CN1252238A - 稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂 - Google Patents
稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂 Download PDFInfo
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- CN1252238A CN1252238A CN99118848A CN99118848A CN1252238A CN 1252238 A CN1252238 A CN 1252238A CN 99118848 A CN99118848 A CN 99118848A CN 99118848 A CN99118848 A CN 99118848A CN 1252238 A CN1252238 A CN 1252238A
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Abstract
本发明涉及稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂、其制法和其作为食品、化妆品、药品和动物饲料的添加剂的应用。
Description
本发明涉及稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂、其制法和其作为食品、化妆品、药品和动物饲料的添加剂的应用。
番茄红素属于类胡萝卜素类物质,广泛存在于自然界。因此,具有大约20mg/kg番茄的番茄红素含量的番茄形成了最重要的这种红色颜料的天然来源。
流行病学研究表明,比较经常和规律地食用番茄或番茄产品可降低慢性疾病、尤其是心脏和循环疾病的危险,并且对癌症的预防具有积极的作用。番茄红素的该保护性功能可以从其作为非常有效的抗氧剂的作用中看出。
无论是对食品和饲料工业还是对药物技术来说,番茄红素,例如作为人造着色剂的替代品,代表着重要的染料,并且由于在本文开头所述的作为健康食品添加剂的理由具有重要的意义。
番茄红素的合成被描述在尤其是EP-A-382067和EP-A-000140中。WO97/48287描述了从番茄中提取番茄红素作为天然类胡萝卜素。
象所有的类胡萝卜素一样,番茄红素也不溶于水,虽然溶于脂肪和油类,但其仅微溶。该有限的溶解度和对氧化的高敏感性妨碍在食品和饲料的着色中直接使用比较粗粒的结晶番茄红素,这是因为粗晶形式的纯物质太不稳定,不能被充分吸收,因此着色效果差。
只有使用特殊制备的、其中活性化合物以细分形式存在并且如果适当的话被保护性胶体保护以抗氧化的制剂才可以在食品的直接着色中产生改进的颜色。
鉴于番茄红素与其它类胡萝卜素相比特别低的对氧化的稳定性和与之有关的低的颜色稳定性和储存稳定性,所以对这些制剂要求很高。
对于类胡萝卜素,已经泛泛地描述了许多制剂和其制备方法。
这样,例如,番茄红素可以以Lyc-O-Mato(LycoRed,以色列)名称作为6%的油分散液得到。它是根据WO97/48287作为天然类胡萝卜素从番茄中提取的。由于在Lyc-O-Mato中的高磷脂含量以及所述油分散液的高粘度,该制剂的使用性质,尤其是水可分散性不是令人满意的。
EP-A-0410236描述了一种制备类胡萝卜素干粉的方法,其中将类胡萝卜素的悬浮液在高沸点的油中短暂加热,将该熔融的类胡萝卜素和油的混合物在胶体的水溶液中乳化,然后将该乳液喷雾干燥。
DE-A-1211911描述了类胡萝卜素产品,其制备是首先将类胡萝卜素溶解在水不溶性溶剂中,然后将该溶液乳化到保护性胶体水溶液中并喷雾干燥。
EP-A-0065193描述了一种制备粉状类胡萝卜素产品的方法,该方法包括,将类胡萝卜素在升高的温度下短暂地溶解在水可混溶的有机溶剂中,通过迅速与保护性胶体的水溶液混合立即以胶体分散的形式从所得溶液中沉淀类胡萝卜素并将产生的分散液转化成干粉。
