CN105636934A - N-酰化的2-氨基异丁酸化合物和包含它们的香味组合物 - Google Patents
N-酰化的2-氨基异丁酸化合物和包含它们的香味组合物 Download PDFInfo
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- CN105636934A CN105636934A CN201380080059.XA CN201380080059A CN105636934A CN 105636934 A CN105636934 A CN 105636934A CN 201380080059 A CN201380080059 A CN 201380080059A CN 105636934 A CN105636934 A CN 105636934A
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Abstract
式(I)的化合物或其可食用盐(式应该***在这里),其中R与它所连接的羰基一起为羧酸残基。该化合物可以用于可食用组合物,例如食品和饮料,以便给所述组合物传递香味和口感或改进其香味和口感。
Description
本发明涉及N-酰化的2-氨基异丁酸化合物、包含所述化合物的香味组合物和所述化合物作为香味调节剂在可食用产品例如饮料和食品中的用途。
GB1130480公开了一些酰化的氨基酸羧酸金属盐。认为这些化合物用作表面活性剂且具有在硬水中特别良好的表面活性剂特性。
申请人已经发现,在氨基酸残基的羧酸羰基的α位碳原子上具有偕二甲基取代基模式的酰化氨基羧酸在添加到食品或饮料中时具有香味改良和口感特性。
本发明在其方面之一中提供式(I)的化合物或其可食用盐,
其中
R与它所连接的羰基一起为羧酸残基。
可食用盐包括典型地用于食品和饮料工业的那些盐且包括氯化物、硫酸盐、磷酸盐、葡糖酸盐、钠、柠檬酸盐、碳酸盐、乙酸盐和乳酸盐。
在本发明的一个具体的实施方案中,羧酸残基是脂肪酸残基。
脂肪酸残基可以是C8-C22脂肪酸残基。脂肪酸可以是哺乳动物或非哺乳动物的脂肪酸。哺乳动物脂肪酸是天然或合成脂肪酸,其在结构上与一种在哺乳动物中天然产生的脂肪酸相同,包括、但不限于肉豆蔻酸、棕榈酸、硬脂酸、油酸、亚油酸、亚麻酸、二十碳三烯酸、花生四烯酸、二十碳五烯酸(eicosapentenoicacid)和二十二碳四烯酸。非哺乳动物脂肪酸是通常不由哺乳动物产生的天然或合成脂肪酸,包括、但不限于十五烷酸;十七烷酸;十九烷酸;二十一烷酸;9-反式-十四烯酸;10-反式-十五烯酸;9-反式-十六烯酸;10-反式-十七烯酸;10-反式-十七烯酸;7-反式-十九烯酸;10,13-十九碳二烯酸;11-反式-二十烯酸;和12-反式二十一烯酸。
脂肪酸残基可以是饱和的或不饱和的。如果它们是不饱和的,则优选它们具有1、2或3个双键,所述双键可以为顺式-或反式-构型。
更具体地,优选的脂肪酸残基是C16-C18,其可以是饱和的或不饱和的。
然而,本领域技术人员可以理解,这些脂肪酸的天然来源例如杏仁油、鳄梨油、蓖麻油、椰子油、玉米油、棉籽油、橄榄油、花生油、米糠油、红花油、芝麻油、大豆油、葵花油、棕榈油和低芥酸菜子油各自由脂肪酸的复杂混合物组成。例如,红花油主要是C18:2亚油酸的来源,但是它可以包含其它脂肪酸,例如亚麻酸(C18:3)和棕榈酸(C16:0)等。因此,本文涉及包含特定脂肪酸残基、例如C18脂肪酸残基的化合物,可以涉及纯的或基本上纯的C18脂肪酸残基或可以涉及具有为C18残基作为主要残基的脂肪酸残基的混合物。优选的脂肪酸残基是C16-C18。
特别优选的式(I)的化合物选自:
可以通过已知方法、使用商购的原料、试剂和溶剂形成式(I)的化合物,且并未在本文中保证详细讨论。在本发明的一个实施方案中,可以通过使氨基酸与羧酸卤化物例如氯化物在碱性条件下在水性条件例如水/THF溶剂***中反应形成共轭物。可以通过给该反应混合物施加热改善收率和反应时间。在可选的实施方案中,可以使羧酸与氨基酸在二噁烷中在DCC(二环己基碳二亚胺)和1-羟基吡咯烷-2,5-二酮的存在下反应。
式(I)的化合物将显著的感官特征传递给添加它们的可食用组合物。具体地,它们给包含它们的可食用组合物传递高度强烈的、真实的和协调的香味和圆和与丰满感。
这种发现更令人惊奇的方面是考虑到,当申请人品尝稀水溶液形式的化合物时,它们展示出令人失望的、微弱的脂肪味道特性。照此,它们显然十分不适用于香味用品。仅它们与香味辅助成分的组合及其使用水平的甚重选择能够发现这些化合物的显著的感官特性。其对可食用产品的效果十分罕见的方面在于它们实际上补充、提升或加强掺入它们的食品或饮料的基本或真实的香味和口感特征。因此,本发明的化合物应用于食品和饮料工业以及健康和保健中的广泛用品。
因此,在另一个方面,本发明提供赋予可食用组合物香味和/或口感或改善其味道和/或口感的方法,该方法包括向所述组合物中添加本文定义的式(I)的化合物。
当将式(I)的化合物掺入包含一种或多种香味辅助成分的可食用组合物中时,观察到显著的感官效应。
香味辅助成分可以是糖类、脂肪、盐(例如氯化钠)、MSG、钙离子、磷酸根离子、有机酸、蛋白质、嘌呤类及其混合物。
