CN1942106A - 生产一种或多种类胡萝卜素的干粉的方法 - Google Patents
生产一种或多种类胡萝卜素的干粉的方法 Download PDFInfo
- Publication number
- CN1942106A CN1942106A CNA2005800038953A CN200580003895A CN1942106A CN 1942106 A CN1942106 A CN 1942106A CN A2005800038953 A CNA2005800038953 A CN A2005800038953A CN 200580003895 A CN200580003895 A CN 200580003895A CN 1942106 A CN1942106 A CN 1942106A
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- China
- Prior art keywords
- carotenoid
- dry powder
- water
- mixture
- astaxanthin
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Abstract
本发明涉及生产一种或多种类胡萝卜素的干粉的方法，该方法特征在于：a)将一种或多种类胡萝卜素悬浮在由海藻糖和至少一种含蛋白的保护性胶体组成的混合物的分子分散水溶液或胶体分散水溶液中，和b)通过分离水并且任选分离额外使用的溶剂以及随后任选在涂敷材料存在下干燥，将形成的悬浮液转化为干粉。
Description
本发明涉及一种生产一种或多种类胡萝卜素的干粉的方法，优选生产含叶黄素的干粉的方法，尤其是生产含选自虾青素、角黄素、黄体素、玉米黄质、桔黄素(citranaxanthin)和β-阿朴-8’-胡萝卜素酸乙酯的叶黄素的干粉的方法。
类胡萝卜素类物质被分为两个主要组，即胡萝卜素和叶黄素。胡萝卜素为纯的多烯烃，例如β-胡萝卜素或番茄红素，它们不同于还具有氧官能度如羟基、环氧基和/或羰基的叶黄素。后一组的典型代表尤其是虾青素、角黄素、黄体素和玉米黄质。
含氧类胡萝卜素还包括桔黄素和β-阿朴-8’-胡萝卜素酸乙酯。
含氧类胡萝卜素广泛分布于自然界中且尤其存在于玉米(玉米黄质)、菜豆(黄体素)、红辣椒(辣椒红)、蛋黄(黄体素)以及虾和鲑鱼(虾青素)中，从而使这些食品具有其特征性颜色。
这些多烯可通过合成得到且可由天然源分离得到，它们是用于人用食品和动物饲料工业以及药物领域的重要着色材料且正如虾青素的情况一样，它们是在鲑鱼中具有维生素A原活性的活性物质。
胡萝卜素和叶黄素均不溶于水，而在油脂中仅具有低溶解性。该有限的溶解性和对氧化的高敏感性阻止了由化学合成得到的较粗颗粒状产品在人用食品和动物饲料着色中的直接使用，因为粗晶形式的物质贮存过程中不稳定并且仅提供不良的着色结果。这些对叶黄素在实际使用中不利的效果在含水介质中特别明显。
在人用食品的直接着色中改进给色量(color yield)仅可通过特殊生产的配制剂达到，在这些配制剂中，活性物质呈细碎形式且合适的话，由保护性胶体加以保护以防氧化。此外，这些配制剂在动物饲料中的应用导致类胡萝卜素或叶黄素的生物利用率更高，因而间接导致着色效果得到改进，例如在蛋黄或鱼着色中。
对于改进给色量和增加可吸收性或生物利用率而言，已经提出了各种各样的方法，且它们均以降低活性物质微晶的尺寸并使颗粒尺寸达到低于10μm的范围为目的。
尤其描述于Chimia(化学)21，329(1967)、WO91/06292和WO94/19411中的许多方法涉及使用胶体磨研磨类胡萝卜素并从而达到2-10μm的粒度。
还存在许多结合的乳化/喷雾干燥方法，例如DE-A-12 11 911或EP-A-0410 236中所述。
根据欧洲专利EP-B-0 065 193，呈细碎粉末形式的类胡萝卜素产品通过将类胡萝卜素在高温下、合适的话在高压下溶于挥发性、水混溶性有机溶剂中，通过与保护性胶体水溶液混合而沉淀该类胡萝卜素并随后喷雾干燥而生产。
生产细碎粉末形式的类胡萝卜素产品的类似方法描述于EP-A-0 937412中，其使用水不混溶性溶剂。
然而，如EP-B-0 065 193所述生产的叶黄素活性物质的纳米颗粒分散体经常出现下列现象。
