CN102239132B - α-支化链烯酸以及α-支化链烷酸和链烯酸作为香料的用途 - Google Patents
α-支化链烯酸以及α-支化链烷酸和链烯酸作为香料的用途 Download PDFInfo
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- CN102239132B CN102239132B CN200980148270.4A CN200980148270A CN102239132B CN 102239132 B CN102239132 B CN 102239132B CN 200980148270 A CN200980148270 A CN 200980148270A CN 102239132 B CN102239132 B CN 102239132B
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- 235000012141 vanillin Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及式(I)的α-支化链烷酸和链烯酸,
Description
本发明涉及α-支化链烷酸和链烯酸及其作为增香剂的用途。本发明进一步涉及它们的生产方法和包含它们的香料组合物。
在香料工业中持续需要增强、改变或改善气味香型的新化合物。令人吃惊地,现在发现了如下定义的式(I)的α-支化链烷酸和链烯酸构成了极强的乳香、柑橘香的增香剂,而相应的不含取代基X的羧酸被描述为具有脂肪味、蜡味、发酵味和酸味的香型。
因此,本发明在一方面涉及式(I)化合物作为香料的用途,
其中
X选自甲基和乙基;
R选自C4-C6烷基(例如戊基)和C4-C6链烯基(例如丁-2-烯基、丁-3-烯基、戊烯基如戊-3-烯基、戊-4-烯基和己-4-烯基)。
式(I)化合物可以包括一个或几个手性中心或E或Z构型的双键,因而可以作为立体异构混合物存在,或者可以将它们拆分为异构体纯形式。拆分立体异构体增加了制造和纯化这些化合物的复杂性,因此仅仅出于经济原因,优选使用其立体异构体混合物形式的化合物。然而,如果希望制备单一的立体异构体,则可以根据本领域已知的方法来实现,所述的方法例如制备型HPLC和GC、结晶或立体选择性合成。
非限制性实例为式(I)化合物,其中X为甲基和R为直链C4-C6烷基,以及式(I)化合物,其中X为乙基和R为直链C4-C6烷基。
此外,非限制性实例为式(I)化合物,其中X为甲基和R为直链C4-C6链烯基,以及式(I)化合物,其中X为乙基和R为直链C4-C6链烯基。
在特定实施方案中,式(I)化合物选自2-甲基癸酸、2-甲基十一烷酸、2-乙基癸酸、2-乙基十一烷酸、2-甲基十一碳-9-烯酸、2-甲基十一碳-10-烯酸、2-甲基十一碳-8-烯酸、2-甲基十一碳-7-烯酸和2-甲基十二烷酸。
在式(I)化合物中,可提到的一个是2-甲基十一烷酸,其为香料商最为赏识的一个化合物。该化合物具有极强且扩散性醛香和天然树脂香香型,其主要为乳香和没药香,兼有明快(sparkling)的榄香特征以及鸢尾草和秋葵子的底香。该化合物具有与天然乳香脂(frankincense)相关的所有气味特征,而所述天然乳香是需要急于研制的典型的香料香型。
式(I)化合物可以单独使用、以其混合物的形式使用、或与基质材料结合使用。在此使用的“基质材料”包括所有已知的增香剂分子,所述增香剂分子选自宽范围的目前可获得的天然产品和合成分子,如精油、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/或与一种或多种通常与香料组合物中的增香剂结合使用的成分或赋形剂,例如载体材料,以及其他常用在本领域中的助剂结合使用。
在此使用的“香料组合物”是指任何组合物,其包含至少一种式(I)化合物和基质材料,例如通常与增香剂一起使用的稀释剂,如一缩二丙二醇(DPG)、肉豆蔻酸异丙酯(IPM)、柠檬酸三乙酯(TEC)和醇(例如乙醇)。
