CN101056538A - 环糊精包合复合物和其制备方法 - Google Patents
环糊精包合复合物和其制备方法 Download PDFInfo
- Publication number
- CN101056538A CN101056538A CNA2004800440843A CN200480044084A CN101056538A CN 101056538 A CN101056538 A CN 101056538A CN A2004800440843 A CNA2004800440843 A CN A2004800440843A CN 200480044084 A CN200480044084 A CN 200480044084A CN 101056538 A CN101056538 A CN 101056538A
- Authority
- CN
- China
- Prior art keywords
- cyclodextrin
- mixture
- inclusion complexes
- emulsifier
- pectin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 124
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 117
- 238000000034 method Methods 0.000 title claims abstract description 111
- 239000000203 mixture Substances 0.000 claims abstract description 71
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- 238000002156 mixing Methods 0.000 claims abstract description 5
- 239000000796 flavoring agent Substances 0.000 claims description 46
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- 229920001277 pectin Polymers 0.000 claims description 38
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- 239000001814 pectin Substances 0.000 claims description 36
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- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims description 20
- -1 nutriment Substances 0.000 claims description 19
- 238000001035 drying Methods 0.000 claims description 18
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- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 claims description 12
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- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 3
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Abstract
环糊精包合复合物和制备环糊精包合复合物的方法。在一些实施方案中，制备环糊精包合复合物的方法可以包括干混环糊精和乳化剂而形成干混物，以及使溶剂和客体与所述干混物混合而形成环糊精包合复合物。在一些实施方案中，制备环糊精包合复合物的方法可以包括使环糊精和乳化剂混合而形成第一混合物，使第一混合物与溶剂混合，形成第二混合物，以及使客体与第二混合物混合，形成第三混合物。
Description
背景技术
以下美国专利公开了使用环糊精来复合各种客体分子，由此通过引入而将其全部结合在此：Borden的美国专利4,296,137、4,296,138和4,348,416(在口香糖、牙粉、化妆品等中使用的调味料)；Gandolfo等人的4,265,779(洗涤组合物中的泡沫抑制剂)；Hyashi等人的3,816,393和4,054,736(用作医药品的前列腺素)；Mifune等人的3,846,551(杀虫和杀螨组合物)；Noda等人的4,024,223(薄荷醇、水杨酸甲酯等)；Akito等人的4,073,931(硝基-甘油)；Szjetli等人的4,228,160(茚甲新)；Bernstein等人的4,247,535(补充抑制剂)；Kawamura等人的4,268,501(抗哮喘活性剂)；Szjetli等人的4,365,061(强无机酸络合物)；Pitha的4,371,673(类维生素A)；Szjetli等人的4,380,626(激素植物生长调节剂)、Wagu等人的4,438,106(用于降低胆固醇的长链脂肪酸)；Sato等人的4,474,822(茶香精络合物)；Szjetli等人的4,529,608(蜜香)、Kuno等人的4,547,365(烫发活性-络合物)；Pitha的4,596,795(性激素)；Hirai等人的4,616,008(抗菌络合物)；Shibanai的4,636,343(杀虫络合物)、Ninger等人的4,663,316(抗生素)；Fukazawa等人的4,675,395(日扁柏素)；Shibanai等人的4,732,759和4,728,510(洗浴添加剂)；Karl等人的4,751,095(天冬氨酸(aspartamane))；4,560,571(咖啡提取物)；Okonogi等人的4,632,832(速溶奶油粉)；Trinh等人的5,571,782、5,660,845和5,635,238(香味剂、调味剂和医药品)；Kubo等人的4,548,811(烫发水(waving lotion))；Prasad等人的6,287,603(香味剂、调味剂和医药品)；Pera的4,906,488(增嗅剂、调味剂、药剂和杀虫剂)；以及Qi等人的6,638,557(鱼油)。
