CN1362406A - 一种或多种氧化的类胡萝卜素干粉的制备方法 - Google Patents
一种或多种氧化的类胡萝卜素干粉的制备方法 Download PDFInfo
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- CN1362406A CN1362406A CN01145432A CN01145432A CN1362406A CN 1362406 A CN1362406 A CN 1362406A CN 01145432 A CN01145432 A CN 01145432A CN 01145432 A CN01145432 A CN 01145432A CN 1362406 A CN1362406 A CN 1362406A
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- carotenoid
- dry powder
- dispersion
- water
- hydrolysis
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Abstract
本发明公开了制备一种或多种氧化类胡萝卜素干粉的方法,通过a)将一种或多种氧化的类胡萝卜素分散于保护性胶体的水分子分散体或胶态分散体中以及b)在存在或没有表面覆盖剂的情况下通过除去水和所有添加的溶剂并干燥,将形成的分散体转变成干粉,其中包括在制备方法步骤a)中将至少一种水解度大于5%的部分水解的大豆蛋白质用作保护性胶体。
Description
技术领域
本发明涉及制备一种或多种氧化的类胡萝卜素干粉的方法,特别是含有选自虾青素、斑蝥黄、叶黄素、玉米黄质、citranaxanthin和β-阿朴-8’-类胡萝卜酸乙酯的类胡萝卜素干粉。
背景技术
可将类胡萝卜素类物质分成两大类,胡萝卜素和叶黄素。与全部是多烯烃的胡萝卜素例如β-胡萝卜素或番茄红素相比,在叶黄素中还存在氧官能团如羟基,环氧基和/或氧基。该类的典型代表特别是虾青素、斑蝥黄、叶黄素和玉米黄质。
氧化的类胡萝卜素在自然界中广泛分布并特别存在于玉米(玉米黄质),嫩荚菜豆(叶黄素),辣椒(辣椒红),蛋黄(黄体素)和蟹以及鲑鱼类(虾青素)中,每种情况下使上述食品获得特有的着色。
不仅可以通过合成,而且还可由天然物质中分离获得的上述聚醚是食品和饲料工业以及医药领域中的重要颜料,并且象虾青素在鲑鱼体内还是具有前维生素A活性的活性化合物。
与所有类胡萝卜素一样,叶黄素不溶于水,而可溶于脂肪和油中,但是发现仅有很低的溶解度。有限的溶解度和高氧化灵敏度要求不能在食品和饲料的着色中直接使用合成获得的相对粗粒产品,因为在粗结晶形式的这些物质仅能获得很差的着色效果。叶黄素实际应用时的这些不利作用在含水介质中表现得特别明显。
仅通过特殊制备的制剂,其中活性化合物以细碎的形式存在,并且如需要用保护胶体保护以防止氧化,这样在食品的直接染色中可提高得色量。此外,饲料工业中使用的上述制剂可获得更高的叶黄素生物利用率,并因此间接地改进例如在蛋黄或鱼的色素形成中的着色效果。
为增加得色量并增加可吸收性和生物利用率,已公开了各种方法,所有方法的目的都是降低活性化合物的微晶大小并使颗粒尺寸范围小于10μm。
多种方法,尤其是公开在Chimia 21,329(1967),WO91/06292和WO94/19411中的方法,使用胶体磨研磨的类胡萝卜素,从而获得了2-10μm的粒子大小。
此外还有很多结合乳化作用/喷雾干燥方法,如DE-A-12 11911和EP-A-0 410236所述方法。
根据欧洲专利EP-B-0 065 193,细碎的粉状的类胡萝卜素制剂是通过在升温条件下,如果可行并在升压条件下,将类胡萝卜素溶解在挥发性的水混溶性有机溶剂中,与保护性胶体水溶液混合沉淀出类胡萝卜素,然后喷雾干燥而制备。
生产细碎的粉状类胡萝卜素制剂的类似方法公开在EP-A-0 937 412中,使用水不混溶性溶剂。
然而,当根据EP-B-0 065 193生产叶黄素纳米颗粒活性化合物分散体时,经常可观察到下述现象。
含有叶黄素的活性化合物水分散体经常,特别是在浓缩时,为不稳定胶体。由于活性化合物颗粒的絮凝,在上述过程中形成部分沉积物,部分水浆,因此不可能再将分散体进一步转化为干粉。
此外当使用含有羰基官能团的叶黄素时,用作保护性胶体的明胶可交联,形成凝胶并因此不能再分散且也不能将其转化成干粉。
由于上述方法中存在的问题,因比就着色效果和生物利用率而论,制备的高规格的含叶黄素制剂总是不能令人满意。
明胶的缺点还在于它们的高粘合特性。应用液体系统常用的干燥方法,如喷雾干燥,或喷雾流化床干燥时,使用含有明胶产品常出现成丝或包壳现象。
此外,含有明胶的产品已不再受消费者的欢迎。
