CN106420394A - 一种增强叶酸光稳定性的方法 - Google Patents
一种增强叶酸光稳定性的方法 Download PDFInfo
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- CN106420394A CN106420394A CN201610921126.1A CN201610921126A CN106420394A CN 106420394 A CN106420394 A CN 106420394A CN 201610921126 A CN201610921126 A CN 201610921126A CN 106420394 A CN106420394 A CN 106420394A
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- acid
- folic acid
- folic
- hydroxy cinnamic
- derivative
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- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 title claims abstract description 177
- 235000019152 folic acid Nutrition 0.000 title claims abstract description 90
- 239000011724 folic acid Substances 0.000 title claims abstract description 90
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 title claims abstract description 89
- 229960000304 folic acid Drugs 0.000 title claims abstract description 89
- 238000000034 method Methods 0.000 title claims abstract description 25
- 230000002708 enhancing effect Effects 0.000 title abstract 2
- 229940074360 caffeic acid Drugs 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- -1 hydroxyl cinnamic acid derivative Chemical class 0.000 claims abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000002537 cosmetic Substances 0.000 claims abstract description 3
- 235000013305 food Nutrition 0.000 claims abstract 2
- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical class OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 16
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims description 14
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- XXLFLUJXWKXUGS-UHFFFAOYSA-N 6-methoxyquinoline-4-carboxylic acid Chemical compound N1=CC=C(C(O)=O)C2=CC(OC)=CC=C21 XXLFLUJXWKXUGS-UHFFFAOYSA-N 0.000 claims description 8
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 claims description 8
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007853 buffer solution Substances 0.000 claims description 7
- 235000004883 caffeic acid Nutrition 0.000 claims description 7
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 claims description 7
- 238000005728 strengthening Methods 0.000 claims description 6
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 claims description 5
