CN101500656A - 环戊烷/环戊烯醛或酮衍生物和它们作为增香剂的用途 - Google Patents
环戊烷/环戊烯醛或酮衍生物和它们作为增香剂的用途 Download PDFInfo
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- CN101500656A CN101500656A CNA2007800299577A CN200780029957A CN101500656A CN 101500656 A CN101500656 A CN 101500656A CN A2007800299577 A CNA2007800299577 A CN A2007800299577A CN 200780029957 A CN200780029957 A CN 200780029957A CN 101500656 A CN101500656 A CN 101500656A
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- thiazolinyl
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- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- USMNOWBWPHYOEA-MRTMQBJTSA-N α-thujone Chemical compound O=C([C@@H]1C)C[C@@]2(C(C)C)[C@@H]1C2 USMNOWBWPHYOEA-MRTMQBJTSA-N 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61K8/35—Ketones, e.g. benzophenone
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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Abstract
本发明涉及式(I)的龙脑醛缩合物,其中R1-R5具有说明书中给出的相同含义。进一步涉及它们的制备方法和包含它们的香料组合物与芳香用品。
Description
本发明涉及新类型的具有有益的类似木香-紫罗兰酮香型的龙脑醛缩合物,和它们作为增香剂的用途。本发明还涉及它们的制备方法和包含它们的香料组合物。
香料工业中,一直存在对于在香型方面增强、改性或改进的新化合物的需求。
迄今为止还不能够在结构与气味之间得到完整的相关性,且由此通常不能够预测何种化合物具有有益或令人愉悦的气味,或任意给定化合物将是何种特定气味种类。
令人吃惊地,现在已发现,通过缩短发香团中心(即氧原子)与环体系(即分子的亲脂性部分)之间的间隔基团一个碳原子,可以获得新类型的化合物,其具有花香、木香、柠檬型、果香(覆盆子)、茴香气味,几乎完全不具有现有技术化合物的明显檀香香型。
由此,本发明在其一方面涉及式(I)化合物作为香料或香精成分的用途,
其中,
R1和R2独立地为氢或C1-C3烷基,例如乙基;
C-1连接于C-1,或C-4’;
C-1与C-2之间的虚线与碳-碳键一起表示双键或单键;
C-3’与C-4’之间的虚线与碳-碳键一起表示双键或单键;
I)R3和R4与它们所连接的碳原子一起形成羰基;和
R5为氢,C1-C6烷基,例如乙基、丁基或异丙基,或C2-C6烯基,例如丁烯基或异丙烯基;
或
II)R3为羟基;和
R4和R5彼此独立地为氢、C1-C6烷基或C2-C6烯基;
条件是R1、R2、R4和R5中至少一个不为氢;
且该式(I)化合物包含不多于20个碳原子,优选11-18个,例如12、13、14或15个。
式(I)化合物可以包括几个手性中心且由此可以以立体异构体的混合物出现,或可以以异构体纯形式将它们拆分。拆分立体异构体增加了制备和纯化这些化合物的复杂性,且由此仅出于经济原因优选以它们立体异构体的混合物使用该混合物。但是,如果期望制备单一立体异构体,可以根据本领域中已知的方法实现这一点,例如,制备性HPLC和GC、结晶或通过从手性原材料出发,例如,从光学异构纯的或富集的原材料如萜类出发,和/或通过采用立体选择性合成。
特定实施方案中为式(I)化合物,其中环体系的相对构型为1’R或1’S,如式(Ia)和(Ib)所示。
(Ia) (Ib)
双键是E或是Z。
特别优选的式(I)化合物为4-(2,2,3-三甲基环戊-3-烯基)丁-3-烯-2-酮、(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-酮和(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-醇。