下列清单包括已知的增香剂分子的实例,其可以与本发明的化合物结合:
-精油和提取物,例如树苔净油、罗勒油、果油如香柠檬油和橘子油、香桃木油、玫瑰草油、广藿香油、橙叶油、茉莉油、玫瑰油、檀香油、苦艾油、熏衣草油或依兰-依兰油;
-醇类,例如肉桂醇、顺式-3-己烯醇、香茅醇、EbanolTM、丁子香酚、法呢醇、香叶醇、Super MuguetTM、芳樟醇、薄荷醇、橙花醇、苯乙醇、玫瑰醇、SandaloreTM、萜品醇或TimberolTM;
-醚类和缩醛类,例如AmbroxTM、香叶草基甲醚、氧化玫瑰或SpirambreneTM;
-杂环化合物类,例如异丁基喹啉。
根据式(I)化合物可以用在宽范围的香料应用中,例如在精细和功能香料的任何领域中,如香水、空气护理产品、家用产品,洗衣产品、身体护理产品和化妆品。精细香料的更多实例为香水(Eau deperfume)、化妆水(Eau de Toilette)、古龙水(Eau de Cologne)和古龙水拍敷装(Splash Cologne)。精细香料产品通常以醇溶液作为稀释剂。然而使用油或蜡作为稀释剂的精细香料产品也包括在本发明的含义内。取决于特定应用以及其他增香剂成分的性质和质量,该化合物可以以宽范围变化的用量使用。其比例通常为用品的0.0001-10重量%。在一个实施方案中,本发明的化合物可以0.0001-0.04重量%的量用在织物软化剂中。在另一实施方案中,本发明的化合物可以0.01-10重量%,更优选0.01-5重量%(例如至多2重量%)的量用在精细香料中。然而这些值仅仅是以例子的形式给出,因为有经验的香料商还可以通过较低或较高浓度获得效果或者可以得到新颖的谐香。
简单地通过将式(I)化合物或其混合物或香料组合物与消费品基质直接混合就可以将上文所述的化合物用在消费品基质中,或者可以在在前的步骤中用捕集材料对其进行捕集,所述捕集材料例如为聚合物、胶囊、微胶囊和纳米胶囊、脂质体、成膜剂、吸收剂如碳或沸石、环状低聚糖及其混合物,或者其可以化学键结合在基质上,键合后的物质在经历诸如光、酶等外部刺激时易于释放香料分子,随后释放物再与消费品基质混合。
因此,本发明另外提供一种制造香料用品的方法,所述方法包括使用常规技术和方法,或者通过将化合物直接混入消费品基质中,或者通过混合包括式(I)化合物的香料组合物,随后可以将其混入到消费品基质中,从而将式(I)化合物作为香料成分结合进来。通过加入嗅觉可接受量的如上文所述的本发明的化合物或其混合物,将改善、增强或改变消费品基质用品的气味香型。
因此,本发明另外提供一种通过向其中加入嗅觉可接受量的式(I)化合物或其混合物来改善、增强或改变消费品基质的方法。
本发明还提供一种香料用品,所述用品包含:
a)作为增香剂的式(I)化合物或其混合物;和
b)消费品基质;和
c)任选的另外的增香剂分子。
在此使用的“消费品基质”是指用作消费品以满足诸如清洁、软化和护理等特定作用的组合物。这类产品的实例包括精细香料,例如香水和化妆水;织物护理品、家用产品和个人护理产品如洗衣护理洗涤剂、冲洗调理剂、个人清洁组合物、洗碗机用洗涤剂、表面清洁剂;洗衣产品,例如乳化剂、漂白剂、洗涤剂;身体护理产品,例如洗发香波、洗浴凝胶;空气护理产品和化妆品,例如除臭剂、洁面乳。所列产品只是用于说明,不应将其视为以任何方式进行限制。
式(I)化合物可由相应的醛通过有机合成领域技术人员已知的氧化方法制备。
现在将参考下列非限制性实施例对本发明作进一步描述。这些实施例仅仅用于说明,并且应当理解本领域技术人员可以对其作出改变或改进。
除非另有说明,记录的NMR谱在CDCl3中测量;化学位移(δ)以ppm表示,以TMS为内标;耦合常数J以Hz为单位。
快速色谱:Merck硅胶60(230-400目)。
实施例1:2-甲基十一烷酸
