CN113166023B - 用于调节味道的癸二酸组合物和方法 - Google Patents
用于调节味道的癸二酸组合物和方法 Download PDFInfo
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- CN113166023B CN113166023B CN201980080927.1A CN201980080927A CN113166023B CN 113166023 B CN113166023 B CN 113166023B CN 201980080927 A CN201980080927 A CN 201980080927A CN 113166023 B CN113166023 B CN 113166023B
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- sebacic acid
- acid
- sweetness
- mouthfeel
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/82—Acid flavourants
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
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Abstract
描述了癸二酸用于增强含有碳水化合物甜味剂或调味剂的消费品的甜度和口感的组合物和方法中。
Description
相关申请的交叉引用
本申请要求享有2018年12月6日提交的美国临时专利申请序列号62/776,150的优先权权益,该申请的内容通过引用整体并入本文。
背景技术
癸二酸为白色片状或粉末状晶体,微溶于水。癸二酸及其衍生物例如壬二酸具有多种工业用途,如用作增塑剂、润滑剂、液压液、化妆品和蜡烛。它也用于合成聚酰胺和醇酸树脂,并用作芳族化合物、防腐剂和涂料的中间体。
发明简述
本发明提供了一种由碳水化合物甜味剂或调味剂和癸二酸组成的消费品,其中该消费品可以是食品、药物组合物、膳食补充剂、营养保健品、牙科卫生组合物、桌面甜味剂、饮料或化妆品。还提供了一种通过向消费品添加癸二酸来增强该消费品的甜度或口感的方法。在某些实施方案中,所述组合物和方法进一步包括使用愈伤酸和/或其异构体,例如3-十二碳烯二酸。
发明详述
现已发现,癸二酸显示出甜味增强作用以及口感改良功能。因此,本发明提供了组合物和方法,该组合物和方法使用癸二酸作为添加剂来增强消费品的甜度和口感。
如本领域中已知的,癸二酸(sebacic acid或decanedioic acid)(CAS号111-20-6)是直链的饱和二羧酸。用于本发明中的癸二酸可以从天然来源获得或通过合成方法制备。癸二酸的天然来源包括蜂王浆(Moutsatsou,et al.(2010)PLoS ONE 5:e15594)、苎麻(Boehmeria nivea)、金凤花(Caesalpinia pulcherrima)和龙舌兰(Agave americana)(Matic(1956)Biochem.J.63(1):168-176)。可以通过以下方法从这些天然来源中的一种或多种分离出癸二酸:醚提取以及按顺序碱化、酸化和醚萃取(Brown&Freure(1959)Can.J.Chem.37:2042-2046);或在升高的温度(例如50-100℃)下用水溶液提取,然后分离两个不混溶的相,并通过冷却水相来沉淀二羧酸(US 2,798,093)。