根据本发明的化合物可以单独地或与选择多种范围的目前可获得的天然和合成分子的已知增香剂分子组合使用,如精油和提取物、醇类、醛类和酮类、醚类和缩醛类、酯类和内酯类、大环化合物类和杂环化合物类,和/或与一种或多种在香料组合物中通常与增香剂结合使用的成分或赋形剂混合,例如,载体材料,和本领域中通常使用的其它助剂,例如,溶剂如二丙二醇、肉豆蔻酸异丙酯和柠檬酸三乙酯。
如下序列包括了可以与本发明化合物结合的已知增香剂分子的实例。
-精油和提取物,例如橡苔净油、罗勒油、热带果油(如香柠檬油和橘子油)、纯乳香、香桃木油、玫瑰草油、广藿香油、橙叶油、苦艾油、熏衣草油、玫瑰油、茉莉油、依兰-依兰油和檀香油。
-醇类,例如,顺式-3-己烯醇、肉桂醇、香茅醇、EbanolTM、丁子香酚、法呢醇、香叶醇、薄荷醇、橙花醇、玫瑰醇、Super MuguetTM、芳樟醇、苯乙醇、SandaloreTM、萜品醇和TimberolTM(1-(2,2,6-三甲基环己基)己-3-醇)。
-醛类和酮类,例如,柠檬醛、羟基香茅醛、Lilial、甲基壬基乙醛、茴香醛、烯丙基紫罗兰酮、马鞭烯酮、诺卡酮、香叶基丙酮、α-戊基肉桂醛、GeorgywoodTM、羟基香茅醛、Iso E (甲基紫罗兰酮)、麦芽醇、甲基柏木酮和香草醛。
-酯类和内酯类,例如,乙酸苄酯、乙酸柏木酯、γ-癸内酯、γ-十一烷酸内酯、乙酸岩兰草酯、丙酸肉桂酯、乙酸香茅酯、乙酸癸酯、二甲基苄基甲基乙酸酯、乙酰乙酸乙酯、乙酰乙酸乙酯、异丁酸顺式-3-己烯酯、乙酸芳樟酯和乙酸香叶酯。
-大环类,例如,黄葵内脂、巴西酸亚乙酯或
-杂环类,例如,异丁基喹啉。
本发明的化合物可以用于多种芳香用品(fragrance application),例如,在精细香料和功能香料的任何领域中,如香水、家用产品、洗衣产品、身体护理产品和化妆品。可以以宽泛变化的数量使用该化合物,根据特定的应用和其它增香剂分子的性能与数量。比例典型地为该用品的0.001-20wt%。一种实施方案中,本发明的化合物可以以0.001-0.05wt%的数量用于织物柔软剂中。另一实施方案中,本发明的化合物可以以0.1-30wt%的数量用于醇类溶液中,更优选为5-20wt%。但是,这些数值仅是作为示例给出的,因为有经验的香料制造者也可以采用更低或更高浓度(例如,基于香料组合物不多于约50wt%)达到效果或可以形成新的谐香。
本发明的化合物可以简单地通过将香料组合物与芳香用品直接混合而应用到芳香用品中,或可以在更早的步骤中采用俘获材料如聚合物、胶囊、微胶囊和纳米胶囊、脂质体、成膜剂、吸附剂如碳或沸石、环状低聚糖及其混合物将它们俘获,和/或可以将它们化学键合于基质,使该基质适应于在施加外部刺激如光、酶等时释放出香料分子,并随后与用品混合。
由此,本发明另外提供了制备芳香用品的方法以及由此获得的消费品。该方法包括采用常规的技术和方法,或者通过直接将该化合物混合到用品中,或者通过将包含式(I)化合物或其前体的香料组合物掺混,随后可以将其混合到芳香用品中,从而在其中引入作为香料成分的式(I)化合物。通过加入嗅觉上可接受量的如上所述的本发明化合物,芳香用品的香型将得到改进、增强或改善。
“前体”特别地含义为,式(I)的醛/酮、即其中R3和R4与它们所连接的碳原子一起形成羰基的式(I)化合物,与包含至少一个选自伯胺、仲胺、巯基(硫醇)、羟基和羧基的官能团的化合物的反应产物,其中在至少一个式(I)化合物的碳原子与至少一个所述包含至少一个官能团的化合物的杂原子(即N、S和/或O)之间形成共价键。
由此,本发明另外提供了改进、增强或改善芳香用品的方法,通过在其中加入嗅觉上可接受量的式(I)化合物或其混合物。
本发明还提供了芳香用品,其包括:
a)作为增香剂的式(I)化合物或其混合物;和
b)消费品基材。
本文中使用的“芳香用品”含义为任意产品,如精细香料,例如香水和化妆水(eaux de toilette);家用产品,例如用于洗碗机、表面清洁器、空气清新器的清洁剂;洗衣产品,例如柔软剂、漂白剂、清洁剂;身体护理产品,例如剃须后洗液、香波、洗浴凝胶、沐浴液和浴盐、卫生产品;和化妆品,例如除臭剂、雪花膏,包含增香剂。该序列产品是通过例证的方式给出的且并不认为以任意方式进行限定。
本文中使用的“香料组合物”含义为包含至少一种增香剂分子和香料组合物中与增香剂通常组合使用的稀释剂(如二丙二醇(DPG)、肉豆蔻酸异丙酯(IMP)、柠檬酸三乙酯(TEC)和醇(例如乙醇))的任意组合物。
本文中使用的“消费品基材”含义为作为消费品用于实现特定作用如清洁、软化和护理等的组合物。该产品的实例包括织物护理和个人护理产品如洗衣护理清洁剂、漂洗调节剂、个人清洁组合物。该组合物可以包括多种活性成分如表面活性剂、聚合物、填料和助剂如染料和溶剂。
