CN101861296B - 广藿香醇增味剂 - Google Patents
广藿香醇增味剂 Download PDFInfo
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- CN101861296B CN101861296B CN2008801164196A CN200880116419A CN101861296B CN 101861296 B CN101861296 B CN 101861296B CN 2008801164196 A CN2008801164196 A CN 2008801164196A CN 200880116419 A CN200880116419 A CN 200880116419A CN 101861296 B CN101861296 B CN 101861296B
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/36—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.4.0) system, e.g. naphols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
- C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
- C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
- C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms
- C11B9/0053—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms both rings being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及8a-烷基-全氢-萘酚衍生物作为加香成分赋予木质-土质类型气味香调的用途。
Description
技术领域
本发明涉及香料领域。更具体地,其涉及一些用作木质-土质增味剂的通式(I)的全氢萘酚衍生物。本发明涉及所述化合物在香料工业中的用途以及含有所述化合物的组合物或制品。
背景技术
据我们所知,本发明化合物是新的,并且没有任何已知的结构接近的类似物作为加香成分。
发明内容
我们现在已经令人惊奇地发现了通式(I)的化合物可用作加香成分,例如赋予木质-土质类型的气味香调,
其中R1表示氢原子或甲酰基或乙酰基;
R2表示甲基或乙基;并且
每个R相互独立地表示氢原子或甲基,并且至少两个所述R是甲基。
根据本发明的一个实施方案,所述化合物(I)中R1是氢原子。
根据本发明的一个实施方案,所述化合物(I)中R2是甲基。
根据本发明的一个实施方案,所述化合物(I)为通式(II)的化合物,
其中两个R表示氢原子,另外两个R表示甲基。
作为本发明化合物的典型实例,可以列举全氢-6,8,8a-三甲基-1-萘酚。所述化合物拥有木质-土质气味,结合了令人感兴趣的草本-桉树底香。该木质香调缺乏任何琥珀内涵,后者常常存在于萘酚衍生物的木质增味剂中。而且,整个气味,特别是土质香调,非常接近于森林地被物的气味,并实际上非常强烈地令人想起纯广藿香醇的气味。由香料或气味的观点看,全氢-6,8,8a-三甲基-1-萘酚代表最接近纯广藿香醇的合成类似物。
此外该化合物由于缺乏广藿香油典型的酚的、辛辣的香调而将其本身与其它具有广藿香类型香调的加香成分区分开来。
还令人感兴趣地指出,在各种洗涤剂试验中,全氢-6,8,8a-三甲基-1-萘酚被证明是其气味家族中最具香味牢度的化合物之一。
如以上提及的,本发明涉及通式(I)化合物作为加香成分的用途。换言之,其涉及一种赋予、提高、促进或改变加香组合物或已加香制品的气味特性的方法,该方法包括向所述组合物或制品加入有效量的至少一种通式(I)的化合物。“通式(I)的化合物的用途”在此也必须理解为包含化合物(I)的任何组合物的用途,且它可以有利地用于香料工业作为活性成分。
实际上可以有利地用作加香成分的所述组合物,也是本发明的一个目的。
因此,本发明的另一个目的是一种加香组合物,其包含:
i)至少一种如上定义的本发明化合物作为加香成分;
ii)至少一种选自香料载体和香料基料的成分;和