将琼斯试剂(61ml,含163mmol CrO3和280mmol H2SO4)在20分钟内逐滴添加到冷却(-25℃)的2-甲基十一醛(45.0g,245mmol)的丙酮(80ml)溶液中。将溶液在-5℃下进一步搅拌15分钟,然后倒入10%NaOH水溶液(400g)和甲苯(400ml)的双相混合物中并充分搅拌15分钟。在分液漏斗中分离该相(通过添加少量EtOH和固体NaCl使乳液破乳)。将碱性水层转入锥形瓶中,与甲苯(大约100ml)混合,并通过添加6NHCl水溶液(200ml,1.2mol)酸化。然后将水层用甲苯萃取,用半饱和NaCl水溶液洗涤至中性并通过MgSO4干燥。在除去溶剂后,将粗产物在0.05mbar/111-123℃下短程蒸馏,之后在0.05mbar/118-121℃下通过维格罗分馏柱精馏,从而得到20.1g(41%)的2-甲基十一烷酸,无色油。
IR(薄膜):2923m,2854m,1703vs,1465w,1236w,938w。
1H-NMR(400MHz,CDCl3):11.76(br.s,1H);2.44(hex,J=7.0Hz,1H);1.71-1.63(m,1H);1.46-1.37(m,1H);1.35-1.23(m,14H);1.16(d,J=6.8Hz,3H);0.87(t,J=7.0Hz,3H)。
13C-NMR(100MHz,CDCl3):183.7(s),39.4(d),33.5(t),31.9(t),29.6(t),29.5(t),29.5(t),29.3(t),27.1(t),22.7(t),16.8(q),14.1(q)。
MS(EI,70eV):200(2,M+),185(<1),171(1),157(5),143(11),129(7),87(41),74(100)。
气味描述:乳香、榄香、柑橘香。
实施例2:2-甲基癸酸
按照实施例1的方案,从2-甲基癸醛起始制备2-甲基癸酸。在0.05mbar/115-130℃下通过维格罗分馏柱精馏而纯化标题化合物(无色油,产率49%)。
IR(薄膜):2924m,2855m,1703vs,1465w,1238w,938w。
1H-NMR(400MHz,CDCl3):11.59(br.s,1H);2.44(hex,J=6.9Hz,1H);1.73-1.62(m,1H);1.47-1.37(m,1H);1.36-1.22(m,12H);1.16(d,J=6.8Hz,3H);0.87(t,J=7.0Hz,3H)。
13C-NMR(100MHz,CDCl3):183.5(s),39.4(d),33.5(t),31.9(t),29.5(t),29.4(t),29.2(t),27.1(t),22.7(t),16.8(q),14.1(q)。
MS(EI,70eV):186(2,M+),143(9),129(11),87(39),74(100),55(20)。
气味描述:柑橘香、醛香、树脂香、乳香。
实施例3:2-甲基十二烷酸
按照实施例1的方案,从2-甲基十二醛起始制备2-甲基十二烷酸。
气味描述:醛香、树脂香、覆盆子香。
实施例4:更多的化合物
按照实施例1的方案可制备下列化合物:2-乙基癸酸;2-乙基十一烷酸;2-甲基十一碳-9-烯酸;和2-甲基十一碳-10-烯酸。
实施例5:2-甲基十一碳-9-烯酸和2-甲基十一碳-10-烯酸
a)在10℃下将硫酸(62%,88.7g,0.56mol,1.1当量)添加到二乙胺(81.4g,1.1mol,1.1当量)中。在15℃下将甲醛(36.5%在水中,93.3g,1.12mol,1.12当量)添加到白色悬浮液中。在相同温度下于25分钟内逐滴添加BHT(0.67g)的异C11醛(E-/Z-9-十一碳烯醛和10-十一碳烯醛的混合物;168g,1mol)溶液。将混合物在室温下进一步搅拌1.5h,在110℃下3.5小时和在室温下16小时。将混合物用环己烷稀释并将有机层用水洗涤3次,饱和NaHCO3溶液一次和盐水两次。将用MgSO4干燥有机层并除去溶剂后获得的粗产物在0.06mbar/90℃下通过短程蒸馏进行纯化以分离出119g(66%)无色油,将其在0.05mbar/71-79℃下精馏以分离出104g(58%)2-亚甲基十一碳-9-烯醛(1)和2-亚甲基十一碳-10-烯醛(2)的混合物,无色液体。