在一个具体的实施方案中,糖类以占可食用组合物总重0.001%-90%、更具体地为0.001%-50%、仍然更具体地为0.001%-20%的量存在。
在一个具体的实施方案中,脂肪以占可食用组合物总重0.001%-100%、更具体地为0.001%-80%、更具体地为0.001%-30%、仍然更具体地为0.001%-5%的量存在。
在一个具体的实施方案中,盐(例如氯化钠)以占可食用组合物总重0.001%-20%、更具体地为0.001%-5%的量存在。
在一个具体的实施方案中,MSG以占可食用组合物总重0.001%-2%的量存在。
在一个具体的实施方案中,钙以占可食用组合物总重0.001%-50%、更具体地为0.001%-20%、仍然更具体地为0.001%-1%的量存在。
在一个具体的实施方案中,有机酸以占可食用组合物总重0.001%-10%、更具体地为0.001%-7%的量存在。
有机酸的类型包括柠檬酸、苹果酸、酒石酸、富马酸、乳酸、乙酸和琥珀酸。包含有机酸的可食用组合物的类型包括饮料,例如碳酸软饮料、不充气饮料、果汁、粉状软饮料、液体浓缩物、酒精性饮料和功能性饮料。
在一个具体的实施方案中,磷的存在量至多占可食用组合物重量的0.5%。典型地,磷作为磷酸盐或磷酸存在。
在一个具体的实施方案中,嘌呤类的存在量至多占可食用组合物重量的0.5%。术语“嘌呤类”包括核糖核苷酸,例如IMP和GMP。
式(I)的化合物便利地以储备溶液的形式呈现。化合物在储备溶液中的浓度需要平衡考量。一方面,化合物相当有效且为了易于操作少量有效材料,通常便利地将它们掺入大量稀释剂;而另一方面,可能不想使用过多的溶剂,因为这牵涉成本的增加,大量溶剂可能导致不良的审美效应,并且生成将化合物加工成香味组合物和可食用产品带来的问题。然而,优选地,在储备溶液中,化合物可以以至多5%重量、更具体地至多10%重量、仍然更具体地至多20%重量、仍然更具体地至多25%重量的浓度存在。
适合的溶剂包括与水可溶混的醇类,例如乙醇、甘油、丙二醇或其衍生物,例如三醋精;或miglyol。
在另一个方面,提供式(I)的化合物的储备溶液,其浓度至多为5%重量,更具体地至多为10%重量,仍然更具体地至多为20%重量,仍然更具体地至多为25%重量。
所述储备溶液可以包含如下文更完整地描述的其它材料,例如载体材料和/或助剂。在一个具体的实施方案中,所述储备溶液包含抗氧化剂,其选自维生素C、维生素E、迷迭香提取物、叔丁基对甲氧酚(antrancine)、丁羟茴醚(BHA)和丁羟甲苯(BHT)。抗氧化剂优选用于防止或显著地减少作为式(I)的化合物降解结果的挥发性异味的生成。当式(I)的化合物具有不饱和脂肪酸残基时,特别优选抗氧化剂。如果脂肪酸残基包含1个以上双键,则特别优选抗氧化剂。确定抗氧化剂的有效量属于本领域技术人员的范围,然而,基于储备溶液的重量可以存在约10ppm-1000ppm范围内的用量。
在制备本发明的香味组合物的过程中,式(I)的化合物可以以任意物理形式使用。可以以净形式、储备溶液的形式使用它们;可以以乳液形式使用它们;或可以以粉末形式使用它们。如果式(I)的化合物以粉末形式呈现,则可以通过分散蒸发法生产粉末形式,例如作为下文中更充分地描述的喷雾干燥法。液体制品可以包括包含式(I)的化合物的溶液、混悬液或乳液。具体地,液体制品可以采用上文所述的储备溶液的形式。液体制品可以包含其它成分,例如如下文更充分地描述的载体材料和/或助剂。
包含式(I)的化合物的粉末构成本发明的另一个方面。
可以将式(I)的化合物单独地或以包含一种或多种香味辅助成分的香味组合物的形式掺入可食用组合物。
包含式(I)的化合物的香味组合物构成本发明的另一个方面。
在本发明的一个实施方案中,所述香味组合物包含式(I)的化合物和至少一种香味辅助成分。
在本发明的一个具体的实施方案中,所述香味组合物包含:
i)式(I)的化合物;
ii)至少一种香味辅助成分;
iii)任选的载体材料;和
iv)任选的至少一种助剂。
所谓术语“香味辅助成分”是能够以积极或令人愉快的方式给可食用组合物贡献或传递或改变味道的成分。
所有形式的香料均可以用于本发明的组合物,包括、但不限于天然香料、人造香料、香料调味品、作料等。香味辅助成分包括合成香味油和加香香料和/或油、来源于植物、叶、花、果实等的油性树脂、精油、蒸馏物和提取物和包含上述成分的至少一种的组合。
香味油包括留兰香油、肉桂油、冬青油(水杨酸甲酯)、胡椒薄荷油、日本薄荷油、丁香油、桂花油、八角茴香油、桉叶油、百里香油、香柏叶油、肉豆蔻油、多香果、鼠尾草油、肉豆蔻、苦杏仁油和桂皮油;有用的增香剂包括人造、天然和合成水果香料,例如香草和柑橘油,包括柠檬、橙、白柠檬、葡萄柚、yazu、史达橘(sudachi)和水果香精包括苹果、梨、桃、葡萄、蓝莓、草莓、覆盆子、樱桃、李子、洋李、葡萄干、可乐、瓜拉那、橙花油、菠萝、杏子、香蕉、甜瓜、杏子、ume、樱桃、覆盆子、黑莓、热带水果、芒果、山竹果、石榴、番木瓜等。
