CN1711234A - 反式-佩利特灵作为芳香物质的用途 - Google Patents
反式-佩利特灵作为芳香物质的用途 Download PDFInfo
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- CN1711234A CN1711234A CNA2003801032090A CN200380103209A CN1711234A CN 1711234 A CN1711234 A CN 1711234A CN A2003801032090 A CNA2003801032090 A CN A2003801032090A CN 200380103209 A CN200380103209 A CN 200380103209A CN 1711234 A CN1711234 A CN 1711234A
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- pellitorin
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- isobutyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G4/00—Chewing gum
- A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
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Abstract
本发明涉及2E,4E-癸二烯酸-N-异丁基酰胺(反式-佩利特灵)作为芳香物质,特别是作为具有诱导唾液作用的芳香物质的用途,优选用在营养或者口腔卫生中或者休闲消费的制品中。本发明还涉及包含反式-佩利特灵的制品和半成品以及香味、芳香和风味物质组合物,以及制备反式-佩利特灵的方法。
Description
本发明涉及2E,4E-癸二烯酸N-异丁基酰胺(反式-佩利特灵(trans-pellitorin))作为芳香物质的用途,特别是作为诱导唾液的芳香物质的用途,优选用在营养或口腔卫生或休闲消费的制品中。本发明还涉及包含反式-佩利特灵的制品和半成品以及香味、芳香和风味物质组合物,以及制备反式-佩利特灵的方法。
例如,为了治疗临床口腔干燥症,刺激食欲,或者还为了改善口腔卫生,而使用诱导唾液的物质,原因在于唾液流量的增加会将有害物质从口腔中洗去。为此,在食品制品中通常使用可食用酸例如柠檬酸、酒石酸或者苹果酸。刺激唾液腺的特定物质,例如从毛果芸香树中提取的毛果芸香碱被应用于临床口腔干燥症中(Acta Med.Croatica 2000,54,65-67)。然而,这些高效的胆碱能拟副交感神经药物通常具有严重的副作用而且有些具有高毒性。
在长链脂肪酸烷基酰胺中,2E,6Z,8E-癸三烯酸-N-异丁基酰胺(千日菊酰胺)已被描述为强烈诱导唾液和造成刺痛感。然而,千日菊酰胺同时首先是刺激的、强麻痹性的以及收敛性的(Lebensm.-Wiss.U.-Technol.1992,25,417-421)。而其他长链多烯酸N-异丁基酰胺或多炔酸-N-异丁基酰胺似乎具有更强的诱导唾液的作用,它们还额外地提供苦的味觉(参见上述引用)。
本发明的目的是开发一种具有诱导唾液和/或刺痛作用且具有不同的、基本上为中性的芳香特性的物质,其可作为芳香物质加入制品中,尤其是用在营养、口腔卫生或者休闲消费的制品中。
因此本发明涉及2E,4E-癸二烯酸-N-异丁基酰胺(反式-佩利特灵)作为芳香物质的用途,优选作为具有诱导唾液和/或刺痛作用的芳香物质,特别优选作为用在营养、口腔卫生或休闲消费的制品中的具有诱导唾液和/或刺痛作用的芳香物质。
本发明还提供了包含2E,4E-癸二烯酸-N-异丁基酰胺,优选包含合成的2E,4E-癸二烯酸-N-异丁基酰胺的制品和半成品以及香味、芳香和风味物质组合物。
根据本发明的反式-佩利特灵的感观评定表明,其提供了一种相对持久的、令人愉快的诱导唾液和弱刺痛的感观知觉。令人惊奇的是,如果其在成品,例如最终制品中的浓度低于20ppm,特别是低于10ppm,则只能观察到刺激唾液的作用。此时,不能检测到其他感观知觉,因而其味道特性非常中性。基本中性的味道特性构成了在加入制品方面的主要优势,因为反式-佩利特灵不会导致制品味道特性的变化或者不纯。