色谱分离通常包括柱色谱法,并且可以是基于分子大小、电荷、溶解度和/或极性。取决于色谱方法的类型,可使用由例如葡聚糖、琼脂糖、聚丙烯酰胺或二氧化硅组成的基质材料进行柱色谱法,并且可包括溶剂,例如二甲亚砜、吡啶、水、二甲基甲酰胺、甲醇、盐水、二氯乙烷、氯仿、丙醇、乙醇、异丁醇、甲酰胺、二氯甲烷、丁醇、乙腈、异丙醇、四氢呋喃、二氧六环、氯仿/二氯甲烷等。通常,将色谱步骤的产物收集为多个部分,然后对其可以使用任何合适的分析技术(例如,薄层色谱法、质谱法)测试所需化合物的存在。然后可以选择富含所需化合物的部分进行进一步纯化。
或者,可以合成癸二酸。例如,癸二酸可以通过蓖麻油电氧化法合成(US 4,237,317),其从容易获得的己二酸产生高纯度的癸二酸。该方法包括以下步骤:将己二酸部分酯化以形成己二酸单甲酯;使在甲醇和水的混合物中的己二酸单甲酯的钾盐进行电解,给出癸二酸二甲酯;以及将癸二酸二甲酯水解为癸二酸。在其他实施方案中,癸二酸获自商业来源,例如Cayman Chemical(AnnArbor,MI)或Sigma-Aldrich(St.Louis,MO)。在特定的实施方案中,将癸二酸纯化至至少95%、96%、97%、98%、99%或100%的同质性。
尽管在本发明中可以使用癸二酸的盐,但优选地,癸二酸不被衍生化或不与另一分子缀合,即癸二酸是未缀合的癸二酸。
如本文所述,癸二酸增强了消费品的味道和风味。包括癸二酸的消费品的味道和风味特征可以比不包括癸二酸作为添加剂的对比消费品的比较味道和风味特征增强或更强烈(例如,增强了5%、10%、20%、30%或更强烈)。此外,相对于不包括癸二酸的对比消费品的口感,包括癸二酸的消费品的口感可以得到了改善。
在特定的实施方案中,癸二酸增强了含有碳水化合物甜味剂或调味剂的消费品的甜度和口感。如本文所用,术语“甜度”或“甜度强度”是指由个体(例如人)所观察到或感受到的甜味感觉的相对强度,或通过品尝者(taster)检测到的甜度的程度或量,例如根据American Societyfor Testing Materials,Special Technical Publication-434:“Manual on Sensory Testing Methods,”ASTM International,West Conshohocken,Pa.(1996)中描述的程序在感官评价中使用的0(无)至8(非常强)的程度。物质的口感与特定食品在口中产生的物理感觉有关。举例来说,“甜腻口感(sugary mouthfeel)”是个体例如人在食用糖时观察到或经历的物理感觉。根据本发明,癸二酸增强了甜/甜腻口感以及任选的脂肪口感。
如本文所用,消费品包括所有食品、药物组合物、膳食补充剂、营养保健品、牙科卫生组合物、桌面甜味剂、饮料或化妆品。在一些实施方案中,消费品包括一种或多种碳水化合物甜味剂或调味剂。碳水化合物甜味剂或调味剂可固有地存在于消费品中(例如,在含有水果的食品中),或将碳水化合物甜味剂或调味剂添加到消费品中(即,外源性甜味剂或调味剂)。本发明的合适的碳水化合物甜味剂包括但不限于蔗糖、果糖、葡萄糖、高果糖玉米糖浆(含有果糖和葡萄糖)、木糖、阿拉伯糖、鼠李糖和糖醇,例如赤藓糖醇、木糖醇、甘露糖醇、山梨糖醇或肌醇。在一个实施方案中,碳水化合物甜味剂是蔗糖、果糖、葡萄糖、高果糖玉米糖浆、木糖、阿拉伯糖或鼠李糖,优选蔗糖、果糖或葡萄糖。在该实施方案的一方面,碳水化合物甜味剂是蔗糖。在该实施方案的另一方面,碳水化合物甜味剂是葡萄糖。在该实施方案的另一方面,碳水化合物甜味剂是果糖。在另一个实施方案中,碳水化合物甜味剂是糖醇,例如赤藓糖醇、木糖醇、甘露糖醇、山梨糖醇或肌醇。