环糊精还记载在以下文献中，这些文献也通过引用而结合在此：(1)Reineccius，T.A.等人″Encapsulation of flavors using cyclodextrins：comparisonof flavor retention in alpha，beta，and gamma types.″
Journal of Food Science.2002；67(9)：3271-3279；(2)Shiga，H.等人″Flavor encapsulation and releasecharacteristics of spray-dried powder by the blended encapsulant of cyclodextrinand gum arabic.″
Marcel Dekker，Incl.，www.dekker.com.2001；(3)Szente L.等人″Molecular Encap-sulation of Natural and Synthetic Coffee Flavor withβ-cyclodextrin.″
Journal of Food Science.1986；51(4)：1024-1027；(4)Reineccius，G.A.等人″Encapsulation of Artificial Flavors byβ-cyclodextrin.″
Perfumer & Flavorist(ISSN 0272-2666)An Allured Publication.1986：11(4)：2-6；以及(5)Bhandari，B.R.等人″Encap-sulation of lemon oil by paste method usingβ-cyclodextrin：encapsulation efficiency and profile of oil volatiles.″
J.Agric. Food Chem.1999；47：5194-5197。
发明内容
本发明的一些实施方案提供了一种制备环糊精包合复合物的方法。所述方法可以包括干混环糊精和乳化剂形成干混物，以及使溶剂和客体与所述干混物混合，形成环糊精包合复合物。
在本发明的一些实施方案中，提供了一种制备环糊精包合复合物的方法。所述方法可以包括使环糊精和乳化剂混合，形成第一混合物，使第一混合物与溶剂混合，形成第二混合物，以及使客体与第二混合物混合，形成第三混合物。
本发明的一些实施方案提供了一种制备环糊精包合复合物的方法。所述方法可以包括干混环糊精和果胶，形成第一混合物，使第一混合物与水混合，形成第二混合物，以及使二乙酰(diacetyl)与第二混合物混合，形成第三混合物。
本领域技术人员经阅读以下详细说明书、权利要求书和附图，就可以清楚本发明的其他特征和方面。
附图说明
图1是具有空腔并且客体分子收容于空腔内的环糊精分子的示意图。
图2是由自组装的环糊精分子和客体分子形成的纳米结构的示意图。
在详细说明本发明任何实施方案之前，应该理解，本发明的应用不限于以下说明书中所述或附图中所示的结构细节和组成排列。本发明可以具有其他实施方案并能够以各种方式实施。此外，应该理解，本文中所用的短语和术语用于说明目的，不起限制作用。使用″包含″、″包括″或″具有″和其变体是指包括所列出的项和其等同物以及额外项。
具体实施方式
一般来说，本发明涉及环糊精包合复合物以及其形成方法。本发明的一些环糊精包合复合物用于封装挥发性和反应性客体分子。在一些实施方案中，封装客体分子可以提供至少一种以下作用：(1)防止挥发性或反应性客体从市售产品逸出，这样可以防止在市售产品中风味浓度差；(2)使能够与其他成分相互作用和反应的客体分子与形成气味的其他成分分离；(3)使客体分子对降解(例如，水解、氧化等)稳定；(4)从其他产品或化合物中选择性提取客体分子；(5)增强客体分子的水溶解度；(6)市售产品的味道或气味改进或增强；(7)客体在微波和常规烘焙应用中受到热保护；(8)缓慢和/或持续释放香剂或气味(例如，在环糊精包合复合物中使用二乙酰作为客体分子的实施方案中，其可以提供黄油熔化的感觉)；以及(9)安全处理客体分子。
本文中，术语″环糊精″可以指通过使淀粉发生酶转化形成的环状糊精分子。特定的酶，例如各种形式的环状糖基转移酶(CGTase)，可以破坏淀粉中的螺旋结构，形成具有三维多葡萄糖环，例如6、7或8个葡萄糖分子的特定环糊精分子。例如，α-CGTase可以使淀粉转化成具有6个葡萄糖单元的α-环糊精，β-CGTase可以使淀粉转化成具有7个葡萄糖单元的β-环糊精，γ-CGTase可以使淀粉转化成具有8个葡萄糖单元的γ-环糊精。所述环糊精包括但不限于α-环糊精、β-环糊精、γ-环糊精、和其组合中的至少一种。
环糊精分子10的三维环状结构(即，大环结构)示意性地示于图1中。环糊精分子10包括外部12，其包括一级和二级羟基，并且是亲水性的。环糊精分子10还包括三维空腔14，其包括碳原子、氢原子和醚键，并且是疏水性的。环糊精分子的疏水性空腔14可用作主体，并容纳包括疏水性部分的各种分子或客体16，以形成环糊精包合复合物。
本文中，术语″客体″可以指其至少一部分被容纳或扑获在环糊精分子的三维空腔中的任何分子，其包括但不限于调味剂、增嗅剂(olfactant)、药剂、营养剂(netraceutical)、和其组合中的至少一种。
