N-[(5-氯-3,4-二氢-8-羟基-3-甲基-1-氧代-1H-2-苯并吡喃-7-基)羰基]-L-苯基丙氨酸甲酯 | 16281-44-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 赭曲霉毒素及相关物质
• 中文名称: N-[(5-氯-3,4-二氢-8-羟基-3-甲基-1-氧代-1H-2-苯并吡喃-7-基)羰基]-L-苯基丙氨酸甲酯
• 英文名称: ochratoxin A methyl ester
• 英文别名: methyl (2S)-2-[[(3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoate
• CAS: 16281-44-0
• 化学式: C₂₁H₂₀ClNO₆
• 分子量: 417.846
• InChiKey: IHPSAIGCKPYNDR-BZNIZROVSA-N

物化性质

• 沸点：
  605.3±55.0 °C(Predicted)
• 密度：
  1.353±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 赭曲霉毒素A 在 盐酸 作用下， 反应 24.0h， 生成 N-[(5-氯-3,4-二氢-8-羟基-3-甲基-1-氧代-1H-2-苯并吡喃-7-基)羰基]-L-苯基丙氨酸甲酯
  参考文献：
  名称：

  Identification of ochratoxins and some of their metabolites in bile and urine of rats

  摘要：

  The objectives of this study were to develop and evaluate procedures for the confirmation of ochratoxin A (OA), lactone opened OA (OP-OA), ochratoxin B (OB), hydroxy OA (OA-OH) and ochratoxin alpha (O alpha) and metabolites formed in the rats from these toxins, and to demonstrate that many ochratoxin metabolites can he identified in the bile and urine of rats injected with the different ochratoxins. An esterification procedure in acidified methanol and a lactone hydrolysis procedure in strong base yielded two additional forms of most of the different ochratoxins. The esterification procedure provided a simple, fast and reliable method for the confirmation of the ochratoxins. A total of 20 different metabolites of OA, OP-OA, OB, OA-OH and O alpha were detected in the urine and the bile of rats of which several were identified. Among these, OA and the recently discovered and toxic form of OA (OP-OA) were readily formed in vivo when either were injected. Procedures developed in this study can be used to confirm and isolate ochratoxins in biological samples and hare shown that a new form of OA (OP-OA) along with many other metabolites are formed from OA and related ochratoxins in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0278-6915(99)00153-2

文献信息

• Liquid Chromatographic Determination of Ochratoxin A in Pure and Adulterated Soluble Coffee Using an Immunoaffinity Column Cleanup Procedure
  作者：Alain Pittet、Dominique Tornare、Anthony Huggett、Rinantonio Viani

  DOI：10.1021/jf9602939

  日期：1996.1.1

  An immunoaffinity column/HPLC procedure was developed to quantify low levels of ochratoxin A (OTA) in green coffee beans, roasted coffee beans, and soluble (instant) coffee with greater than 80% recoveries. The method was used to survey 116 soluble coffee samples from various countries and different manufacturers and showed contamination levels ranging from ''not detectable'' to 15.9 mu g/kg. The highest levels of OTA were detected among soluble coffees that had been adulterated with coffee husks and/or coffee parchments (mean contamination level: 5.9 mu g/kg). By comparison, OTA concentrations in pure soluble coffee samples were significantly lower, with a mean cont;amination level of 1.1 mu g/kg. Although higher than normal figures have been found in some products purchased in East European countries, the results of this survey indicate that pure soluble coffee is not a major source of OTA in the diet, with estimated intakes being well within safety limits.
• Identification of ochratoxins and some of their metabolites in bile and urine of rats
  作者：S Li、R.R Marquardt、A.A Frohlich

  DOI：10.1016/s0278-6915(99)00153-2

  日期：2000.2

  The objectives of this study were to develop and evaluate procedures for the confirmation of ochratoxin A (OA), lactone opened OA (OP-OA), ochratoxin B (OB), hydroxy OA (OA-OH) and ochratoxin alpha (O alpha) and metabolites formed in the rats from these toxins, and to demonstrate that many ochratoxin metabolites can he identified in the bile and urine of rats injected with the different ochratoxins. An esterification procedure in acidified methanol and a lactone hydrolysis procedure in strong base yielded two additional forms of most of the different ochratoxins. The esterification procedure provided a simple, fast and reliable method for the confirmation of the ochratoxins. A total of 20 different metabolites of OA, OP-OA, OB, OA-OH and O alpha were detected in the urine and the bile of rats of which several were identified. Among these, OA and the recently discovered and toxic form of OA (OP-OA) were readily formed in vivo when either were injected. Procedures developed in this study can be used to confirm and isolate ochratoxins in biological samples and hare shown that a new form of OA (OP-OA) along with many other metabolites are formed from OA and related ochratoxins in vivo. (C) 2000 Elsevier Science Ltd. All rights reserved.