根据EP-A-0832569,其中活性化合物颗粒以X-射线无定型形式大量存在的类胡萝卜素干粉通过热处理按照EP-A-0065193在40℃-90℃之间的温度下制备的分散液和随后喷雾干燥得到。
WO98/16204描述了一种制备粉状类胡萝卜素产品的方法,该方法包括,在升高的温度和压力下在高压釜中将类胡萝卜素溶解在甲醚中,然后通过非常迅速地减压再一次除去溶剂。
许多方法,尤其是描述在Chimia 21,329(1967)、WO91/06292和WO94/19411中的方法,都利用了通过胶体磨研磨类胡萝卜素如β-胡萝卜素,由此得到2-10μm的粒度。
虽然在该领域有许多公开物,但是在该先有技术中述及的文章中没有一篇在关于类胡萝卜素制剂的一般说明之外给出解决番茄红素的稳定性问题的信息。
因此,本发明的目的是制备可利用的粉状的番茄红素制剂,其中番茄红素对氧化和光是特别稳定的,并且没有上述先有技术的缺点。
我们发现,该目的根据本发明通过稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂可以实现。
在本发明制剂中的番茄红素的结晶度可以例如通过X-射线衍射测量法测定,一般在大于20%、优选在25-100%、特别优选在30-95%、非常特别优选在40-80%之间的范围内。
关于双键的异构问题,在所述的粉状制剂中所含的番茄红素可以不受限制地以所有的异构形式存在,例如以全反、5-顺式或9,13-二顺式形式存在。优选的粉状制剂是含有具有至少50%全反含量的番茄红素、特别优选具有52-100%全反含量的番茄红素、非常特别优选具有55-90%全反含量的番茄红素的那些制剂。
番茄红素在本发明制剂中的含量基于制剂的干重在0.5-25%重量、优选2-21%重量、特别优选5-16%重量、非常特别优选8-12%重量的范围内。
干粉中番茄红素的平均粒度在10μm以下、优选5.0μm以下、特别优选在0.05-1μm的范围内。
为了增加粉状番茄红素制剂的稳定性,除了活性化合物之外,于制剂中掺入保护性胶体、增塑剂和/或稳定剂是有利的。
所用的保护性胶体是例如明胶、鱼胶、淀粉、糊精、植物蛋白、果胶、阿拉伯树胶、酪蛋白、酪蛋白酸盐或其混合物。然而,也可以使用聚乙烯醇、聚乙烯吡咯烷酮、甲基纤维素、羧甲基纤维素、羟丙纤维素和藻酸盐。有关更详细的情况,参见R.A.Morton,Fat Soluble Vitamins,Intern.Encyclopedia of Food and Nutrition,Vol.9,Pergamon Press 1970,pp.128-131。为了增加最终产品的机械稳定性,方便地于胶体中加入增塑剂如糖或糖醇如蔗糖、葡萄糖、乳糖、转化糖、山梨糖醇、甘露醇或甘油。
保护性胶体和增塑剂与类胡萝卜素溶液的比率一般选择得使得得到的最终产品含有0.5-25%重量的番茄红素、10-50%重量、优选15-35%重量的保护性胶体、20-70%重量、优选30-60%重量的增塑剂,所有百分率都是基于粉末的干重,并且,如果适当,含有少量的稳定剂。
为了增加活性化合物对氧化降解的稳定性,加入基于干制剂的0-10%重量、优选0.5-7.5%重量的一种或多种稳定剂如α-生育酚、叔丁基羟基甲苯、叔丁基羟基苯甲醚、抗坏血酸或乙氧喹可能是有利的。
此外,可以使用乳化剂例如抗坏血酸棕榈酸酯(ascorbyl palmitate)、聚甘油脂肪酸酯、脱水山梨糖醇脂肪酸酯、丙二醇脂肪酸酯或卵磷脂,基于番茄红素,其浓度为0-200%重量、优选5-150%重量、特别优选10-80%重量。
在某些情况下,另外使用生理上可接受的油如芝麻油、玉米油、棉籽油、豆油或花生油和中链植物脂肪酸的酯也可以是有利的,基于番茄红素,其浓度为0-500%重量、优选10-300%重量、特别优选20-100%重量。