大多数式(I)化合物在上面首次进行描述且由此其本身是新的。就我们所知,仅仅3个落入式(I)定义之内的化合物先前在文献中得到描述。全部三个,即4-(2,2,3-三甲基环戊-3-烯基)丁-2-酮、4-(2,3,3-三甲基环戊-1-烯基)丁-2-酮和3-甲基-5-(2,3,3-三甲基环戊-1-烯基)戊-l-烯-3-醇都由Ribas等(Anales de Quimica,Serie C:Quimica Organica yBioquimica(1982,78(1),48-52)描述为用于制备cecropia C17保幼激素类似物的中间体。
由此,本发明在另一方面涉及式(I)化合物,
其中,
R1和R2独立地为氢或C1-C3烷基(例如乙基);
C-1连接于C-1’或C-4’;
C-1与C-2之间的虚线与碳-碳键一起表示双键或单键;
C-3’与C-4’之间的虚线与碳-碳键一起表示双键或单键;
I)R3和R4与它们所连接的碳原子一起形成羰基;和
R5为氢、C1-C6烷基(例如乙基、丁基或异丙基)或C2-C6烯基(例如丁烯基或异丙烯基);
或
II)R3为羟基;和
R4和R5彼此独立地为氢、C1-C6烷基或C2-C6烯基;
条件是R1、R2、R4和R5中至少一个不为氢;
且该式(I)化合物包含不多于20个碳原子,优选为11-18个,例如12、13、14或15个;
条件是不包括4-(2,2,3-三甲基环戊-3-烯基)丁-2-酮、4-(2,3,3-三甲基环戊-1-烯基)丁-2-酮和3-甲基-5-(2,3,3-三甲基环戊-1-烯基)戊-1-烯-3-醇。
式(I)化合物可以由龙脑醛((S)-(+)龙脑醛或(R)-(-)龙脑醛)或2,3,3-三甲基环戊-1-烯甲醛出发来制备。它们可以通过采用相应醛/酮在酸性或碱性条件下醇醛型缩合,或通过采用(三苯基亚膦基)烷酮如1-(三苯基亚膦基)-2-丙酮或3-(三苯基亚膦基)-2-丁酮在本领域技术人员众所周知的条件下维悌希(Wittig)型偶合来制备。但是在酸性条件下,可以获得相应重排的([1,2]-甲基变换的)2-取代的1,5,5-三甲基环戊烯-衍生物,即其中侧链在C-4’上连接的式(I)化合物,在碱性或维悌希型条件下,保持4-取代的1,5,5-三甲基环戊烯-衍生物的未改变的碳骨架,即其中侧链在C-1’上连接的式(I)化合物。
所述重排,即[1,2]-甲基变换,也可以在缩合步骤之前进行。由此,将龙脑醛用酸如磷酸或硫酸进行处理,且随后可以使由此获得的2,3,3-三甲基环戊-1-烯甲醛进一步转化为式(I)化合物。
由此获得的式(I)的酮/醛可以采用硼氢化钠或是氢化铝锂进行还原,获得其它式(I)化合物,即相应的醇。
同样,可以通过与有机金属物质如格氏试剂或有机锂试剂在本领域中众所周知的条件下反应,将酮/醛转化为相应的原醇。
另外,可以使环中C-3’与C-4’之间和/或由上述醇醛缩合或维悌希型反应在侧链中形成的C-1与C-2之间的双键,在贵金属催化剂如木炭上的钯在本领域中众所周知的条件下,一起或区域选择地进行氢化。
实施例中提供了关于反应条件的进一步特定内容。
现在本发明将进一步参照如下非限定性实施例进行描述。这些实施例仅是出于例证的目的且认为本领域技术人员可以进行变化和改进。
在Merck硅胶60(230-400目)上进行快速色谱分析。如果未相反指出,所报道的NMR光谱都是在CDCl3中测量的;化学位移(δ)是以ppm为单位由TMS向低场进行报道;耦合常数J以Hz计。
实施例1:龙脑醛
A)4-((1E)-2-(2,2,3-三甲基环戊-3-烯基)乙烯基)吗啉
使龙脑烯醛(138g,0.9mol)和吗啉(95.7g,1.1mol)的混合物溶解于环己烷(400ml)中,并加入催化量的p-甲苯磺酸(1g)。将混合物加热到回流同时搅拌。在迪安-斯达克(Dean-Stark)条件下,在3小时内收集到约18g水。冷却到室温之后,将混合物用水(200ml)清洗、在硫酸钠之上干燥并在真空下浓缩以提供粗吗啉烯胺(235g)。通过在减压下5cm-Vigreux柱子上蒸馏对其进行纯化,由此提供浅黄色油状的目标化合物(186g),沸点110℃(0.1mabr)。
1H-NMR:δ 5.80(1H,d,J=13.8,=CHN),5.25-5.23(1H,m,=CH),4.48(1H,dd,J=13.8,9.2,=CH),3.73(4H,表观t,J=4.9,2 x OCH2),2.80(4H,表观t,J=4.9,2 x NCH2),2.27-2.21(2H,m,CH和CHH),2.08-1.97(1H,m,CHH),1.62-1.60(3H,m,Me),0.92(3H,s,Me),和0.74(3H,s,Me)。13C-NMR:δ 148.3(s),139.8(d),121.6(d),103.2(d),66.5(t),52.6(d),49.6(t),47.7(s),36.9(t),25.1(q),20.2(q),和12.9(q)。MS:221(M+,100),206(93),178(13),139(33),126(25),119(32),113(29),91(24),79(16),67(14),55(16),41(24)。