调味剂的实例可以包括但不限于基于醛、酮或醇的调味剂。醛调味剂的实例可以包括但不限于以下的至少一种：乙醛(苹果)；苯甲醛(樱桃、杏仁)；茴香醛(甘草、茴芹)；肉桂醛(肉桂)；柠檬醛，即α柠檬醛(柠檬、酸橙)；橙花醛，即β柠檬醛(柠檬、酸橙)；癸醛(橙子、柠檬)；乙基香草醛(香草、乳酪)；洋茉莉醛，即胡椒醛(香草、乳酪)；香草醛(香草、乳酪)；a-戊基肉桂醛(加香料的果味调味剂)；丁醛(黄油、奶酪)；戊醛(黄油、奶酪)；香茅醛(变化，许多类型)；癸烯醛(柑桔果实)；醛C-8(柑橘果实)；醛C-9(柑桔果实)；醛C-12(柑桔果实)；2-乙基丁醛(浆果)；己烯醛，即反式-2(浆果)；甲苯醛(樱桃、杏仁)；藜芦醛(香草)；2，6-二甲基-5-庚烯醛，即MelonalTM(瓜)；2，6-二甲基辛醛(绿色果实)；2-十二烯醛(柑橘、蜜柑)；以及其组合。
酮调味剂的实例可以包括但不限于以下的至少一种：d-香芹酮(香菜)；1-香芹酮(绿薄荷)；二乙酰(黄油、奶酪、″乳酪″)；二苯甲酮(果味和加香料的调味剂、香草)；甲基乙基酮(浆果)；麦芽醇(浆果)、薄荷酮(薄荷)、甲基戊基酮、乙基丁基酮、二丙基酮、甲基己基酮、乙基戊基酮(浆果、核果)；丙酮酸(烟熏、坚果调味剂)；乙酰茴香醚(山楂、向日葵)；二氢香芹酮(绿薄荷)；2，4-二甲基苯乙酮(胡椒薄荷)；1，3-二苯基-2-丙酮(杏仁)；乙酰异丙基苯(鸢尾草和罗勒，加香料的)；异茉莉酮(茉莉)；d-异甲基紫罗兰酮(鸢尾草类、紫罗兰)；异丁基乙酰乙酸酯(白兰地类)；姜油酮(姜)；蒲勒酮(胡椒薄荷-樟脑)；d-薄荷酮(有薄荷味的)；2-壬酮(玫瑰和茶类)；以及其组合。
醇调味剂的实例可以包括但不限于以下的至少一种：茴香醇或对甲氧基苄醇(果味，桃子)；苄醇(果味)；香芹酚或2-对-伞花醇(辛辣温和味的)；香芹醇；肉桂醇(花香味)；香茅醇(玫瑰类)；癸醇；二氢香芹醇(含香料的、胡椒味)；四氢香叶醇或3，7-二甲基-1-辛醇(玫瑰味)；丁子香酚(丁香)；对薄荷-1，8-二烯-7-醇或紫苏子醇(花香-松树)；以及其组合。
增嗅剂的实例可以包括但不限于以下增嗅剂中的至少一种：天然香料、合成香料、合成精油、天然精油、和其组合。
合成香料的实例可以包括但不限于以下的至少一种：萜烯烃、酯、醚、醇、醛、酚、酮、缩醛、肟、和其组合。
萜烯烃的实例可以包括但不限于以下的至少一种：酸橙萜烯、柠檬萜烯、柠檬烯二聚体、和其组合。
酯的实例可以包括但不限于以下的至少一种：γ-十一烷酸内酯、乙基甲基苯基缩水甘油酸酯、己酸烯丙酯、水杨酸戊酯、苯甲酸戊酯、乙酸戊酯、乙酸苄酯、苯甲酸苄酯、水杨酸苄酯、丙酸苄酯、乙酸丁酯、丁酸苄酯、苯基乙酸苄酯、乙酸柏木酯、乙酸香茅酯、甲酸香茅酯、乙酸对甲苯酯、乙酸2-叔戊基-环己酯、乙酸环己酯、乙酸顺式-3-己烯酯、水杨酸顺式-3-己烯酯、乙酸二甲基苄酯、邻苯二甲酸二乙酯、δ-癸内酯、邻苯二甲酸二丁酯、丁酸乙酯、乙酸乙酯、苯甲酸乙酯、乙酸葑酯、乙酸香叶酯、γ-十二烷酸内酯、二氢茉莉酮酸甲酯、乙酸异冰片酯、水杨酸β-异丙氧基乙酯、乙酸里哪酯、苯甲酸甲酯、乙酸邻叔丁基环己酯、水杨酸甲酯、巴西酸亚乙酯、十二烷酸亚乙酯、乙酸甲基苯酯、异丁酸苯基乙酯、乙酸苯基乙基苯酯、乙酸苯基乙酯、乙酸甲基苯基甲酯、3，5，5-三甲基己基乙酸酯、乙酸萜品酯、柠檬酸三乙酯、乙酸对叔丁基环己酯、乙酸香根酯、和其组合。
醚的实例可以包括但不限于以下的至少一种：对甲苯基甲基醚、二苯基醚、1，3，4，6，7，8-六氢-4，6，7，8，8-六甲基环戊-β-2-苯并吡喃、苯基异戊基醚、和其组合。
醇的实例可以包括但不限于以下的至少一种：正辛醇、正壬醇、β-苯基乙基二甲基甲醇、二甲基苄基甲醇、卡必醇、二氢月桂烯醇、二甲基辛醇、己二醇、里哪醇、叶醇、橙花醇、苯氧基乙醇、γ-苯基-丙醇、β-苯基乙醇、甲基苯基甲醇、萜品醇、tetraphydroalloocimenol、四氢里哪醇、9-癸烯-1-醇、和其组合。
醛的实例可以包括但不限于以下的至少一种：正壬醛、十一烯醛、甲基壬基乙醛、茴香醛、苯甲醛、樱草醛、2-己基己醛、己基肉桂醛、苯基乙醛、4-(4-羟基-4-甲基戊基)-3-环己烯-1-羧醛、对叔丁基-a-甲基氢-肉桂醛、羟基香茅醛、α-戊基肉桂醛、3，5-二甲基-3-环己烯-1-羧醛、和其组合。
酚的实例可以包括但不限于甲基丁子香酚。
酮的实例可以包括但不限于以下的至少一种：1-香芹酮、α-damascon、紫罗酮、4-叔戊基环己酮、3-戊基-4-乙酰氧基四氢吡喃、薄荷酮、甲基紫罗酮、对-叔戊基环己酮、乙酰基柏木烯、和其组合。
缩醛的实例可以包括但不限于苯基乙醛二甲基缩醛。
肟的实例可以包括但不限于5-甲基-3-庚酮肟。
客体还可以包括但不限于以下的至少一种：脂肪酸、内酯、萜烯、二乙酰、二甲硫、脯氨酸、呋喃酮、里哪醇、乙酰丙酰、天然香精(例如，橙子、番茄、苹果、肉桂、树莓等)、精油(例如、橙子、柠檬、酸橙等)、和其组合。
本文中，术语″环糊精包合复合物″指通过在三维空腔内扑获并容纳客体分子而由一种或多种环糊精分子封装一种或多种客体分子的至少一部分所形成的络合物(分子水平上的封装)。客体可以通过氢键和亲水-疏水相互作用中的至少一种在范德华力作用下收容位于空腔内。当环糊精包合复合物在水中溶解时，可以从空腔释放出客体。
本文中，术语″水性胶体″通常指与水形成凝胶的物质。水性胶体可以包括但不限于以下的至少一种：黄原胶、果胶、阿拉伯树胶(或阿拉伯树胶)、黄芪胶、瓜尔胶、角叉菜胶(carrageenan)、刺槐豆胶、和其组合。
本文中，术语″果胶″指可以在植物组织中(例如，在成熟果实和蔬菜中)出现的水性胶体多糖。果胶可以包括但不限于以下至少一种：甜菜果胶、果实果胶(例如，从柑橘皮得到)、和其组合。所用的果胶可以是各种分子量的。
本发明的环糊精包合复合物可用于各种应用中，包括但不限于以下至少一种：食物(如爆米花、谷类食品、咖啡、饼干、核仁巧克力饼、其他烘焙物等)、口香糖、糖果、调味剂、香料、医药品、营养品、化妆品、农业应用(如除草剂、杀虫剂等)、感光乳剂、和其组合。在一些实施方案中，环糊精包合复合物可用作中间体分离基质以进一步处理、分离和干燥(例如用作废料流)。