加香剂递送的另外的示例性香精包括牛奶香精、黄油香精、干酪香精、奶油香精和酸奶香精;香草香精;茶或咖啡香精例如绿茶香精、乌龙茶香精、茶香精、可可香精、巧克力香精和咖啡香精;薄荷香精例如薄荷香精、留兰香香精和日本薄荷香精;香辣香精例如阿魏香精、香旱芹香精、大茴香香精、当归属香精、小茴香香精、多香果香精、肉桂香精、黄春菊香精、芥茉香精、小豆蔻香精、葛缕子香精、小茴香子香精、丁香香精、胡椒香精、芫荽子香精、黄樟香精、香旱芹菜香精、川花椒香精、紫苏香精、杜松子香精、姜香精、八角茴芹香精、辣根香精、百里香香精、龙艾香精、莳萝子香精、辣椒香精、肉豆蔻香精、罗勒香精、马郁兰香精、迷迭香香精、月桂叶香精和绿芥末(日本辣根)香精;坚果香精例如杏仁香精、榛子香精、坚果香精、花生香精、美洲山核桃香精、阿月浑子香精和胡桃香精;酒精香精例如葡萄酒香精、威士忌酒香精、白兰地酒香精、甜酒香精、杜松子酒香精和利口酒香精;花香精;和蔬菜香精例如洋葱香精、大蒜香精、甘蓝香精、胡萝卜香精、芹菜香精、香茹香精和蕃茄香精。
在一些实施方案中,所述香味辅助成分包括醛类和酯类,例如可以使用乙酸肉桂酯、肉桂醛、柠檬醛二乙基缩醛、乙酸二氢香芹酯、丁子香酚49甲酸酯、对-甲基茴香醇(amisol)等。醛香料的另外的实例包括乙醛(苹果)、苯甲醛(樱桃,杏仁)、茴香醛(甘草,大茴香)、肉桂醛(肉桂)、柠檬醛即α-柠檬醛(柠檬,白柠檬)、橙花醛即β-柠檬醛(柠檬,白柠檬)、癸醛(橙,柠檬)、乙基香草醛(香草,奶油)、天芥菜即胡椒醛(香草,奶油)、香草醛(香草,奶油)、α-戊基肉桂醛(辛香水果香精)、丁醛(黄油,干酪)、戊醛(黄油,干酪)、香茅醛(改性剂,许多类型)、癸醛(柑橘类水果)、醛C-8(柑橘类水果)、醛C-9(柑橘类水果)、醛C-12(柑橘类水果)、2-乙基丁醛(浆果类)、己烯醛即反式-2(浆果类)、甲苯醛(樱桃,杏仁)、藜芦醛(香草)、2,6-二甲基-5-庚烯醛即甜瓜醛(甜瓜)、2,6-二甲基辛醛(青香果实)和2-十二碳烯醛(柑橘,橘子)等。
其它香味辅助成分的另外的实例可以在NationalAcademyofSciences的“ChemicalsUsedinFoodProcessing”,1274卷,63-258页中找到。
香味辅助成分还可以包括咸味促味剂、鲜味促味剂和调味的香味化合物。非限制性实例包括:NaCl、KCl、MSG、鸟苷一磷酸(GMP)、肌苷一磷酸(IMP)、核糖核苷酸类例如肌苷酸二钠、鸟苷酸二钠、N-(2-羟基乙基)-乳酰胺、N-乳酰基-GMP、N-乳酰基酪胺、γ氨基丁酸、烯丙基半胱氨酸、1-(2-羟基-4-甲氧基苯基)-3-(吡啶-2-基)丙-1-酮、精氨酸、氯化钾、氯化铵、琥珀酸、N-(2-甲氧基-4-甲基苄基)-N'-(2-(吡啶-2-基)乙基)草酰胺、N-(庚-4-基)苯并(D)(1,3)间二氧杂环戊烯-5-甲酰胺、N-(2,4-二甲氧基苄基)-N'-(2-(吡啶-2-基)乙基)草酰胺、N-(2-甲氧基-4-甲基苄基)-N'-2(2-(5-甲基吡啶-2-基)乙基)草酰胺、环丙基-E,Z-2,6-壬二烯酰胺。
在本发明的具体实施方案中,香味辅助成分选自WO2005102701、WO2006009425、WO2005096843、WO2006046853和WO2005096844中公开的化合物和组合物,将所有这些参考文献完整地引入本文参考。
香味辅助成分可以包括已知的咸味促味剂、鲜味促味剂和调味的香味化合物。非限制性实例包括:NaCl、KCl、MSG、鸟苷一磷酸(GMP)、肌苷一磷酸(IMP)、核糖核苷酸类例如肌苷酸二钠、鸟苷酸二钠、N-(2-羟基乙基)-乳酰胺、N-乳酰基-GMP、N-乳酰基酪胺、γ氨基丁酸、烯丙基半胱氨酸、1-(2-羟基-4-甲氧基苯基)-3-(吡啶-2-基)丙-1-酮、精氨酸、氯化钾、氯化铵、琥珀酸、N-(2-甲氧基-4-甲基苄基)-N'-(2-(吡啶-2-基)乙基)草酰胺、N-(庚-4-基)苯并(D)(1,3)间二氧杂环戊烯-5-甲酰胺、N-(2,4-二甲氧基苄基)-N'-(2-(吡啶-2-基)乙基)草酰胺、N-(2-甲氧基-4-甲基苄基)-N'-2(2-(5-甲基吡啶-2-基)乙基)草酰胺、环丙基-E,Z-2,6-壬二烯酰胺。
载体材料可以用于将组合物的其它成分包封或俘获在本发明组合物的基质中。载体材料的作用可以仅在于加工助剂或填充剂的作用,或可以用于屏蔽或防止其它成分受到湿气或氧或任意其它攻击性介质的影响。载体材料还可以在消费时作为控制香味从可食用组合物中释放的用品起作用。
载体材料可以包括单糖、二糖或三糖、天然或改性淀粉、水胶体、纤维素衍生物、聚乙酸乙烯酯、聚乙烯醇、蛋白质或果胶。具体的载体材料的实例包括蔗糖、葡萄糖、乳糖、左旋糖、果糖、麦芽糖、核糖、右旋糖、异麦芽酮糖醇(isomalt)、山梨糖醇、甘露糖醇、木糖醇、乳糖醇、麦芽糖醇、戊糖醇(pentatol)、***糖、戊糖、木糖、半乳糖、麦芽糖糊精、糊精、化学修饰的淀粉、氢化淀粉水解物、琥珀酰化或水解淀粉、琼脂、角叉菜胶、***树胶、金合欢树胶(gumaccacia)、黄蓍胶、藻酸盐、甲基纤维素、羧甲基纤维素、羟乙基纤维素、羟丙基甲基纤维素、其衍生物和混合物。当然,本领域技术人员可以理解,所引述的材料作为实例并入本文且不解释为限制本发明。
所谓“香味助剂”是指能够将额外添加的有益性例如颜色、耐光性、化学稳定剂等赋予给本发明组合物的成分。适合的助剂包括溶剂(包括水、醇、乙醇、三醋精、油、脂肪、植物油和miglyol)、粘合剂、稀释剂、崩解剂、润滑剂、着色剂、防腐剂、抗氧化剂、乳化剂、稳定剂、消结块剂等。在一个具体的实施方案中,所述香味组合物包含抗氧化剂。所述抗氧化剂可以包括维生素C、维生素E、迷迭香提取物、叔丁基对甲氧酚、丁羟茴醚(BHA)和丁羟甲苯(BHT)。
