CN109280005A - 一种复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途 - Google Patents
一种复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途 Download PDFInfo
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- CN109280005A CN109280005A CN201710596489.7A CN201710596489A CN109280005A CN 109280005 A CN109280005 A CN 109280005A CN 201710596489 A CN201710596489 A CN 201710596489A CN 109280005 A CN109280005 A CN 109280005A
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- Prior art keywords
- carnitine
- zinc salt
- alkanoyl
- zinc
- lemon acid
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Abstract
本发明实施例提供了一种复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途,其中,具有以下的结构通式;其中R代表碱性氨基酸、L‑肉碱或烷酰基L‑肉碱,所述烷酰基为具有2~5个碳原子的直链或支链烷酰基。通过上述可知,本发明提供的复合柠檬酸锌盐,将柠檬酸锌与碱性氨基酸、L‑肉碱和/或烷酰基L‑肉碱相结合,形成利于保存、运输和易于被人体吸收等特点的多种形式的复合柠檬酸锌盐,大大改善了单一复合柠檬酸锌盐的理化特性,增加了碱性氨基酸、L‑肉碱和/或烷酰基L‑肉碱的功能,因而大大拓展了它的应用范围。
Description
技术领域
本发明特别涉及一种复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途。
背景技术
天然柠檬酸在自然界中分布很广,天然的柠檬酸存在于植物如柠檬、柑橘、菠萝等果实和动物的骨骼、肌肉、血液中。人工合成的柠檬酸是用砂糖、糖蜜、淀粉、葡萄等含糖物质发酵而制得的,可分为无水和水合物两种。纯品柠檬酸为无色透明结晶或白色粉末,无臭,有一种诱人的酸味。
柠檬酸的功效已有很多报道,具有多种功能:因为柠檬酸有温和爽快的酸味,普遍用于各种饮料、汽水、葡萄酒、糖果、点心、饼干、罐头果汁、乳制品等食品的制造。其还可用作调味剂,也可用作食用油的抗氧化剂。另外,柠檬酸能够改善食品的感官性状,增强食欲和促进体内锌、磷物质的消化吸收。无水柠檬酸大量用于固体饮料。柠檬酸的盐类如柠檬酸锌和柠檬酸铁是某些食品中需要添加锌离子和铁离子的强化剂。柠檬酸的酯类如柠檬酸三乙酯可作无毒增塑剂,制造食品包装用塑料薄膜,是饮料和食品行业的酸味剂,防腐剂。柠檬酸具有防止和消除皮肤色素沉着的作用。
L-精氨酸是一种营养增补剂,它是鸟氨酸循环中的一个组成成分具有极其重要的生理功能,多吃精氨酸,可以增加肝脏中精氨酸(arginase)的活性,有助于将血液中的氨转变为尿素而排泄出去。所以,精氨酸对高氨血症,肝脏机能障碍有帮助。L-精氨酸也是精子蛋白的主要成分,有促进精子的质量,提高精子运动能量的作用。L-精氨酸可有效提高免疫力、促进免疫系统分泌自然杀手细胞、吞噬细胞、白血球内烯素(interleukin-1)等内生性物质,有利于对抗癌细胞及预防病毒感染。另外,L-精氨酸是鸟氨酸(L-ornithine)及脯氨酸(L-proline)的前趋物,脯氨酸是构成胶原蛋白的重要元素,补充精氨酸对于严重外伤、烧伤等需要大量组织修护的康护,具有明显的帮助,同时具有降低感染及发炎的效果。