B)龙脑醛(2,2,3-三甲基环戊-3-烯甲醛)
使4-((1E)-2-(2,2,3-三甲基环戊-3-烯基)乙烯基)吗啉(45g,0.2mol)溶解于乙腈(200ml)中并加入氯化亚铜(I)(1g,0.01mol)。随后,在25-30℃和强力搅拌下使氧气流从溶液中起泡3.5小时,之后将初始吗啉烯胺全部消耗。将混合物倒入冰/水(500ml)中并采用己烷(3×250ml)进行萃取。将结合的有机相用氯化铵溶液(饱和水溶液,250ml)清洗、在硫酸钠之上干燥并在真空下浓缩,由此获得浅黄色到浅绿色液体的粗产物(29.6g)。使其通过6cm-Widmer柱子在减压下蒸馏,由此提供极浅黄色油状的所需龙脑醛(22.5g),沸点67-68℃(~15mbar)。
1H-NMR:δ 9.76(1H,d,J=3.2,CHO),5.26-5.24(1H,m,=CH),2.69-2.65(1H,m,CH),2.63-2.55(1H,m,CHH),2.41-2.31(1H,m,CHH),1.63-1.60(3H,m,Me),1.21(3H,s,Me),和1.00(3H,s,Me)。13C-NMR:δ204.5(d),146.8(s),121.0(d),61.5(d),48.9(s),29.3(t),25.6(q),21.6(q),和11.7(q)。MS:138(M+,26),123(58),109(22),95(100),79(20),67(48),55(28),41(23)。
由(R)-龙脑烯醛(~80%ee)出发时,旋光度为:[α]D 22=+9.8°(EtOH中5.09)。由(S)-龙脑烯醛(~30%ee)出发时,旋光度为:[α]D 22=-3.8°(EtOH中5.01)。
实施例2:4-(2,2,3-三甲基环戊-3-烯基)丁-3-烯-2-酮
将在二甘油二甲醚(40ml)中的龙脑醛(来自实施例1,6g,0.04mol)和(三苯基亚膦基)丙酮(15g,0.04mol)的混合物在搅拌下加热到170℃,并保持在温度下15分钟。使混合物冷却到低于100℃并倒入水(200ml)中,由此三苯基膦氧化物沉淀。采用己烷(3×200ml)萃取该混合物并使结合的有机相在硫酸钠之上进行干燥和在真空下进行浓缩(7.4g)。通过快速色谱(MTBE/己烷1:6)将粗产物进行纯化,由此提供极浅黄色油状的期望产物(5.8g,81%),E:Z-异构体的混合物(7:2比例)。
1H NMR(主要的,E-异构体):δ 6.86(1H,dd,J=16,8.5,=CH),6.09(1H,dd,J=16,1,=CH),5.26-5.24(1H,m,=CH),2.58(1H,dq,J=7.5,1,CH),2.38-2.31(1H,m,CHH),2.27(3H,s,COMe),2.25-2.18(1H,m,CHH),1.63-1.60(3H,m,Me),1.03(3H,s,Me),和0.82(3H,s,Me)。13C NMR(主要的,E-异构体):δ 198.3(s),149.3(d),147.7(s),131.4(d),121.0(d),53.7(d),49.1(s),34.6(t),26.9(q),25.5(q),20.6(q),12.4(q)。MS:178(M+,13),163(24),145(26),135(43),121(28),107(28),105(31),96(44),95(41),93(55),91(37),81(33),79(28),77(27),55(20),43(100),41(28),39(10)。
由衍生自(S)-龙脑烯醛(~30%ee)的龙脑醛出发时,旋光度为:[α]D 22=+2.1°(CHCl3中1.12)。
气味描述:乡土香(agrestic)、木香(侧柏酮型)、甜香、粉香、紫罗兰酮、花香、乳香。
由衍生自(R)-龙脑烯醛(~80%ee)的龙脑醛出发时,旋光度为:[α]D 22=-5.5°(CHCl3中1.05)。
气味描述:花香、α紫罗兰酮、木香、果香。
实施例3:(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-酮
使龙脑醛(34.5g,0.27mol)、丁-2-酮(72g,1.0mol)和Amberlyst 15(10g)的混合物在回流下搅拌过夜。短程蒸馏之后,通过快速色谱将粗产物(27g)进行纯化(MTBE/己烷1∶19;12g,25%产率,无色的油)。