用于本发明中的调味剂包括但不限于Natural Sweet Flavor#2(WO2012/129451)、甜菊苷、莱鲍迪苷A、莱鲍迪苷B、莱鲍迪苷C、莱鲍迪苷D、莱鲍迪苷E、莱鲍迪苷F、杜克苷A、杜克苷B、甜叶菊、α-葡糖基甜叶菊、果糖基甜叶菊、半乳糖基甜叶菊、β-葡糖基甜叶菊、赛门苷、罗汉果苷IV、罗汉果苷V、罗汉果甜味剂、莫纳甜及其盐、甘草酸及其盐(例如,如在MAGNASWEET中发现的)、仙茅甜蛋白、奇异果甜蛋白、应乐果甜蛋白、马槟榔甜蛋白、布那珍甜蛋白、hernandulcin、叶甜素、菝葜苷、根皮苷、trilobtain、白元参苷、欧亚水龙骨甜素、水龙骨皂苷A(polypodoside A)、枫杨皂苷A(pterocaryoside A)、枫杨皂苷B、无患子倍半萜苷(mukurozioside)、糙苏苷I、巴西甘草甜素I、相思子三萜苷A、青钱柳苷I或它们的组合。在某些实施方案中,调味剂是Natural Sweet Flavor#2(也称为NSF-02),其含有糖基化甜菊醇糖苷和糊精。
当添加到消费品中作为添加剂时,癸二酸以有效增强碳水化合物甜味剂或调味剂的甜度或口感且不会表现出任何异味的量使用。可使用提供所需程度的甜度或口感增强的任何量的癸二酸。优选地,消费品中存在的癸二酸的量为低至0.05ppm的量、低至0.2ppm的量、低至1ppm的量或低至10ppm的量。在消费品中可以高达1000ppm的量、高达500ppm的量、或者高达100ppm的量包括癸二酸。癸二酸可以进一步以任何一对前述值限定的任何范围内(例如在0.2ppm至1000ppm之间,或例如在1ppm至100ppm之间)的量存在。本文中所用的术语“ppm”是指按重量或体积计每百万份的份数,例如,每升溶液的组分重量(以毫克计),即μg/ml。
在一些实施方案中,本发明包括癸二酸和愈伤酸(CAS号6402-36-4)和/或其异构体3-十二碳烯二酸(CAS号189034-80-8)的组合。在特定实施方案中,愈伤酸(或其异构体)与癸二酸的重量比为至少1:1、2:1、3:1、4:1、5:1、6:1、7:1、8:1或9:1。
本文中所用的词语“食品”包括但不限于水果、蔬菜、果汁、肉类产品(例如火腿、培根和香肠);蛋制品、果汁浓缩液、明胶和明胶样产品(例如果酱、果冻和蜜饯等);奶制品(例如冰淇淋、酸奶油以及冻果子露);糖衣、糖浆(包括糖蜜);玉米产品、小麦产品、黑麦产品、大豆产品、燕麦产品、水稻产品和大麦产品;坚果仁和坚果产品;蛋糕、饼干、糖果(例如奶糖、口香糖、水果味滴剂和巧克力)、泡泡糖、薄荷糖、奶油、冰淇淋、派和面包,以及饮料,例如咖啡、茶、碳酸软饮料(例如以商标名和/>销售的软饮料)、非碳酸软饮料、果汁和其他果汁饮料、运动饮料(例如以商标名/>销售的那些运动饮料)、酒精饮料(例如啤酒、红酒和烈酒),以及以商标名/>销售的风味饮料。食品进一步包括调味品(例如香草、香料和佐料)以及风味增强剂(例如味精(monosodiumglutamate))。食品还包括配制的产品包,例如饮食甜味剂(dietetic sweeteners)、液体甜味剂、当与水重构时提供非碳酸饮料的粒状调味混合料、速溶布丁混合料、速溶咖啡和茶、咖啡伴侣、麦乳精混合料、宠物食物、家畜饲料、烟草和烘焙用途的材料(例如用于制备面包、饼干、蛋糕、烙饼、甜甜圈等的粉状烘焙混合料)。食品还包括含有少量或不含蔗糖的节食或低卡路里食物和饮料。尤其优选的食品是碳酸饮料。优选地,其中甜度或口感增强的消费品含有降低水平的碳水化合物甜味剂。例如,通过添加癸二酸,可生产出具有与已知的碳酸软饮料相同的甜度但具有更低的糖含量的改良的碳酸软饮料。