L-赖氨酸是帮助其它营养物质被人体充分吸收和利用的关键物质,人体只有补充了足够的L-赖氨酸才能提高食物蛋白质的吸收和利用,达到均衡营养,促进生长发育。其作用有:提高智力,促进生长,增强体质;增进食欲,改善营养不良状况;改善失眠,提高记忆力;帮助产生抗体,激素和酶,提高免疫力,增加血色素;帮助锌的吸收,治疗防止骨质疏松症;降低血中甘油三酯的水平,预防心脑血管疾病的产生。
L-肉碱的功效也有很多报道,L-肉碱是一种重要的食品营养强化剂,已广泛应用于食品工业,如婴儿奶粉,减肥食品,运动员营养品和中老年营养补剂中以及饲料加工业中,此外还有医药方面的疗效,心血管疾病、肝脏疾病、肾脏疾病、高脂血症、糖尿病、神经肌肉疾病等均可通过服用L-肉碱及其系列产品而使病症得到改善。
乙酰L-肉碱是存在于人体内的一种自然物质,尤其在肌肉、大脑及精子中含量特别丰富,在人体内参与一系列重要的代谢过程,它从细胞中带走乙酰基并协助能量转移,有报道说乙酰L-肉碱还可以提高生殖能力。
丙酰L-肉碱通过刺激丙酮酸脱氢酶活性,提高能量底物的产生,提高葡萄糖的氧化利用能力,可作为自由基清除剂和活性氧的保护剂,保护心肌细胞免受氧化损伤,治疗心血管疾病,如充血性心衰、心律不齐、外周血管病和急性缺血。另外,丙酰L-肉碱能比L-肉碱更快地进入心肌细胞抑制自由基的产生。改善受损心肌的物质与能量代谢是丙酰L-肉碱的主要药理活性表现,丙酰L-肉碱在高剂量能直接扩张骨骼肌血管床,提高组织代谢水平。丙酰L-肉碱在某些啮齿动物血管炎症模型有抗炎活性。在具备嗜中性粒细胞和血小板组织缺血和其他炎症疾病中具有保护作用。与L-肉碱相比,丙酰L-肉碱具有三个潜在的优势:具有为三羧酸循环补充介质的能力;对肌纤维膜载体具有更大的亲和力;在完整心脏在局部缺血后能更大的影响肌肉应力。
锌是人体必需的微量元素之一,在人体生长发育过程中起着极其重要的作用,常被人们誉为“生命之花”和“智力之源”,日常含锌丰富的食物在海鲜类食物中,每周建议吃两三次海鲜。锌有以下重要作用:
1、促进人体的生长发育。处于生长发育期的儿童、青少年如果缺锌,会导致发育不良,肠道菌群失衡。缺乏严重时,将会导致"侏儒症"和智力发育不良。
2、维持人体正常食欲。缺锌会导致味觉下降,出现厌食、偏食甚至异食、肠道菌群失衡。
3、增强人体免疫力。锌元素是免疫器官胸腺发育的营养素,只有锌量充足才能有效保证胸腺发育,正常分化T淋巴细胞,促进细胞免疫功能。
4、促进伤口和创伤的愈合。补锌剂最早被应用于临床就是用来治疗皮肤病。
5、影响维生素A的代谢和正常视觉。锌在临床上表现为对眼睛有益,就是因为锌有促进维生素A吸收的作用。维生素A的吸收离不开锌。维生素A平时储存在肝脏中,当人体需要时,将维生素A输送到血液中,这个过程是靠锌来完成“动员”工作的。
6、维持男性正常的生精功能。锌元素大量存在于男性睾丸中,参与精子的整个生成、成熟和获能的过程。男性一旦缺锌,就会导致精子数量减少、活力下降、精液液化不良,最终导致男性不育。缺锌还会导致青少年没有第二性征出现、不能正常生殖发育。
综上,无论是柠檬酸、氨基酸还是微量元素锌,都是很重要的营养元素,但在现有技术中,至今还缺少一种能够同时补充前述的氨基酸、柠檬酸及锌元素的营养物质。
发明内容
本发明的目的在于提供复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途,用于解决现有技术中缺少一种能够同时补充氨基酸、柠檬酸及锌元素的营养物质的问题。具体技术方案如下:
本发明首先提供了一种复合柠檬酸锌盐,具有以下的结构通式:
其中R代表碱性氨基酸、L-肉碱或烷酰基L-肉碱,所述烷酰基为具有2~5个碳原子的直链或支链烷酰基。