经常,仅能将较低浓度的脂溶性物质加入其他经常使用的保护性胶体,例如阿拉伯树胶,淀粉,糊精,果胶或黄蓍胶中。另外,过去由于阿拉伯树胶收获量不足,不是总能获得,品质也差。
合成胶体如聚乙烯吡咯烷酮或部分合成的聚合物如纤维素衍生物也表现出有限的乳化能力并且不能总令人满意,特别是在食品工业领域。
DE-A-44 24 085公开了使用部分水解的大豆蛋白质作为脂溶性活性化合物的保护性胶体。此处公开的大豆蛋白质的水解度为0.1-5%。
上述大豆蛋白质的缺点常常是它们的水溶性差,不充分的乳化性能以及它们易于交联,这些情况是不理想的,特别是对于生产可再分散于水中的干粉。
因此本发明目的是提供一种使用没有上述现有技术缺点的保护性胶体来生产氧化的类胡萝卜素干粉的方法。
发明内容
令人惊奇地发现,通过下述的用于制备一种或多种氧化的类胡萝卜素干粉的方法实现了本发明目的,
a)将一种或多种氧化的类胡萝卜素分散于保护性胶体的水分子分散体或胶态分散体中以及
b)在存在或没有表面覆盖剂的情况下,通过除去水和所有另加的溶剂并干燥将形成的分散体转变成干粉,
其中包括在制备方法步骤a)中将至少一种水解度大于5%的部分水解的大豆蛋白质用作保护性胶体。
根据本发明,保护性胶体是部分水解的大豆蛋白质,其水解度(DH)大于5%,优选6-20%,特别优选6-12%,更特别优选6-9%。水解度“DH”如下定义:
DH=裂解的肽键数量/肽键总数量×100%
水解度的测定是通过C.F.Jacobsen等人在“Methods of BiochemicalAnalysis”,第IV卷,第171-210页中所公开的“pH-Stat-Method”,IntersciencePublishers Inc.,New York 1957。
通常部分水解是使用可以想到的酶进行,适合的酶如来自植物、微生物和真菌的蛋白酶,或来自动物蛋白酶。优选,部分水解是使用植物蛋白酶菠萝蛋白酶进行的。
使用的大豆蛋白质是常规的市售大豆蛋白质分离物和大豆蛋白质浓缩物,蛋白质含量为70-90重量%,其余为10-30重量%或多或少不确定的其他植物组分。本发明优选使用的大豆蛋白质是没有进行遗传修饰的大豆蛋白质。
优选在50-70℃和pH为7-9条件下将大豆蛋白质分离物在含水介质中用酶酶解。每种情况下可通过实验室试验根据所需水解度确定蛋白质与酶的适当比例,这是本领域技术人员很容易做到的。
通常大豆蛋白质水解产物的水溶液是由蛋白质含量为6-10重量%的大豆蛋白质制备的。
本发明使用的部分水解大豆蛋白质的重均分子量通常为15000-250000,优选25000-220000,特别优选50000-200000,更特别优选120000-180000。
在本发明方法中不同水解度的部分水解大豆蛋白质混合物,或部分水解和没有水解的大豆蛋白质混合物也可用作保护性胶体。这些混合物,它们的重均分子量也在上述范围内。
术语分散优选产生水悬浮液和水乳液。特别优选,分散步骤a)是在部分水解大豆蛋白质的水分子分散体或胶态分散体中制备一种或多种氧化的类胡萝卜素悬浮液其中分散相包括至少一种活性化合物纳米颗粒。
上述方法的优选实施方案中,该方法步骤a)中制备的悬浮液在制成干粉前进行研磨。在这种情况下,优选研磨操作前将活性化合物以结晶形状悬浮。
这里采用已知方式进行研磨,例如使用球磨机。根据使用的磨的类型,研磨至Fraunhofer diffraction D[4,3]测定的颗粒的平均颗粒大小为0.1-100μm,优选0.2-50μm,特别优选0.2-20μm,更特别优选0.2-5μm,特别是0.2-0.8μm。术语D[4,3]表示体积-重量平均直径(参见Handbook to Malvern Mastersizer S,Malvern Instruments Ltd.,UK)。
关于研磨及其使用的装置的进一步详述,可特别在下述文献中找到:Ullmann’s Encyclopedia of Industrial Chemistry,第6版,1999年,ElectronicRelease,Size Reduction,3.6.章:Wet Grinding,和EP-A-0 498 824。
还优选本发明方法的另一种变化方式,步骤a)中的分散包括下述步骤:
a1)将一种或多种氧化的类胡萝卜素溶解在水混溶性有机溶剂或水和水混溶性有机溶剂的混合物中或
a2)将一种或多种氧化的类胡萝卜素溶解在水不混溶性有机溶剂中以及
a3)将a1)或a2)获得的溶液与水解度大于5%的部分水解的大豆蛋白质水分子分散体或胶态分散体混合,将类胡萝卜素的疏水相制成纳米分散相。
根据使用的溶剂类型,步骤a3)中的纳米分散相可以是固体纳米颗粒(悬浮液)或纳米液滴(乳液)。