消费品还可以是药物组合物。优选的组合物是含有癸二酸以及一种或多种药学可接受的赋形剂的药物组合物。这些药物组合物可用于配制含有一种或多种活性剂的药物,该活性剂施加甜度增强之外的生物效应。药物组合物优选进一步包括一种或多种施加生物效应的活性剂。此类活性剂包括药物制剂和生物制剂,其具有不同于增强味道的活性。此类活性剂是本领域中熟知的。参见,例如The Physician's Desk Reference。可根据本领域中已知的方法,例如,如Remington's Pharmaceutical Sciences,Mack Publishing Co.,Easton,PA中描述的方法,制备此类组合物。在一个实施方案中,此类活性剂包括支气管扩张剂、减食欲剂、抗组胺剂、营养补充剂、缓泻剂、镇痛剂、麻醉剂、抗酸剂、H2受体拮抗剂、抗胆碱能药、止泻剂、缓和剂、镇咳药、抗呕吐剂、抗微生物剂、抗细菌剂、抗真菌剂、抗病毒剂、祛痰剂、抗炎剂、退热剂、及其混合物。在一个实施方案中,活性剂是退热剂或镇痛剂,例如布洛芬、对乙酰氨基酚或阿司匹林;缓泻剂,例如酚酞二辛基磺基琥珀酸钠;食欲抑制剂,例如安非他命、苯丙醇胺、苯丙醇胺盐酸盐;或咖啡因;抗酸剂,例如碳酸钙;抗喘药,例如茶碱;抗利尿剂,例如盐酸地芬诺酯;有效抗胃肠胀气剂,例如二甲基硅油(simethecon);偏头痛药剂,例如酒石酸麦角胺;精神药理学药剂,例如氟哌啶醇;解痉药或镇静剂,例如苯巴比妥;抗高动力学药剂,例如甲基多巴或哌甲酯;镇定剂,例如苯二氮卓、hydroxinmeprobramate或吩噻嗪;抗组胺剂,例如阿司咪唑、马来酸氯苯那敏、马来酸吡啶胺、琥珀酸多西拉敏、马来酸溴苯那敏、柠檬酸苯托沙敏、盐酸氯环嗪、马来酸非尼拉敏或酒石酸苯茚胺;减充血剂,例如盐酸苯丙醇胺、盐酸脱氧肾上腺素、盐酸伪麻黄碱、硫酸伪麻黄碱、重酒石酸苯丙醇胺或麻黄碱;β-受体阻滞剂,例如普萘洛尔;戒酒剂,例如二硫龙;镇咳药,例如苯佐卡因、右美沙芬、右美沙芬氢溴酸盐、诺斯卡品、柠檬酸卡贝他汀或盐酸氯苯达诺;氟补充剂,例如氟化钠;局部抗生素,例如四环素或cleocine;皮质类固醇补充剂,例如泼尼松或泼尼松龙;抗甲状腺肿形成剂,例如秋水仙碱或别嘌呤醇;抗癫痫药,例如苯妥英钠;抗脱水剂,例如电解质补充剂;防腐剂,例如西吡氯铵;NSAID,例如对乙酰氨基酚、布洛芬、萘普生或其盐;胃肠道活性剂,例如洛哌丁胺和法莫替丁;生物碱,例如磷酸可待因、硫酸可待因或吗啡;微量元素补充剂,例如氯化钠、氯化锌、碳酸钙、氧化镁或其他碱金属盐或碱土金属盐;维生素;离子交换树脂,例如消胆胺;胆固醇抑制剂或降脂物质;抗心律失常药,例如N-乙酰普鲁卡因酰胺;或祛痰剂,例如愈创甘油醚。
在一些实施方案中,消费品是膳食补充剂或营养保健品。具有不合意的味道的此类组合物的实例包括但不限于用于治疗营养缺乏、创伤、手术、克罗恩病、肾脏疾病、高血压、肥胖等以促进运动性能、肌肉增强或一般健康或治疗先天性代谢障碍(例如苯丙酮酸尿)的肠内营养产品。特别地,此类组合物可含有一种或多种具有苦味或金属味或余味的氨基酸。此类氨基酸包括但不限于必需氨基酸例如亮氨酸、异亮氨酸、组氨酸、赖氨酸、蛋氨酸、苯丙氨酸、苏氨酸、色氨酸、酪氨酸和缬氨酸的L异构体。
在进一步的实施方案中,本发明的消费品是含有碳水化合物甜味剂或调味剂以及癸二酸的牙科卫生组合物。牙科卫生组合物是本领域已知的,包括但不限于牙膏、嗽口水、牙菌斑冲洗剂、牙线、牙齿止痛剂(例如ANBESOLTM)等。在一个实施方案中,牙科卫生组合物包括一种碳水化合物甜味剂。在另一个实施方案中,牙科卫生组合物包括超过一种碳水化合物甜味剂。在某些实施方案中,牙科卫生组合物包括蔗糖和玉米糖浆,或蔗糖和阿斯巴甜。