可选地,所述碱性氨基酸包括L-精氨酸、L-赖氨酸中的至少一种。
可选地,所述烷酰基L-肉碱包括:乙酰L-肉碱和丙酰L-肉碱中的至少一种。
在本发明的一种具体实施方案中,R代表L-精氨酸,本发明提供的复合柠檬酸锌盐为L-精氨酸柠檬酸锌盐,且L-精氨酸、柠檬酸及锌的摩尔比1∶1∶1。其结构式如下:
在本发明的一种具体实施方案中,R代表L-赖氨酸,本发明提供的复合柠檬酸锌盐为L-赖氨酸柠檬酸锌盐,且L-赖氨酸、柠檬酸及锌摩尔比1∶1∶1。其结构式如下:
在本发明的一种具体实施方案中,R代表L-肉碱,本发明提供的复合柠檬酸锌盐为L-肉碱柠檬酸锌盐,且L-肉碱、柠檬酸及锌摩尔比1∶1∶1。其结构式如下:
在本发明的一种具体实施方案中,R代表乙酰L-肉碱,本发明提供的复合柠檬酸锌盐为乙酰L-肉碱柠檬酸锌盐,且乙酰L-肉碱、柠檬酸及锌摩尔比1∶1∶1。其结构式如下:
在本发明的一种具体实施方案中,R代表丙酰L-肉碱,本发明提供的复合柠檬酸锌盐为丙酰L-肉碱柠檬酸锌盐,且丙酰L-肉碱、柠檬酸及锌摩尔比1∶1∶1。其结构式如下:
本发明还提供了上述的复合柠檬酸锌盐的制备方法,包括:
1)将柠檬酸及锌源加入到水中,溶解成水溶液;
2)向步骤1)的水溶液中加入碱性氨基酸、L-肉碱和/或烷酰基L-肉碱,在0-100℃下反应2-8小时,得到反应液;
3)将所得到反应液滴加到有机溶剂,优选为乙醇中进行析晶,对所析出的晶体进行分离、干燥处理。
在本发明的具体实施方式中,步骤1)中在将柠檬酸及锌源加入到水中,溶解透明后,还可以包括过滤步骤,以去除由锌源所引入的杂质。另外,对于步骤1)中所用的溶剂水的量,只要其能够充分溶解各反应物即可,并没有特殊要求,水的具体量可以由本领域普通技术人员根据实际情况进行确定,例如,以柠檬酸计,柠檬酸与水的比例可以为1:(1-3)mol/L。
可以理解的的是,当步骤3)中人有机溶剂优选为乙醇时,本发明所涉及的溶剂只有水和乙醇(也称为无水乙醇),既环保又有利于乙醇的回收循环利用,更能节省成本。
更令人惊讶的是,发明人发现,在步骤3)中,反应结束后,如果向反应液中加入有机溶剂,例如乙醇进行析晶时,并不会出现所期望的晶体;相反,如果向有机溶剂中,例如以倾倒的方式加入反应液,则虽然可以析出一定量的晶体,但晶体的收率很小,只有40-50%。发明人通过深入研究,不限于任何理论的发现,将所得到反应液滴加到有机溶剂,例如乙醇中进行析晶时,晶体的收率很高,可以达到97%以上。需要说明的是,在本发明中,晶体收率是指摩尔收率,摩尔收率的计算方法为:所得到的晶体的摩尔数除以用量最大的原料的摩尔数,当各原料的摩尔比为1:1:1时,摩尔收率的计算方法可以为:所得到的晶体的摩尔数除以任意一原料的摩尔数,再乘以100%。所说的原料指的是碱性氨基酸、L-肉碱和/或烷酰基L-肉碱、柠檬酸及锌源。
本发明所用的锌源可以是任选的能够在酸性条件下溶于水的,含有锌元素的化合物,优选地,所述锌源选氢氧化锌及碳酸锌中的至少一种。
在本发明的具体实施方式中,碱性氨基酸、L-肉碱和/或烷酰基L-肉碱的摩尔数与柠檬酸及锌源及氨基酸的摩尔数的比为1:1:1,以最大化的减少物料的浪费。
在本发明的具体实施方式中,步骤2)中的反应温度为20-90℃,优选为40-90℃,更优选为70-80℃,反应时间为3-7小时,优选为4-6小时,更优选为4小时。
在实际应用中,步骤3)中所述分离具体可以为过滤,当然,本领域普通技术人员也可以采用其它的方式,过滤步骤可以采用现有技术中的常规方法进行。例如,可以是通过使得结晶后的母液自然流过过滤器,或者采用抽吸、加压等方法进行强制过滤,例如减压过滤等。
在实际应用中,干燥步骤优选地通过连续干燥器、直热旋转式干燥器、转鼓式干燥器、带式干燥器、喷雾干燥器或流化床干燥器实施所述干燥步骤。干燥步骤可以采用现有技术中的常规方法进行。例如,可以将过滤得到的晶体分批或连续地进料到干燥器中,并且按照常规方法进行干燥。