1H-NMR(400MHz,CDCl3):9.54(s,1H),6.24(s,1H),5.98(s,1H),5.85-5.75(m,0.14H),5.43-5.31(m,1.6H),4.99-4.88(m,0.29H),2.23(t,J=7.6,2H),2.03-1.90(m,2H),1.62-1.56(m,2H),1.45-1.39(m,3H),1.35-1.23(m,8H)。
MS(EI,70eV):(1)180(M+,2),165(2),151(8),123(9),109(17),95(29),81(33),67(41),55(100)。
b)将如上制备的2-亚甲基十一碳-9-烯醛(1)和2-亚甲基十一碳-10-烯醛(2)的混合物(18g,100mmol)用三乙基硅烷(12.2g,105mmol,1.05当量)和三(三苯基膦)氯铑(I)(100mg,0.1mmol,0.1mol%)处理,并将所形成的溶液在50℃下搅拌1小时和在60℃下搅拌2小时。将深色混合物用己烷稀释并将溶液用水洗涤3次。在将有机层通过MgSO4干燥并除去溶剂后,获得黄色油(30.1g),将其在0.06mbar/105-133℃下蒸馏以得到无色油(20.8g,70%)。
将该产品(15g,50.6mmol)溶于甲苯(50ml)中。将溶液冷却到5℃并在4分钟内逐滴添加四丁基氟化铵(1M在THF中,20ml,20mmol,0.4当量),之后添加固体氟化钾(5.8g,100mmol,2当量)和甲醇(50ml)。将所形成的白色悬浮液在0-5℃下搅拌3小时,然后用饱和NaHCO3水溶液(80ml)处理并充分搅拌15分钟。将混合物用甲基叔丁基醚萃取并将有机层用盐水/水1∶1洗涤3次。将有机层干燥通过MgSO4干燥并除去溶剂。在己烷/甲苯1∶1的条件下通过硅胶的快速柱色谱纯化所形成的无色油(15g)以得到5.74g(31%)无色油,将其在0.05mbar/58-62℃下通过蒸馏进一步纯化以得到2.2g(7%)无色油。将1.09g(6mmol)该产品溶于乙醇(20ml)中并添加硝酸银(2.24g,13.2mmol,2.2当量)的水(10ml)溶液,之后添加12.5%wt/wt氢氧化钠水溶液(30g,94mmol)。在添加期间,使温度升到35℃。在室温下将灰色乳液强烈搅拌22小时。通过过滤除去沉淀并用乙醇充分清洗滤饼。将乙醇从滤液除去并用甲基叔丁基醚稀释残留的碱性水溶液。将水相分离并用4N NaOH水溶液萃取有机层。将混合的碱性水层用甲基叔丁基醚洗涤,然后用稀盐酸酸化至pH 1并用甲基叔丁基醚萃取。将有机层用盐水洗涤,通过MgSO4干燥并在旋转蒸发器中浓缩。将残留物在0.06mbar/140-150℃下通过减压蒸馏(bulb-to-bulb蒸馏)纯化以分离出1.15g(96%)无色油,其由E-2-甲基十一碳-9-烯酸(3a,56.3%)、Z-2-甲基十一碳-9-烯酸(3b,32.4%)和2-甲基十一碳-10-烯酸(4,11.3%)的混合物组成。
IR(薄膜):3500-2600br,2925m,2855w,1703vs。
1H-NMR(400MHz,CDCl3):δppm 11.8(br.s,1H),5.80(m,0.2H),5.39(m,1.8H),4.94(m,0.4H),2.44(td,J=13.8,6.9Hz,1H),1.99(m,2H),1.64(m,3H),1.36(m,10H),1.16(d,J=6.7Hz,3H)。
MS(EI,70eV):(3a)198(M+,4),180(5),165(<1),125(11),87(32),74(89),69(65),55(100)。
(3b)198(M+,4),180(7),165(<1),125(13),87(30),74(91),55(100)。
(4)198(M+,2),180(5),165(<1),125(9),87(24),74(100)。
气味描述:熏香、乳香。
实施例6:更多的化合物
按照实施例5的方案可制备下列化合物:2-甲基十一碳-8-烯酸和2-甲基十一碳-7-烯酸。