步骤a1)中使用的水混溶性溶剂主要是仅含有碳,氢和氧的水混溶性、热稳定性、挥发性溶剂,如醇、醚、酯、酮和缩醛。有利的是,使用下述溶剂:至少10%水混溶性,沸点低于200℃和/或少于10个碳原子的溶剂。特别优选甲醇、乙醇、正丙醇、异丙醇、1,2-丁烷-1-二醇甲醚、1,2-丙烷-1-二醇正丙基醚、四氢呋喃或丙酮。
针对本发明,水不混溶性有机溶剂是在大气压下水溶性低于10%的有机溶剂。可以考虑的溶剂尤其是卤代脂族烃,例如二氯甲烷,氯仿和四氯化碳,羧酸酯,例如碳酸二甲酯、碳酸二乙酯、碳酸异丙烯酯、甲酸乙酯、乙酸甲酯、乙酸乙酯或乙酸异丙酯,以及醚类如甲基叔丁基醚。优选的水不混溶性有机溶剂选自下述化合物:碳酸二甲酯、碳酸异丙烯酯、甲酸乙酯、乙酸乙酯、乙酸异丙酯和甲基叔丁基醚。
本发明方法中优选制备选自虾青素、斑蝥黄、叶黄素、玉米黄质citranaxanthin和β-阿朴-8’-类胡萝卜酸乙酯的氧化类胡萝卜素干粉。
特别优选,在本发明方法中,
a)高于30℃条件下将虾青素和/或斑蝥黄溶解在水混溶性有机溶剂或水和水混溶性有机溶剂的混合物中,
b)将所得溶液与水解度为6-9%的部分水解大豆蛋白质的水分子分散体或胶态分散体混合以及
c)将形成的分散体制成干粉。
更特别优选,该方法是含有虾青素干粉的生产方法。
上述干粉优选以这样一种方式制备,即将至少一种氧化类胡萝卜素溶解在水混溶性有机溶剂中,温度为高于30℃,优选50℃-240℃,特别是100℃-200℃,特别优选140℃-180℃,如需要可在加压条件下进行。
由于高温作用,某些情况下可降低全反式异构体的预期的高含量,因此将类胡萝卜素尽可能快,例如几秒钟分散,例如0.1-10秒,特别优选少于1秒。为快速制备分子分散体,优选升压,例如20巴-80巴,优选30-60巴。
然后将所得分子分散体与未冷却的或冷却的保护性胶体的水分子分散体或胶态分散体直接混合,设定混合温度约为35℃-80℃。
在上述过程中溶剂组分转成水相而类胡萝卜素疏水相形成纳米分散相。
涉及上述分散的方法和装置更详细的描述,参见EP-B-0 065 193。
特别是存在或没有表面覆盖剂的条件下通过喷雾干燥,喷雾冷却,冷冻干燥或流化床干燥方法转化为干粉。适合的表面覆盖剂例如是玉米淀粉,硅酸或磷酸三钙。
为增加最终产品的机械稳定性,有利的是某些情况下向胶体中加入增塑剂如糖或糖醇,例如蔗糖,葡萄糖,葡萄糖浆,糊精,乳糖,转化糖,山梨糖醇,甘露糖醇或甘油。
为增加活性化合物对氧化降解的稳定性,优选加入稳定剂如α-生育酚,丁化羟基甲苯,丁基化羟基苯甲醚,抗坏血酸或乙氧基喹。可将它们加入水相或加入溶剂相,但优选与活性化合物一起溶解在溶剂相中。
某些情况下优选在溶剂相中再溶解生理上可接受的油,例如芝麻油,玉米油,棉籽油,大豆油或花生油,以及中链植物脂肪酸的酯,以叶黄素为基准计算,浓度为0-500重量%,优选10-300重量%,特别优选20-100重量%,然后在与水相混合时将油与活性化合物和所述添加剂一起以极细碎的分散态沉淀出来。
通常选择保护性胶体和增塑剂与氧化类胡萝卜素的比例以使获得的最终产品其中包括0.1-30重量%,优选1-25重量%,特别优选5-20重量%的类胡萝卜素,10-70重量%的保护性胶体,10-70重量%的增塑剂,所有百分比都是以粉末的干物质为基准计,并可含有少量稳定剂。
本发明还涉及可用开头说明的各种方法之一获得的氧化类胡萝卜素干粉。
优选上述干粉是含有选自虾青素、斑蝥黄、叶黄素、玉米黄质、citranaxanthin和β-阿朴-8’-类胡萝卜酸乙酯的氧化类胡萝卜素干粉,特别优选斑蝥黄和虾青素,更特别优选虾青素。
本发明干粉中活性化合物含量为0.1-30重量%,优选1-25重量%,特别优选5-20重量%,更特别优选8-15重量%。
本发明干粉的特点尤其是它们可很容易地再分散于水体系中以获得活性化合物的均匀细粒分布,颗粒大小小于1μm。
而且,已发现获得的氧化类胡萝卜素的胶体稳定和非交联纳米颗粒活性化合物分散体其粘度特性大致相当于牛顿液体。这种类型的液体的特点是它们由牛顿公式τ=h·D定义的流动阻力在一定的温度下为物理常数(τ=剪切应力,D=剪切梯度,h=动态粘度)。牛顿液体的流动特性图解表明在给定温度下大致为一条直线。特别是,活性化合物分散体的粘度在剪切10-2秒-1至10+2秒-1条件下40℃和60℃的变化小于±50%。
这种近似牛顿液体粘度特性的优点,尤其是活性化合物分散体,特别在浓缩后与原有粘度分散体的情况相比可更容易地泵送。此外,在喷雾干燥过程中,近似牛顿液体的活性化合物分散体的优越之处是可更容易地优化喷头参数,并且喷头中对上述分散体特性的要求并不是很严格。
与水解度<5%的部分水解大豆蛋白质相比,通过使用本发明大豆蛋白质,可获得具有提高了颜色强度和改进冷水再分散能力的含叶黄素干粉。
令人惊奇的是水解度大于5%的部分水解大豆蛋白质表现出与开头所述的水混溶性溶剂更好的相容性。因此,可采用更浓缩操作方式,从而以更经济的生产方法获得本发明干粉。