这尤其令人感到惊奇,因为在J.Am.Chem.Soc.1953,第75卷,2584-2586中除了描述唾液流动增加外,还描述了在品尝纯态的反式-佩利特灵时对舌头的明显灼烧效果。反式-佩利特灵的感观知觉还被描述为主要是使人感到麻痹(J.Agric.FoodChem.,1981,第29卷,第115及以后页,或者Fitoterapia,2001,第72卷,第197及以后页)。
纯2E,4E-癸二烯酸-N-异丁基酰胺的天然存在已经在文献中被广泛描述;例如,其存在于胡椒中(综述于G.M.Strunz,Stud.Nat.Prod.,Chem.2000,第24卷(BioactiveNatural Products(Part E)),683-738)。
包含反式-佩利特灵的天然产物,例如天然提取物,具有额外的芳香效果并且因此不具有中性的味道特性。当加入制品中时,这经常是天然产物的一个不期望的特性。为此,在本发明中优选使用合成的,即人造的反式-佩利特灵。
在本发明的一个特别优选的实施方案中,将2E,4E-癸二烯酸-N-异丁基酰胺与其他诱导唾液的、刺痛、刺激和/或辛辣物质或者植物提取物组合使用。由此,可以有目的地实现特别全面的感观特性。
其他诱导唾液的、刺痛、刺激和/或辛辣的物质可以是,例如:可食用酸(例如柠檬酸、苹果酸、酒石酸);辣椒素;二氢辣椒素;姜醇;姜酮酚;生姜酚;胡椒碱;羧酸-N-香草基酰胺,尤其是壬酸N-香草基酰胺;2-烷链烯酸酰胺,尤其是2-壬酸-N-异丁基酰胺、千日菊酰胺、2-壬酸-N-4-羟基-3-甲氧基苯基酰胺;4-羟基-3-甲氧基苄醇的烷基醚,尤其是4-羟基-3-甲氧基苄基-n-丁基醚;4-酰氧基-3-甲氧基苄醇的烷基醚,尤其是4-酰氧基-3-甲氧基苄基-n-丁基醚和4-酰氧基-3-甲氧基苄基-n-己基醚;3-羟基-4-甲氧基苄醇的烷基醚;3,4-二甲氧基苄醇的烷基醚;3-乙氧基-4-羟基苄醇的烷基醚;3,4-亚甲二氧基苄醇的烷基醚;(4-羟基-3-甲氧基苯基)乙酰胺,尤其是(4-羟基-3-甲氧基苯基)乙酸-N-n-辛基酰胺、阿魏酸苯乙基酰胺;烟碱醛;烟酸甲酯;烟酸丙酯;2-丁氧基乙基烟酸酯;烟酸苄基酯;1-乙酰氧基佳味酚;蓼二醛;isodrimeninol或毛果芸香碱。
反式-佩利特灵可以有利地与至少一种选自癸酸、2E-癸烯酸、2E,4Z-癸二烯酸、2Z,4E-癸二烯酸、2Z,4Z-癸二烯酸、2E,4Z,7Z-癸三烯酸、3Z,5E-癸二烯酸或者3Z,5E,7Z-癸三烯酸的其它N-异丁基酰胺共同使用。优选为至少80wt.%的2E,4E-癸二烯酸-N-异丁基酰胺和至多20wt.%的2E,4Z-癸二烯酸-N-异丁基酰胺的混合物。
诱导唾液的、刺痛、刺激和/或辛辣的植物提取物可以是适合营养或口腔卫生的、引起诱导唾液的、刺痛、刺激和/或热的感观知觉的植物提取物中的任一种。例如,胡椒提取物(Piper ssp.,特别是Piper nigrum)、水蓼提取物(Polygonum ssp.,特别是Polygonum hydropiper)、Allium ssp.提取物(特别是洋葱和大蒜提取物)、萝卜提取物(Raphanus ssp.)、辣根提取物(Cochlearia armoracia)、黑芥末提取物(Brassica nigra)、田芥菜或黄芥末(Sinapis ssp.,特别是Sinapis arvensis和Sinapis alba)、除虫菊根提取物(Anacyclus ssp.,特别是Anacyclus pyrethrum L.)、紫松果菊提取物(Echinaceaessp.)、四川胡椒提取物(Zanthoxylum ssp.,特别是Zanthoxylum piperitum)、千日菊属(spilanthes)提取物(Spilanthes ssp.,特别是Spilanthes acmella)、辣椒提取物(Capsicum ssp.,特别是Capsicum frutescens)、乐园籽提取物(Aframomum ssp.,特别是Aframomum melegueta[Rose]K.Schum.)、姜提取物(Zingiber ssp.,特别是Zingiberofficinale)、良姜提取物(Kaempferia galanga或Alpinia galanga)和毛果芸香提取物(Pilocarpus种,特别是Pilocarpus iaborandi)作为植物提取物是优选的。