实施例7:制备香料谐香剂
基础谐香剂(base accord):
*Givaudan Schweiz AG,Vernier
5.1:用4%的在一缩二丙二醇中的10%2-甲基癸酸替代上述基础谐香剂配方中的4%的一缩二丙二醇,带来清新、明快、自然、柑橘香型以及浓郁的天然木材的松香香型,具有冷杉特征。
5.2:用在一缩二丙二醇中的10%2-甲基十一烷酸替代上述基础谐香剂配方中的4%的一缩二丙二醇,赋予强烈、浓郁且天然的乳香香型,具焦香乳香特征。
Claims (7)
1.式(I)化合物作为香料的用途
其中
X为甲基;
R选自C4-C6烷基和C4-C6链烯基。
2.根据权利要求1的用途,其中式(I)化合物选自2-甲基癸酸、2-甲基十一烷酸、2-甲基十一碳-9-烯酸、2-甲基十一碳-10-烯酸、2-甲基十一碳-8-烯酸、2-甲基十一碳-7-烯酸和2-甲基十二烷酸。
3.香料用品,所述用品包含作为增香剂的上述权利要求之一所定义的式(I)化合物或其混合物和消费品基质。
4.权利要求3的香料用品,其中所述消费品基质选自精细香料、家用产品、洗衣产品、身体护理产品、化妆品和空气护理产品。
5.香料组合物,所述组合物包含如权利要求1所定义的式(I)化合物或其混合物和基质材料。
6.改善、增强或改变消费品基质的方法,所述方法通过向所述消费品基质中加入嗅觉可接受量的如权利要求1所定义的式(I)化合物或其混合物来进行。
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CN101267860A (zh) * | 2005-09-21 | 2008-09-17 | 吉万奥丹股份有限公司 | 有机化合物 |
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HA,J.K et.al.Volatile branched-chain fatty acids and phenolic compounds in aged ltalian cheese flavors.《journal of food science》.1991,第56卷(第5期),1241-1247. |
Volatile branched-chain fatty acids and phenolic compounds in aged ltalian cheese flavors;HA,J.K et.al;《journal of food science》;19911231;第56卷(第5期);1241-1247 * |
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US10011554B2 (en) | 2018-07-03 |
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BRPI0922778B1 (pt) | 2017-06-06 |
US9745245B2 (en) | 2017-08-29 |
US20110263725A1 (en) | 2011-10-27 |
EP2370391A1 (en) | 2011-10-05 |
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EP2370391B1 (en) | 2014-02-12 |
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GB0822091D0 (en) | 2009-01-07 |
JP5689070B2 (ja) | 2015-03-25 |
BRPI0922778A2 (pt) | 2016-01-05 |
US20170327452A1 (en) | 2017-11-16 |
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