环糊精包合复合物可用于增强客体的稳定性，使其转化成自由流动的粉末，或改变其溶解度、输送性或性能。可被封装的客体分子的量与客体分子的分子量直接相关。在一些实施方案中，1摩尔环糊精封装1摩尔客体。根据这种摩尔比，仅举例来说，在使用作为客体的二乙酰(分子量86道尔顿)和β-环糊精(分子量1135道尔顿)的实施方案中，最大理论保持率是(86/(86+1135))×100＝7.04重量％。
在一些实施方案中，环糊精可以在溶液中自组装而形成纳米结构，如图2所示的纳米结构20，可以将3摩尔客体分子与2摩尔环糊精分子组合。例如，在使用二乙酰作为客体的实施方案中，二乙酰可以保持10.21重量％。其他复合增强剂如果胶可以有助于自组装过程，并可在干燥过程中保持3∶2摩尔比的客体∶环糊精。在一些实施方案中，由于环糊精分子自组装成纳米结构，因此可以是5∶3摩尔比的客体∶环糊精。
环糊精包合复合物在溶液中形成。干燥过程临时地将至少一部分客体闭合在环糊精的空腔中，因此可以产生干燥、自由流动的粉末。
环糊精空腔的疏水性(水不溶性)在以更水溶性(亲水性)客体为代价下优先更易于扑获诸如(疏水性的)客体。与常规喷雾干燥相比，这种现象使各成分不平衡，并且总收率差。
在本发明的一些实施方案中，通过选择关键组分以分别封装，可避免亲水性和疏水性作用之间的竞争。例如，在黄油调味剂的情况下，脂肪酸和内酯比二乙酰更易于形成环糊精包合复合物。然而，这些化合物不是与黄油相关的关键特性影响化合物，并且它们会降低二乙酰和其他水溶性和挥发性组分的总收率。在一些实施方案中，黄油调味剂中的关键组分(即，二乙酰)被最大化以产生高影响、更稳定和更经济的产品。举例来说，在柠檬调味剂情况下，大部分柠檬调味剂成分很好地封装在环糊精中。然而，萜烯(柠檬调味剂的成分)具有较小的调味值，然而却占柠檬调味剂混合物的约90％，而柠檬醛是柠檬调味剂的关键调味组分。在一些实施方案中，仅封装了柠檬醛。通过选择关键组分(例如，二乙酰、柠檬醛等)以分别封装，可以降低原料的复杂度，从而优化工程步骤并使过程经济。
在一些实施方案中，通过加入过摩尔量的客体驱使形成环糊精包合复合物的包合过程完成。例如，在一些实施方案中，客体与环糊精以3∶1摩尔比的客体∶环糊精混合。
在一些实施方案中，控制通过在溶剂中混合环糊精和客体分子形成的悬浮液、乳状液或混合物的粘度，并且保持在没有其他调节如增加固含量下与常用喷雾干燥技术的相容性。可以加入乳化剂(例如，增稠剂、胶凝剂、多糖、水性胶体)来保持环糊精和客体的紧密接触，并促进包合过程。特别地，可以使用低分子量的水性胶体。一种优选的水性胶体是果胶。乳化剂可以促进包合过程，而不需使用高热量或助溶剂(例如，乙醇、丙酮、异丙醇等)来增大溶解度。
在一些实施方案中，悬浮液、乳状液或混合物的水含量降低到基本上迫使客体表现出疏水性化合物的行为。这种过程甚至可以增大相对亲水性客体如乙醛、二乙酰、二甲硫等的保持性。降低水含量也可以最大化通过喷雾干燥器的产量，并降低挥发性客体在此过程中排出去的可能，这种排除会使总收率降低。
在本发明的一些实施方案中，可以通过以下方法形成环糊精包合复合物，所述方法包括以下步骤的一些或所有步骤：
(1)干混环糊精和乳化剂(例如，果胶)；
(2)使环糊精和乳化剂的干混物与热液体或溶剂如水在反应器中混合，并且搅拌；
(3)加入客体并搅拌(例如，约5～8小时)；
(4)冷却反应器(例如，打开冷却夹套)；
(5)搅拌混合物(例如，约12～36小时)；
(6)乳化(例如，使用罐内快速混合器或高剪切吸入式混合器)；以及
(7)干燥环糊精包合复合物，形成粉末。
这些步骤不必须依所列顺序进行。此外，上述方法被证实极有效，因为该方法可以在各种温度、混合时间和其他过程参数下进行。
在一些实施方案中，上述方法中的步骤1可以使用反应器中的罐内混合器进行，并在步骤2中向其中加入热水。例如，在一些实施方案中，使用安装有控温用夹套和直线式(inline)高剪切混合器的1000加仑反应器完成上述过程，并且反应器与喷雾干燥器直接连接。在一些实施方案中，环糊精和乳化剂可以在分开的装置(例如，带式混合器等)中干混，然后加到完成上述方法其余部分的反应器中。
可以使用各种重量百分比的乳化剂∶环糊精，包括但不限于乳化剂∶环糊精的重量百分数至少约0.5％、特别是至少约1％，和更特别是至少约2％。此外，也可以使用乳化剂∶环糊精的重量百分数小于约10％、特别是小于约6％、和更特别是小于约4％。
上述方法中的步骤2可以在带有加热、冷却或二者都有的夹套的反应器中进行。反应器大小取决于生产规模。例如，可以使用100加仑反应器。反应器可以包括桨式搅拌器和冷凝单元。在一些实施方案中，步骤1在反应器中完成，并且在步骤2中，热的去离子水被加入同一反应器中的环糊精和果胶的干混物中。
步骤3可以在密封的反应器中进行，或者在加入客体时可以将反应器临时暴露于环境中，并可以在加入客体之后再次密封反应器。
步骤4可以使用包括冷却夹套的冷却剂系统进行。例如，可以使用具有丙二醇冷却剂和冷却夹套的冷却反应器。
可以通过摇动、搅拌、翻倒和其组合中的至少一种完成步骤2中的搅拌、步骤3中的搅拌、和步骤5中的搅拌。
在步骤6中，可以使用高剪切混合器(例如，ROSS-牌混合器，10,000RPM下90秒)、快速混合器、或简单混合，然后转移至作为喷雾干燥器一部分的均质化泵中，和其组合中的至少一种使环糊精、乳化剂、水和客体的混合物乳化。
可以通过使用空气干燥、真空干燥、喷雾干燥(例如，使用喷嘴喷雾干燥器、转盘喷雾干燥器等)、烘箱干燥、和其组合中的至少一种进行上述方法中的步骤7。
上述方法可用于提供各种应用中使用的具有各种客体的环糊精包合复合物。例如，本发明的一些实施方案提供一种具有包括二乙酰的客体的环糊精包合复合物，其可用于各种食物中(例如，在微波爆米花、烘焙物品等中)起黄油调味作用。此外，一些实施方案提供一种具有包括柠檬醛的客体的环糊精包合复合物，其可用于酸稳定的饮料中。此外，一些实施方案提供一种具有调味分子的组合作为客体的环糊精包合复合物，其可模拟二乙酰的黄油调味作用。例如，环糊精包合复合物还可包括二甲硫(挥发性硫化合物)、脯氨酸(氨基酸)和呋喃酮(甜味增强剂)中的至少一种作为客体。这种没有二乙酰的环糊精包合复合物可用于对如上述那些食物提供黄油调味作用。
以下实施例阐述了本发明的各特征和方面。
实施例1：具有β-环糊精和二乙酰的环糊精包合复合物以及其形成方法