此外发现使用本发明方法可避免叶黄素附聚形成H聚集体。
文献中已知类胡萝卜素的聚集现象并在大量出版物上公开[P.Song,T.A.Moore,Photochemistry and Photobiology,19,435-441(1974);A.V.Ruban,P.Horton,A.J.Young,J.Photochem.Photobiol.B:Biol.,21,229-234(1993);V.R.Salares,N.M.Young,P.R.Carey,H.J.Bemstein,Journal of RamanSpectroscopy,6(6),282-288(1977)]。
例如可通过将溶于水混溶性有机溶剂,例如异丙醇、乙醇、丙酮或四氢呋喃中的类胡萝卜素溶液与水混合来制备类胡萝卜素聚集体。
因此,如上述文献所述,选择适当的水和有机溶剂质量比,可以获得H或J聚集体。
H聚集体是多烯链的牌墩式(card-stack)聚集体,其特征在于紫外/可见谱在320-400nm区出现新的光谱带,这与单体产生的光吸收类型相比浅色基位移。相比之下,J聚集体代表多烯的直线头尾聚集或人字形聚集体形式。两种排列都使得多烯的UV吸收谱向红移。
鲑鱼饲喂试验发现叶黄素的H聚集体特别是虾青素的H聚集体比相应的J聚集体的生物利用率更差,这是本发明方法生产的干粉的另一优点。
上述干粉特别适于作为食品和饲料工业添加剂以及作为药物制剂添加剂。动物饲料领域中含类胡萝卜素干粉应用的典型领域,例如水产养殖中鱼的色素生成和蛋黄的色素生成以及养鸡业中肉用仔鸡的皮肤着色。
在下述实施例中,将对本发明方法步骤进行更详细的描述。
具体实施方式
实施例1
通过酶降解生产大豆蛋白水解产物
将600ml水和40g大豆蛋白分离物(蛋白质含量为85重量%)装入2升玻璃烧杯中并搅拌下加热至60℃。然后用1M氢氧化钠溶液将pH调到9.0,加入0.5g菠萝蛋白酶并将混合物在60℃进一步搅拌45分钟。然后用1M氢氧化钠溶液再将pH调至9.0。以消耗的氢氧化钠溶液计,计算出的DH为7%。然后通过将溶液加热至100℃2分钟使酶失活。
实施例2
虾青素干粉
可加热容器中,温度为30℃将48g晶状虾青素和20gα-生育酚悬浮于室温下的350g的共沸异丙醇/水混合物中。然后将活性化合物悬浮液加热至100℃,并以2.1kg/h的流速,先后与温度为226℃以及流速为2.6kg/h的另一部分异丙醇/水共沸混合物、在压力为60巴以及混合物温度为172℃下溶解的虾青素混合。然后将上述活性化合物溶液立即与水相混合,水相是由72g水解度为7%的部分水解大豆蛋白质,200g葡萄糖浆的6000g蒸馏水溶液组成,其中用1M NaOH将pH调至pH9.5,流速为35.8kg/h。
混合中形成的活性化合物颗粒在异丙醇中为颗粒大小为174nm的水混合物,E1/1值为119。
然后将活性化合物悬浮液在薄膜式蒸发器上浓缩以使活性化合物含量约为3.4%浓度并喷雾干燥。干粉中虾青素含量为12.3重量%。再分散于水中的干粉的颗粒大小为200nm以及E1/1值为101。
实施例3
虾青素干粉
首先室温下将48g晶状虾青素,1.6g棕榈酸抗坏血酸酯和20gα-生育酚悬浮于350g共沸异丙醇/水混合物。然后将上述活性化合物悬浮液加热至88℃并以2.1kg/h的流速连续与流速为2.7kg/h的另一部分热异丙醇/水共沸混合物,以及溶解在60巴压力下的165℃混合物温度下的虾青素混合。然后将活性化合物溶液与流速为60kg/h的水相混合,水相由103g根据实施例1制备的部分水解大豆蛋白质和163g葡萄糖的10800g蒸馏水溶液组成,其中已用1M NaOH将pH调至pH9.5。
混合过程中形成的活性化合物颗粒在异丙醇/水混合物中的颗粒大小为153nm,E1/1值为124。然后将活性化合物分散体在薄膜式蒸发器上浓缩以使活性化合物含量约为3.6%浓度并喷雾干燥。干粉中虾青素含量为13.0重量%。再分散于水中的干粉的平均颗粒大小为400nm以及E1/1值为106。
实施例4
斑蝥黄干粉
首先室温下将48g晶状斑蝥黄,4g棕榈酸抗坏血酸酯和16gα-生育酚悬浮于350g共沸异丙醇/水混合物。然后将上述活性化合物悬浮液加热至88℃并以2.9kg/h的流速连续与流速为4.8kg/h的另一部分热异丙醇/水共沸混合物,以及溶解在60巴压力下的175℃混合物温度下的斑蝥黄混合。然后将活性化合物溶液与流速为52kg/h的水相混合,水相由120g水解度为7%的部分水解大豆蛋白质和197g葡萄糖的7400g蒸馏水溶液组成,其中已用1M NaOH将pH调至pH9.5。
混合过程中形成的活性化合物颗粒在异丙醇/水混合物中的颗粒大小为139nm,E1/1值为134。然后将活性化合物悬浮液在薄膜式蒸发器上浓缩以使活性化合物含量约为3.3%浓度并喷雾干燥。干粉中斑蝥黄含量为12.5重量%。再分散于水中的干粉的平均颗粒大小为224nm以及E1/1值为125。