iii)非强制选择的至少一种香料佐剂。
“香料载体”在此表示从香料的观点来看实际上是中性的材料,即不显著改变加香成分的感官特性。所述载体可以是液体或固体。
作为液体载体可以列举作为非限制性实例的乳化体系,即溶剂和表面活性剂体系,或通常用于香料的溶剂。通常用于香料的溶剂的性质和类型的详细描述是不可能穷举的。然而,可以列举作为非限制性实例的溶剂如一缩二丙二醇、邻苯二甲酸二乙酯、肉豆蔻酸异丙酯、苯甲酸苄酯、2-(2-乙氧基乙氧基)-1-乙醇或柠檬酸乙酯,它们是最通常使用的。
作为固体载体可以列举作为非限制性实例的吸收胶或聚合物,或还有包封材料。这类材料的实例可以包括成壁和增塑材料,如单糖、二糖或三糖,天然或改性淀粉,水解胶体,纤维素衍生物,聚乙酸乙烯酯,聚乙烯醇,蛋白质或果胶,或另外在参考文献如H.Scherz,Hydrorolloids:Stabilisatoren,Dickungs-und Gehermittel inLebensmittel,Band 2 der Schriftenreihe Lebensmittelchemie,Behr’s VerlagGmbH&Co.,汉堡,1996中列举的材料。包封是本领域技术人员公知的工艺,并可以通过例如使用如喷雾干燥、附聚或还有挤出的技术进行;或由包括凝聚和复合凝聚技术的涂料包封组成。
“香料基料”在此表示包括至少一种加香助成分的组合物。
所述加香助成分不是通式(I)化合物。另外,“加香助成分”在此表示一种化合物,该化合物用于加香制剂或组合物以赋予一种令人享受的效果。换言之,考虑到作为一种加香物质,这样的助成分必须为本领域技术人员所认知能够以积极或令人愉快的方式赋予或改变组合物的气味,而不仅仅是具有气味。
基料中存在的加香助成分的性质和类型在此不保证更详细的描述,它在任何情况下都无法穷举,本领域技术人员能够在其常知的基础上并根据想要的用途或应用和预期的感官效果选择它们。在通常意义上,这些加香助成分属于如下多种的化学品类别:醇、醛、酮、酯、醚、乙酸酯、腈、萜烯烃、含氮或含硫杂环化合物和精油,且所述加香助成分可以为天然或合成来源。无论如何许多这些加香助成分在参考文献中列出,例如书籍S.Arctander,Perfume and Flavor Chemicals,1969,Montclair,新泽西,USA,或它的更近版本,或相似种类的其它作品,以及香料领域丰富的专利文献。还理解的是所述助成分也可以是已知以受控方式释放各种类型加香化合物的化合物。
对于包括香料载体和香料基料两者的组合物,除先前说明的那些以外的其它合适香料载体也可以是醇、水/醇混合物、柠檬烯或其它萜烯、异链烷烃如以商标Isopar(来源:Exxon Chemical)已知的那些,或二醇醚和二醇醚酯如以商标Dowanol(来源:DowChemical Company)已知的那些。
“香料佐剂”在此表示能够赋予额外附加的益处如颜色、特定耐光性、化学稳定性等的成分。通常用于加香基料的佐剂的性质和类型的详细描述是不可能穷举的,但必须提及的是所述成分是本领域技术人员公知的。
由至少一种通式(I)的化合物和至少一种香料载体组成的本发明组合物,以及包含至少一种通式(I)的化合物、至少一种香料载体、至少一种香料基料和非强制选择的至少一种香料佐剂的加香组合物,都代表本发明的特定实施方案。
在此有用地提及在以上提及的组合物中含有多于一种通式(I)的化合物的可能性是重要的,这是由于它使得香水调配者能够制备调和物、香水,拥有本发明各种化合物的气味调子(tonality),从而产生用于他们工作的新工具。
优选的,任何由化学合成直接得到的混合物,例如未经足够净化的,其中本发明的化合物会涉及作为起始、中间或最终产物,都不能认为是根据本发明的加香组合物。
另外,本发明的组合物还可以有利地用于所有现代香料领域以积极赋予或改变向其中加入所述化合物(I)的消费品的气味。因此,包含如下物质的已加香制品也是本发明的目的:
i)作为加香成分的至少一种如上定义的通式(I)的化合物或本发明的加香组合物;和
ii)一种消费品基料。
为清楚起见,必须提及的是“消费品基料”在此表示与加香成分相容的消费品。换言之,根据本发明的已加香制品包含功能配制剂,以及非强制选择的对应于消费品(如洗涤剂或空气清新剂)的额外的有益试剂,和嗅觉有效量的至少一种本发明化合物。
消费品的组分的性质和类型在此不保证更详细的描述,它无论如何都无法穷举,本领域技术人员能够在常识的基础上并根据所述产品的性质和所需效果选择它们。