用于香味组合物的这种载体材料或助剂的实例可以在例如“PerfumeandFlavourMaterialsofNaturalOrigin”,S.Arctander,Ed.,Elizabeth,N.J.,1960;“PerfumeandFlavourChemicals”,S.Arctander,Ed.,第I&II卷,AlluredPublishingCorporation,CarolStream,USA,1994;“Flavourings”,E.Ziegler和H.Ziegler(ed.),Wiley-VCHWeinheim,1998;和“CTFACosmeticIngredientHandbook”,J.M.Nikitakis(ed.),第1版,TheCosmetic,ToiletryandFragranceAssociation,Inc.,Washington,1988中找到。
香味组合物的其它适合的和期望的成分描述在标准教科书例如“HandbookofIndustrialChemicalAdditives”,ed.M.和I.Ash,第2版(Synapse2000)中。
本发明的香味组合物可以以任意适合的物理形式提供。例如,它们可以是在适用于可食用组合物的水性液体或有机液体中的油、乳液或分散液形式或固体形式,例如粉末。
如果以粉末组合物形式提供所述香味组合物,则可以通过本领域一般公知的分散蒸发技术例如喷雾干燥制备它们。
因此,在本发明的另一个实施方案中,提供了形成粉末组合物的方法,所述方法包括下列步骤:提供包含式(I)的化合物和一种或多种任选的成分的液体组合物,所述任选的成分选自至少一种香味辅助成分、载体材料和助剂;和分散蒸发所述液体组合物,以形成粉末组合物。
按照这种方式,可以将式(I)的化合物或包含所述化合物的香味组合物制成粉末形式。
用于制备粉末的液体组合物可以是溶液、乳液、分散液或淤浆的形式。所述液体可以包含水和/或有机液体,例如对用于可食用组合物可接受的乙醇、甘油、三醋精、miglyol(MCT)。
可以根据本领域中用于工业化规模生产粉末的方法和设备制备本发明的粉末组合物。特别适合的方法是喷雾干燥。喷雾干燥技术和设备是本领域众所周知的且无需在本文中详细讨论。描述在US2005/0031769和US2013/0022728中的喷雾干燥技术、设备和方法以及那些对比文件中所述的那些技术、设备和方法适合于生产本发明的粉末组合物,并且将这些文献完整地引入本文参考。
将式(I)的化合物掺入本发明的粉末香味组合物的方式并不关键。例如。可以将所述化合物加入上述液体组合物中并且与香味组合物的所有其它成分一起进行分散蒸发工艺。或者,可以将化合物在形成粉末后加入香味组合物。
上文所述的许多香味辅助成分是挥发性的和/或可能对氧化降解敏感,特别是在接触升温和湿度条件下时。因此,在使上述香味辅助成分进行分散蒸发工艺例如喷雾干燥时,具体问题可能增多。可能特别敏感的成分的非穷举性清单包括:那些包含人造、天然或合成水果香精的成分,例如香草、巧克力、咖啡、可可和柠檬油,包括柠檬、橙、葡萄、白柠檬和葡萄柚,和水果香糖,包括苹果、梨、桃、草莓、覆盆子、樱桃、李子、菠萝、杏子等。这些香味辅助成分的挥发性成分可以包括、但不限于乙醛、二甲硫、乙酸乙酯、丙酸乙酯、丁酸甲酯和丁酸乙酯。包含挥发性醛类或酯类的香味辅助成分包括,例如乙酸肉桂酯、肉桂醛、柠檬醛、乙缩醛、乙酸二氢葛缕醇酯、甲酸丁子香酯和对-甲基茴香醚。可以作为辅助成分呈现的挥发性化合物的另外的实例包括乙醛(苹果)、苯甲醛(樱桃,杏仁)、肉桂醛(肉桂)、柠檬醛即α-柠檬醛(柠檬,白柠檬)、橙花醛即β-柠檬醛(柠檬,白柠檬)、癸醛(橙,柠檬)、乙基香草醛(香草,奶油)、天芥菜即胡椒醛(香草,奶油)、香草醛(香草,奶油)、α-戊基肉桂醛(辛香水果香精)、丁醛(黄油,干酪)、戊醛(黄油,干酪)、香茅醛(改性剂,许多类型)、癸醛(柑橘类水果)、醛C-8(柑橘类水果)、醛C-9(柑橘类水果)、醛C-12(柑橘类水果)、2-乙基丁醛(浆果类)、己烯醛即反式-2(浆果类)、甲苯醛(樱桃,杏仁)、藜芦醛(香草)、2,6-二甲基-5-庚烯醛即甜瓜醛(甜瓜)、2,6-二甲基辛醛(青香果实)和2-十二碳烯醛(柑橘,橘子)、樱桃或葡萄及其混合物。
申请人令人惊奇地发现,在粉末香味组合物中包含式(I)的化合物,能够得到暗示香味油的香味品质。
因此,本发明在其另一个方面提供维持粉末香味组合物的香味品质的方法,所述方法包括在所述粉末香味组合物中包括式(I)的化合物的步骤。
如上文所述,可以将式(I)的化合物或包含这类化合物的香味组合物掺入可食用组合物,且包含这类化合物的可食用组合物或香味组合物构成本发明的另外的方面。
术语“可食用组合物”是指受试者、典型地通过口腔消费(尽管消费可以通过非口腔的方式进行,例如吸入)的产品,其至少一个目的在于享乐、营养或健康和保健有益性。可食用组合物可以以任意形式存在,包括、但不限于液体、固体、半固体、片剂、胶囊、锭剂、条状物、粉末、凝胶、树胶、糊剂、淤浆、糖浆、气雾剂和喷雾剂。该术语还指,例如膳食和营养补充剂。可食用组合物包括在弃去前置于口腔中一定时间期限、不吞咽的组合物。可以将其在消费前置于口腔中,或将其保留在口腔中一定时间期限,然后弃去。如上文所定义的可食用组合物包括这样的组合物,其味道以本文所述的方式通过添加式(I)的化合物改变,或其味道通过加工如此改变,使得它富含式(I)的化合物。