除了番茄红素,制剂中也可以含有其它类胡萝卜素如β-胡萝卜素、胭脂树橙、玉米黄质、隐黄质、citranaxanthin、鸡油菌黄素、β-脱辅基(apo)-4-carotenal、β-脱辅基-8-carotenal、β-脱辅基-8-胡萝卜素酸酯、虾青素或叶黄素,它们可被单独地或作为混合物含有。
本发明也涉及一种制备本文开头所述的稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂的方法,该方法包括
a).在高于30℃的温度下在水可混溶的有机溶剂或水与水可混溶的有机溶剂的混合物中制备番茄红素的分子分散溶液,如果适当的话与乳化剂和/或可食用油一起制备,
b).将该溶液与保护性胶体的水溶液混合,亲水性溶剂组分被转移到了水相中,而疏水的类胡萝卜素相作为毫微分散(nanodisperse)相产生,以及
c).将形成的分散液从用于制备水可分散的干粉的溶剂和水中分离出来,并且,如果适当,在涂覆物质存在下干燥。
特别适用于用来进行本发明方法的是水可混溶的、热稳定的、挥发性的仅含有碳、氢和氧的溶剂如醇类、醚类、酯类、酮类和缩醛类。优选使用乙醇、正丙醇、异丙醇、1,2-丁二醇1-甲基醚、1,2-丙二醇1-正丁基醚或丙酮。一般来说,可方便地使用的溶剂是至少10%水可混溶的、沸点低于200℃和/或有少于10个碳原子的那些溶剂。
在本方法的优选实施方案中,在步骤a)中,在50-240℃、特别优选在140-180℃的温度下制备分子分散的番茄红素溶液,随后在步骤b)中立即与保护性胶体的水溶液混合,混合温度设定在大约35-80℃,特别优选55-70℃。
因为高温的作用可以降低所需的高的全反异构体的含量,所以尽可能快地将番茄红素溶解,例如在数秒钟如0.1-10秒钟内,特别优选在不到1秒钟的时间内。为了迅速制备所述的分子分散溶液,使用高压如20-100bar、优选30-80bar可能是有利的。
根据所用的保护性胶体的类型和量,由方法步骤b)得到深颜色的粘稠液体。溶剂可以通过例如用与水不混溶的溶剂进行提取来除去,或,根据沸点,以本身已知的方法如通过蒸馏,如果适当在减压下蒸馏来除去。在这种情况下,已证实是方便和可能的是直接使用在使用异丙醇时得到的共沸物,而不用除去水。然而,优选地,通过喷雾干燥或喷雾制粒将水和溶剂一起除去。
关于该方法和设备的更详细的描述,具体参见EP-A-0065193。
通过上述方法制备的番茄红素干粉的特征是无论在热水还是在冷水中都具有非常好的可再分散性。
现已发现,由上述方法制备的粉状番茄红素制剂与相应的β-胡萝卜素和鸡油菌黄素制剂相比具有出人意料的性能。β-胡萝卜素和鸡油菌黄素以具有仅仅10%的结晶度、主要是无定型形式存在于根据EP-A-0065193制备的干粉中,而借助X-射线衍射图测得的本制剂中番茄红素的结晶度在大于20%、优选25-100%、特别优选30-95%、非常特别优选40-80%的范围内。
图1是表1中所述的番茄红素、β-胡萝卜素和鸡油菌黄素干粉各自的X-射线衍射图。广角X-射线图在1°≤2Θ≤40°的角范围内记录。活性化合物结晶度WCW的测定根据WCW=FCW/F100·CW在11°≤2Θ≤31°的图段进行,其中大部分活性化合物发生了干涉。在该种情况下,F100是在可比较的条件下测定的并在同样的角范围内通过测面法得到的纯活性化合物的结晶散射,而CW是活性化合物在制剂中的浓度。
出人意料的还有,通过这种方法制备的本发明的番茄红素制剂与相应的β-胡萝卜素和鸡油菌黄素制剂相比在光化学稳定性试验中具有特别的光稳定性(参见表1)。
表1
1)根据实施例1制备2)在光稳定性试验中在最大吸收时初始消光减至一半时的照射时间3)3)在光稳定性试验中,将每种情况下待试验的干粉分散在去矿化的水中,用柠檬酸调至pH3并在通于大气的50ml石英安瓿中在SuntestCPS仪器(Heraeus)中照射。作为照射时间的函数测定UV/VIS光谱。