含叶黄素的活性物质的含水分散体通常是胶体上不稳定的，尤其在浓缩时。活性物质颗粒部分因沉降且部分因分层而絮凝，使得该分散体不可能随后转化为干粉。
因此，对含叶黄素的配制剂在着色效应和生物利用率上的高要求由于对上述方法所述的问题而不能总是得到满足。
明胶的另一缺点是它们具有强粘附性能。在使用含明胶的产品时，采用常用于液态体系的干燥方法如喷雾干燥可能会成丝或结块。
另一因素是消费者不大愿意接受含明胶的产品。
在其他常用的保护性胶体如阿拉伯树胶、淀粉、糊精、果胶或黄蓍胶中，通常可以仅引入较低浓度的脂溶性物质。此外，由于产量低，阿拉伯树胶尤其在过去并不总是能够以足够量得到。
合成胶体如聚乙烯基吡咯烷酮或半合成聚合物如纤维素衍生物同样显示有限的乳化能力且并不总是被接受，尤其在人用食品领域。
DE-A-4 424 085描述了将部分降解的大豆蛋白用作脂溶性活性物质的保护性胶体。其中所公开的大豆蛋白的水解度为0.1-5％。用这些保护性胶体生产的配制剂的着色强度并不总是令人满意。
德国公开的说明书DE-A-101 04 494描述了通过大豆蛋白和乳糖一起使用作为保护性胶体生产类胡萝卜素干粉的方法。尽管其中公开的类胡萝卜素制剂具有改进的冷水再分散能力和提高的着色强度，可是这些配制剂在贮存期间的稳定性，特别是活性物质含量高时，并不总是令人满意。
本发明的目的是提供生产含类胡萝卜素的干粉的方法，尤其是生产含氧类胡萝卜素的干粉的方法，该方法不显示现有技术的上述缺点并且能够实现制剂中高的类胡萝卜素含量。
我们发现该目的由一种生产一种或多种类胡萝卜素的干粉的方法实现，该方法包括：
a)将一种或多种类胡萝卜素悬浮在海藻糖与至少一种含蛋白的保护性胶体的混合物的分子水溶液或胶体水溶液中，和
b)通过除去水并且合适的话除去额外使用的溶剂以及随后合适的话在涂敷材料存在下干燥而将形成的悬浮液转化为干粉。
适合的含蛋白的保护性胶体是：明胶，例如猪明胶或鱼明胶，尤其是起霜数(bloom number)范围为0-250的酸降解或碱降解的明胶，非常特别优选明胶A100和A200，以及起霜数为0且分子量为15 000-25 000D的低分子量酶催降解明胶类，例如Collagel A和Gelitasol P(来自Stoess，Eberbach)和这类明胶的混合物；酪蛋白和/或酪蛋白酸盐，例如，酪蛋白酸钠；植物蛋白如大豆蛋白、稻米蛋白和/或小麦蛋白，这些植物蛋白可以是部分降解或不降解的形式。
优选用于本发明的保护性胶体是酪蛋白或酪蛋白酸盐或它们的混合物。作为特别优选的保护性胶体应被提及的是酪蛋白酸钠。
上述方法的优选实施方案包括在转化成干粉之前研磨在工艺步骤a)中制备的悬浮液。此时活性物质[类胡萝卜素]优选在研磨之前以结晶形式悬浮。
研磨可以用本身已知的方式进行，例如使用球磨机。取决于所用磨机的类型，研磨一直进行到颗粒具有的由Fraunhofer衍射测定的平均粒度D[4.3]为0.1-100μm，优选0.2-50μm，特别优选0.2-20μm，非常特别优选0.2-5μm，尤其是0.2-0.8μm。术语D[4.3]指体积加权平均直径(参见MalvernMastersizer S手册，Malvern Instruments Ltd.，UK)。
研磨及其所用设备的其他详情尤其可在Ullmann工业化学大全(Ullmann’s Encyclopedia of Industrial Chemistry)第6版，2000，电子版，磨碎，第3.6章：湿研磨和EP-A-0 498 824中找到。
本发明方法的同样优选的方案包括在步骤a)中的悬浮包括下列步骤：
a1)将一种或多种类胡萝卜素溶于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)将一种或多种类胡萝卜素溶于水不混溶性有机溶剂中，和
a3)将在a1)或a2)中得到的溶液与海藻糖和至少一种含蛋白的保护性胶体的混合物的分子水溶液或胶体水溶液混合，形成作为纳米分散相的类胡萝卜素疏水相。
用于步骤a1)中的水混溶性溶剂尤其是水混溶性、热稳定的挥发性溶剂，其仅含碳、氢和氧，如醇、醚、酯、酮和缩醛。便于使用的溶剂是具有至少10％水混溶性、沸点低于200℃和/或低于10个碳的那些。特别优选使用的是甲醇、乙醇、正丙醇、异丙醇、1，2-丁二醇1-甲基醚、1，2-丙二醇1-正丙基醚、四氢呋喃或丙酮。
