、永久和半永久头发着色剂、头发定型组合物如冷烫剂和头发柔顺组合物、生发水、发膏和发乳,除臭剂和止汗剂,例如腋下喷雾剂、卷剂(roll-on)、除臭棒和除臭膏,装饰性化妆品,例如眼线、眼影、指甲油、彩妆品、唇膏和睫毛膏,和口腔牙齿卫生产品,如牙膏、牙线、漱口水、口气清新剂、牙用泡沫、牙用凝胶和牙带。
卫生制品可选自线香(joss stick)、杀虫剂、驱虫剂、推进剂、除锈剂、加香清新擦巾、腋窝垫、婴儿尿布、卫生巾、厕纸、化妆棉、手帕纸、洗碗机除臭剂。
清洁组合物,例如固体表面清洁剂,可选自加香的酸性、碱性和中性清洁剂,例如地板清洁剂、窗户清洁剂、手洗和机洗使用的洗碗组合物、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、蜡和抛光剂如家具抛光剂、地板蜡、鞋油、消毒剂、表面消毒剂和卫生清洁剂、刹车盘清洁剂、管道清洁剂、除水垢剂、烤架和烤箱清洁剂、藻类和苔藓清除剂、去霉剂、立面清洁剂。
纺织品洗涤剂组合物可选自液体洗涤剂、粉末洗涤剂、洗衣预处理剂如漂白剂、浸泡剂和去渍剂、织物柔软剂、洗涤皂、洗涤片。
食品是指生的、煮熟的或加工过的可食用物质、冰、饮料或用于或意图用于完全或部分供人类食用的成分,或口香糖、软糖、果冻和甜食。
食品补充剂是含有旨在进一步增加膳食的营养价值的膳食成分的食用产品。膳食成分可以是下列物质之一或任何组合:维生素、矿物质、草药或其它物质、氨基酸、通过增加总膳食摄入而被人类用于补充饮食的膳食物质、浓缩物、代谢物、成分或提取物。食品补充剂可以许多形式存在,如片剂、胶囊、软胶囊、囊形片(Gel cap)、液体或粉剂。
药物组合物包含意图用于诊断、治愈、减轻、治疗或预防疾病的组合物以及旨在影响人类或其它动物身体的结构或任何功能的制品(非食品)。
作物保护组合物包含意图用于管理破坏农作物和林业的植物疾病、杂草和其它害虫(脊椎动物和无脊椎动物)的组合物。
优选地,根据本发明的组合物进一步包含至少一种辅助剂,其选自防腐剂、磨料、抗痤疮剂、抗皮肤老化剂、抗橘皮剂、去头屑剂、抗炎剂、防刺激剂、刺激减轻剂、收敛剂、防汗剂、防腐剂、抗静电剂、粘合剂、缓冲剂、载体材料、螯合剂、细胞兴奋剂、护理剂、脱毛剂、乳化剂、酶、精油、纤维、成膜剂、固定剂、泡沫形成剂、泡沫稳定剂、防泡剂、泡沫促进剂、杀真菌剂、胶凝剂、凝胶形成剂、护发剂、头发定型剂、头发柔顺剂、保湿剂、增湿物质、湿润剂物质、漂白剂、强化剂、去渍剂、荧光增白剂、浸渍剂、防污剂、减摩剂、润滑剂、保湿霜、软膏、乳浊剂、增塑剂、覆盖剂、抛光剂、光泽剂、聚合物、粉末、蛋白质、加脂剂(refattingagent)、去角质剂、有机硅、皮肤镇静剂、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、皮肤软化剂、冷却剂、皮肤冷却剂、增温剂、温肤剂、稳定剂、紫外线吸收剂、紫外线过滤剂、织物柔软剂、悬浮剂、皮肤美黑剂、增稠剂、维生素、蜡、脂肪、磷脂、饱和脂肪酸、单或多不饱和脂肪酸、α-羟基酸、多羟基脂肪酸、液化剂、染料、颜色保护剂、颜料、防腐蚀剂、多元醇、电解质和有机硅衍生物。
组合物的制备和赋予组合物芳香印象的方法
本发明的一个实施方案涉及一种制备式(I)的化合物的组合物的方法,所述组合物包含:
(i)至少一种不同于根据本发明的化合物的芳香化学品(X),或
(ii)至少一种非芳香化学载体,或
(iii)(i)和(ii)。
本发明还涉及一种增进组合物的芳香印象的方法,其中该方法包含将至少一种式(I)的化合物并入组合物中。
特别地,本发明涉及一种制备香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物或作物保护组合物的方法,其包含将至少一种式(I)的化合物包括在香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物或作物保护组合物中。
在一个实施方案中,本发明涉及一种赋予香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物或作物保护组合物令人想起甜美香调、香豆香调、金合欢香调和/或木质香调元素的香调的方法,其包含将至少一种式(I)的化合物包括在香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物或作物保护组合物中。
