N¹⁰-formylfolic acid | 134-05-4

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: N¹⁰-formylfolic acid
• 英文别名: N-(10-formyl-pteroyl)-L-glutamic acid；N-(10-Formyl-pteroyl)-L-glutaminsaeure；10-Formylfolic acid；(2S)-2-[[4-[(2-amino-4-oxo-3H-pteridin-6-yl)methyl-formylamino]benzoyl]amino]pentanedioic acid
• CAS: 134-05-4
• 化学式: C₂₀H₁₉N₇O₇
• 分子量: 469.414
• InChiKey: UGWUWNVTCLDEOG-ZDUSSCGKSA-N

物化性质

• 熔点：
  >193°C (dec.)
• 密度：
  1.67±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶、加热、超声处理）、甲醇（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  217
• 氢给体数：
  5
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

制备方法与用途

用途

10-甲酰叶酸是一种叶酸衍生物。叶酸是重要且具有营养价值的水溶性B族维生素，主要包括四氢叶酸及其衍生物。这类物质由蝶啶、对氨基苯甲酸和谷酰基链组成。作为一碳供体，叶酸参与嘌呤、嘧啶的合成以及氨基酸之间的相互转化。

反应信息

• 作为反应物：
  描述：

  N¹⁰-formylfolic acid 生成 亚叶酸
  参考文献：
  名称：

  亚叶酸的合成

  摘要：

  在亚叶酸钙（5-甲酰基-5,6,7,8-四氢叶酸钙）的合成中，使用胺碱转化无水亚叶酸（5,10-甲基-5,6,7,8-四氢叶酸）酸）转化为亚叶酸意外地直接从反应混合物中产生纯（USP）产物。

  DOI：

  10.1021/ja01133a014
• 作为产物：
  描述：

  DL-叶酸 以60%的产率得到
  参考文献：
  名称：

  ROSOWSKY, ANDRE;BADER, HENRY;FORSCH, RONALD A., PTERIDINES, 1,(1989) N, C. 91-98

  摘要：

  DOI：

文献信息

• Process For The Preparation Of Optically Pure Tetrahydropterins And Derivatives, And Specifically Of Optically Pure Tetrahydrofolic Acid And Derivatives Thereof, By Stereospecific Hydrogenation
  申请人：MULLER Hans Rudolf

  公开号：US20080306263A1

  公开（公告）日：2008-12-11

  Process for the preparation of tetrahydropterin and tetrahydropterin derivatives by hydrogenating pterin and pterin derivatives with hydrogen in the presence of a hydrogenating catalyst, in which the hydrogenation is carried out in a polar reaction medium and metal complexes that are soluble in the reaction medium are employed as the hydrogenation catalysts. The process is suited to the hydrogenation, particularly asymmetric hydrogenation, of folic acid, folio acid salts, folio acid esters, folio acid ester salts or dihydroforms thereof, with the proviso that in the event of using folic acid, carboxylic acid salts thereof or dihydroforms thereof the reaction medium is aqueous, and in the event of using folic acid esters, folic acid ester salts or dihydroforms thereof the reaction medium is an alcohol. The process opens up straightforward access to achiral and chiral pterin derivatives.

  通过在存在氢化催化剂的情况下，用氢气氢化葉酸和葉酸衍生物制备四氢生物葉酸和四氢生物葉酸衍生物的过程，其中氢化是在极性反应介质中进行的，并且可溶于反应介质的金属配合物被用作氢化催化剂。该过程适用于葉酸、葉酸盐、葉酸酯、葉酸酯盐或其二氢形式的氢化，特别是不对称氢化，但若使用葉酸、其羧酸盐或二氢形式，则反应介质为水，若使用葉酸酯、葉酸酯盐或其二氢形式，则反应介质为醇。该过程为得到无手性和手性葉酸衍生物提供了直接途径。
• Folates are potential ligands for ruthenium compounds in vivo
  作者：Tom G. Scrase、Simon M. Page、Paul D. Barker、Sally R. Boss

  DOI：10.1039/c4dt00081a

  日期：——

  A labile ruthenium(ii) complex has been observed to chelate to folates under physiologically relevant conditions. The diastereomeric complexes formed would interfere with the one-carbon carrying role of folatein vivo. This highlights the importance of considering small molecules alongside macromolecules when determining the chemical origins of cytotoxicity of metallodrug candidates.