在再一实施方案中,本发明的消费品是含有碳水化合物甜味剂或调味剂以及癸二酸的化妆品。例如但不作为限制,该化妆品可以是面霜、唇膏和唇彩等。本发明的其他合适的组合物包括润唇膏,例如以商标名或BURT'S/>销售的润唇膏。
当在本发明的方法和组合物中使用时,将癸二酸以有效增强包括碳水化合物甜味剂或调味剂的消费品的甜度或口感的量添加到消费品中(即,癸二酸不是消费品的内源性组分)。在这方面,可以减少添加到消费品中的碳水化合物甜味剂或调味剂的量,同时保持所需的甜度水平。因此,本发明还提供了通过将碳水化合物甜味剂和/或调味剂与癸二酸组合来增强碳水化合物甜味剂和/或调味剂的甜度和口感并减少消费品中碳水化合物甜味剂和/或调味剂的量的方法和组合物。在一些实施方案中,碳水化合物甜味剂或调味剂和癸二酸以10000∶1、1000∶1或100∶1的比例使用。在一个实施方案中,本发明提供了一种消费品,其包含有效量的癸二酸和减少量的碳水化合物甜味剂或调味剂的组合以便达到与以传统量单独使用碳水化合物甜味剂或调味剂时相同水平的甜度。在这方面,可使消费品中使用的碳水化合物甜味剂或调味剂的量减少了至少约5%、10%、20%或30%。除非另有说明,百分数(%)均按重量计。
通过以下非限制性实施例更详细地描述本发明。
实施例1:对糖水中不同量的癸二酸的感官评价
制备糖水(在饮用水中的4%的蔗糖)并将其用作基础溶液。将不同量的癸二酸添加至基础溶液中,并进行描述性感官评价(表1)。
表1
癸二酸(ppm) | 味道评价 |
0.02 | 微甜和口感增强,几乎不可检测的 |
1000 | 强甜和口感增强,具有强的化学品异味 |
实施例2:使用癸二酸调节味道
在不同应用中使用不同量的癸二酸进行描述性感官评价。与不存在癸二酸的相同应用相比,该分析的结果列于表2中。
表2
实施例3:加糖奶中癸二酸和愈伤酸的感官评价
制备加糖奶(含2%蔗糖的2%脂肪奶),并用作基础溶液(“基础”)。将癸二酸和愈伤酸添加到该基础溶液中,并进行描述性感官评估(表3)
表3
该分析的结果表明,癸二酸(2ppm)和愈伤酸(2ppm)各自增加了加糖奶的甜度和口感。当一起使用时,癸二酸(2ppm)和愈伤酸(2ppm)提供了甜度和口感的最大增加。
此外,在2ppm下,将癸二酸的甜度和口感增强以及异味掩盖与包括己二酸、庚二酸、辛二酸、十一烷二酸、十二烷二酸、1,11-十一烷二羧酸、十四烷二酸和十六烷二酸的一系列类似物进行了比较。在所有的测试化合物中,癸二酸的作用最强,持续时间最长,明显优于所有其他化合物。
Claims (5)
1.一种增强包括碳水化合物甜味剂或调味剂的消费品的甜度或口感的方法,其包括以有效地增强所述消费品的甜度或口感的量向所述消费品添加癸二酸,
其中,癸二酸以0.05ppm至1000ppm的量存在。
2.根据权利要求1所述的方法,其进一步包括向所述消费品添加愈伤酸、3-十二碳烯二酸或它们的组合。
3.根据权利要求1所述的方法,其中,癸二酸的量在0.2ppm至1000ppm的范围内。
4.根据权利要求1所述的方法,其中,癸二酸的量在1ppm至100ppm的范围内。
5.根据权利要求1所述的方法,其中,所述消费品是食品、药物组合物、膳食补充剂、营养保健品、牙科卫生组合物、桌面甜味剂、饮料或化妆品。
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