下列物质的干粉1) | 含量[%重量] | 全反含量[%] | 结晶度[%] | 半衰期2)(分钟) |
番茄红素 | 10 | 72 | 64 | 160 |
β-胡萝卜素 | 10 | 78 | 10 | 28 |
鸡油菌黄素 | 10 | 73 | 0 | 34 |
此外,本发明还涉及另一种制备稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂的方法,该方法包括,在保护性胶体存在下在水介质中研磨全反异构体含量为至少50%的结晶番茄红素并干燥所得到的番茄红素悬浮液以制备干粉。这样得到的干粉又可以容易地再分散到水中例如用于着色目的。
关于该方法和设备的更详细的描述,具体参见EP-A-0498824。
令人惊奇的是,在上述所要求保护的用于制备番茄红素干粉的研磨方法中,可以通过改变研磨时间和/或研磨温度来调节番茄红素的结晶度。
除了已经描述的本发明的番茄红素干粉的有利的着色稳定性外,还观察到了非常好的储存稳定性。因此,通过研磨方法制备的含番茄红素的制剂例如在药物产品如多维片中显示出显著的储存稳定性(参见表2)。
表2
1)根据实施例3制备2)在多维/矿物片中在40℃和75%空气湿度条件下储存后的番茄红素的储存稳定性
下列物质的干粉1) | 含量[%重量] | 结晶度[%] | 储存3个月的时间后的含量2)[%] |
番茄红素 | 10 | 33 | 89 |
番茄红素 | 10 | 25 | 80 |
番茄红素 | 10 | 19 | 60 |
除了本发明的制备番茄红素制剂的方法外,其它制备方法,尤其是在本文开头作为先有技术所引用那些,任选地也可以被想到,例如结合的乳化和喷雾干燥方法。
本发明还涉及稳定的、含有结晶度大于20%的番茄红素的番茄红素水分散液。
这些分散液例如通过在本发明的制备番茄红素干粉的方法中省去干燥步骤如喷雾干燥步骤来获得。
正象粉状番茄红素制剂一样,番茄红素水分散液显示出非常好的光稳定性。
本发明的番茄红素制剂适合于尤其是在人和兽医领域作为食品的添加剂、作为制备药品和化妆品和制备食品添加剂产品的组分。
在食品领域中典型的使用方面是例如饮料、奶制品如酸乳酪、奶饮品或奶基冰淇淋的着色和牛奶冻粉、蛋产品、烘烤混合物和糖食的着色。
在食品领域中,番茄红素制剂可被用于例如在家禽饲养中对蛋黄和烤皮着色。
在化妆品领域,番茄红素干粉可以用于例如作为用于装饰性的身体护理组合物的着色剂。
本发明还涉及含有上述番茄红素制剂的食品添加剂、动物饲料、食品、药物制剂和化妆品。
含有本发明的番茄红素制剂的食品添加剂产品和药物制剂应被理解为是指尤其是片剂、包衣片和硬和软明胶胶囊。
可以含有本发明的番茄红素制剂的化妆品是例如可局部使用的制剂,特别是装饰性身体护理组合物如唇膏、面霜、洗液、粉末或作为胭脂。
本发明的番茄红素制剂在下列实施例中被更详细地解释。
实施例1
10%浓度的番茄红素干粉的制备
将25g结晶番茄红素悬浮在4.6g抗坏血酸棕榈酸酯和3.6gα-生育酚在300g异丙醇中的溶液中。在2.0kg/h的进料速率和50bar的系统压力下将该悬浮液与400g异丙醇(进料速率2.6kg/h)混合,通过热交换器进行加热。将在170℃的温度下在此过程中形成的分子分散溶液在混合室中与72.4g鱼胶和108g葡萄糖浆在4776g水中的溶液湍流地混合,以30.5kg/h排出,以形成番茄红素微分散相在水/异丙醇的混合物中的分散液(番茄红素含量0.3%)。将该分散液在真空蒸发器中浓缩(番茄红素含量3.0%),除去了异丙醇,然后通过喷雾干燥转化成干粉。光度法测得的番茄红素含量是9.8%。
通过准弹性光散射测得的平均粒度是134nm。通过HPLC测得的全反含量是72%;通过广角X-射线散射测得的番茄红素的结晶度是64%。
实施例2
20%浓度的番茄红素干粉的制备