1H NMR:δ 7.26(br.s,1H),2.67-2.61(m,2H),2.38(s,3H),1.93(d,J=1.0,3H),1.73-1.69(m,2H),1.72(t,J=2.0,3H),1.05(s,6H)。13CNMR:δ 200.5(s),154.2(s),135.7(d),134.7(s),131.5(s),46.8(s),39.1(t),32.6(t),26.0(2q),25.7(q),12.6(q),10.9(q)。MS:192(M+,4),177(9),159(14),144(5),136(10),137(100),119(8),107(7),105(8),91(15),77(9),55(6),43(32),41(10)。
气味描述:木香、花香、类似食品、(甲基)紫罗兰酮、甘草、鸢尾草、鸢尾酮、Koavone、油脂香、增浓乳香。
实施例4:(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-醇
在0-10℃下将氢化铝锂(0.1g,2.6mmol)分成五份加到实施例3中的酮(2.0g,10mmol)在THF(20ml)的溶液中。使反应混合物升温到室温并在继续搅拌0.5h。在0-10℃下相继地加入水(0.1g)、氢氧化钠16%溶液(0.1g)和再次水(0.3g)。15min.搅拌之后,过滤掉固体并使滤液在真空下浓缩且通过快速色谱(MTBE/己烷1:3)进行催化剂,由此提供无色油状的期望产物(1.5g)。
1H NMR:δ 6.07(br.s,1H),4.28(q,J=6.4,1H),2.56-2.41(m,2H),1.75(br.s,3H),1.65(t,J=7.1,2H),1.58-1.55(m,3H),1.29(d,J=6.4,3H),1.00(s,6H)。13C NMR:δ 145.0(s),139.0(s),131.0(s),120.8(d),74.2(d),46.3(s),39.3(t),33.2(t),26.3(q),26.2(q),21.7(q),13.2(q),10.3(q)。MS:194(M+,8),179(25),161(30),133(6),119(16),107(100),105(19),95(15),91(24),79(15),77(13),55(13),45(4),43(20)。
气味描述:木香、土香/苔香、花香、蜜香、Isoraldeine(甲基紫罗兰酮)、天然香味、Cetonal。
实施例5:2,3,3-三甲基环戊-1-烯甲醛
使龙脑醛(实施例1的,10.0g,0.72mol)和Amberlyst 15(12g)和甲基环己烷(30ml)的混合物在回流下搅拌4.5h。过滤之后,在真空下浓缩粗产物并通过球管至球管(bulb-to-bulb)蒸馏进行纯化,由此提供浅黄色油状的期望的醛(4.0g,93%GC-纯度)。
1H NMR:δ 10.0(s,1H),2.50-2.42(m,2H),2.04(t,J=1.7,3H),1.70(t,J=7.3,2H),1.10(s,6H)。13C NMR:δ 189.2(d),168.6(s),136.4(s),49.2(s),37.8(t),26.9(t),25.5(2q),10.0(q)。MS:138(M+,32),123(32),95(100),92(9),79(10),77(13),67(32),55(18),53(13),41(15),39(14)。
实施例6:香料组合物
化合物/成分 重量份
广霍香油 20
乙酸岩兰草酯 40
β紫罗兰酮 45
铃兰醛 75
桃醛(Peach Pure)(γ-十一烷酸内酯) 15
新洋茉莉醛(Tropional)(α-甲基-1,3-
苯并二氧杂环戊烯基-5-丙醛) 45
环己醛(Cyclohexal) 20
乙基香草醛 7
芫荽子油 10
羟基香茅醛 30
玫瑰油 1
乙基芳樟醇 250
格蓬酮(Galbanone)(1-(5,5-二甲基-1-环己烯-1-基)-
4-戊烯-1-酮))10%在二丙二醇中 8
甲基二氢异茉莉酮酸酯 250
Moxalone(6,7-环氧-1,1,2,4,4,7-六甲基-1,2,3,4,5,6,7,8-
八氢-萘)50%在柠檬酸三乙酯中 20
二丙二醇 134
将30份(S)-(-)-4-(2,2,3-三甲基环戊-3-烯基)丁-3-烯-2-酮加到上述组合物中,增大了体积、舒适性和感觉性。其增强了这种素心兰型(Chypre-type)香精的果香动物香方面且在干时保留了柔和的花香木香气味。
Claims (10)
2、权利要求1的用途,其中式(I)化合物环体系的相对构型为1’R。
3、权利要求1的用途,其中式(I)化合物环体系的相对构型为1’S。