本发明还提供了一种营养组合物,其包含有前述的复合柠檬酸锌盐及可食用的载体或赋形剂。
在本发明的一种具体实施方式中,上述的营养组合物,具体可以以粉剂、颗粒剂、片剂、胶囊、口服液或饮料的形式存在。
本发明还提供了前述的复合柠檬酸锌盐或前述的营养组合物在人用饮食或营养增补剂或作为兽用营养增补剂中的用途。
在实际应用中,本发明所提供了的复合柠檬酸锌盐或营养组合物可以作为人用饮食/营养增补剂或作为兽用营养增补剂,其中所述营养组合物包含本发明提供的任意一种复合柠檬酸锌盐作为活性成份。本发明提供的营养组合物可以制成适于口服、饮用、稳定的药学可接受的复合柠檬酸锌盐的组合物,该组合物还可以包含有可选的一种或多种药理学上可接受的赋形剂,以及药学和食品工艺学专家熟知的活性成分。
通过上述可知,本发明提供的复合柠檬酸锌盐,将柠檬酸锌与碱性氨基酸、L-肉碱和/或烷酰基L-肉碱相结合,形成利于保存、运输和易于被人体吸收等特点的多种形式的复合柠檬酸锌盐,大大改善了单一柠檬酸锌盐的理化特性,增加了碱性氨基酸、L-肉碱和/或烷酰基L-肉碱的功能,因而大大拓展了它的应用范围。本发明提供的复合柠檬酸锌盐是一个固态新化合物,不吸湿,在25℃相对湿度60±5%时暴露24小时,无结团发粘现象,抗吸湿性良好。可以做成消费者需要的各种剂型,同时也可以应用于食品、饮料、医药等各个领域,前景非常宽广。
具体实施方式
下面将结合具体实施例对本发明的技术方案进行描述,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1:L-精氨酸柠檬酸锌盐的制备
将一水柠檬酸21克(0.1mol)溶于100ml水中,加入氧化锌8.1克(0.1mol),常温溶解,溶液透明后过滤,除去氧化锌中的SiO2等杂质,在洁净的滤液中加入L-精氨酸17.4克(0.1mol),于70-80℃搅拌反应4小时,然后把反应液滴入无水乙醇中析晶,降温过滤干燥,所得的L-精氨酸柠檬酸锌盐42.2克,具有良好的流动性和抗吸湿性,收率98.2%。
[α]D 20=+5.4°(C=5,H2O),L-精氨酸HPLC含量41.1%,柠檬酸HPLC含量43.8%,锌含量15.1%。
实施例2:L-赖氨酸柠檬酸锌盐的制备
将一水柠檬酸21克(0.1mol)溶于100ml水中,加入人氢氧化锌9.9克(0.1mol),常温溶解,溶液透明后过滤,除去氢氧化锌中的SiO2等杂质,在洁净的滤液中加入L-赖氨酸14.6克(0.1mol),于70-80℃搅拌反应2小时,然后把反应液滴入无水乙醇中析晶,降温过滤干燥,所得的L-赖氨酸柠檬酸锌盐39.2克,具有良好的流动性和抗吸湿性,收率97.6%。
[α]D 20=+4.4°(C=5,H2O),L-赖氨酸HPLC含量36.8%,柠檬酸HPLC含量47.0%,锌含量16.2%。
实施例3:L-肉碱柠檬酸锌盐的制备。
将一水柠檬酸21克(0.1mol)溶于100ml水中,加入碳酸锌12.5克(0.1mol),常温溶解,溶液透明后过滤,除去碳酸锌中的SiO2等杂质,在洁净的滤液中加入L-肉碱16.1克(0.1mol),于70-80℃搅拌反应8小时,然后把反应液滴入无水乙醇中析晶,降温过滤干燥,所得的L-肉碱柠檬酸锌盐40.7克,具有良好的流动性和抗吸湿性,收率97.6%。
[α]D 20=-10.8°(C=5,H2O),L-肉碱HPLC含量38.2%,柠檬酸HPLC含量45.8%,锌含量16.0%。
实施例4:乙酰L-肉碱柠檬酸锌盐的制备。
将一水柠檬酸21克(0.1mol)溶于200ml水中,加入氧化锌8.1克(0.1mol),常温溶解,溶液透明后过滤,除去氧化锌中的SiO2等杂质,在洁净的滤液中加入乙酰L-肉碱20.3克(0.1mol),于70-80℃搅拌反应4小时,然后把反应液滴入无水乙醇中析晶,降温过滤干燥,所得的乙酰L-肉碱柠檬酸锌盐45.2克,具有良好的流动性和抗吸湿性,收率98.4%。