将50g结晶番茄红素悬浮在4.6g抗坏血酸棕榈酸酯和3.6gα-生育酚在275g异丙醇中的溶液中。在2.0kg/h的进料速率和50bar的系统压力下将该悬浮液与433g异丙醇(进料速率2.6kg/h)混合,通过热交换器进行加热。将在170℃的温度下在此过程中形成的分子分散溶液在混合室中与72.4g鱼胶和108g葡萄糖浆在4773g水中的溶液湍流地混合,以30.5kg/h排出,以形成番茄红素微分散相在水/异丙醇的混合物中的分散液。将该分散液在真空蒸发器中浓缩(番茄红素含量4.8%),然后通过喷雾干燥转化成干粉。光度法测得的番茄红素含量是20%。
通过准弹性光散射测得的平均粒度是244nm。通过HPLC测得的全反含量是52%;通过广角X-射线散射测得的番茄红素的结晶度是51%。
实施例3
结晶番茄红素的研磨
在保护性气体下,将15g结晶番茄红素加到加热至60℃的、21g 240Bloom A明胶和1.5g抗坏血酸钠在150ml水中的溶液中。将该悬浮液用球磨机(DynoMillType KDL)研磨7小时。加入20g明胶、35g蔗糖和1.5g生育酚后,将悬浮液喷雾干燥。得到了番茄红素含量为10%重量的干粉。通过HPLC测得的全反含量是91%;通过广角X-射线散射测得的番茄红素的结晶度是33%。
Claims (17)
1.稳定的、含有结晶度大于20%的番茄红素的粉状番茄红素制剂。
2.根据权利要求1的番茄红素制剂,包含全反异构体含量至少为50%的番茄红素。
3.根据权利要求1或2的番茄红素制剂,包含0.5-25%重量的番茄红素、10-50%重量的保护性胶体、20-70%重量的增塑剂、0-10%重量的稳定剂,所有百分率都是基于粉末的干重。
4.根据权利要求1-3任一项的番茄红素制剂,包含粒度小于10μm的番茄红素。
5.根据权利要求1-4任一项的番茄红素制剂,其是水可分散的。
6.制备如权利要求1中定义的稳定的粉状番茄红素制剂的方法,该方法包括
a).在高于30℃的温度下在水可混溶的有机溶剂或水与水可混溶的有机溶剂的混合物中制备番茄红素的分子分散溶液,如果适当的话与乳化剂和/或可食用油一起制备,
b).将该溶液与保护性胶体的水溶液混合,亲水性溶剂组分被转移到了水相中,而疏水的类胡萝卜素相作为毫微分散相产生,以及
c).将形成的分散液从用于制备水可分散干粉的溶剂和水中分离出来,并且,如果适当,在涂覆物质存在下干燥。
7.根据权利要求6的方法,其中,在步骤a)中,在50-240℃的温度下制备分子分散的番茄红素溶液,随后在步骤b)中立即与保护性胶体的水溶液混合,混合温度设定在大约35-80℃。
8.一种稳定的、含有具有大于20%结晶度的番茄红素的番茄红素水分散液。
9.根据权利要求8的稳定的番茄红素水分散液,它是由省去了干燥步骤的权利要求6的方法制备的。
10.制备如权利要求1中定义的稳定的粉状番茄红素制剂的方法,该方法包括,在保护性胶体存在下在水介质中研磨全反异构体含量为至少50%的结晶番茄红素并干燥所得到的用来制备干粉的番茄红素悬浮液。
11.根据权利要求10的方法,其中可以通过改变研磨时间和/或研磨温度来调节粉状制剂中的番茄红素的结晶度。
12.根据权利要求8的稳定的番茄红素水分散液,它是通过省去了干燥步骤的权利要求10中所定义的方法制备的。
13.权利要求1中所定义的稳定的粉状番茄红素制剂用于制备食品添加剂和作为食品、动物饲料、药物制品和化妆品的添加剂的应用。
14.根据权利要求13的稳定的粉状番茄红素制剂作为着色剂的应用。
15.权利要求8中所定义的稳定的番茄红素水分散液用于制备食品添加剂和作为食品、动物饲料、药物制品和化妆品的添加剂的应用。
16.根据权利要求15的稳定的番茄红素水分散液作为着色剂的应用。
17.含有权利要求1和8任一项所定义的番茄红素制剂的食品添加剂、动物饲料、食品、药物制剂或化妆品。
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-