4、权利要求1的用途,其中式(I)化合物选自4-(2,2,3-三甲基环戊-3-烯基)丁-3-烯-2-酮、(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-酮和(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-醇。
5、包含前述权利要求中任一项所定义的式(I)化合物的香料或香精组合物。
6、一种芳香用品,包含:
a)权利要求1-4中任一项中定义的式(I)化合物;和
b)消费品基材。
7、权利要求6的芳香用品,其中该消费品基材选自精细香料、家用产品、洗衣产品、身体护理产品和化妆品。
8、一种制备香料或香精组合物的方法,包含如下步骤:将有效量的权利要求1-4中任一项所定义的式(I)化合物或其混合物结合到基础材料中。
9、式(I)化合物
其中,
R1和R2独立地为氢或C1-C3烷基;
C-1连接于C-1’或C-4’;
C-1与C-2之间的虚线与碳-碳键一起表示双键或单键;
C-3’与C-4’之间的虚线与碳-碳键一起表示双键或单键;
I)R3和R4与它们所连接的碳原子一起形成羰基;和
R5为氢、C1-C6烷基或C2-C6烯基;
或
II)R3为羟基;和
R4和R5彼此独立地为氢、C1-C6烷基或C2-C6烯基;
条件是R1、R2、R4和R5中至少一个不为氢;
且该式(I)化合物包含不多于20个碳原子;条件是不包括4-(2,2,3-三甲基环戊-3-烯基)丁-2-酮、4-(2,3,3-三甲基环戊-1-烯基)丁-2-酮和3-甲基-5-(2,3,3-三甲基环戊-1-烯基)戊-1-烯-3-醇。
10、权利要求9的化合物,其选自4-(2,2,3-三甲基环戊-3-烯基)丁-3-烯-2-酮、(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-酮和(3E)-3-甲基-4-(2,3,3-三甲基环戊-1-烯基)丁-3-烯-2-醇。
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GBGB0616002.2A GB0616002D0 (en) | 2006-08-11 | 2006-08-11 | Organic compounds |
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EP (1) | EP2063964A1 (zh) |
JP (1) | JP2010500421A (zh) |
CN (1) | CN101500656A (zh) |
BR (1) | BRPI0716426A2 (zh) |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103160375A (zh) * | 2011-12-14 | 2013-06-19 | 西姆莱斯有限公司 | 含有环戊-2-烯基乙酸乙酯的香料混合物 |
CN104433927A (zh) * | 2014-10-23 | 2015-03-25 | 广东比伦生活用纸有限公司 | 一种手帕纸的加香工艺及制得的香味手帕纸 |
CN105517985A (zh) * | 2013-09-06 | 2016-04-20 | 高砂香料工业株式会社 | 香料组合物 |
Families Citing this family (1)
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GB0802526D0 (en) | 2008-02-12 | 2008-03-19 | Givaudan Sa | Organic compounds |
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DE2536543A1 (de) * | 1975-08-16 | 1977-02-24 | Basf Ag | Substituierte cyclopentene und verfahren zu ihrer herstellung |
US4052341A (en) * | 1976-04-29 | 1977-10-04 | Givaudan Corporation | 3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pentan-2-ol compound and perfume compositions |