广泛地说,可食用组合物包括、但不限于所有种类的食品、糖食产品、烘烤制品、甜品、风味产品、发酵产品、乳制品、饮料和口腔护理产品。
在一个具体的实施方案中,术语“可食用组合物”是指由受试者、典型地通过口腔消费的产品(不过,消费可以通过非口腔方式例如吸入进行),目的之一在于享乐或营养。
在一个更具体的实施方案中,术语“可食用组合物”是指由受试者、典型地通过口腔消费的目的在于享乐的产品(不过,消费可以通过非口腔方式例如吸入进行)。更具体地,该术语是指食品和饮料。
在一个具体的实施方案中,术语“可食用组合物”不涉及药物组合物。
在一个具体的实施方案中,术语“可食用组合物”不涉及营养补剂。
示例性食品包括、但不限于速冻小吃、甜和风味极佳的小吃、水果小吃、油煎土豆片/炸土豆片、膨化休闲食品、玉蜀黍饼/玉米片、爆玉米花、椒盐卷饼、坚果、其它甜和风味极佳的点心、小吃、低脂肪小饼干、早餐棒、能量棒、水果棒、其它小吃、膳食替代品、减肥产品、恢复性饮料、即食餐、罐头即食餐、冷冻即食食品、干燥好的饭、冷冻即食餐、混合方便饭、速冻比萨、冷冻比萨、汤、汤品罐头、汤粉、速溶汤粉、冷汤、超高温汤、冷冻汤、意面、罐装意面、干意面、冷冻/新鲜意面、面条、阳春面、方便面、杯装/碗装方便面、袋装方便面、油醋汁凉面、方便面、干燥食品、什锦点心、酱油、调料和调味品、草药和香料调味品、糊状食品、果酱和蜜饯、蜂蜜、巧克力酱、基于坚果的酱和基于发酵的粉酱。
示例性糖食产品包括、但不限于口香糖(包括糖化口香糖、无糖口香糖、功能性口香糖和泡泡糖)、夹心糖食、巧克力和其它巧克力糖食、含药糖食、脆性硬糖、片剂、软果糕、薄荷糖、标准薄荷糖、强力薄荷糖、软糖、硬糖、硬糖果、呼吸和其它口腔护理膜或条、拐杖糖、棒糖、粘糖、果冻、乳脂软糖、焦糖、硬和脆松糖、乳脂糖、太妃糖、甘草、胶糖、橡皮糖、豆形胶质软糖、奶油杏仁糖、微晶糖膏、一种或多种上述的组合和掺入上述一种或多种的可食用香味组合物。
示例性烘烤制品包括、但不限于夹心饼干(alfajores)、面包、包装/工业化面包、散装的/手工面包、面粉糕饼、蛋糕、包装/工业化蛋糕、散装的/手工蛋糕、饼干、巧克力糖皮饼干、三明治饼干、有馅饼干、加调味料的饼干和薄脆饼干、面包替代品。
示例性甜品包括、但不限于早点用谷物片、可即食(“rte”)谷物、家庭早点用谷物片、薄片、早餐食品、其它可即食谷物、儿童早点用谷物片、热谷物。
示例性的风味产品包括、但不限于含盐零食(马铃薯片、薄脆、坚果、炸玉米粉圆饼、椒盐卷饼、干酪零食、玉米零食、马铃薯零食、可即食爆玉米花、可微波烹饪的爆玉米花(microwaveablepopcorn)、猪肉皮、坚果、薄脆饼干、薄脆零食、早点用谷物片、肉类、肉冻、腌肉(火腿、咸猪肉)、午餐/早餐肉(热狗、冷吃的肉片、香肠)、番茄产品、人造黄油、花生酱、汤(清汤、罐装汤、奶油、即食汤、UHT)、罐装蔬菜、面酱。
示例性的乳制品包括、但不限于干酪、干酪调味品、基于干酪的产品、冰淇淋、兴消费的冰淇淋、单份牛奶冰淇淋、单份水冰淇淋、一包多件包装的牛奶冰淇淋、一包多件包装的水冰淇淋、带回家的冰淇淋、带回家的牛奶冰淇淋、冰淇淋甜点、散装冰淇淋、带回家的水冰淇淋、冷冻酸奶、手工冰淇淋、乳制品、乳品、新鲜/巴氏灭菌牛奶、全脂新鲜/巴氏灭菌牛奶、半脱脂新鲜/巴氏灭菌牛奶、保存期较长的/超高温奶、全脂保存期较长的/超高温奶、半脱脂保存期较长的/超高温奶、无脂保存期较长的/超高温奶、羊奶、炼乳/脱水奶、纯炼乳/脱水奶、加味的、功能性和其它炼乳、香味奶饮料、只有调味乳饮料乳制品、含果汁的香味奶饮料、豆浆、酸乳饮料、发酵奶饮料、咖啡白化剂、奶粉、香味奶粉饮料、奶油、酸奶、纯/天然酸奶、加味酸奶、加水果的酸奶、益生菌酸奶、饮用酸奶、定期饮用酸奶、益生菌饮用酸奶、冷冻点心和耐储存点心、基于乳品的点心、基于大豆的点心。
示例性饮料包括、但不限于调味的水、软饮料、果汁饮料、基于咖啡的饮料、基于茶的饮料、基于果汁的饮料(包括水果和蔬菜)、基于奶的饮料、胶冻饮料、碳酸或非碳酸饮料、粉末饮料、酒精或非酒精性饮料。
示例性的发酵食品包括、但不限于干酪和干酪产品、肉和肉制品、大豆和大豆制品、鱼和鱼制品、谷物和谷物制品、水果和水果制品。
在一个具体的实施方案中,消费品选自大豆酱油、干酪、汤、热和冷调料、水果、蔬菜、番茄酱、茶、咖啡、零食例如马铃薯片或挤出的零食。
式(I)的化合物在添加到香味组合物和/或可食用组合物中时对组合物起作用,以补充其香味和/或赋予其更多的美味和真实感。这些作用可能是暂时的或与强度相关,例如化合物可以通过增强、加强、软化、锐化香味或形成更多的唾液分泌起作用。式(I)的化合物还可以影响香味的暂时特性,即它们可以影响香味的起始印象、香味的本体感或其逗留不去的效果。
式(I)的化合物可以改进可食用组合物的味道或香味的短暂特性的任意方面。具体地,所述化合物改善口感并且传递更多的奶油和脂肪样感觉。