在大气压下，在100加仑反应器中，将49895.1600g(110.02磅)β-环糊精与997.9g(2.20磅)甜菜果胶干混(2重量％的果胶：β-环糊精；XPQ EMP 5甜菜果胶，从Degussa-France得到)，形成干混物。100加仑反应器被套上加热和冷却用的夹套，并包括桨式搅拌器和包括冷凝单元。向反应器供应约40(4.5℃)的丙二醇冷却剂。丙二醇冷却剂系统开始时关闭，夹套某种程度上用作反应器的隔热体。将124737.9g(275.05磅)热去离子水加到β-环糊精和果胶的干混物中。水温为约118(48℃)。使用反应器的桨式搅拌器将混合物搅拌约30min。然后临时打开反应器，加入11226.4110g(24.75磅)二乙酰。再次封闭反应器，所得混合物在未加热下搅拌8小时。然后，将反应器夹套与丙二醇冷却剂系统连接。打开冷却剂到约40(4.5℃)，对混合物搅拌约36小时。然后使用如常用在喷雾干燥操作中的高剪切罐内混合器使混合物乳化。其后混合物在入口温度约410(210℃)和出口温度约221(105℃)的喷嘴干燥器中喷雾干燥。实现的二乙酰在环糊精包合复合物中的保持百分率为18.37重量％。水分含量测得为4.0％。环糊精包合复合物包括小于0.3％的表面二乙酰，经测量具有通过80目筛子粒径的环糊精包合复合物为99.7％。
实施例2：具有α-环糊精和二乙酰的环糊精包合复合物以及其形成方法
使用α-环糊精代替实施例1的β-环糊精，并与1重量％的果胶干混(即，1重量％的果胶：β-环糊精；XPQ EMP 5甜菜果胶，从Degussa-France得到)。按实施例1所述的方法处理混合物并干燥。二乙酰在环糊精包合复合物中的保持百分率为11.4重量％。
实施例3：具有β-环糊精和橙子香精的环糊精包合复合物以及其形成方法
将橙汁生产后的废水流的橙子香精作为水相加到根据实施例1所述方法形成的β-环糊精和2重量％果胶的干混物中。未加入额外的水，固体含量约28％。按实施例1所述的方法形成环糊精包合复合物。干燥的包合复合物含有约3～4重量％的乙醛，约5～7重量％的丁酸乙酯，约2～3重量％的里哪醇以及其他柑橘增味剂。得到的环糊精包合复合物可用于高味觉饮料中。
实施例4：具有β-环糊精和乙酰丙酰的环糊精包合复合物以及其形成方法
将过摩尔量的乙酰丙酰加到按实施例1所述方法形成的β-环糊精和2重量％果胶水溶液的干混物中。乙酰丙酰在环糊精包合复合物中的保持百分率为9.27重量％。所述混合物用于高味觉无二乙酰的黄油体系中。
实施例5：橙油调味品以及其形成方法
将橙油(即，Orange Bresil；75g)加到包括635g水、403.75g麦芽糖糊精和21.25g甜菜果胶(从Degussa-France得到，产品号XPQ EMP 5)的水相中。温和搅拌下将橙油加到水相中，然后在10,000RPM的剧烈搅拌下形成混合物。然后使混合物通过250bar下的均质器，形成乳液。使用入口温度约180℃和出口温度约90℃的NIRO牌喷嘴干燥器干燥乳液，形成干燥产品。然后用100g干燥产品中的油量(单位：g)除以原料混合物中的油含量来定量调味剂保持百分率。橙油的保持百分率为约91.5％。
实施例6：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、297.50g麦芽糖糊精和127.50g阿拉伯树胶(从
Naturels International得到)的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约91.5％。
实施例7：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、297.50g麦芽糖糊精、123.25g阿拉伯树胶(从
Naturels International得到)和4.25g解聚的柑橘果胶的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约96.9％。
实施例8：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、297.50g麦芽糖糊精、123.25g阿拉伯树胶(从
Naturels International得到)和4.25g甜菜果胶(从Degussa-France得到，产品号XPQ EMP 5)的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约99.0％。
实施例9：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、403.75g麦芽糖糊精和21.25g解聚的柑橘果胶的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约90.0％。
实施例10：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、340.00g麦芽糖糊精和85.00g阿拉伯树胶(从
Naturels International得到)的水相中。将橙油加到水相中，并安装实施例5所述的方法干燥。调味剂的保持百分率为约91.0％。
实施例11：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水和425.00g麦芽糖糊精的水相中。将橙油加到水相中，并安装实施例5所述的方法干燥。调味剂的保持百分率为约61.0％。
实施例12：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、420.75g麦芽糖糊精和4.25g果胶的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约61.9％。
实施例13：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、403.75g麦芽糖糊精和21.50g果胶的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约71.5％。