实施例5
citranaxanthin干粉
室温下将100g晶状citranaxanthin,59g水解度为7%的部分水解大豆蛋白质和50g抗坏血酸钠悬浮于280g去离子水中。然后将活性化合物悬浮液与约400g的直径为1mm的氧化锆陶瓷研磨珠一起分散于高性能分散机(Red-Devil,Erichsen,德国)上的1000ml玻璃烧瓶中。研磨1小时后,将磨碎的悬浮液在氮气下加入130g水解度为7%的部分水解的大豆蛋白质,200g蔗糖水溶液,同时存在1g棕榈酸抗坏血酸酯和1.5gα-生育酚。将混合物均化后,然后将悬浮液喷雾冷却干燥。获得活性化合物含量为13重量%的citranaxanthin干粉。
Claims (14)
1.制备一种或多种氧化类胡萝卜素干粉的方法,通过
a)将一种或多种氧化的类胡萝卜素分散于保护性胶体的水分子分散体或胶态分散体中以及
b)在存在或没有表面覆盖剂的情况下通过除去水和所有添加的溶剂并干燥,将形成的分散体转变成干粉,
其中包括在制备方法步骤a)中用作保护性胶体的至少一种水解度大于5%的部分水解的大豆蛋白质。
2.权利要求1的方法,其中分散步骤a)是在水解度大于5%的部分水解大豆蛋白质的水分子分散体或胶态分散体中制备的一种或多种氧化类胡萝卜素悬浮液。
3.权利要求2的方法,其中步骤a)中制备的悬浮液在转变成干粉前进行研磨。
4.权利要求1的方法,其中步骤a)的分散包括下述步骤:
a1)将一种或多种氧化的类胡萝卜素溶解在水混溶性有机溶剂或水和水混溶性有机溶剂的混合物中或
a2)将一种或多种氧化的类胡萝卜素溶解在水不混溶性有机溶剂中以及
a3)将a1)或a2)获得的溶液与水解度大于5%的部分水解的大豆蛋白质水分子分散体或胶态分散体混合,将类胡萝卜素的疏水相制成纳米分散相。
5.权利要求1-4中任一项的方法,其中保护性胶体是至少一种水解度为6-12%的部分水解的大豆蛋白质。
6.权利要求1-5中任一项的方法,其中氧化类胡萝卜素选自虾青素、斑蝥黄、叶黄素、玉米黄质、citranaxanthin和β-阿朴-8’-类胡萝卜酸乙酯。
7.权利要求6的方法,其中
a)高于30℃条件下将虾青素和/或斑蝥黄溶解在水混溶性有机溶剂或水和水混溶性有机溶剂的混合物中,
b)将所得溶液与水解度为6-9%的部分水解大豆蛋白质的水分子分散体或胶态分散体混合以及
c)将形成的分散体制成干粉。
8.权利要求7的方法,其中类胡萝卜素是虾青素。
9.权利要求1-8中任一项所述方法获得的氧化类胡萝卜素干粉。
10.权利要求9的干粉,包括选自虾青素、斑蝥黄、叶黄素、玉米黄质、citranaxanthin和β-阿朴-8’-类胡萝卜酸乙酯的氧化类胡萝卜素。
11.权利要求9或10的干粉,其中类胡萝卜素含量为0.1-30重量%。
12.权利要求9-11中任一项的干粉,包括5-20重量%的虾青素。
13.权利要求9-11中任一项的干粉,包括5-20重量%的斑蝥黄。
14.权利要求9-13中任一项的干粉作为食品、药物和/或动物饲料添加剂的用途。
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SI (1) | SI1219292T1 (zh) |
TR (1) | TR200402694T4 (zh) |
Cited By (3)
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CN102341006A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 虾青素衍生物的粉状组合物ii |
CN112772923A (zh) * | 2021-02-02 | 2021-05-11 | 山东农业大学 | 一种基于大豆肽聚集体的β-胡萝卜素包埋乳液及其制备方法 |
CN113575945A (zh) * | 2021-07-20 | 2021-11-02 | 万华化学集团股份有限公司 | 一种纳米级高全反式类胡萝卜素干粉的制备方法 |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1405572A1 (en) * | 2002-10-04 | 2004-04-07 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Modified lupin proteins for the preparation of water dispersible product forms of fat soluble compounds |