根据本发明的植物提取物可以从相应的新鲜或干的植物或植物器官获得,而具体得自于白、绿或黑胡椒子、水蓼籽、洋葱和大蒜、萝卜根、辣根、芥末籽、紫松果菊根、除虫菊根、来自花椒(Zanthoxylum)变种的植物器官、来自千日菊属(spilanthes)变种的植物器官、辣椒荚、乐园籽或者姜根或者良姜根,以及毛果芸香。传统地,使用适用于食品和休闲消费产品的溶剂,优选乙醇、水、己烷、庚烷或者乙醇/水混合物,在从0℃至各溶剂或溶剂混合物的沸点温度下对干植物器官,优选预先粉碎过的干植物器官进行提取,然后过滤,完全或部分地浓缩滤液,优选通过蒸馏、冷冻干燥或者喷雾干燥进行浓缩。然后对如此得到的粗提取物进行进一步加工,例如以通常压力为0.01毫巴至标准压力的蒸汽来处理,和/或溶解在适用于食品和休闲消费的产品的溶剂中。
适用于食品和休闲消费的产品的溶剂可以是例如:水、乙醇、甲醇、丙二醇、甘油、丙酮、二氯甲烷、乙酸乙酯、二乙醚、己烷、庚烷、三乙酸甘油酯、植物油或者脂肪,以及超临界二氧化碳或者上述溶剂的混合物。
迄今在文献中所描述的反式-佩利特灵合成方法是多步法,而且产率中等至偏低(J.Am.Chem.Soc.1953,第75卷,2584-2586),或者使用有毒试剂,例如有毒的二氧化硒(Bull.Chem.Soc.Jpn.,1984,第57卷,第3013及以后页)。
因此本发明还涉及2E,4E-癸二烯酸-N-异丁基酰胺的制备方法,其特征在于
a)在催化剂存在下,使2E,4E-或2E,4Z-癸二烯酸酯或其混合物与异丁基胺反应,以及
b)使步骤a)形成的产物,任选在纯化步骤之后,异构化生成2E,4E-癸二烯酸-N-异丁基酰胺;
或者
i)使2E,4Z-癸二烯酸酯或者2E,4E-和2E,4Z-癸二烯酸酯的混合物异构化为2E,4E-癸二烯酸酯,以及
ii)使步骤a)形成的产物,任选在纯化步骤之后,在催化剂存在下与异丁基胺反应。
步骤i)可以自然省略,而且可以直接提供2E,4E-癸二烯酸与异丁基胺反应。
一种有利方法的特征在于与异丁基胺的反应在催化剂,优选酶,尤其是具有脂肪酶活性的酶的存在下进行,其中所述酶作为游离蛋白或者结合载体存在。
得到的反应混合物任选地与未反应的2,4-癸二烯酸酯进行皂化反应,优选在存在于水性介质或者用水稀释的碱中的酶的作用下,特别优选无机碱性盐的水溶液。
分离形成的2,4-癸二烯酸酯,优选使用萃取方法,
使纯化或未纯化的粗产物异构化为2E,4E-癸二烯酸-N-异丁基酰胺,以及
然后通过物理化学方法,优选通过结晶、色谱、蒸馏或共蒸馏方法来纯化该混合物。
参照以下图解通式说明该方法:
已经惊喜地确定了本发明的方法提供了获得高产率、易纯化的所需2E,4E-癸二烯酸-N-异丁基酰胺的非常简单的途径。而且,以这种方式,当使用管理芳香物质的条例含义内的天然试剂时,可以得到天然的反式-佩利特灵。
有利地是,2E,4E-和2E,4Z-癸二烯酸酯是2E,4E-和2E,4Z-癸二烯酸与具有1-20个碳原子的脂肪族单羟基醇的酯,而所述醇具体是甲醇、乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、2-甲基-1-丙醇、2-甲基-2-丙醇、1-戊醇、2-戊醇、3-戊醇、1-己醇、2-己醇、3-己醇、1-庚醇、2-庚醇、3-庚醇、4-庚醇、1-辛醇、2-辛醇、1-壬醇、1-癸醇、1-十一醇、1-十二醇、1-十三醇、1-十四醇、1-十五醇、1-十六醇、1-十七醇、1-十八醇、1-十九醇、1-二十醇。
或者2E,4E-和2E,4Z-癸二烯酸酯是2E,4E-和2E,4Z-癸二烯酸与具有2-18个碳原子的多羟基醇的酯,所述醇是例如乙二醇;1,2-丙二醇;1,3-丙二醇;甘油;季戊四醇;糖醇,如赤藻糖醇、山梨糖醇、葡萄糖醇、甘露醇;单糖,如四糖,例如赤藓糖或苏糖;戊糖例如阿拉伯糖、核糖、来苏糖、木糖;己糖,例如阿洛糖、阿卓糖、半乳糖、甘露糖、古洛糖、艾杜糖、葡萄糖、塔罗糖、果糖;多糖,例如麦芽糖、棉子糖、蔗糖、低聚麦芽糖或乳糖,其中多羟基醇的其他OH基团可与脂肪族饱和或不饱和羧酸及其混合物或者具有4-20个碳原子的饱和或不饱和羟基羧酸的混合物发生酯化反应,所述羧酸或其混合物就其本身而言可以与上述醇发生酯化反应。
本发明含义范围内的有利的脂肪族饱和或不饱和羧酸是具有2-26个碳原子的饱和或者单-或多不饱和线性羧酸,而具体是乙酸;丙酸;丁酸;戊酸;己酸;庚酸;辛酸;壬酸;2E-壬酸;癸酸;2E-癸酸;癸二烯酸或癸三烯酸的各种异构体,例如2E,4E-癸二烯酸、2E,4Z-癸二烯酸、2E,4Z,7Z-癸三烯酸、3Z,5E-癸二烯酸、3Z,5E,7Z-癸三烯酸、癸-2,8-二烯-4,6-二炔酸、癸-2-烯-4,6,8-三炔酸;十一酸;十二酸;十三酸;十四酸;十五酸;十六酸;9E-或9Z-十六烯酸;十七酸;十八酸;9E-或9Z-或11E-或11Z-十八烯酸;9,12-十八碳二烯酸的、6,9,12-十八碳三烯酸的、9,12,15-十八碳三烯酸的、6,9,12,15-十八碳四烯酸的各种几何异构体;十九酸;二十酸;二十酸的、11,14-二十碳二烯酸的、8,11,14-二十碳三烯酸的、5,8,11,14-二十碳四烯酸的、5,8,11,14,17-二十碳五烯酸的、10,13,16-二十二碳三烯酸的、7,10,13,16-二十二碳四烯酸的、4,7,10,13,16-二十二碳五烯酸的以及4,7,10,13,16,19-二十二碳六烯酸的各种几何异构体。