实施例14：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、420.75g麦芽糖糊精和4.75g解聚的柑橘果胶的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约72.5％。
实施例15：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、420.75g麦芽糖糊精和4.75g甜菜果胶(从Degussa-France得到，产品号XPQ EMP 5)的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约78.0％。
实施例16：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、414.40g麦芽糖糊精和10.60g解聚的柑橘果胶的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约85.0％。
实施例17：橙油调味品以及其形成方法
将橙油(75g)加到包括635g水、414.40g麦芽糖糊精和10.60g甜菜果胶(从Degussa-France得到，产品号XPQ EMP 5)的水相中。将橙油加到水相中，并按照实施例5所述的方法干燥。调味剂的保持百分率为约87.0％。
所述权利要求书阐述了本发明的各特征和方面。
Claims (44)
1.一种制备环糊精包合复合物的方法，所述方法包括：
干混环糊精和乳化剂，形成干混物；以及
使溶剂和客体与所述干混物混合，形成环糊精包合复合物。
2.权利要求1的方法，其中使所述溶剂和所述客体与所述干混物混合以形成环糊精包合复合物形成了包含环糊精包合复合物的混合物，并且所述方法还包括干燥所述混合物。
3.权利要求2的方法，其中干燥包括空气干燥、真空干燥、喷雾干燥、烘箱干燥、和其组合中的至少一种。
4.权利要求2的方法，其还包括在干燥之前使用罐内混合器和高剪切吸入式混合器中的至少一种使所述混合物乳化。
5.权利要求2的方法，其中所述混合物包含溶剂成分，所述方法还包括在干燥所述混合物之前减少所述混合物的溶剂成分。
6.权利要求1的方法，其中使所述客体和所述溶剂与所述干混物混合包括使所述溶剂和所述干混物混合，然后使所述客体与其混合。
7.权利要求1的方法，其中所述乳化剂包括水性胶体。
8.权利要求1的方法，其中所述乳化剂包括黄原胶、果胶、阿拉伯树胶、黄芪胶、瓜尔胶、角叉菜胶、刺槐豆胶、和其组合中的至少一种。
9.权利要求1的方法，其中所述乳化剂包括果胶。
10.权利要求9的方法，其中所述果胶包括甜菜果胶、果实果胶、和其组合中的至少一种。
11.权利要求1的方法，其中所述溶剂包括水。
12.权利要求1的方法，其中所述环糊精包括α-环糊精、β-环糊精、γ-环糊精、和其组合中的至少一种。
13.权利要求1的方法，其中所述客体包括调味剂、增嗅剂、药剂、营养剂、和其组合中的至少一种。
14.权利要求13的方法，其中所述调味剂包括醛、酮、醇、和其组合中的至少一种。
15.权利要求13的方法，其中所述增嗅剂包括天然香料、合成香料、合成精油、天然精油、和其组合中的至少一种。
16.权利要求1的方法，其中所述客体包括脂肪酸、内酯、萜烯、二乙酰、二甲硫、脯氨酸、呋喃酮、里哪醇、乙酰丙酰、天然香精、精油、和其组合中的至少一种。
17.权利要求1的方法，其中所述客体包括二乙酰。
18.权利要求1的方法，其中所述环糊精包合复合物至少部分地由包括环糊精和客体的纳米结构限定。
19.权利要求18的方法，其中所述纳米结构包括摩尔比至少约3∶2的客体∶环糊精。
20.权利要求1的方法，其中使客体和溶剂与所述干混物混合包括使所述客体和环糊精以摩尔比约3∶1的客体∶环糊精混合。
21.权利要求1的方法，其中所述环糊精包合复合物在没有额外热量或助溶剂下形成。
22.权利要求1的方法，其中使所述客体和所述溶剂与所述干混物混合包括搅拌所述客体、所述溶剂和所述干混物。
23.权利要求22的方法，其中搅拌所述客体、所述干混物和所述溶剂进行约5～8小时。
24.权利要求1的方法，其中使溶剂和客体与所述干混物混合以形成环糊精包合复合物包括形成包括环糊精包合复合物的混合物，并且所述方法还包括冷却所述混合物。
25.权利要求24的方法，其中冷却所述混合物包括打开反应器的冷却夹套。
26.权利要求1的方法，其中使客体和溶剂与所述干混物混合在密封的反应器中进行。
27.权利要求1的方法，其中干混环糊精和乳化剂包括干混乳化剂∶环糊精的重量百分数为至少约0.5重量％的环糊精和乳化剂。
28.权利要求1的方法，其中干混环糊精和乳化剂包括干混乳化剂∶环糊精的重量百分数为小于约10重量％的环糊精和乳化剂。
29.一种根据权利要求1所述方法制备的环糊精包合复合物。
30.权利要求29的环糊精包合复合物，其中在所述环糊精包合复合物中客体∶环糊精的重量百分数为至少约10重量％。
31.权利要求29的环糊精包合复合物，其中所述环糊精包合复合物用于食物、口香糖、糖果、调味剂、香料、医药品、营养品、化妆品、农业应用、感光乳剂、废料流体系、和其组合的至少一种中。
32.一种制备环糊精包合复合物的方法，所述方法包括：
使环糊精和乳化剂混合，形成第一混合物；
使所述第一混合物与溶剂混合，形成第二混合物；以及
使客体与所述第二混合物混合，形成第三混合物。
33.权利要求32的方法，其还包括干燥所述第三混合物。
34.权利要求32的方法，其中使环糊精和乳化剂混合包括干混。
35.权利要求32的方法，其中所述乳化剂包括黄原胶、果胶、阿拉伯树胶、黄芪胶、瓜尔胶、角叉菜胶、刺槐豆胶、和其组合中的至少一种。
36.权利要求32的方法，其中所述乳化剂包括果胶。
37.权利要求32的方法，其中所述客体包括调味剂、增嗅剂、药剂、营养剂、和其组合中的至少一种。
38.权利要求32的方法，其中所述客体包括二乙酰。
39.一种根据权利要求32的方法制备的环糊精包合复合物。
40.一种制备环糊精包合复合物的方法，所述方法包括：