NZ554476A (en) | 2004-09-28 | 2010-09-30 | Chemaphor Inc | Compositions and methods for promoting weight gain feed conversion |
JP2008524266A (ja) * | 2004-12-22 | 2008-07-10 | コラローム インコーポレイティド | 天然の水−不溶性カプセル化組成物及びその製造法 |
GB0501365D0 (en) * | 2005-01-21 | 2005-03-02 | Promar As | Compositions |
DE102005053862A1 (de) | 2005-11-04 | 2007-05-10 | Pharmasol Gmbh | Verfahren und Vorrichtung zur Herstellung hochfeiner Partikel sowie zur Beschichtung solcher Partikel |
KR20090017502A (ko) * | 2006-04-05 | 2009-02-18 | 체마폴, 인코포레이티드. | 식료품 보충제 및 그의 용도 |
EP2124615A1 (de) * | 2007-01-16 | 2009-12-02 | Basf Se | Ölige formulierungen |
DK2111125T4 (en) | 2007-01-16 | 2017-02-27 | Basf Se | LIQUID FORMULATIONS CONTAINING CAROTINOIDS |
MX2009008269A (es) * | 2007-02-23 | 2009-08-12 | Basf Se | Proceso para la modulacion del sabor en composiciones de sustancias nuevas que comprenden al menos un edulcorante de alta intensidad (his). |
EP2139347B1 (de) * | 2007-02-23 | 2011-01-12 | B.R.A.I.N. Biotechnology Research And Information Network AG | Verwendung von wasserdispergierbaren carotinoid-nanopartikeln als geschmacksmodulatoren, geschmacksmodulatoren, enthaltend wasserdispergierbare carotinoid-nanopartikel, und verfahren zur geschmacksmodulation |
JP2011500733A (ja) * | 2007-10-26 | 2011-01-06 | ケマファー インコーポレーテッド | 免疫応答を増強するための組成物および方法 |
EP2224823B2 (de) | 2007-11-29 | 2021-11-17 | Basf Se | Pulverförmige carotinoidzubereitung für die färbung von getränken |
CN102176833B (zh) | 2008-10-07 | 2018-03-16 | 巴斯夫欧洲公司 | 即用型稳定乳液 |
JP5185068B2 (ja) * | 2008-10-31 | 2013-04-17 | 日本メナード化粧品株式会社 | 水溶性カロテノイド組成物 |
CN102341004B (zh) | 2009-03-05 | 2014-04-16 | 巴斯夫欧洲公司 | 虾青素衍生物的粉状组合物i |
EP2403360B1 (de) | 2009-03-05 | 2016-08-10 | Basf Se | Formulierung von astaxanthin-derivaten und deren verwendung iii |
AU2010242502B2 (en) | 2009-04-30 | 2016-11-10 | Avivagen Inc. | Methods and compositions for improving the health of animals |
KR102392078B1 (ko) * | 2016-04-01 | 2022-04-29 | 디에스엠 아이피 어셋츠 비.브이. | 제분된 루테인의 안정한 과립을 포함하는 음료 |