本发明含义范围内的2,4-癸二烯酸酯优选为以天然或者经浓缩处理的例如来自柿苓油或者作为甲酯或乙酯的甘油三酸酯的形式存在。特别优选由柿苓油在乙醇中的酶促酯交换反应后蒸馏而得到的级分,该级分的特征在于其包含至少80wt.%的2E,4Z-癸二烯酸乙酯。
本发明含义范围内的异构化是指将不对应于反式-佩利特灵的2,4-癸二烯酸酸根的其他可能的几何异构体(2E,4Z-、2Z,4Z-或2Z,4E-)通过本身已知的方法转化为2E,4E-异构体。优选通过使用碘处理或者使用紫外光辐射(波长为250-320nm)来将2E,4Z-异构体转化为2E,4E-异构体。可以对2,4-癸二烯酸-N-异丁基酰胺或者2,4-癸二烯酸酯进行该异构化。
本发明还提供了用于营养或者休闲消费的制品,其包括具有有效量的2E,4E-癸二烯酸-N-异丁基酰胺和任选其他常规用于食品和休闲消费产品的原料、助剂和添加剂。以制品的总重量计,这些制品通常包含0.000001wt.%(0.01ppm)-0.05wt.%(500ppm),优选0.00001wt.%(0.1ppm)-0.005wt.%(50ppm),特别优选0.00001wt.%(0.1ppm)-0.0015wt.%(15ppm)的2E,4E-癸二烯酸-N-异丁基酰胺。以制品的总重量计,可以包含0.000001-99.999999wt.%,优选10-80wt.%的其他常规用于食品或休闲消费产品的原料、助剂和添加剂。以制品的总重量计,所述制品可以进一步含有最高99.999999wt.%,优选5-80wt.%含量的水。
本发明含义范围内的用于营养或者休闲消费的制品是,例如焙烤产品(例如面包、饼干、蛋糕、其他焙烤产品)、糖果(例如巧克力、水果口香糖、硬质和软质太妃糖、口香糖)、酒精饮料或非酒精饮料(例如咖啡、茶、葡萄酒、含葡萄酒的饮料、啤酒、含啤酒的饮料、甜酒、烈酒、白兰地、含水果的碳酸饮料、等渗饮料、活力饮料、果汁饮料、水果和蔬菜汁、水果或蔬菜汁制品)、即溶饮料、肉制品(例如火腿、新鲜香肠或者未烹煮的香肠制品)、蛋或蛋制品(干蛋粉、蛋白、蛋黄)、谷物产品(例如早餐谷物、什锦早餐棒)、奶制品(例如乳制饮料、牛奶冻、酸奶、酸乳酒、未熟奶酪、软质奶酪、硬质奶酪、干奶粉、乳清、黄油、酪乳)、水果制品(例如果酱、水果冰、水果酱)、蔬菜制品(例如蕃茄酱、酱油、干菜)、快餐制品(例如焙烤或油炸的薯条或者土豆团制品、基于玉米或花生的压出制品)、基于脂肪和油或其乳液的制品(例如蛋黄酱、调味蛋黄酱、调味品)、用于快餐的预制的菜肴和汤、香料、调味品混合物以及特别是用于喷洒的调味品(调料)。本发明含义范围内的制品还可以作为半成品用来制作用于营养或者休闲消费的其他制品。本发明含义范围内的制品还可以作为以胶囊、片剂(未包衣以及包衣片剂,例如抗胃液的包衣)、糖衣丸、颗粒、球粒、固体混合物、液相中的分散体的形式的营养添加物、作为乳液、作为粉末、作为溶液、作为浆体或者作为可以吞服或者咀嚼的其他制品存在。
包含具有有效量的2E,4E-癸二烯酸-N-异丁基酰胺和任选用于这些制品的其他常规原料、助剂和添加剂的口腔卫生制品,尤其是牙齿护理产品例如牙膏、牙粉、嗽口水、口香糖和其他口腔护理产品,是本发明特别优选的实施方案。以制品的总重量计,所述制品通常包含0.000001wt.%(0.01ppm)-0.05wt.%(500ppm),优选0.00001wt.%(0.1ppm)-0.005wt.%(50ppm),特别优选0.00001wt.%(0.1ppm)-0.0015wt.%(15ppm)的2E,4E-癸二烯酸-N-异丁基酰胺。以制品的总重量计,可以包含0.000001-99.999999wt.%,优选10-80wt.%的其他常规用于食品或休闲消费产品的原料、助剂和添加剂。以制品的总重量计,所述制品还可以包含最高99.999999wt.%,优选5-80wt.%含量的水。