干混环糊精和果胶，形成第一混合物；
使所述第一混合物与水混合，形成第二混合物；以及
使二乙酰与所述第二混合物混合，形成第三混合物。
41.权利要求40的方法，其还包括干燥所述第三混合物。
42.权利要求40的方法，其中所述环糊精和果胶以果胶∶环糊精的重量百分数为至少约0.5重量％干混。
43.权利要求40的方法，其中所述环糊精和果胶以果胶∶环糊精的重量百分数为小于约10重量％干混。
44.一种根据权利要求40的方法制备的环糊精包合复合物。
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| NZ (1) | NZ553909A (zh) |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101648126B (zh) * | 2009-08-26 | 2011-06-15 | 江南大学 | 一种利用环糊精母液制备丁香油微胶囊的方法 |
| CN103271991A (zh) * | 2013-05-25 | 2013-09-04 | 江苏丰园生物技术有限公司 | 一种薄荷精油与混合环糊精包合物及其制备方法 |
| CN103271996A (zh) * | 2013-05-25 | 2013-09-04 | 江苏丰园生物技术有限公司 | 一种肉桂精油与混合环糊精包合物及其制备方法 |
| CN110463695A (zh) * | 2019-08-23 | 2019-11-19 | 无锡迈莱博生物科技有限公司 | 水溶性植物精油消毒剂及其制备方法和应用 |
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| EP1891083A1 (en) * | 2005-06-13 | 2008-02-27 | Cargill Incorporated | Cyclodextrin inclusion complexes and methods of preparing same |
| CA2610000A1 (en) * | 2005-06-13 | 2006-12-28 | Cargill, Incorporated | Cyclodextrin inclusion complexes and methods of preparing same |
| EP2027136A4 (en) * | 2006-06-13 | 2011-08-03 | Cargill Inc | Large part cyclicxtrin inclusion complexes and method for their preparation |
| BRPI0720888A2 (pt) * | 2006-12-27 | 2014-03-25 | Cargill Inc | Complexos de inclusão de ciclodextrina e métodos de preparar os mesmos |
| US20080283693A1 (en) * | 2007-05-15 | 2008-11-20 | Evans Michael J F | Propulsion apparatus and system |
| JP2013521796A (ja) * | 2010-03-13 | 2013-06-13 | イーストポンド・ラボラトリーズ・リミテッド | 脂肪結合性組成物 |
| CA2797307A1 (en) * | 2010-04-26 | 2011-11-03 | Aalborg Universitet | Method for functionalizing a solid material surface with self assembling or self aggregating cyclodextrins and products thereof |
| US20120171184A1 (en) | 2010-12-31 | 2012-07-05 | Lajos Szente | Cellular hydration compositions |
| BR112013016809A2 (pt) | 2010-12-31 | 2016-09-27 | Eastpond Lab Ltd | composições de hidratação celular |
| JP5906518B2 (ja) * | 2011-08-11 | 2016-04-20 | 地方独立行政法人鳥取県産業技術センター | シクロデキストリン包接化合物含有組成物の製造方法 |
| WO2013188366A2 (en) * | 2012-06-12 | 2013-12-19 | Cornell University | Nanosystems for formulation of effective minimum risk biocides |
| FR3000080B1 (fr) * | 2012-12-20 | 2015-01-30 | Oreal | Polycondensat de cyclodextrine insoluble dans l'eau ; utilisations comme agent de capture |
| RU2741848C1 (ru) * | 2019-03-16 | 2021-01-29 | Иванова Мария Ивановна | Способ получения клатратных комплексов летучих веществ |
| EP4132294A1 (en) | 2020-04-06 | 2023-02-15 | Eastpond Laboratories Limited | Compositions for promoting cellular hydration |
| CN111592934A (zh) * | 2020-06-15 | 2020-08-28 | 上海应用技术大学 | 一种茉莉缓释香精及其制备方法 |