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 claims description 5
- 229940074393 chlorogenic acid Drugs 0.000 claims description 5
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 claims description 4
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 claims description 4
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- 235000001368 chlorogenic acid Nutrition 0.000 claims description 4
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 claims description 4
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 claims description 4
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- KKSDGJDHHZEWEP-UHFFFAOYSA-N m-hydroxycinnamic acid Natural products OC(=O)C=CC1=CC=CC(O)=C1 KKSDGJDHHZEWEP-UHFFFAOYSA-N 0.000 claims description 4
- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 claims description 4
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 claims description 4
- PMOWTIHVNWZYFI-AATRIKPKSA-N trans-2-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1O PMOWTIHVNWZYFI-AATRIKPKSA-N 0.000 claims description 4
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 2
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- 235000013985 cinnamic acid Nutrition 0.000 description 6
- 229930016911 cinnamic acid Natural products 0.000 description 6
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 6
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
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- 229930005346 hydroxycinnamic acid Natural products 0.000 description 4
- 235000010359 hydroxycinnamic acids Nutrition 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-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)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 WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 3
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- HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical compound C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 description 2
- IXAFVLCVPFFCSD-UHFFFAOYSA-N CCO.OC(=O)C=Cc1ccccc1 Chemical compound CCO.OC(=O)C=Cc1ccccc1 IXAFVLCVPFFCSD-UHFFFAOYSA-N 0.000 description 2
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- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical group NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 229940014144 folate Drugs 0.000 description 1