含2E,4E-癸二烯酸-N-异丁基酰胺的牙齿护理产品通常由磨料体系(擦洗剂或磨光剂),例如硅酸、碳酸钙、磷酸钙、氧化铝和/或羟基磷灰石;表面活性剂例如十二烷基硫酸钠、十二烷基肌氨酸钠和/或椰子油酰丙基甜菜碱(cocamidopropylbetaine);湿润剂例如甘油和/或山梨糖醇;增稠剂例如羧甲基纤维素、聚乙二醇、角叉菜(carragheen)和/或Laponite;甜味剂例如糖精;稳定剂和活性成分例如氟化钠,单氟磷酸钠,氟化锡(II),氟化季胺盐,柠檬酸锌,硫酸锌,焦磷酸锡,氯化锡(II),各种焦磷酸盐的混合物、三氯生、十六烷基氯化吡啶鎓、乳酸铝、柠檬酸钾、硝酸钾、氯化钾、氯化锶、过氧化氢、香料和/或重碳酸钠所组成。
包含2E,4E-癸二烯酸-N-异丁基酰胺的口香糖通常由口香糖胶基即咀嚼时变成塑性的咀嚼物质、各种类型的糖、糖的替代物、甜味剂、糖醇、湿润剂、增稠剂、乳化剂、香料和稳定剂组成。
根据本发明的制品还优选用在喷洒调味品即所谓的调料中,以避免当食用玉米粉、土豆粉或者米粉的松脆物和点心时出现的口腔干涩感并改善整体感观知觉。
合适的喷洒调味品包括,例如合成的、天然的或者等同天然的芳香物质,以及载体物质例如麦芽糖糊精,盐例如常用盐,调味料例如红辣椒和胡椒,甜味剂例如糖精,以及香味增强剂例如谷氨酸一钠和/或次黄苷单磷酸。
可以制备包含2E,4E-癸二烯酸-N-异丁基酰胺的本发明的制品,使得2E,4E-癸二烯酸-N-异丁基酰胺在不使用溶剂的情况下、作为溶液或者以与固体或液体载体物质的混合物的形式加入用在营养或者口腔卫生中的或者休闲消费的制品中。有利的是,以溶液形式存在的、包含2E,4E-癸二烯酸-N-异丁基酰胺的本发明制品还可以通过喷雾干燥转化成固体制品。
为了制备所述制品,还可以在另一优选实施方案中首先将2E,4E-癸二烯酸-N-异丁基酰胺和任选根据本发明制品的其他组分加入由由适用于食品和休闲消费产品的基质,例如淀粉、淀粉衍生物、其他多糖、天然脂肪、天然蜡,或者蛋白质例如明胶缩制成的乳液、脂质体,例如以卵磷脂开始、微球体、纳米球体或者胶囊中。另一个实施方案在于首先将2E,4E-癸二烯酸-N-异丁基酰胺与合适的复合剂例如环糊精或者环糊精衍生物,优选以环糊精复合,并以该形式使用它。
作为根据本发明的用在营养中或者休闲消费的制品中的其他组分,可以使用用于食品或者休闲消费产品的其他常规原料、助剂和添加剂,例如水、新鲜或加工过的植物-或动物基原料(例如未加工、油炸、干燥、发酵、烟熏和/或炖肉、蛋、骨、软骨、鱼、甲壳类动物和贝类、蔬菜、水果、香草、坚果、蔬菜或水果汁或酱,或其混合物)、可消化或不可消化的碳水化合物(蔗糖、麦芽糖、果糖、葡萄糖、糊精、直链淀粉、支链淀粉、菊糖、木聚糖、纤维素)、糖醇(例如山梨糖醇、甘露糖醇、木糖醇)、天然或氢化脂(例如牛脂、猪油、棕榈油、椰子油、氢化蔬菜油)、脂肪油(例如葵花籽油、花生油、玉米油、蓟油、橄榄油、胡桃油、鱼油、豆油、芝麻籽油)、脂肪酸或其盐(例如硬脂酸钾、棕榈酸钾)、蛋白质或非蛋白质氨基酸以及相关化合物(例如牛磺酸、肌氨酸、肌氨酸酐)、肽、天然或加工过的蛋白质(例如明胶)、酶(例如肽酶、葡糖苷酶、脂肪酶)、核酸、核苷酸(磷酸肌醇酯)、调味物质(例如谷氨酸一钠、2-苯氧基丙酸)、乳化剂(例如卵磷脂、二酰甘油)、稳定剂(例如角叉菜、藻酸盐、角豆荚粉、果阿胶)、防腐剂(例如苯甲酸、山梨酸)、抗氧化剂(例如生育酚、抗坏血酸)、螯合剂(例如柠檬酸)、有机或无机酸化剂(例如苹果酸、乙酸、柠檬酸、酒石酸、磷酸)、苦味物质(例如奎宁、咖啡因、柠檬苦素)、甜味剂(例如糖精、环磺酸盐、阿斯巴甜、纽甜(neotame)、新橙皮苷二氢查耳酮)、矿物质盐(例如氯化钠、氯化钾、氯化镁、磷酸钠)、防止酶褐变的物质(例如亚硫酸盐、抗坏血酸)、精油、植物提取物、天然或合成着色剂或有色颜料(例如类胡萝卜素、类黄酮、花色甙、叶绿素及其衍生物)、调味品以及香味物质、合成、天然或等同天然的芳香和调味物质。
根据本发明的制品还优选包含芳香组合物,以丰富或者改善制品的味道和/或气味。合适的芳香组合物包含例如合成的、天然的或者等同天然的芳香物质以及香味物质,但是尤其还包含其他诱导唾液的、刺痛、刺激或者辛辣物质或者植物提取物。
本发明还提供作为半制成品的本发明制品的用途,用于给由其制备的作为最终产品的制品添加香味。
本发明还提供包含2E,4E-癸二烯酸-N-异丁基酰胺的香味、芳香和风味物质。以制品的总重量计,这些组合物通常包含0.001wt.%-5wt.%,优选0.01wt.%-2wt.%,特别优选0.05wt.%-1wt.%的2E,4E-癸二烯酸-N-异丁基酰胺。
参考下面的实施例解释本发明。
实施例
实施例1:
通过与2E,4Z-癸二烯酸乙酯的酶促反应而后异构化得到的2E,4E-癸二烯酸-N-异丁基酰胺(反式-佩利特灵)
与异丁基胺反应:
将10g 2E,4Z-癸二烯酸乙酯、4.7g Chirazym L-2(见C2,lyo.,Catalogue No.1859242,Roche Diagostics,Basle,Switzerland)和4g异丁基胺在55℃下搅拌4天。在该批料中加入100ml二乙醚而后过滤,真空下蒸发滤液(粗产量15.2g)。于室温下将该产物在10%的KOH/甲醇(1∶1的混合物)中搅拌45分钟,用醚萃取,醚相用硫酸钠干燥,过滤,蒸发滤液。将粗中间产物在硅胶60(洗脱液为己烷/乙酸乙酯10∶1(v/v))上进行色谱分离。产量为9.1g(GC:99.4%)。
1H-MNR(CDCl3;200MHz):δ=7.56(1H,ddd,11.5Hz,14.9Hz,1.0Hz),6.08(1H,dddd 11.5Hz,10.8Hz,1.4Hz,0.6Hz),5.82(1H,d,14.9Hz),5.79(1H,dtd 10.8Hz,7.8Hz,0.9Hz),5.50(1H,bs),3.18(2H,dd,6.8Hz,6.1Hz),2.36-2.22(2H,m),1.81(1H,m,6.7Hz),1.50-1.22(6H,m),0.93(6H,d,6.7Hz),0.88(3H,m)ppm。
13C-NMR(CDCl3;50MHz):δ=166.34(C),140.07(CH),135.76(CH),126.28(CH),123.78(CH),46.96(CH2),31.41(CH2),29.14(CH2),28.63(CH),28.15(CH2),22.52(CH2),20.15(CH3),14.02(CH3)ppm。
异构化:
将227mg纯化的2E,4E-癸二烯酸-N-异丁基酰胺与29mg碘于室温下在10ml甲苯中搅拌1小时。使用己烷/乙酸乙酯5∶1(v/v)作为洗脱液在硅胶60上进行色谱分离。产量:61mg(纯度大于95%,NMR)。
1H-MNR(CDCl3;200MHz):δ=7.19(1H,dd,14.9Hz,9.7Hz),6.13(1H,dd 15.1Hz,9.6Hz),6.07(1H,dd,15.1Hz,6.4Hz),5.75(1H,d,14.9Hz),5.50(1H,bs),3.17(2H,dd,6.9Hz,6.1Hz),2.14(2H,dd,7Hz,6.4Hz),1.80(1H,m,6.7Hz),1.42(2H,m,7.1Hz),1.37-1.22(4H,m),0.93(6H,d,6.7Hz),0.89(3H,m)ppm。
异构化变体1:
将60mg碘加入溶于20ml甲苯的由与异丁基胺的反应得到的3.1g粗中间产物中,在室温下搅拌该混合物持续26小时。加入30ml正己烷,将该混合物在约18℃下放置1小时。滤出结晶产物(GC:86%的2E,4E-异构体,10.5%的2E,4Z-异构体)。通过从约30ml正己烷中重结晶得到纯度为95%的产物(产量1.6g)。
异构化变体2:
将由与异丁基胺的反应得到的3.1g粗中间产物溶解在100乙醇中,冷却的同时用具有石英玻璃管的汞蒸气高压灯辐射持续8小时。蒸发溶液并通过色谱法纯化油状残余物(GC:22%的2E,4E-异构体,62%的2E,4Z-异构体)(产量约400mg)。
实施例2:试味
将反式-佩利特灵溶解在乙醇中,然后用11wt.%的糖溶液稀释该乙醇溶液(最终浓度:c)。为了试味,每种情况下吞服约5ml的糖溶液。由6-8个测试者组成的测试组来品尝该溶液:
c=10ppm:诱导唾液、略微刺痛,且不刺激
c=20ppm:诱导唾液、略微感到麻痹、略微油腻、弱水果味、刺痛、持久且不刺激
实施例3:用于牙膏
部分 | 成分 | 含量以wt.%表示 |
A | 软化水 | 22.00 |
山梨糖醇(70%) | 45.00 | |
SolbrolM,钠盐(Bayer AG,对羟基苯甲酸烷基酯) | 0.15 | |
磷酸三钠 | 0.10 | |
糖精,450倍甜度 | 0.20 | |
单氟磷酸钠 | 1.12 | |
聚乙二醇1500 | 5.00 | |
B | Sident 9(研磨二氧化硅) | 10.00 |
Sident 22 S(增稠二氧化硅) | 8.00 | |
羧甲基纤维素钠 | 0.90 | |
二氧化钛 | 0.50 | |
C | 软化水 | 4.53 |
十二烷基硫酸钠 | 1.50 | |
D | 芳香组合物,包含0.1wt.%的2E,4E-癸二烯酸-N-异丁基酰胺 | 1 |
将A和B部分的成分各自预混,然后将其一起在25-30℃下真空充分搅拌30min。预混C部分,将其加入A和B中;再加入D,并且在25-30℃下真空充分搅拌该混合物30min。松弛以后,即制成牙膏并可以被装填。