术语“水不混溶性有机溶剂”在本发明中意指在大气压力下在水中溶解度低于10％的有机溶剂。就此而论，可能的溶剂尤其是卤代脂族烃，如二氯甲烷、氯仿和四氯甲烷，羧酸酯如碳酸二甲酯、碳酸二乙酯、碳酸亚丙酯、甲酸乙酯、乙酸甲酯、乙酸乙酯或乙酸异丙酯以及醚如甲基叔丁基醚。优选的水不混溶性有机溶剂是下列化合物：碳酸二甲酯、碳酸亚丙酯、甲酸乙酯、乙酸乙酯、乙酸异丙酯和甲基叔丁基醚。
本发明方法优选包括生产含氧类胡萝卜素的干粉，特别优选选自虾青素、角黄素、黄体素、玉米黄质、桔黄素和β-阿朴-8’-胡萝卜素酸乙酯的化合物的干粉，非常特别优选虾青素和角黄素的干粉。
上述干粉有利的是以如下方式生产，其中将至少一种类胡萝卜素在30℃以上的温度、优选50-240℃、特别是100-200℃、特别优选140-180℃，合适的话在加压下溶于水混溶性有机溶剂中。
因为在高温下暴露有时会降低全反式异构体的所需高比例，因此类胡萝卜素的溶解应尽快进行，例如在数秒内，如0.1-10秒内，特别优选低于1秒。为了快速制备分子溶液，可能有利的是使用高压，如20-80巴，优选30-60巴。
然后向如此得到的分子溶液中直接加入海藻糖和至少一种含蛋白的保护性胶体的混合物的分子水溶液或胶体水溶液，合适的话将后者冷却，加入方式应使混合温度为约35-80℃。
在此过程中，溶剂组分转移到水相中且类胡萝卜素疏水相成为纳米分散相。
有关前述分散的方法和装置的详细描述参考EP B-0 065 193。
本发明同样涉及一种用于生产虾青素干粉的方法，其中
a)在30℃以上的温度下将虾青素溶于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)将所得溶液与海藻糖和酪蛋白或酪蛋白酸盐的混合物或者海藻糖和酪蛋白及酪蛋白酸盐的混合物的分子水溶液或胶体水溶液混合，和
c)将形成的悬浮液转化为干粉。
本发明中，用海藻糖与酪蛋白和/或酪蛋白酸钠的混合物，尤其是海藻糖与酪蛋白酸钠的混合物生产含虾青素的干粉的方法是非常特别优选的。
向干粉的转化尤其可以通过喷雾干燥、喷雾冷却、冷冻干燥或在流化床中干燥而进行，合适的话还存在涂敷材料。合适的涂敷剂尤其是玉米淀粉、二氧化硅或磷酸三钙。
为了增加活性物质对氧化降解的稳定性，有利的是加入基于粉末干重的浓度为2-10重量％，优选3-7重量％的稳定剂如α-生育酚、叔丁基羟基甲苯、叔丁基羟基苯甲醚、抗坏血酸、抗坏血酸钠或乙氧基喹。它们可以加入水相或溶剂相中，但优选与活性物质一起溶于溶剂相中。
为了增加活性物质对微生物降解的稳定性，有利的是向制剂中加入防腐剂，例如4-羟基苯甲酸甲酯、4-羟基苯甲酸丙酯、山梨酸或苯甲酸或它们的盐。
在某些情况下也有利的是额外将生理上可接受的油如芝麻油、玉米油、棉籽油、大豆油或花生油以及中链长度的植物脂肪酸酯，基于叶黄素以0-500重量％，优选10-300重量％，特别优选20-100重量％的浓度溶于溶剂相中，然后以极细的颗粒与活性物质和所述添加剂一起在与水相混合时沉淀。
保护性胶体和海藻糖与类胡萝卜素的比率通常选择得使所得最终产品含有0.1-40重量％、优选1-35重量％、特别优选5-30重量％，非常特别优选10-25重量％的至少一种类胡萝卜素，1-40重量％，优选2-30重量％，特别优选3-20重量％，非常特别优选5-15重量％的至少一种保护性胶体和10-80重量％，优选20-75重量％，特别优选30-70重量％，非常特别优选40-60重量％的海藻糖，并且合适的话还包括少量稳定剂和防腐剂，所有百分数均基于粉末的干重。
本发明还涉及可由开头所述的方法之一得到的类胡萝卜素干粉。
优选的干粉包含选自虾青素、角黄素、黄体素、玉米黄质、桔黄素和β-阿朴-8’-胡萝卜素酸乙酯的含氧类胡萝卜素，特别优选角黄素和虾青素，非常特别优选虾青素。
本发明制剂中虾青素含量优选为10-25重量％。
本发明的干粉的特征尤其在于它们能够无问题地再分散于含水体系中，得到粒度低于1μm的活性物质的均匀细分布。
使用海藻糖和含蛋白的保护性胶体，特别是酪蛋白或酪蛋白酸钠组合作为配制赋形剂与其他糖类如乳糖或蔗糖相比具有的优点是用其生产的类胡萝卜素制剂显示特别高的贮存稳定性(见表)。
上述干粉特别适合加入到人用食品和动物饲料中以及加入到药物制剂中。含类胡萝卜素的干粉在动物饲料方面的典型应用领域例如是水产养殖中的鱼类着色以及家禽饲养中的蛋黄和童子鸡(broiler)皮肤着色。
本发明方法的程序在下列实施例中详细说明。
实施例1
用海藻糖和酪蛋白酸钠的组合生产虾青素干粉