- 125000003929 folic acid group Chemical group 0.000 description 1
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Abstract
本发明公开了一种增强叶酸光稳定性的方法,属于医药配置品技术领域。本发明的方法是向叶酸中添加质量浓度≥1/100叶酸质量浓度的羟基肉桂酸衍生物并混合,制成叶酸‑羟基肉桂酸衍生物混合液。本发明所制备的叶酸‑羟基肉桂酸衍生物混合液中叶酸的光稳定性好,以1:1的质量比配制的叶酸‑对香豆酸或叶酸‑咖啡酸混合液中,即使在紫外光照射了240分钟后叶酸残留率仍为100%,能够完全抑制叶酸的光降解,可应用于药品、食品、化妆品。
Description
技术领域
本发明一种增强叶酸光稳定性的方法,属于医药配置品技术领域。
背景技术
叶酸(Folic acid),又称蝶酰谷氨酸,是一类水溶性B族维生素,由蝶呤、对氨基苯甲酸与谷氨酸部分组成。叶酸是人体许多生理过程中必不可少的物质,但人类不能靠自身合成叶酸,因此常需在饮食中添加叶酸。叶酸在体内转化为活性的辅酶形式,参与一碳单位的转移,对核酸和蛋白质的生物合成、氨基酸相互转化、细胞的分裂生长、以及人体神经系统的正常发育具有特别重要的作用。然而,叶酸对光非常敏感,在紫外光照射下易降解,失去活性。如何保护叶酸抑制其光降解便成为研究者广泛关注的问题。
太阳辐射的紫外线部分根据波长可分为介于320nm和400nm的UVA,介于280nm和320nm波段的UVB和介于200nm和280nm之间的UVC。其中,UVC和少量UVB可被地球大气臭氧层吸收。而可照射到地球表面的紫外线中,95%为UVA。
因此,为了延缓或抑制UVA对叶酸的破坏,加入β-环糊精与叶酸形成包合物,使叶酸分子进入β-环糊精的空腔,减少了被光照的机会,因而降低了其结构破坏的机率,降低了降解速率。但市售的β-环糊精纯度不高,且此包合物制备较繁琐,所以一般不采用。也有研究选取了蛋白质与叶酸形成复合物,在一定程度上延缓或抑制了叶酸的光降解。然而由于原料成本过高而限制了其工业化应用。
发明内容
本发明的第一个目的是提供一种组合物,含有叶酸和羟基肉桂酸衍生物,其中羟基肉桂酸衍生物:叶酸的质量比≥1/100。
在本发明的一种实施方式中,所述羟基肉桂酸衍生物结构通式为其中R1、R2、R3、R4、R5包括H、羟基、甲氧基、结构式如所示的将奎宁酸六元环上第2位羟基的氢去掉后的一价基团。
在本发明的一种实施方式中,所述羟基肉桂酸衍生物选自咖啡酸、阿魏酸、对香豆酸、邻香豆酸、间香豆酸、芥子酸、绿原酸中的任一种。
在本发明的一种实施方式中,所述组合物是将质量浓度为0.5~2g/L的叶酸和质量浓度为0.5~2g/L的羟基肉桂酸衍生物进行混合。
在本发明的一种实施方式中,所述混合是在pH为6.0~8.0的缓冲液中进行,具体是以pH为6.0~8.0的缓冲液为溶剂,使羟基肉桂酸衍生物:叶酸的质量比≥1/100;所述缓冲液包括磷酸盐缓冲液、Tris-盐酸缓冲液。
本发明的第二个目的是提供一种增强叶酸光稳定性的方法,所述方法是将叶酸与大于叶酸质量浓度的1/100的羟基肉桂酸衍生物进行混合。
在本发明的一种实施方式中,所述羟基肉桂酸衍生物结构通式为其中R1、R2、R3、R4、R5包括H、羟基、甲氧基、结构式如所示的将奎宁酸六元环上第2位羟基的氢去掉后的一价基团。
在本发明的一种实施方式中,所述羟基肉桂酸衍生物选自咖啡酸、阿魏酸、对香豆酸、邻香豆酸、间香豆酸、芥子酸、绿原酸中的任一种。
本发明的第三个目的是提供所述组合物的应用。
在本发明的一种实施方式中,所述应用包括制备含有叶酸的口服液、化妆品和医药配制品。
本发明的第四个目的是提供所述方法的应用。所述应用包括将所述羟基肉桂酸衍生物添加至口服液制剂,叶酸强化饮品中,作为抗氧化剂或防晒滤光剂添加到含叶酸的化妆用或皮肤病用的配制品。
有益效果:本发明采用小分子羟基肉桂酸衍生物增强叶酸光稳定性。在中心波长为365nm,功率为4W的紫外灯照射下,叶酸的残留率在120分钟后降至约15%。以10:0.1的质量比配制的叶酸-对香豆酸混合液在紫外光照射120分钟后叶酸的残留率为56%;叶酸-咖啡酸混合液中,叶酸的残留率仍高于90%,叶酸的残留率分别提高了41%和75%。以10:10的质量比配制的叶酸-对香豆酸或叶酸-咖啡酸混合液中,即使在紫外光照射了240分钟后叶酸残留率仍为100%,能够完全抑制叶酸的光降解。本发明成本低,方法简便,易于工业化推广应用。
附图说明
图1为肉桂酸和羟基肉桂酸衍生物对叶酸在光照射过程中的荧光强度的影响曲线图;
图2为肉桂酸和羟基肉桂酸衍生物对叶酸在光照射过程中的荧光强度的影响曲线图;
图3为咖啡酸和对香豆酸对叶酸在光照射过程中的残留率的影响曲线图。
具体实施方式
叶酸残留率计算:在中心波长为365nm,功率为4W的紫外灯下照射240分钟,采用高效液相色谱法测定叶酸的含量,并计算叶酸残留率。叶酸的残留率按下列公式求得:
实施例1
将质量浓度为1g/L的叶酸溶液与质量浓度为1g/L的肉桂酸-乙醇溶液或羟基肉桂酸衍生物-乙醇溶液中的任一种,在pH为6.0~8.0的磷酸盐缓冲液中进行混合,用缓冲液调节叶酸和羟基肉桂酸衍生物或叶酸和肉桂酸质量比为10:0.1(100g叶酸:1g羟基肉桂酸衍生物),制成叶酸-肉桂酸混合液或叶酸-羟基肉桂酸衍生物混合液。
