2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid | 21891-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid
• 英文别名: 2-(3-hydroxy-5-hydroxymethyl-2-methylpyridin-4-yl)thiazolidine-4-carboxylic acid；2-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-thiazolidine-4-carboxylic acid；2-<3-Hydroxy-2-methyl-5-hydroxymethyl-pyridyl-(4)>-thiazolidin-carbonsaeure-(4)；2-Methyl-3-hydroxy-5-hydroxymethyl-4-(4-carboxy-thiazolidinyl-2)-pyridin；N,S-pyridoxylidene-cysteine；2-[3-Hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]-1,3-thiazolidine-4-carboxylic acid
• CAS: 21891-56-5
• 化学式: C₁₁H₁₄N₂O₄S
• 分子量: 270.309
• InChiKey: CDNKRUFYOOECEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid 、 乙酸酐 在 甲苯 作用下， 以 水 为溶剂， 反应 1.0h， 以to give N-acetyl-2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid as an amorphous solid (0.64 g)的产率得到N-acetyl-2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  CYSTEINE DERIVATIVE

  摘要：

  以下式子所代表的半胱氨酸化合物，其中每个符号如说明书所定义的，并且其盐，具有更好的稳定性，更少的气味，表现出黑色素生成抑制作用，并且可用作化妆品剂。

  公开号：

  US20160060234A1
• 作为产物：
  描述：

  N-pyridoxylidene-L-cysteine 以 乙醇 、 水 为溶剂， 生成 2-[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]thiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Specific features of the reaction of l-cysteine with pyridoxal and N-pyridoxylidene-β-alanine

  摘要：

  The mechanisms of condensation of l-cysteine, l-methionine, and l-serine with pyridoxal and of transaldimination of N-pyridoxylidene-beta-alanine with l-cysteine were studied by the kinetic method. Unlike methionine and serine, the condensation of cysteine with pyridoxal and transaldimination with Npyridoxylidene-beta-alanine involves intermediate formation of stable product having a thiazolidine ring. Its structure was determined by elemental analysis, UV, and IR spectroscopy, and quantum-chemical calculations. The thiazolidine fragment in the pyridoxal condensation product with l-cysteine is turned through an angle of similar to 90A degrees with respect to the pyridine ring plane due to mutual repulsion of the negatively charged oxygen atom in the ortho position of the pyridine ring and sulfur and nitrogen atoms in the thiazolidine ring.

  DOI：

  10.1134/s1070363212070146

文献信息

• Cysteine derivative
  申请人：AJINOMOTO CO., INC.

  公开号：US09212154B2

  公开（公告）日：2015-12-15

  Cysteine compounds represented by the following formula wherein each symbol is as defined in the specification, and salts thereof, are superior in stability, have less odor, exhibit an eumelanin production suppressive effect, and are useful as cosmetic agents.

  以下式子所代表的半胱氨酸化合物及其盐，每个符号如规范所定义，具有更好的稳定性，较少的气味，表现出黑色素生成抑制效果，并可用作化妆品。
• EP2578203
  申请人：——

  公开号：——

  公开（公告）日：——
• EP2578203B1
  申请人：——

  公开号：EP2578203B1

  公开（公告）日：2015-04-01
• US9212154B2
  申请人：——

  公开号：US9212154B2

  公开（公告）日：2015-12-15
• Specific features of the reaction of l-cysteine with pyridoxal and N-pyridoxylidene-β-alanine
  作者：F. V. Pishchugin、I. T. Tuleberdiev

  DOI：10.1134/s1070363212070146

  日期：2012.7

  The mechanisms of condensation of l-cysteine, l-methionine, and l-serine with pyridoxal and of transaldimination of N-pyridoxylidene-beta-alanine with l-cysteine were studied by the kinetic method. Unlike methionine and serine, the condensation of cysteine with pyridoxal and transaldimination with Npyridoxylidene-beta-alanine involves intermediate formation of stable product having a thiazolidine ring. Its structure was determined by elemental analysis, UV, and IR spectroscopy, and quantum-chemical calculations. The thiazolidine fragment in the pyridoxal condensation product with l-cysteine is turned through an angle of similar to 90A degrees with respect to the pyridine ring plane due to mutual repulsion of the negatively charged oxygen atom in the ortho position of the pyridine ring and sulfur and nitrogen atoms in the thiazolidine ring.