在可加热接收器中将66g结晶虾青素和15gα-生育酚在30℃下悬浮于496g室温下的共沸异丙醇/水混合物中。然后将活性物质悬浮液加热到90℃并以3.6kg/h的流速连续与流速为4.6kg/h且温度为220℃的其他异丙醇/水共沸物混合，虾青素在55巴的压力下于设定为165℃的混合温度下溶解。将该活性物质溶液立即与由29g酪蛋白酸钠和166g海藻糖在8724g蒸馏水中的溶液组成的水相以55kg/h的流速混合，其中用1M NaOH将pH调至9.5。
混合时产生的活性物质颗粒在异丙醇/水混合物中的粒度为130nm，E1/1值1)为117。
然后将活性物质悬浮液在薄膜蒸发器中浓缩至活性物质干含量为约27.4％的浓度并喷雾干燥。该干粉的虾青素含量为22.4重量％。再分散于水中的该干粉具有的粒度为141nm且E1/1值为120。
1)E1/1值在此定义为在1cm比色杯中20重量％干粉的0.5％浓度的水分散体在最大吸收时的比消光。
实施例2(对比例)
使用乳糖和酪蛋白酸钠的组合生产虾青素干粉
在可加热接收器中将83.5g结晶虾青素和20gα-生育酚在30℃下悬浮于626g室温下的共沸异丙醇/水混合物中。然后将活性物质悬浮液加热到90℃并以2.1kg/h的流速连续与流速为2.6kg/h且温度为220℃的其他异丙醇/水共沸物混合，虾青素在55巴的压力下于设定为165℃的混合温度下溶解。将该活性物质溶液立即与由83.5g酪蛋白酸钠和177g乳糖在20580g蒸馏水中的溶液组成的水相以60kg/h的流速混合，其中用1M NaOH将pH调至9.5。
混合时产生的活性物质颗粒在异丙醇/水混合物中的粒度为133nm，E1/1值为123。
然后将活性物质悬浮液在薄膜蒸发器中浓缩至活性物质干含量为约6.9％的浓度并喷雾干燥。该干粉的虾青素含量为22.5重量％。再分散于水中的该干粉具有的粒度为167nm且E1/1值为123。
实施例3(对比例)
使用乳糖和大豆蛋白的组合生产虾青素干粉
在可加热接收器中将83.5g结晶虾青素和20gα-生育酚在30℃下悬浮于626g室温下的共沸异丙醇/水混合物中。然后将活性物质悬浮液加热到90℃并以2.1kg/h的流速连续与流速为2.6kg/h且温度为220℃的其他异丙醇/水共沸物混合，虾青素在55巴的压力下于设定为165℃的混合温度下溶解。将该活性物质溶液立即与由83.5g大豆蛋白和177g乳糖在11010g蒸馏水中的溶液组成的水相以32.5kg/h的流速混合，其中用1M NaOH将pH调至9.5。
混合时产生的活性物质颗粒在异丙醇/水混合物中的粒度为107nm，E1/1值为124。
然后将活性物质悬浮液在薄膜蒸发器中浓缩至活性物质干含量为约23.7％的浓度并喷雾干燥。该干粉的虾青素含量为23重量％。再分散于水中的该干粉具有的粒度为317nm且E1/1值为101。
实施例4(对比例)
使用葡萄糖浆粉(Glucidex47，来自Roquette Freres)和酪蛋白酸钠的组合生产虾青素干粉
在可加热接收器中将66g结晶虾青素和15gα-生育酚在30℃下悬浮于496g室温下的共沸异丙醇/水混合物中。然后将活性物质悬浮液加热到90℃并以3.6kg/h的流速连续与流速为4.6kg/h且温度为220℃的其他异丙醇/水共沸物混合，虾青素在55巴的压力下于设定为165℃的混合温度下溶解。然后将该活性物质溶液立即与由28.7g酪蛋白酸钠和165.6g Glucidex 47在8724g蒸馏水中的溶液组成的水相以56kg/h的流速混合，其中用1M NaOH将pH调至9.5。
混合时产生的活性物质颗粒在异丙醇/水混合物中的粒度为144nm，E1/1值为115。
然后将活性物质悬浮液在薄膜蒸发器中浓缩至活性物质干含量为约19.4％的浓度并喷雾干燥。该干粉的虾青素含量为23.6重量％。再分散于水中的该干粉具有的粒度为623nm且E1/1值为119。
实施例5(对比例)
使用葡萄糖浆粉(Glucidex47，来自Roquette Freres)和酪蛋白酸钠的组合生产虾青素干粉
在可加热接收器中将83.5g结晶虾青素和20gα-生育酚在30℃下悬浮于626g室温下的共沸异丙醇/水混合物中。然后将活性物质悬浮液加热到90℃并以3.6kg/h的流速连续与流速为4.6kg/h且温度为220℃的其他异丙醇/水共沸物混合，虾青素在55巴的压力下于设定为165℃的混合温度下溶解。然后将该活性物质溶液立即与由83.5g酪蛋白酸钠和177g Glucidex47在11010g蒸馏水中的溶液组成的水相以56kg/h的流速混合，其中用1MNaOH将pH调至9.5。