实施例2
将质量浓度为1g/L的叶酸溶液与质量浓度为1g/L的肉桂酸-乙醇溶液或羟基肉桂酸衍生物-乙醇溶液中的任一种,以质量终浓度10:1的比例(10g叶酸:1g羟基肉桂酸衍生物)将叶酸和肉桂酸及羟基肉桂酸衍生物在pH为6.0~8.0的缓冲液中进行混合,制成叶酸-肉桂酸混合液或叶酸-羟基肉桂酸衍生物混合液。
实施例3
取实施例1、2的样品,与混合液中同浓度的叶酸溶液比较,在紫外灯下照射240分钟,通过荧光光谱法测定在激发波长为360nm、发射波长为445nm处的荧光强度,并以单独叶酸照射240分钟后的荧光强度进行归一化处理,结果以相对荧光强度表示。
如图1和2所示,叶酸本身的荧光强度几乎可忽略,在紫外光照射下荧光强度显著增强,表明叶酸分子在光照下不断发生断裂、降解。随着紫外照射时间延长至120分钟后,荧光强度的增加渐渐减缓;在照射200分钟后荧光强度不再增加,表明叶酸已基本降解完全。由图1可知,对于以本发明实施例1配制的混合液,除了肉桂酸的加入对叶酸在紫外照射过程中的荧光强度无明显影响外,当以叶酸和羟基肉桂酸衍生物终质量浓度比例为10:0.1,将羟基肉桂酸衍生物加入到叶酸溶液中时,叶酸在紫外光照射过程中荧光强度的增加明显变慢,以咖啡酸、阿魏酸、对-香豆酸为例。当分别加入对香豆酸、阿魏酸和咖啡酸时,在照射120分钟后荧光强度仅分别为叶酸空白的13%、10%和9%;在照射240分钟后荧光强度分别为叶酸空白的86%、85%和34%。由图2可知,以本发明实施例2配制叶酸-羟基肉桂酸衍生物混合液,在紫外光照射240分钟后叶酸的荧光强度仍无明显增加。由此可知,本发明采用羟基肉桂酸衍生物可以抑制叶酸的光降解,增强其稳定性。
实施例4
对实施例1、2制备的组合物中叶酸残留率进行检测,结果如图3所示,在紫外光照射下,叶酸的降解逐渐加速,其残留率在120分钟后降至约15%;在200分钟后叶酸基本降解完全。按实施例1方法配制的叶酸-对香豆酸混合液在紫外光照射120分钟后叶酸的残留率为56%,在照射200分钟后叶酸降解完全。以本发明实施例1配制的叶酸-咖啡酸混合液中,在紫外光照射120分钟后叶酸的残留率仍高于90%,然后叶酸降解加速,在照射240分钟时叶酸残留率约为12%。以本发明实施例2配制的叶酸-对香豆酸或叶酸-咖啡酸混合液中,即使在紫外光照射了240分钟后叶酸残留率仍为100%。由此可知,本发明采用羟基肉桂酸衍生物可显著增强叶酸的光稳定性。
实施例5
参照实施例1的方法制备叶酸-羟基肉桂酸衍生物混合物,其区别在于叶酸与羟基肉桂酸衍生物的质量比为10:0.01。按实施例3、4的方法对混合物的叶酸稳定性进行检测,结果显示在紫外光照射下羟基肉桂酸衍生物的加入对叶酸的荧光强度变化及叶酸的残留率的影响并不明显。表明在此浓度比例下羟基肉桂酸衍生物无法提高叶酸的光稳定性。
实施例6
参照实施例1的方法制备叶酸-羟基肉桂酸衍生物混合物,其区别在于,以1:1的质量比配制的叶酸-对香豆酸或叶酸-咖啡酸混合液,按实施例3、4的方法对混合物的叶酸稳定性进行检测,结果显示即使在紫外光照射了240分钟后叶酸残留率仍为100%,能够完全抑制叶酸的光降解。
采用上述相同步骤制备叶酸-阿魏酸、叶酸-芥子酸、叶酸-绿原酸混合物,并对叶酸稳定性进行检测,均具有增强叶酸光稳定性的作用。
虽然本发明已以较佳实施例公开如上,但其并非用以限定本发明,任何熟悉此技术的人,在不脱离本发明的精神和范围内,都可做各种的改动与修饰,因此本发明的保护范围应该以权利要求书所界定的为准。
Claims (10)
1.一种组合物,其特征在于,含有叶酸和羟基肉桂酸衍生物,其中羟基肉桂酸衍生物:叶酸的质量比≥1/100。
2.根据权利要求1所述的组合物,其特征在于,所述羟基肉桂酸衍生物结构通式为其中R1、R2、R3、R4、R5包括H、羟基、甲氧基、结构式如所示的将奎宁酸六元环上第2位羟基的氢去掉后的一价基团。
3.根据权利要求1所述的组合物,其特征在于,所述羟基肉桂酸衍生物选自咖啡酸、阿魏酸、对香豆酸、邻香豆酸、间香豆酸、芥子酸、绿原酸中的任一种。
4.根据权利要求1所述的组合物,其特征在于,所述组合物是将质量浓度为0.5~2g/L的叶酸和质量浓度为0.5~2g/L的羟基肉桂酸衍生物进行混合。
5.根据权利要求4所述的组合物,其特征在于,所述混合是在pH为6.0~8.0的缓冲液中进行;具体是以pH为6.0~8.0的缓冲液为溶剂,使羟基肉桂酸衍生物:叶酸的质量比≥1/100;所述缓冲液包括磷酸盐缓冲液、Tris-盐酸缓冲液。
6.一种增强叶酸光稳定性的方法,其特征在于,向叶酸中添加质量浓度≥1/100叶酸质量浓度的羟基肉桂酸衍生物并混合。
7.根据权利要求6所述的方法,其特征在于,所述羟基肉桂酸衍生物结构通式为其中R1、R2、R3、R4、R5包括H、羟基、甲氧基、结构式如所示的将奎宁酸六元环上第2位羟基的氢去掉后的一价基团。
8.根据权利要求6所述的方法,其特征在于,所述羟基肉桂酸衍生物选自咖啡酸、阿魏酸、对香豆酸、邻香豆酸、间香豆酸、芥子酸、绿原酸中的任一种。
9.权利要求1~5任一所述组合物的应用。
10.权利要求6~9任一所述的方法在制备含有叶酸的食品、药品、化妆品中的应用。
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