量
通常,式(I)的化合物在根据本发明的组合物、方法和用途中的总量通常适应特定的预期用途或预期应用,并因此可以在宽范围内变化。通常,使用芳香化学品,优选香料的常规标准商业量。
优选地,根据本发明的组合物包含基于组合物的总重量计0.001至99.9重量%的总量的式(I)的化合物。
特别地,该组合物包含基于组合物的总重量计0.001至99.5重量%,优选50至99重量%,更优选80至95重量%,特别是90至95重量%的总量的式(I)的化合物。
特别地,该组合物包含基于组合物的总重量计0.005至80重量%,优选0.1至30重量%,更优选1至20重量%,特别是5至15重量%的总量的式(I)的化合物。
特别地,该组合物包含基于组合物的总重量计0.001至20重量%,优选0.005至6重量%,更优选0.05至4重量%,特别是0.1至3重量%的总量的式(I)的化合物。
术语化合物(I)和式(I)的化合物在本说明书通篇可互换使用。术语多种化合物(I)和多种式(I)的化合物在本说明书通篇也可互换使用。
实施方案
下面提供一系列实施方案以进一步例示本公开而无意将本公开限制于下列具体实施方案。
1.式(I)的化合物或其立体异构体用于赋予组合物芳香印象的用途。
2.根据权利要求1的用途,其中所述式(I)的化合物包括单一对映异构体I(a)或I(b),或I(a)和I(b)的任何比率的混合物。
3.一种赋予组合物香调的方法,其至少包括将至少一种根据实施方案1的式(I)的化合物添加到组合物中的步骤。
4.根据实施方案1-3中任一项的用途或方法,其中所述组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物和作物保护组合物。
5.根据实施方案1-3中任一项的用途或方法,其中所述芳香印象选自甜美香调、香豆香调、金合欢香调和木质香调。
6.根据实施方案1-3中任一项的用途或方法,其中所述式(I)的化合物以基于组合物的总重量计≥0.001重量%至≤70.0重量%存在。
7.一种组合物,其包含至少一种根据实施方案1至2中任一项的式(I)的化合物,和
(i)至少一种不同于式(I)的化合物的芳香化学品(X),或
(ii)至少一种非芳香化学载体,或
(iii)(i)和(ii)。
8.根据实施方案7的组合物,其中式(I)的化合物以基于组合物的总重量计≥0.001重量%至≤70.0重量%存在。
9.根据实施方案7的组合物,其中所述至少一种非芳香化学载体(ii)选自表面活性剂、油组分、抗氧化剂、除臭活性剂和溶剂。
10.根据实施方案7-9中任一项的组合物,其中所述组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物和作物保护组合物。
实施例:
通过下面的非限制性实施例详细例示本发明。更特别地,下文规定的试验方法是本申请的一般公开的一部分并且不限于具体实施例。
1.分析方法:
通过13C-NMR和1H-NMR进行表征。在Bruker DPX-500能谱仪上测量13C-NMR和1H-NMR谱。
2.合成
实施例1
(化合物A(式(I)的化合物-5-甲基-5-(4-甲基戊-3-烯基)呋喃-2-酮)的制备)
将由芳樟醇通过羰基化制备的(E/Z)-4,8-二甲基-3,7-壬二烯酸(13.9克,76.4毫摩尔)溶解在置于配备内部温度计和磁搅拌棒的1升三颈烧瓶中的THF(160毫升)中,并用NaHCO3水溶液(10克在250毫升水中)处理。将溶液搅拌20分钟并将烧瓶包装在铝箔中以避光保存。将碘化钾(58.1克,350毫摩尔)和碘(132毫摩尔,33.6克)溶解在水(200毫升)中并加入。将所得混合物搅拌小时。
加入Na2S2O3(饱和水溶液)。分离相,水相用EtOAc(4×40毫升)萃取。合并的有机萃取物用NaHCO3水溶液(40毫升)洗涤,经硫酸镁干燥。在真空中除去溶剂。
将含有碘内酯的所得粗制残渣溶解在甲苯(100毫升)中并置于配备回流冷凝器的250毫升三颈烧瓶中。该溶液用NEt3(22.2克,220毫摩尔)处理并在100℃下搅拌。悬浮液变成深棕色。GC控制表明在100℃下搅拌4小时后起始材料完全消耗。加入水(50毫升)并分离相。水相用EtOAc(3x 20毫升)萃取。合并的有机萃取物用NaCl水溶液(30毫升)洗涤,经硫酸镁干燥并在真空中除去溶剂。通过Kugelrohr蒸馏纯化得到作为浅黄色油的外消旋5-甲基-5-(4-甲基戊-3-烯基)呋喃-2-酮(化合物A)(11.1克,78%收率)。