  一种不稳定的铑（II）配合物已被观察到在生理条件下与叶酸螯合。形成的对映异构体配合物会干扰叶酸在体内携带一碳的作用。这突显了在确定金属药物候选物的细胞毒性的化学起源时，考虑小分子和大分子的重要性。
• Process for the preparation of tetrahydrofolates
  申请人：Eprova AG

  公开号：US05006655A1

  公开（公告）日：1991-04-09

  For the preparation of 5,10-methenyl-(6R)-, 5-formyl-(6S)- or 5-methyl-(6S)-tetrahydrofolic acid or salts thereof, 5,10-methenyl-(6R,S)-tetrahydrofolic acid, the inner salt thereof or one of the salts thereof with strong acids is subjected to diastereomer separation by fractional crystallization and, if desired, the resulting 5,10-methenyl-(6R)-tetrahydrofolic acid is converted by treatment with a hydrolyzing agent into 5-formyl-(6S)-tetrahydrofolic acid or by treatment with a reducing agent into 5-methyl-(6S)-tetrahydrofolic acid, and the resulting free acid may be converted into one of its salts by treatment with a base.

  为制备5,10-甲烯基-(6R)-、5-甲酰基-(6S)-或5-甲基-(6S)-四氢叶酸或其盐，将5,10-甲烯基-(6R,S)-四氢叶酸、其内盐或其强酸盐之一通过分馏结晶进行对映异构体分离，如果需要的话，可以通过加水解剂使得得到的5,10-甲烯基-(6R)-四氢叶酸转化为5-甲酰基-(6S)-四氢叶酸，或通过还原剂使其转化为5-甲基-(6S)-四氢叶酸，而得到的游离酸可以通过加碱转化为其盐。
• Treatment of neurodegenerative disorders
  申请人：Wageningen Centre for Food Sciences

  公开号：EP1645276A1

  公开（公告）日：2006-04-12

  The present invention is dedicated to the treatment of neurodegenerative disorders, in particular age related cognitive decline and age related hearing loss. These disorders can be alleviated by increasing 10-formyltetrahydrofolate or increasing thymidylate synthesis. The invention is of particular benefit to subjects that are MTHFR 677CT heterozygote and MTHFR 677CC homozygote. The substance that increases 10-formyltetrahydrofolate or increases thymidylate synthesis is selected from 10-formyltetrahydrofolate, 5-formyltetrahydrofolate, 5,10-methenyltetrahydrofolate, 5,10-methylentetrahydrofolate, methionine, S-adenosylmethionine and poly-glutamate forms of 10-formyltetrahydrofolate, 5-formyltetrahydrofolate, 5,10-methenyltetrahydrofolate and 5,10-methylentetrahydrofolate and the substance may be in an acid or salt or ester form.

  本发明致力于治疗神经退行性疾病，特别是与年龄相关的认知能力下降和与年龄相关的听力损失。这些疾病可以通过增加 10-甲酰四氢叶酸或增加胸苷酸合成来缓解。本发明对 MTHFR 677CT 杂合子和 MTHFR 677CC 同合子的受试者特别有益。 增加10-甲酰基四氢叶酸或增加胸苷酸合成的物质选自10-甲酰基四氢叶酸、5-甲酰基四氢叶酸、5,10-亚甲基四氢叶酸、5,10-亚甲基五氢叶酸、蛋氨酸、10-甲酰基四氢叶酸、5-甲酰基四氢叶酸、5,10-亚甲基四氢叶酸、5,10-甲基五氢叶酸、蛋氨酸、S-腺苷蛋氨酸和多谷氨酸的形式，该物质可以是酸或盐或酯的形式。
• Compositions comprising pantothenic acid or derivatives thereof and their use for stimulating appetite
  申请人：N.V. Nutricia

  公开号：EP2002830A1

  公开（公告）日：2008-12-17

  The present invention relates to the field of food compositions. In particular compositions comprising at least 15 En% protein and pantothenic acid, or equivalents thereof, are provided, which are suitable for stimulating appetite.

  本发明涉及食品组合物领域。特别是提供了由至少 15 En% 的蛋白质和泛酸或其等价物组成的组合物，适用于刺激食欲。