可以将式(I)的化合物或包含它们的香味组合物以广泛携带量加入到可食用组合物中。用量取决于所加香的可食用组合物的性质和期望的效果以及存在于所述香味组合物中的成分的性质。为了得到归因于存在的式(I)的化合物的显著的有益效果,香味组合物应当以这样的用量使用,使得式(I)的化合物的存在量为占可食用组合物总重的每十亿份中1份至每百万份中10份。尽管可以使用高于它的用量,但是有益效果明显相当低且不期望的异味可能逐步变得明显。
当以1-100ppb的水平使用式(I)的化合物时,可以在包含盐或酒精或清凉化合物的可食用组合物中实现有意义的感官效果,例如咸、酒精或清凉加强效果。
当以100-250ppb的水平使用式(I)的化合物时,可以在包含鲜味促味剂的可食用组合物中实现有意义的感官效果,例如鲜味加强效果。
当以250-500ppb的水平使用式(I)的化合物时,可以在可食用组合物中实现有意义的感官效果,特别是口感加强效果。
当以500-1000ppb的水平使用式(I)的化合物时,可以在包含脂肪的可食用组合物中实现有意义的感官效果,例如脂肪加强效果。
特别有利的是将式(I)的化合物掺入在高温条件下例如烘烤、油煎形成或通过热处理例如巴氏消毒或UHT条件下加工的可食用组合物。在高制备或加工温度下,挥发性香味成分可能丧失或被降解,结果是香味强度可能下降且基本和真实的香味特征可能减少。这类可食用产品包括乳制品、零食、烘焙食品、粉状软饮料和类似干燥混合物等、脂肪和作料、蛋黄酱、调味品、汤和肉汤和饮料。
本发明的一种特别优选类型的可食用组合物是粉状软饮料和类似的干燥混合物用品。干燥混合物用品是本领域公知的且包括预期在消费前再溶解的粉末形式的产品。它们包括汤粉、粉状蛋糕混合料、粉状巧克力饮料、速溶咖啡、调味品和方坦糖(fonds)等。
通过分散蒸发法例如喷雾干燥形成的干粉代表将香味油品质的香味递送给可食用组合物的极为便利的载体。
令人遗憾地,香味油且特别是橘子香味油可能对分散蒸发法、尤其是在高温下进行的加工特别敏感。香味油倾向于蒸发或降解而形成具有不利异味的产品。粉状香味组合物、特别是包含柠檬油的那些产品可能品质差且作为结果显示相对短的贮存期限。
令人惊奇地,将式(I)的化合物或包含它们的香味组合物掺入粉末组合物导致该粉末组合物显示用于其制备的香味油的冲击和真实感,尤其是维持粉状香味制品中的香味油品质。
因此,本发明在另一个方面提供粉末香味组合物,其包含式(I)的化合物和至少另一种香味辅助成分。
本发明在另一个方面提供包含式(I)的化合物的粉末软饮料组合物或其它干燥混合物组合物。
本发明在另一个方面提供包含含有式(I)的化合物的粉末香味组合物的粉末软饮料组合物或其它干燥混合物组合物。
本发明在另一个方面提供形成粉末香味组合物的方法,所述方法包括将式(I)的化合物掺入所述组合物的步骤。
在另一个具体的实施方案中,可以将式(I)的化合物加入到形成的粉末香味组合物中,或可以将其加入到香味组合物中,然后形成粉末。
本发明可食用组合物的另一种特别优选的种类是快餐食品。快餐食品是食品工业领域普通技术人员众所周知类型的产品。这些产品如上所述且包括、但不限于椒盐卷饼、玉米片、马铃薯片、膨化制品、挤出产品、玉米粉圆饼片等。更具体地,本发明涉及低脂肪快餐食品组合物。低脂肪快餐食品组合物包含低于30%重量的脂肪,更具体地为5-25%重量的脂肪。
在快餐食品组合物中减少脂肪的问题在于味道和质地缺失。脂肪以这样的方式起重要作用,即生面团在加工过程中的行为且显著地影响方便食品的质量、香味和质地。当零食产品中的脂肪含量下降或被其它成分(例如不可消化的脂肪、蛋白质、纤维、树胶)替代时,不良感官效应(例如口腔涂抹、干燥、缺乏脆性和缺乏香味)增加。不良感官效应导致产品的适口性下降。
在设计香味组合物的过程中已经花费了相当的努力来克服与低脂肪快餐食品相关的问题。可以将香料作为干粉和/或液体形式(例如基于油、基于水)的局部涂料涂布于快餐食品上。另一种方法在于向生面团中添加香料。
尽管采取这些不同方法来改善消费者对快餐食品且特别是低脂肪快餐食品的吸引力和适口性,但是仍然需要改进的低脂肪快餐食品,其上涂布有全脂快餐食品的视觉吸引力、香味和质地的涂料。
可以将式(I)的化合物或包含它们的香味组合物掺入快餐食品以赋予有效的香味和具有显著的圆和与丰满感的口感。此外,甚至可以在低脂肪快餐食品中实现所述味道和口感效应。
因此,本发明在其另一个方面中提供了包含如上所述的香味组合物的快餐食品。在本发明的一个具体的实施方案中,所述快餐食品具有的脂肪含量占该快餐食品总重的约40%重量或以下,更具体地约为30%重量或以下,仍然更具体地为25%重量或以下,更具体地约为10%重量或以下,仍然更具体地约为5%重量或以下,仍然更具体地约为3%重量或以下。
快餐食品的实例如上所述且包括通过烤箱烘烤、挤出或油煎加工和由马铃薯和/或玉米和/或不同谷物例如稻米或小麦加工的产品。
本发明的另一种特别优选类型的可食用组合物是酒精性饮料。
申请人令人惊讶地发现,掺入酒精性饮料的式(I)的化合物具有增加该饮料酒精影响的作用。
因此,本发明在其另一个方面中提供了包含式(I)的化合物的酒精性饮料。
在本发明的另一个方面中提供了在酒精性饮料中产生增强的酒精影响的方法,通过将式(I)的化合物掺入所述饮料来进行。
可以将式(I)的化合物以1ppb-1ppm的量掺入所述酒精性饮料。
其它类可食用产品是通过口服摄取的片剂、胶囊、粉末、多颗粒等形式的产品。这种化合物可以包括药物剂型或营养品剂型。