[α]D 20=-9.8°(C=5,H2O),乙酰L-肉碱HPLC含量44.0%,柠檬酸HPLC含量41.6%,锌含量14.4%。
实施例5:丙酰L-肉碱柠檬酸锌盐的制备。
将一水柠檬酸21克(0.1mol)溶于200ml水中,加入氢氧化锌9.9克(0.1mol),常温溶解,溶液透明后过滤,除去氢氧化锌中的SiO2等杂质,在洁净的滤液中加入丙酰L-肉碱21.7克(0.1mol),于70-80℃搅拌反应4小时,然后把反应液滴入无水乙醇中析晶,降温过滤干燥,所得的丙酰L-肉碱柠檬酸锌盐46.6克,具有良好的流动性和抗吸湿性,收率98.5%。
[α]D 20=-9.0°(C=1,H2O),丙酰L-肉碱HPLC含量46.3%,柠檬酸HPLC含量40.5%,锌含量13.2%。
上述实施例1-5的HPLC(高效液相色谱)条件:
柱:HYPERSIL C8(5μm)250×4.6mm
温度:25℃
流动相:0.02M KH2PO4
pH:6.0H3PO4
检测波长:254nm
流速:0.6毫升/分钟
L-精氨酸:Rt=6.2分钟
L-赖氨酸:Rt=7.3分钟
L-肉碱:Rt=8.0分钟
乙酰L-肉碱:Rt=6.4分钟
丙酰L-肉碱:Rt=5.8分钟。
实施例6
应用实施例1制备的L-精氨酸柠檬酸锌盐制备组合物片剂,其中片剂的组份为:
实施例7
应用实施例3制备的L-肉碱柠檬酸锌盐制备组合物配制饮料,其配方如下:
以上对本发明所提供的复合柠檬酸锌盐、其制备方法、包含其的组合物及其用途进行了详细介绍。本文中应用了具体实施例对本发明的原理及实施方式进行了阐述,以上实施例的说明只是用于帮助理解本发明的方法及其中心思想。应当指出,对于本领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以对本发明进行若干改进和修饰,这些改进和修饰也落入本发明权利要求的保护。
Claims (10)
1.一种复合柠檬酸锌盐,其特征在于,具有以下的结构通式:
其中R代表碱性氨基酸、L-肉碱或烷酰基L-肉碱,所述烷酰基为具有2~5个碳原子的直链或支链烷酰基。
2.如权利要求1所述的复合柠檬酸锌盐,其特征在于,所述碱性氨基酸包括L-精氨酸、L-赖氨酸中的至少一种。
3.如权利要求1所述的复合柠檬酸锌盐,其特征在于,所述烷酰基L-肉碱包括:乙酰L-肉碱和丙酰L-肉碱中的至少一种。
4.权利要求1-3中任一项所述的复合柠檬酸锌盐的制备方法,其特征在于,包括:
1)将柠檬酸及锌源加入到水中,溶解成水溶液;
2)向步骤1)的水溶液中加入碱性氨基酸、L-肉碱和/或烷酰基L-肉碱,在0-100℃下反应2-8小时,得到反应液;
3)将所得到反应液滴加到有机溶剂,优选为乙醇中进行析晶,对所析出的晶体进行分离、干燥处理。
5.如权利要求4所述的制备方法,其特征在于,所述锌源选自于氢氧化锌及碳酸锌中的至少一种。
6.如权利要求4所述的制备方法,其特征在于,碱性氨基酸、L-肉碱和/或烷酰基L-肉碱的摩尔数与柠檬酸及锌源及氨基酸的摩尔数的比为1:1:1。
7.如权利要求4所述的制备方法,其特征在于,步骤2)中的反应温度为20-90℃,优选为40-90℃,更优选为70-80℃,反应时间为3-7小时,优选为4-6小时,更优选为4小时。
8.一种营养组合物,其特征在于,包含有权利要求1-3中任一项所述的复合柠檬酸锌盐及可食用的载体或赋形剂。
9.如权利要求8所述的营养组合物,其特征在于,所述营养组合物的具体形式为粉剂、颗粒剂、片剂、胶囊、口服液或饮料。
10.如权利要求1-3所述的复合柠檬酸锌盐或权利要求8-9所述的营养组合物在人用饮食或营养增补剂或作为兽用营养增补剂中的用途。
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