1H NMR(CDCl3,500MHz):δ=6.5(d,1H,2-H),5.6(d,1H,3-H),4.8(t,J=7.5Hz,2H,7-H),1.2-1.7(m,4H,2x CH2),1.6(s,3H,CH3),1.4(s,3H,CH3),1.0(s,3H,CH3).13C NMR(d8-甲苯,125MHz):δ=171.4,159.3,132.0,123.7,120.6,87.6,38.4,25.7,24.0,22.7,17.6ppm。
3.嗅觉印象
为了测试本发明的化合物和混合物的品质和强度,进行香气试纸试验。
为此,将吸水纸的试条浸渍到在柠檬酸三乙酯中含有1至10重量%受试化合物的溶液中。在溶剂蒸发(大约30秒)后,由受过训练的调香师嗅觉评价香气印象。
在下表1中指出本发明的式(I)的化合物-5-甲基-5-(4-甲基戊-3-烯基)呋喃-2-酮的香气印象。将该化合物配制在根据表2和3的香水组合物中并标记为化合物A。
表1:本发明的化合物
4.有利的组合物
将如表1中所示的化合物配制为根据表2和3的组合物。表1中所示的化合物在表2和3中标记为“化合物A”。
表2:组合物1A和1B
表3:组合物2A和2B
根据表2和表3的组合物,即1A、1B、2A、2B可包括在各种组合物中,其选自Deo泵喷雾、干净头发护发素、洗面凝胶(Face wash gel)、泡沫浴浓缩液、发胶、自发泡沐浴液、可喷涂防晒护理乳液、可喷涂防晒乳液、润肤面部凝胶、两相油泡沫浴液、洗发水、淋浴露、水-醇性AP/Deo泵喷雾、气溶胶、水性/含醇AP/Deo卷剂(Aqueous/alcoholic AP/Deo roll-on)、造型凝胶类型"Out of Bed"、剃须泡沫、敏感皮肤婴儿洗发水、用于敏感皮肤的沐浴液、用于敏感头皮的亮泽洗发水、除臭棒、婴儿湿巾、须后膏、面部凝胶、面部日间护理霜、洗面乳、身体乳液、防晒SPF50+喷涂液、手洗餐具洗涤剂-常规、手洗餐具洗涤剂-浓缩、卫生清洁剂-浓缩、通用清洁剂、抗菌织物柔软剂、洗涤剂组合物、粉末洗涤剂组合物和液体洗涤剂组合物。
本领域技术人员精通上述产品的各种一般配方。
组合物1A、1B、2A和2B可以例如配制在如标题为New Aroma Chemicals的IP.comNumber:IPCOM000258614D第6至46页,表1至表D13中公开的特定配方中,其中“FragranceComposition 1A”被相同量的组合物1A、1B、2A或2B替代。
Claims (10)
1.式(I)的化合物或其立体异构体用于赋予组合物芳香印象的用途。
2.根据权利要求1的用途,其中所述式(I)的化合物包括单一对映异构体I(a)或I(b),或I(a)和I(b)的任何比率的混合物。
3.一种赋予组合物香调的方法,其至少包括将至少一种根据权利要求1的式(I)的化合物添加到组合物中的步骤。
4.根据权利要求1-3中任一项的用途或方法,其中所述组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物和作物保护组合物。
5.根据权利要求1-3中任一项的用途或方法,其中所述芳香印象选自甜美香调、香豆香调、金合欢香调和木质香调。
6.根据权利要求1-3中任一项的用途或方法,其中式(I)的化合物以基于组合物的总重量计≥0.001重量%至≤70.0重量%存在。
7.一种组合物,其包含至少一种根据权利要求1-2中任一项的式(I)的化合物,和
(i)至少一种不同于式(I)的化合物的芳香化学品(X),或
(ii)至少一种非芳香化学载体,或
(iii)(i)和(ii)。
8.根据权利要求7的组合物,其中式(I)的化合物以基于组合物的总重量计≥0.001重量%至≤70.0重量%存在。
9.根据权利要求7的组合物,其中所述至少一种非芳香化学载体(ii)选自表面活性剂、油组分、抗氧化剂、除臭活性剂和溶剂。
10.根据权利要求7-9中任一项的组合物,其中所述组合物选自香水组合物、身体护理组合物、卫生制品、清洁组合物、纺织品洗涤剂组合物、散香器用的组合物、食品、食品补充剂、药物组合物和作物保护组合物。
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