| CN111500368A (zh) * | 2020-06-15 | 2020-08-07 | 上海应用技术大学 | 一种西瓜缓释香精及其制备方法 |
| CN115607468A (zh) * | 2022-08-08 | 2023-01-17 | 南京华狮新材料有限公司 | 包裹超分子水杨酸组合物、制备方法及其应用 |
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| CA2610000A1 (en) * | 2005-06-13 | 2006-12-28 | Cargill, Incorporated | Cyclodextrin inclusion complexes and methods of preparing same |
| EP2027136A4 (en) * | 2006-06-13 | 2011-08-03 | Cargill Inc | Large part cyclicxtrin inclusion complexes and method for their preparation |
| BRPI0720888A2 (pt) * | 2006-12-27 | 2014-03-25 | Cargill Inc | Complexos de inclusão de ciclodextrina e métodos de preparar os mesmos |
-
2004
- 2004-11-01 JP JP2007533448A patent/JP2008514198A/ja active Pending
- 2004-11-01 MX MX2007003718A patent/MX2007003718A/es unknown
- 2004-11-01 US US11/575,715 patent/US20090227690A1/en not_active Abandoned
- 2004-11-01 EP EP04810196A patent/EP1793673A4/en not_active Withdrawn
- 2004-11-01 RU RU2007115893/04A patent/RU2362785C2/ru not_active IP Right Cessation
- 2004-11-01 KR KR1020077009452A patent/KR20070062582A/ko not_active Application Discontinuation
- 2004-11-01 BR BRPI0419086-6A patent/BRPI0419086A/pt not_active IP Right Cessation
- 2004-11-01 CA CA002580824A patent/CA2580824A1/en not_active Abandoned
- 2004-11-01 CN CNA2004800440843A patent/CN101056538A/zh active Pending
- 2004-11-01 NZ NZ553909A patent/NZ553909A/en unknown
- 2004-11-01 AU AU2004323721A patent/AU2004323721A1/en not_active Abandoned
- 2004-11-01 WO PCT/US2004/036270 patent/WO2006036159A1/en active Application Filing
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101648126B (zh) * | 2009-08-26 | 2011-06-15 | 江南大学 | 一种利用环糊精母液制备丁香油微胶囊的方法 |
| CN103271991A (zh) * | 2013-05-25 | 2013-09-04 | 江苏丰园生物技术有限公司 | 一种薄荷精油与混合环糊精包合物及其制备方法 |
| CN103271996A (zh) * | 2013-05-25 | 2013-09-04 | 江苏丰园生物技术有限公司 | 一种肉桂精油与混合环糊精包合物及其制备方法 |
| CN110463695A (zh) * | 2019-08-23 | 2019-11-19 | 无锡迈莱博生物科技有限公司 | 水溶性植物精油消毒剂及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
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| JP2008514198A (ja) | 2008-05-08 |
| US20090227690A1 (en) | 2009-09-10 |
| EP1793673A1 (en) | 2007-06-13 |
| RU2007115893A (ru) | 2008-11-10 |
| NO20072066L (no) | 2007-06-26 |
| KR20070062582A (ko) | 2007-06-15 |
| AU2004323721A1 (en) | 2006-04-06 |
| RU2362785C2 (ru) | 2009-07-27 |
| BRPI0419086A (pt) | 2007-12-18 |
| CA2580824A1 (en) | 2006-04-06 |
| MX2007003718A (es) | 2007-04-23 |
| NZ553909A (en) | 2009-02-28 |
| WO2006036159A1 (en) | 2006-04-06 |
| EP1793673A4 (en) | 2009-08-12 |
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