混合时产生的活性物质颗粒在异丙醇/水混合物中的粒度为155nm，E1/1值为116。
然后将活性物质悬浮液在薄膜蒸发器中浓缩至活性物质干含量为约25％的浓度并喷雾干燥。该干粉的虾青素含量为22.3重量％。再分散于水中的该干粉具有的粒度为179nm且E1/1值为117。
表：贮存期间虾青素干粉的稳定性(60℃下的耐热性试验)
| 10天后 | 20天后 | ||||||
| 实施例 | 糖 | 蛋白质 | 虾青素含量 | 含量(％) | 损失(％) | 含量(％) | 损失(％) |
| 1 | 海藻糖 | 酪蛋白酸钠 | 22.4 | 21.3 | 5.0 | 20.6 | 7.8 |
| 2 | 乳糖 | 酪蛋白酸钠 | 22.5 | 14.2 | 36.9 | 12.5 | 44.2 |
| 3 | 乳糖 | 大豆蛋白 | 23.0 | 19.3 | 15.9 | 17.7 | 22.9 |
| 4 | 葡萄糖浆 | 酪蛋白酸钠 | 23.6 | 22.0 | 6.5 | 20.8 | 11.7 |
| 5 | 葡萄糖浆 | 酪蛋白酸钠 | 22.3 | 18.3 | 17.8 | 16.6 | 25.6 |
Claims (12)
1.一种通过如下步骤生产一种或多种类胡萝卜素的干粉的方法，包括：
a)将一种或多种类胡萝卜素悬浮在海藻糖与至少一种含蛋白的保护性胶体的混合物的分子水溶液或胶体水溶液中，和
b)通过除去水并且合适的话除去额外使用的溶剂以及随后合适的话在涂敷材料存在下干燥而将形成的悬浮液转化为干粉。
2.如权利要求1所要求的方法，其中在转化成干粉之前研磨在工艺步骤a)中制备的悬浮液。
3.如权利要求1所要求的方法，其中在步骤a)中的悬浮包括如下步骤：
a1)将一种或多种类胡萝卜素溶于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)将一种或多种类胡萝卜素溶于水不混溶性有机溶剂中，和
a3)将在a1)或a2)中得到的溶液与海藻糖和至少一种含蛋白的保护性胶体的混合物的分子水溶液或胶体水溶液混合，形成作为纳米分散相的类胡萝卜素疏水相。
4.如权利要求1-3中任一项所要求的方法，其中将酪蛋白或酪蛋白酸盐或它们的混合物用作保护性胶体。
5.如权利要求1-4中任一项所要求的方法，其中所用类胡萝卜素是含氧类胡萝卜素。
6.如权利要求5所要求的方法，其中含氧类胡萝卜素是选自虾青素、角黄素、黄体素、玉米黄质、桔黄素和β-阿朴-8’-胡萝卜素酸乙酯的化合物。
7.一种生产虾青素干粉的方法，其中
a)在30℃以上的温度下将虾青素溶于水混溶性有机溶剂或水与水混溶性有机溶剂的混合物中，
b)将所得溶液与海藻糖和酪蛋白或酪蛋白酸盐的混合物或者海藻糖与酪蛋白和酪蛋白酸盐的混合物的分子水溶液或胶体水溶液混合，和
c)将形成的悬浮液转化为干粉。
8.如权利要求7所要求的方法，其中将海藻糖和酪蛋白酸钠的混合物在步骤b)中用作保护性胶体。
9.一种可由权利要求1-8中任一项所定义的方法得到的含类胡萝卜素的干粉。
10.如权利要求9所要求的干粉，类胡萝卜素含量为0.1-40重量％。
11.如权利要求10所要求的干粉，包含10-25重量％的虾青素。
12.如权利要求9-11中任一项所定义的含类胡萝卜素的干粉添加到人用食品、药物和/或动物饲料中的用途。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004006106A DE102004006106A1 (de) | 2004-02-06 | 2004-02-06 | Verfahren zur Herstellung von Trockenpulvern eines oder mehrerer Carotinolde |
| DE102004006106.8 | 2004-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1942106A true CN1942106A (zh) | 2007-04-04 |
Family
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Family Applications (1)