合适消费品基料的实例包括固体或液体洗涤剂和织物柔软剂以及香料中通常的所有其它制品,即香水,古龙水或须后水,香皂,浴盐、沐浴乳、浴油或沐浴露,卫生产品或头发护理产品如香波,身体护理产品,除臭剂或止汗剂,空气清新剂以及化妆品制剂。作为洗涤剂,存在希望的应用如用于洗涤或清洁各种表面的洗涤剂组合物或清洁产品,如希望用于纺织品、盘子或硬表面处理,而不管它们是否希望用于家庭或工业用途。其它已加香制品是织物清新剂、熨烫水、纸张、擦拭用品或漂白剂。
一些上述消费品基料可能代表了本发明化合物的攻击性介质,使得可能必须例如由包封保护本发明化合物以避免引起过早分解。
可以将本发明的化合物加入到各种上述制品或组合物的比例在宽的数值范围内变化。当本发明的化合物与通常用于本领域的加香助成分、溶剂或添加剂混合时,这些数值取决于要加香制品的性质和所需的感官效应以及在给定基料中助成分的性质。
例如,在加香组合物的情况下,基于将它们加入其中的组合物重量,本发明化合物典型的浓度是约0.01%~30%重量或甚至更多。当将这些化合物加入已加香制品时,相对于制品重量的百分数,可以使用低于这些的浓度,如约0.01%~10%重量。
本发明的化合物通过使适当的环己烯酮与适当的二烯(在狄尔斯-阿尔德条件下)反应,然后完全还原所得到的萘酮而制备。以下的实施例提供了该合成方法的具体实例。
具体实施方式
实施例
现在将通过如下实施例进一步详细描述本发明,其中缩写具有本领域的通常含义,温度以摄氏度(℃)指示,NMR光谱数据在CDCl3(如果不另外说明)中采用对于1H和13C的360或400MHz机器记录,化学位移δ关于作为标准物的TMS以ppm表示,以Hz表达偶合常数J。
实施例1
全氢-6,8,8a-三甲基-1-萘酚的合成
I)狄尔斯-阿尔德偶合的通用步骤
在500ml反应器中加入AlEtCl2或AlCl3、0.1g的BHT和甲苯,或CH2Cl2。然后,在剧烈搅拌下,逐滴加入适当的环己烯酮,以保持温度低于30℃。之后,逐滴加入二烯,当反应结束时,用5%的HCl水溶液水解该反应混合物,并用Et2O萃取两次。然后用饱和NaHCO3水溶液、水、盐水洗涤有机层,然后用Na2SO4干燥。蒸发溶剂,层析(SiO2,洗提庚烷/AcOEt 98∶2)和蒸馏得到了不饱和的萘酮。
II)不饱和萘酮氢化为全氢萘酮的通用步骤
在100ml烧瓶中加入适当的不饱和萘酮、乙酸乙酯和相对于不饱和萘酮为10%w/w的Pd/C 5%。由此在室温和H2下搅拌该混合物,直到消耗了理论量的氢。之后,用尼龙6/6过滤反应混合物。蒸发溶剂并蒸馏得到全氢萘酮。
III)全氢萘酮还原为全氢萘酚的通用步骤
在保持在Ar气氛下的100ml烧瓶中加入相对于酮为2摩尔当量的Et2O中的LiAlH4。然后逐滴加入适当的全氢萘酮以保持回流。反应完成后,在回流下搅拌混合物30分钟。之后,用化学当量的NaOH水溶液水解该反应混合物,并用Na2SO4干燥有机层。蒸发溶剂并蒸馏得到全氢萘酚。
-6,8,8a-三甲基-3,4,4a,5,8,8a-六氢-1(2H)-萘酮
根据通用步骤I)用以下量制备:
2-甲基-2-环己烯-1-酮(22g;0.2mol)
二氯乙基铝(1摩尔于己烷中的溶液;40ml;0.04mol)
甲基戊二烯(24.6g;0.3mol),二氯甲烷(200ml)
所得的标题产物的产率为50%(两种异构体;GC比率=27.2∶72.8)
B.p.=85℃(0.015mbar)
1H-NMR:0.78(d,J=7,0.75H);0.91(s,0.75H);1.18(d,J=7,2.25H);1.32(s,2.25H);1.44-2.30(m,8H);1.63(broad s,2.25H);1.68(broad s,0.75H);2.58-2.75(m,2H);5.09(broad s,0.25H);5.23(broad s,0.75H)。
-全氢-6,8,8a-三甲基-1-萘酮
根据通用步骤II)用以下量制备:
6,8,8a-三甲基-3,4,4a,5,8,8a-六氢-1(2H)-萘酮(9.60g,0.05mol)
5%Pd-C(1.0g),EtOAc(100ml)
所得作为异构体的混合物的标题产物的产率为97%(GC比率=66∶22∶6∶6)
B.p.=75℃(0.071mbar)
1H-NMR:0.61-1.25(m,8H);1.30-1.50(m,7H);1.55-2.32(m,6H);2.50-2.65(m,1H)。