WO2020208642A1 (en) * | 2019-04-11 | 2020-10-15 | Technion Research & Development Foundation Limited | Formulations for encapsulation and bioavailability improvement of bioactive compounds based on natural plant based materials |
CN116584656A (zh) * | 2023-04-06 | 2023-08-15 | 东北农业大学 | 一种大豆肽-β-胡萝卜素纳米颗粒的制备方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1211911B (de) | 1959-09-08 | 1966-03-03 | Hoffmann La Roche | Verfahren zur Herstellung eines insbesondere zum Faerben von Lebens- und Futtermitteln geeigneten Carotinoidpraeparates |
US3110598A (en) | 1959-09-08 | 1963-11-12 | Hoffmann La Roche | Process of making a carotenoid preparation |
GB887883A (en) | 1959-09-08 | 1962-01-24 | Hoffmann La Roche | Manufacture of carotenoid preparations |
DE3119383A1 (de) * | 1981-05-15 | 1982-12-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von feinverteilten, pulverfoermigen carotinodpraeparaten |
JPS6042317A (ja) * | 1983-08-18 | 1985-03-06 | Nisshin Oil Mills Ltd:The | 化粧料 |
DK0410236T3 (da) | 1989-07-25 | 1993-12-13 | Hoffmann La Roche | Fremgangsmåde til fremstilling af caratenoidpræparater |
DK546289D0 (da) * | 1989-11-02 | 1989-11-02 | Danochemo As | Carotenoidpulvere |
DE4141351A1 (de) * | 1991-12-14 | 1993-06-17 | Basf Ag | Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung |
DK19393D0 (da) | 1993-02-19 | 1993-02-19 | Danochemo As | Fremgangsmaade til fremstilling af et i vand dispergerbart pulverformigt carotenoidpraeparat |
DE4424085A1 (de) | 1994-07-11 | 1996-01-18 | Basf Ag | Kaltwasserdispergierbare Zubereitungen fettlöslicher Wirkstoffe |
SE503336C2 (sv) * | 1994-09-19 | 1996-05-28 | Asta Carotene Ab | Medel och sätt för att öka produktionen av/hos fjäderfän |
US5827539A (en) * | 1995-12-28 | 1998-10-27 | Amway Corporation | Dry carotenoid-oil powder and process for making same |
EP0807431B1 (en) * | 1996-05-14 | 2004-03-24 | DSM IP Assets B.V. | Process for the manufacture of carotenoid compositions |
CA2261456A1 (en) | 1998-02-23 | 1999-08-23 | F. Hoffmann-La Roche Ag | Preparation of a finely divided pulverous carotenoid preparation |