US4241228A (en) * | 1979-03-22 | 1980-12-23 | International Flavors & Fragrances Inc. | 2,2,3-Trimethyl-3-cyclopenten-1-ylalkenyl and alkylidene secondary alkanols, alkanones, cycloalkanols and cycloalkanones, organoleptic uses thereof in perfume compositions, colognes and perfumed articles and process for producing same |
DE3562901D1 (en) * | 1984-03-23 | 1988-06-30 | Firmenich & Cie | Hydroxylated derivatives of campholenic aldehyde, their use as flavouring agents and flavouring compositions containing them |
US4810813A (en) * | 1986-09-08 | 1989-03-07 | General Electric Company | Method for making reaction products of phosgene and dihydric phenol with stable suspension of dihydric phenol, alkali metal hydroxide and water |
DE10144888A1 (de) * | 2001-09-12 | 2003-03-27 | Cognis Deutschland Gmbh | Verfahren zur Bestimmung des Enantiomerenverhältnisses von Trimethylcyclopenten-Derivaten |
-
2006
- 2006-08-11 GB GBGB0616002.2A patent/GB0616002D0/en not_active Ceased
-
2007
- 2007-08-07 JP JP2009523127A patent/JP2010500421A/ja active Pending
- 2007-08-07 CN CNA2007800299577A patent/CN101500656A/zh active Pending
- 2007-08-07 EP EP07785079A patent/EP2063964A1/en not_active Withdrawn
- 2007-08-07 MX MX2009001378A patent/MX2009001378A/es unknown
- 2007-08-07 BR BRPI0716426-2A2A patent/BRPI0716426A2/pt not_active IP Right Cessation
- 2007-08-07 US US12/376,010 patent/US20090298950A1/en not_active Abandoned
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103160375A (zh) * | 2011-12-14 | 2013-06-19 | 西姆莱斯有限公司 | 含有环戊-2-烯基乙酸乙酯的香料混合物 |
CN103160375B (zh) * | 2011-12-14 | 2017-05-24 | 西姆莱斯有限公司 | 含有环戊‑2‑烯基乙酸乙酯的香料混合物 |
CN105517985A (zh) * | 2013-09-06 | 2016-04-20 | 高砂香料工业株式会社 | 香料组合物 |
CN104433927A (zh) * | 2014-10-23 | 2015-03-25 | 广东比伦生活用纸有限公司 | 一种手帕纸的加香工艺及制得的香味手帕纸 |
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BRPI0716426A2 (pt) | 2014-03-04 |
JP2010500421A (ja) | 2010-01-07 |
US20090298950A1 (en) | 2009-12-03 |
WO2008017183A1 (en) | 2008-02-14 |
EP2063964A1 (en) | 2009-06-03 |
GB0616002D0 (en) | 2006-09-20 |
MX2009001378A (es) | 2009-02-13 |
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