-全氢-6,8,8a-三甲基-1-萘酚
根据通用步骤III)用以下量制备:
全氢-6,8,8a-三甲基-1-萘酮(3g,0.016mmol)
氢化铝锂(0.31g,0.008mol),二乙醚(30ml)
所得作为异构体的混合物的标题产物的产率为98%(GC比率=64∶31∶5)
B.p.=86℃(0.027mbar)
1H-NMR:0.82-1.05(m,9H);1.12-1.54(m,9H);1.60-2.18(m,5H);3.30-3.60(m,1H)。
实施例2
加香组合物的制备
通过混合以下成分制备花香-紫罗兰类型的用于柔软剂基料的香料:
*在一缩二丙二醇中
1)7-丙基-2h,4h-1,5-苯并二氧杂环庚烯-3-酮;来源:FirmenichSA,瑞士
2)环十五烯内酯(pentadecenolide);来源:Firmenich SA,瑞士
3)丙酸(1S,1′R)-2-[1-(3′,3′-二甲基-1′-环己基)乙氧基]-2-甲基丙酯;来源:Firmenich SA,瑞士
4)3-(3,3/1,1-二甲基-5-茚满基)丙醛;来源:Firmenich SA,瑞士
5)甲基紫罗兰酮的混合物;来源:Firmenich SA,瑞士
6)3-(4-叔丁基苯基)-2-甲基丙醛;来源:Givaudan-Roure SA,Vernier,瑞士
7)乙酸4-(1,1-二甲基乙基)-1-环己酯;来源:Firmenich SA,瑞士
8)二氢茉莉酮酸甲酯;来源:Firmenich SA,瑞士
9)1-(5,5-二甲基-1-环己烯-1-基)-4-戊烯-1-酮;来源:FirmenichSA,瑞士
加入60重量份全氢-6,8,8a-三甲基-1-萘酚为这种织物柔软剂香精带来了美好的广藿香效果,甚至在干布料上更显著。
实施例3
加香组合物的制备
通过混合以下成分制备木质-草本类型的男士用古龙香水:
*在一缩二丙二醇中
1)1,2,3,5,6,7-六氢-1,1,2,3,3-五甲基-4-二氢茚酮;来源:International Flavors & Fragrances,美国
2)十二氢-3a,6,6,9a-四甲基-萘并[2,1-b]呋喃的左旋异构体;来源:Firmenich SA,瑞士
3)环十五烯内酯;来源:Firmenich SA,瑞士;
4)二氢茉莉酮酸甲酯;来源:Firmenich SA,瑞士
5)1-(八氢-2,3,8,8-四甲基-2-萘基)-1-乙酮;来源:InternationalFlavors & Fragrances,美国
6)2,5-二甲基-2-茚满甲醇;来源:Firmenich SA,瑞士
7)3-甲基-(4)-环十五碳烯酮;来源:Firmenich SA,瑞士
8)2-叔丁基-1-环己基乙酸酯;来源:International Flavors &Fragrances,美国
9)甲基柏木酮;来源:International Flavors & Fragrances,美国
加入750重量份的全氢-6,8,8a-三甲基-1-萘酚赋予这种男性木质-草本香味以一种土质-广藿香特性,有一点但像真实的广藿香,但其他合成木质香料无法提供这种香味。
Claims (10)
2.一种根据权利要求1的化合物,其特征在于R1表示氢原子。
3.一种根据权利要求1的化合物,其特征在于R2表示甲基。
5.一种根据权利要求1的化合物,其特征在于其是全氢-6,8,8a-三甲基-1-萘酚。
6.一种加香组合物,其包含:
i)至少一种权利要求1~5中任一项定义的本发明化合物;
ii)至少一种选自香料载体和香料基料的成分;以及
iii)非强制选择的至少一种香料佐剂。
7.一种已加香制品,其包含:
i)至少一种权利要求1~5中任一项定义的通式(I)化合物或权利要求6定义的组合物;以及
ii)一种消费品基料。
8.一种根据权利要求7的已加香制品,其特征在于该消费品基料是固体或液体洗涤剂,织物柔软剂,香水,古龙水或须后水,香皂,浴盐、沐浴乳、浴油或沐浴露,卫生产品,香波,身体护理产品,除臭剂或止汗剂,空气清新剂,化妆品制剂,织物清新剂,熨烫水,纸张,擦拭用品或漂白剂。
9.根据权利要求1~5中任一项定义的化合物作为加香成分的用途。
10.根据权利要求9的用途,其特征在于所述化合物用于赋予木质-土质类型的气味香调。
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