一类人存在吞咽片剂或胶囊、粉末、多颗粒等困难的问题。该问题在一些消费者类型中特别显著,例如儿童和极老的老年人或虚弱的人。申请人令人惊讶地发现,式(I)的化合物在摄入口腔中时产生显著的分泌唾液效应。将所述化合物掺入这些形式,特别是作为所述剂型周围包衣衣料的组成部分可以使得消费者的吞咽过程便利,特别是儿童和老年人或虚弱的人。
因此,本发明在其另一个方面中提供了可口服施用的剂型,特别是包含式(I)的化合物的片剂、胶囊、粉末或多颗粒。
另一种优选类型的可食用组合物是烘烤制品。可以局部或在生面团中掺入式(I)的化合物。掺入1ppb-1ppm水平的式(I)的化合物使得烘烤制品干燥程度较低且更具有多汁性。
其它优选类型的可食用组合物是有热量的或无热量的饮料,其包含碳水化合物甜味剂,例如蔗糖、高果糖玉米糖浆、果糖和葡萄糖;或高强度无营养甜味剂,例如阿斯巴甜、乙酰舒泛钾、三氯蔗糖、环己氨基磺酸盐、糖精钠、纽甜、莱鲍迪甙A和/或其它基于甜叶菊的甜味剂;以及其它任选的成分,例如果汁、有机酸例如柠檬酸、醇和功能性成分。
掺入1ppb-10ppm水平的式(I)的化合物给包含低于1%且至多约为20%水平的甜味剂的所述饮料赋予上等的甜味和暗示为糖的口感。
其它优选的可食用产品是风味组合物,特别是为基于大豆的或基于鱼肉的那些组合物。
在包含5-40%盐的基于大豆的组合物(例如大豆酱油)或基于鱼肉的组合物(例如鱼肉调味料)中掺入1ppb-10ppm水平,发现这些组合物显示逗留不去和丰富的强烈鲜味。
另一种优选的可食用组合物是混浊状饮料组合物。
一些饮料例如果汁具有相对较高的浊度且由此具有不透明的外观。通常期望饮料具有相对高的浊度,这可能期望给具有低果汁含量的饮料提供更天然的外观,或可能的原因与掩蔽沉降或“清脆声响(ringing)”(其中在贮存期间香味或色素油升至容器表面)相关。混浊状饮料通常借助于混浊剂形成。混浊剂通常以乳液形式提供,或混浊剂可以是粉状饮料的组成部分,在重构时,形成乳液,从而为饮料提供持久的混浊。
式(I)的化合物除其显著的感官特征外还可以赋予混浊剂和包含它们的饮料组合物稳定性。
因此,本发明在其另一个方面提供包含使饮料混浊的组合物和式(I)的化合物的组合物。
在本发明的一个具体的实施方案中,如本文所定义的香味组合物可以以乳液形式提供。该乳液组合物可以特别地用于混浊状饮料用品,具体地,其中预期使用混浊剂。
在本发明的另一个方面,提供包含混浊剂和式(I)的化合物的混浊状饮料组合物。
其它优选的可食用组合物是通过熟化方法形成的那些组合物。
在食品加工过程中,对于食品而言频繁出现需要在充分确定条件下保持延长时间期限的需求,以得到具有必不可少和公认的品质的食品。用于该过程的常用术语是熟化。熟化是一些类型的干酪、肉类、大豆酱油和葡萄酒以及啤酒香肠、泡菜、印尼豆豉和豆腐加工中众所周知的。还存在因特定原因进行的具体步骤(例如除去水或除去异味),它们对食品产生有益作用。其实例是精炼巧克力和干燥面条、蔬菜和水果。改善食品质量的转化通过化学转化、酶催化的转化或发酵转化诱导。所有这些转化均为缓慢的且由此是昂贵的;它们也不完全可预期或可控。
式(I)的化合物在其添加到掺入它们的可食用组合物的真实味道特征方面具有显著特性,可以将式(I)的化合物在熟化过程中添加到可食用产品中,以便减少贮存时间,而不会对熟化产品的味道品质产生不良影响。
因此,本发明在另一个方面中提供熟化产品的方法,所述产品选自干酪、肉类、大豆酱油和葡萄酒、啤酒、香肠、泡菜、印尼豆豉和豆腐,该方法包括在式(I)的化合物的存在下熟化所述产品的步骤。
本发明在另一个方面中提供了精炼巧克力的方法,该方法包括将式(I)的化合物或包含它的香味组合物添加到巧克力中的步骤。
现在,下面是用于示例本发明的一系列非限制性实施例。
实施例1
式(I)的化合物的合成
用于制备化合物的通用方法:
在室温向2-氨基-2-甲基丙酸(0.69g,6.78mmol)在1:1THF:2NNaOH(50ml:50ml)中的溶液中滴加油酰氯(2.4g,6.78mmol)。将该反应体系在室温搅拌7h。真空除去THF。向该水层中加入浓HCl用于将pH调整至2。然后用EtOAc3X萃取水层,合并有机层。将有机层用水、盐水洗涤,干燥(Na2SO4),浓缩。对残余物进行硅胶色谱(5%MeOH/DCM,0.1%甲酸),得到0.7g(28%)产物,为白色固体。
2-甲基-2-油酰氨基丙酸:28%收率;1HNMR(300MHz,CD3OD)δppm0.92(t,J=7.5Hz,3H),1.31-1.68(m,28H),2.02-2.08(m,2H),2.18(t,J=7.5Hz,2H),5.31-5.41(m,2H)。13CNMR(300MHz,CD3OD)δppm12.96,22.24,23.92,25.37,26.65,26.67,28.70,28.77,28.86,28.89,29.95,29.12,29.35,31.57,35.31,55.24,129.33,129.36,174.07,176.54。