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| CNA2005800038953A Pending CN1942106A (zh) | 2004-02-06 | 2005-02-02 | 生产一种或多种类胡萝卜素的干粉的方法 |
Country Status (8)
| Country | Link |
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| US (1) | US20070173547A1 (zh) |
| EP (1) | EP1713746A2 (zh) |
| JP (1) | JP2007521812A (zh) |
| CN (1) | CN1942106A (zh) |
| CA (1) | CA2552931A1 (zh) |
| DE (1) | DE102004006106A1 (zh) |
| NO (1) | NO20063962L (zh) |
| WO (1) | WO2005075385A2 (zh) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102341007A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 生产虾青素衍生物的溶液的方法 |
| CN102341005A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 虾青素衍生物的配制剂及其应用iii |
| 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 |
| CN105582001A (zh) * | 2015-12-25 | 2016-05-18 | 南京泛成生物化工有限公司 | 一种虾青素组合物、制剂及其制备方法 |
| CN108366605A (zh) * | 2015-12-10 | 2018-08-03 | 帝斯曼知识产权资产管理有限公司 | 维生素制剂 |
| CN108578385A (zh) * | 2018-08-01 | 2018-09-28 | 西南大学 | 一种类胡萝卜素-白蛋白复合物及其制备方法和应用 |
| 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2009048120A1 (ja) * | 2007-10-11 | 2011-02-24 | 日清ファルマ株式会社 | アスタキサンチン含有水溶性組成物 |
| JP2009185023A (ja) * | 2008-01-07 | 2009-08-20 | Fujifilm Corp | 粉末組成物及びその製造方法、並びにこれを含む食品組成物、化粧品組成物及び医薬品組成物 |
| 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 |
| BR112020018548A2 (pt) * | 2018-03-16 | 2020-12-29 | Ajinomoto Co., Inc. | Composição de aditivo de ração de tipo revestido, ração, e, método para melhorar um ganho de peso corporal de gado |
| CN111714466A (zh) | 2019-03-18 | 2020-09-29 | 浙江医药股份有限公司新昌制药厂 | 一种高生物利用度高稳定性的类胡萝卜素制剂的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE19651681A1 (de) * | 1996-12-12 | 1998-06-18 | Basf Ag | Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthopyllen, deren Herstellung und Verwendung |