1999
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- 1999-09-02 DK DK99117236.2T patent/DK0986963T3/en active
- 1999-09-02 ES ES99117236.2T patent/ES2617144T3/es not_active Expired - Lifetime
- 1999-09-08 IL IL13179199A patent/IL131791A/en not_active IP Right Cessation
- 1999-09-10 CA CA002282184A patent/CA2282184C/en not_active Expired - Fee Related
- 1999-09-14 US US09/395,772 patent/US6235315B1/en not_active Expired - Lifetime
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2003028481A1 (fr) * | 2001-09-28 | 2003-04-10 | Xinjiang Jinqi Industry Limited | Procede de preparation de lycopene |
CN101006854B (zh) * | 2006-05-27 | 2011-08-17 | 新疆屯河投资股份有限公司 | 番茄红素粉的制备方法 |
CN101583286B (zh) * | 2007-01-16 | 2013-08-21 | 巴斯夫欧洲公司 | 含有类胡萝卜素的液体配制剂 |
CN101417917B (zh) * | 2008-11-05 | 2013-01-16 | 江苏江山制药有限公司 | 一种高纯度全反式番茄红素晶体的制备方法 |
CN110317685A (zh) * | 2019-07-22 | 2019-10-11 | 辽宁富康源黑果花楸科技开发有限公司 | 不老莓香皂 |
CN110317685B (zh) * | 2019-07-22 | 2021-03-16 | 辽宁富康源黑果花楸科技开发有限公司 | 不老莓香皂 |
CN111714413A (zh) * | 2020-05-26 | 2020-09-29 | 新疆亲努尔生物科技有限公司 | 一种含有番茄红素提取物的抗氧化润唇膏及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP4988081B2 (ja) | 2012-08-01 |
CA2282184C (en) | 2008-07-15 |
US6235315B1 (en) | 2001-05-22 |
CN1125601C (zh) | 2003-10-29 |
ES2617144T3 (es) | 2017-06-15 |
EP0986963A3 (de) | 2003-01-22 |
IL131791A0 (en) | 2001-03-19 |
CA2282184A1 (en) | 2000-03-14 |
DK0986963T3 (en) | 2017-03-20 |
IL131791A (en) | 2004-01-04 |
DE19841930A1 (de) | 2000-03-16 |
EP0986963A2 (de) | 2000-03-22 |
JP2000103733A (ja) | 2000-04-11 |
EP0986963B1 (de) | 2016-12-07 |
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