实施例4:用于不含糖的口香糖
部分 | 成分 | 含量以wt.%表示 |
A | 口香糖胶基,“Jagum T”公司 | 30.00 |
B | 山梨糖醇,粉末状 | 39.00 |
Isomalt(Palatinit GmbH) | 9.50 | |
木糖醇 | 2.00 | |
甘露糖醇 | 3.00 | |
Aspartam | 0.10 | |
AcesulfamK | 0.10 | |
Emulgum(Colloides Naturels有限公司) | 0.30 | |
C | 山梨糖醇,70% | 14.00 |
甘油 | 1.00 | |
D | 芳香组合物,包含0.1wt.%的2E,4E-癸二烯酸-N-异丁基酰胺 | 1 |
将A-D部分进行混合并充分捏和。可将粗物质加工成待用口香糖,例如呈薄片状。
实施例5:用于漱口水
部分 | 成分 | 含量(wt.%) |
A | 乙醇 | 10.00 |
CremophorCO40(BASF,清洁剂) | 1.00 | |
苯甲酸 | 0.12 | |
芳香组合物,包含0.1wt.%的2E,4E-癸二烯酸-N-异丁基酰胺 | 0.25 | |
B | 软化水 | 83.46 |
山梨糖醇,70% | 5.00 | |
糖精钠450 | 0.07 | |
L-Blue 5000e.c.,1wt.%的水溶液(着色剂) | 0.10 |
将A和B部分的成分分别各自混合。将B部分缓慢加入A部分中直至混合物均匀。
实施例6:
在用来喷洒在干炸快餐食品上的调味品中的使用
在100g未调味的玉米饼上喷洒7g用于快餐的奶酪干香料和0.07g 2E,4E-癸二烯酸-N-异丁基酰胺。
实施例7:
在饼干奶油馅中的使用
将100g标准奶油馅与0.4g草莓香料和0.1g 2E,4E-癸二烯酸-N-异丁基酰胺充分混合。
Claims (9)
1. 2E,4E-癸二烯酸-N-异丁基酰胺(反式-佩利特灵)作为芳香物质,特别是作为具有诱导唾液作用的芳香物质,在用在营养或口腔卫生或休闲消费的制品中的用途。
2.根据权利要求1的用途,其特征在于对于最终制品,反式-佩利特灵的用量为0.01-500ppm。
3.包含反式-佩利特灵的用在营养或口腔卫生或休闲消费的制品以及香味、芳香和风味物质组合物。
4.根据权利要求3的制品,其特征在于对于最终制品,所述制品包含0.01-500ppm含量的反式-佩利特灵。
5.根据权利要求3或4的制品,其特征在于所述制品包含至少一种额外的诱导唾液的、刺痛、刺激或辛辣的物质。
6.根据权利要求3-5中任一项的制品,其特征在于所述制品包含至少一种额外的诱导唾液的、刺痛、刺激或辛辣的植物提取物。
7.根据权利要求3的组合物,其特征在于所述组合物包含0.001wt.%-5wt.%的反式-佩利特灵。
8.根据权利要求3-7中任一项的制品或组合物,其特征在于反式-佩利特灵是合成的。
9.一种制备2E,4E-癸二烯酸-N-异丁基酰胺的方法,其特征在于
a)在催化剂存在下,使2E,4E-或2E,4Z-癸二烯酸酯或其混合物与异丁基胺反应,以及
b)使步骤a)形成的产物,任选在纯化步骤之后,异构化形成2E,4E-癸二烯酸-N-异丁基酰胺;
或者
i)使2E,4Z-癸二烯酸酯或者2E,4E-和2E,4Z-癸二烯酸酯的混合物异构化形成2E,4E-癸二烯酸酯,以及
ii)使步骤a)形成的产物,任选在纯化步骤之后,在催化剂存在下与异丁基胺反应。
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DE10253331.8 | 2002-11-14 | ||
DE10253331A DE10253331A1 (de) | 2002-11-14 | 2002-11-14 | Verwendung von trans-Pellitori als Aromastoff |
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CN1711234A true CN1711234A (zh) | 2005-12-21 |
CN1318390C CN1318390C (zh) | 2007-05-30 |
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US (2) | US7776923B2 (zh) |
EP (1) | EP1562893B1 (zh) |
JP (1) | JP4970727B2 (zh) |