2-甲基-2-((9Z,12Z)-十八-9,12-二烯酰氨基)丙酸:20%;1HNMR(300MHz,CD3OD)δppm0.91(t,J=7.8Hz,3H),1.31-1.45(m,21H),1.57-1.62(m,2H),2.03-2.10(m,4H),2.17(t,J=7.5Hz,2H),2.78(t,J=6.3Hz,2H),5.27-5.41(m,4H)。13CNMR(300MHz,CD3OD)δppm12.93,22.12,23.91,25.04,25.36,26.66,26.68,28.68,28.77,28.88,28.97,29.24,31.16,35.29,55.22,127.56,127.58,129.41,129.44,174.07,176.54。
2-甲基-2-硬脂酰氨基丙酸:26%;1HNMR(300MHz,CD3OD)δ0.92(t,J=8.7Hz,3H),1.31-1.65(m,36H),2.18(t,J=7.2Hz,2H).13CNMR(300MHz,CD3OD)δppm14.45,23.74,25.41,26.88,30.20,30.49,30.65,30.74,30.80,33.09,36.81,56.75,175.60,178.09。
2-甲基-2-棕榈酰氨基丙酸:9.6%;1HNMR(300MHz,CD3OD)δ0.91(t,J=8.2Hz,3H),1.25-1.45(m,31H),2.52-1.67(m,2H),2.16(t,J=6.9Hz,2H),8.08(s,1H)。13CNMR(300MHz,CD3OD)δppm12.93,22.23,23.90,25.36,28.69,28.97,29.14,29.28,31.57,35.28,55.26,173.87,176.46。
(Z)-2-(十二-5-烯酰氨基)-2-甲基丙酸:12%;1HNMR(300MHz,CD3OD)δ0.92(t,J=8.4Hz,3H),1.29-1.38(m,8H),1.47(s,6H),1.59-1.70(q,J=7.8Hz,2H),2.02-2.13(m,4H),2.19(t,J=7.8Hz,2H),5.31-5.45(m,2H)。13CNMR(300MHz,CD3OD)δppm14.43,23.72,25.41,26.95,27.62,28.21,30.09,30.85,32.95,36.3256.75,129.91,131.72,175.36,178.02。
2-十二烷酰氨基-2-甲基丙酸:21%1HNMR(300MHz,CD3OD)δ0.90(t,J=8.1Hz,3H),1.29-1.45(m,23H),1.54-1.65(m,2H),2.16(t,J=8.1Hz,2H)。13CNMR(300MHz,CD3OD)δppm12.93,22.22,23.90,25.36,28.68,28.97,29.13,29.23,31.57,35.28,55.21,174.09,176.53。
2-己酰氨基-2-甲基丙酸:6%1HNMR(300MHz,CD3OD)δ0.93(t,J=8.1Hz,3H),1.32-1.36(m,4H),1.47(s,6H),1.56-1.68(m,2H),2.18(t,J=8.1Hz,2H)。13CNMR(300MHz,CD3OD)δppm14.42,23.59,25.58,26.68,32.55,36.88,56.86,175.74,178.20。
实施例2:BlancoVerdundeKikkoman低盐1g盐/100ml
由富有经验的品尝者小组评价样品。
当将0.25ppm2-甲基-2-油酰氨基丙酸施用于Kikkoman大豆酱油中时,小组同意品尝的该样品具有更纯净、更上等的本体感、咸味、更少的发酵味、更上等、更多的咸苦味和甜味、发酵味。
当将0.25ppm2-甲基-2-硬脂酰氨基丙酸施用于Kikkoman大豆酱油中时,小组同意品尝的该样品品尝起来具有上等的咸味、无余味扩展、非负面的苦余味、更上等的咸味、非苦味和甜味、发酵味。
当将0.25ppm2-甲基-2-棕榈酰氨基丙酸施用于Kikkoman大豆酱油中时,小组同意品尝的该样品品尝起来具有强烈咸味、更上等、发酵味、适度苦味和甜味。
Claims (5)
1.式(I)的化合物或其可食用盐,
其中
R与它所连接的羰基一起为羧酸残基。
2.权利要求1的化合物,选自2-甲基-2-油酰氨基丙酸、2-甲基-2-((9Z,12Z)-十八-9,12-二烯酰氨基)丙酸、2-甲基-2-硬脂酰氨基丙酸、2-甲基-2-棕榈酰氨基丙酸、(Z)-2-(十二-5-烯酰氨基)-2-甲基丙酸、2-十二烷酰氨基-2-甲基丙酸和2-己酰氨基-2-甲基丙酸。
3.上述权利要求任一项的化合物作为可食用组合物中的香味成分的用途。
4.香味组合物,包含权利要求1-2任一项的化合物与至少一种选自糖类、脂肪、盐、MSG、钙离子、磷酸根离子、有机酸、蛋白质、嘌呤类及其混合物的香味辅助成分、任选的载体材料和任选的助剂。
5.可食用组合物,包含权利要求1-2任一项的式(I)的化合物或权利要求4的香味组合物。
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US20160213038A1 (en) | 2016-07-28 |
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WO2015050536A1 (en) | 2015-04-09 |
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