| DE19919751A1 (de) * | 1999-04-29 | 2000-11-09 | Basf Ag | Stabile, wäßrige Dispersionen und stabile, wasserdispergierbare Trockenpulver von Xanthophyllen, deren Herstellung und Verwendung |
| DE10104494A1 (de) * | 2001-01-31 | 2002-08-01 | Basf Ag | Verfahren zur Herstellung von Trockenpulvern eines oder mehrerer Carotinoide |
-
2004
- 2004-02-06 DE DE102004006106A patent/DE102004006106A1/de not_active Withdrawn
-
2005
- 2005-02-02 CA CA002552931A patent/CA2552931A1/en not_active Abandoned
- 2005-02-02 EP EP05707139A patent/EP1713746A2/de not_active Withdrawn
- 2005-02-02 CN CNA2005800038953A patent/CN1942106A/zh active Pending
- 2005-02-02 JP JP2006551788A patent/JP2007521812A/ja not_active Withdrawn
- 2005-02-02 WO PCT/EP2005/001016 patent/WO2005075385A2/de not_active Application Discontinuation
- 2005-02-02 US US10/587,562 patent/US20070173547A1/en not_active Abandoned
-
2006
- 2006-09-05 NO NO20063962A patent/NO20063962L/no not_active Application Discontinuation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102341007A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 生产虾青素衍生物的溶液的方法 |
| CN102341005A (zh) * | 2009-03-05 | 2012-02-01 | 巴斯夫欧洲公司 | 虾青素衍生物的配制剂及其应用iii |
| 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 |
| CN108366605A (zh) * | 2015-12-10 | 2018-08-03 | 帝斯曼知识产权资产管理有限公司 | 维生素制剂 |
| CN105582001A (zh) * | 2015-12-25 | 2016-05-18 | 南京泛成生物化工有限公司 | 一种虾青素组合物、制剂及其制备方法 |
| CN108578385A (zh) * | 2018-08-01 | 2018-09-28 | 西南大学 | 一种类胡萝卜素-白蛋白复合物及其制备方法和应用 |
| 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 |
|---|---|
| WO2005075385A2 (de) | 2005-08-18 |
| EP1713746A2 (de) | 2006-10-25 |
| DE102004006106A1 (de) | 2005-08-25 |
| US20070173547A1 (en) | 2007-07-26 |
| NO20063962L (no) | 2006-09-05 |
| WO2005075385A3 (de) | 2007-02-08 |
| JP2007521812A (ja) | 2007-08-09 |
| CA2552931A1 (en) | 2005-08-18 |
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