KR (2) | KR101285264B1 (zh) |
CN (1) | CN1318390C (zh) |
AT (1) | ATE454821T1 (zh) |
AU (1) | AU2003283398A1 (zh) |
BR (1) | BR0316207A (zh) |
DE (2) | DE10253331A1 (zh) |
RU (1) | RU2356886C2 (zh) |
WO (1) | WO2004043906A2 (zh) |
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2002
- 2002-11-14 DE DE10253331A patent/DE10253331A1/de not_active Withdrawn
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2003
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- 2003-11-13 KR KR1020057008494A patent/KR101285264B1/ko active IP Right Grant
- 2003-11-13 CN CNB2003801032090A patent/CN1318390C/zh not_active Expired - Lifetime
- 2003-11-13 DE DE50312345T patent/DE50312345D1/de not_active Expired - Lifetime
- 2003-11-13 AU AU2003283398A patent/AU2003283398A1/en not_active Abandoned
- 2003-11-13 US US10/483,668 patent/US7776923B2/en active Active
- 2003-11-13 KR KR1020127014030A patent/KR101245130B1/ko active IP Right Grant
- 2003-11-13 WO PCT/EP2003/012686 patent/WO2004043906A2/de active Application Filing
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Publication number | Publication date |
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EP1562893B1 (de) | 2010-01-13 |
US20040241312A1 (en) | 2004-12-02 |
KR20050074607A (ko) | 2005-07-18 |
BR0316207A (pt) | 2006-04-11 |
WO2004043906A3 (de) | 2004-10-07 |
AU2003283398A1 (en) | 2004-06-03 |
ATE454821T1 (de) | 2010-01-15 |
US8063107B2 (en) | 2011-11-22 |
KR101285264B1 (ko) | 2013-07-15 |
JP4970727B2 (ja) | 2012-07-11 |
WO2004043906A2 (de) | 2004-05-27 |
EP1562893A2 (de) | 2005-08-17 |
RU2005118091A (ru) | 2006-01-10 |
US7776923B2 (en) | 2010-08-17 |
DE10253331A1 (de) | 2004-06-03 |
CN1318390C (zh) | 2007-05-30 |
RU2356886C2 (ru) | 2009-05-27 |
JP2006506479A (ja) | 2006-02-23 |
KR20120091265A (ko) | 2012-08-17 |
KR101245130B1 (ko) | 2013-03-26 |
DE50312345D1 (de) | 2010-03-04 |
US20100291005A1 (en) | 2010-11-18 |
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