DE19841930A1 (de) | 1998-09-14 | 2000-03-16 | Basf Ag | Stabile, pulverförmige Lycopin-Formulierungen, enthaltend Lycopin mit einem Kristallinitätsgrad von größer 20% |
-
2000
- 2000-12-21 DE DE10064387A patent/DE10064387A1/de not_active Withdrawn
-
2001
- 2001-12-04 EP EP01128813A patent/EP1219292B1/de not_active Expired - Lifetime
- 2001-12-04 DK DK01128813T patent/DK1219292T3/da active
- 2001-12-04 DE DE50103970T patent/DE50103970D1/de not_active Expired - Lifetime
- 2001-12-04 TR TR2004/02694T patent/TR200402694T4/xx unknown
- 2001-12-04 PT PT01128813T patent/PT1219292E/pt unknown
- 2001-12-04 SI SI200130251T patent/SI1219292T1/xx unknown
- 2001-12-04 AT AT01128813T patent/ATE278392T1/de not_active IP Right Cessation
- 2001-12-04 ES ES01128813T patent/ES2228737T3/es not_active Expired - Lifetime
- 2001-12-17 JP JP2001383736A patent/JP3595300B2/ja not_active Expired - Lifetime
- 2001-12-17 US US10/015,560 patent/US6639113B2/en not_active Expired - Fee Related
- 2001-12-21 CN CNB011454326A patent/CN1184201C/zh not_active Expired - Lifetime
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102341006A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 虾青素衍生物的粉状组合物ii |
CN112772923A (zh) * | 2021-02-02 | 2021-05-11 | 山东农业大学 | 一种基于大豆肽聚集体的β-胡萝卜素包埋乳液及其制备方法 |
CN113575945A (zh) * | 2021-07-20 | 2021-11-02 | 万华化学集团股份有限公司 | 一种纳米级高全反式类胡萝卜素干粉的制备方法 |
CN113575945B (zh) * | 2021-07-20 | 2023-12-19 | 万华化学集团股份有限公司 | 一种纳米级高全反式类胡萝卜素干粉的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
EP1219292A1 (de) | 2002-07-03 |
US20020165285A1 (en) | 2002-11-07 |
DK1219292T3 (da) | 2004-11-15 |
EP1219292B1 (de) | 2004-10-06 |
JP2002262824A (ja) | 2002-09-17 |
ES2228737T3 (es) | 2005-04-16 |
TR200402694T4 (tr) | 2004-11-22 |
DE10064387A1 (de) | 2002-06-27 |
ATE278392T1 (de) | 2004-10-15 |
US6639113B2 (en) | 2003-10-28 |
CN1184201C (zh) | 2005-01-12 |
PT1219292E (pt) | 2005-01-31 |
DE50103970D1 (de) | 2004-11-11 |
JP3595300B2 (ja) | 2004-12-02 |
SI1219292T1 (en) | 2005-02-28 |
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