ochratoxin α methyl ester | 159694-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ochratoxin α methyl ester
• 英文别名: methyl (3R)-5-chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carboxylate
• CAS: 159694-36-7
• 化学式: C₁₂H₁₁ClO₅
• 分子量: 270.669
• InChiKey: VHZOHNVDFUPEMO-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ochratoxin α methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以9.0 mg的产率得到5-氯-8-羟基-3-甲基-1-氧代异色满-7-羧酸
  参考文献：
  名称：

  真菌颜料。六十九。(R)-赭曲霉毒素α的全合成和赭曲霉毒素的正式全合成

  摘要：

  (R)-赭曲霉毒素 α 是具有生物活性的二肽赭曲霉毒素 A 的单手性羧酸成分，首次由 (R)-环氧丙烷通过九个步骤合成。该方法构成了功能化二氢异香豆素的通用和通用途径。

  DOI：

  10.1071/ch02014
• 作为产物：
  描述：

  (-)-3,4-dihydro-8-hydroxy-7-methoxycarbonyl-3-methylisocoumarin 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 ochratoxin α methyl ester
  参考文献：
  名称：

  真菌颜料。六十九。(R)-赭曲霉毒素α的全合成和赭曲霉毒素的正式全合成

  摘要：

  (R)-赭曲霉毒素 α 是具有生物活性的二肽赭曲霉毒素 A 的单手性羧酸成分，首次由 (R)-环氧丙烷通过九个步骤合成。该方法构成了功能化二氢异香豆素的通用和通用途径。

  DOI：

  10.1071/ch02014

文献信息

• 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.
• Synthesis and structural elucidation of analogs of ochratoxin A
  作者：Hao Xiao、Ronald R. Marquardt、Andrew A. Frohlich、Yang Z. Ling

  DOI：10.1021/jf00050a050

  日期：1995.2

  Five analogs of ochratoxin A (OA) including the ethylamide of OA (OE-OA), the D-phenylalanine form of OA (d-OA), the decarboxylated OA (DC-OA), the O-methyl ether of OA (OM-OA), and the methyl ester of ochratoxin alpha (M-O alpha) were synthesized using OA or ochratoxin alpha (O alpha) as the starting material. The reactions involved activation of OA to the N-hydroxysuccinimide ester (OA-NHS) and of O alpha to acyl chloride (O alpha-Cl) followed by nucleophilic substitution with primary amines, amino acids, and alcohols to form corresponding amides and esters. All analogs were obtained in pure forms, and all but OM-OA were crystallized. A simplified procedure for the isolation and crystallization of O alpha was also developed. The chemical structures of all analogs were elucidated using EI-MS and H-1 NMR. Other physicochemical parameters such as melting point, UV-vis absorption, fluorescence, and HPLC elution pattern for each analog are presented. The procedures that have been developed for the synthesis of the analogs of OA from OA or O alpha are simple and efficient. The reactions generally result in high yields of the desired compounds. The overall yields of final products range approximately from 85 to 90% of the starting materials. The analogs synthesized together with the natural analogs of OA can be used to establish the structure-activity relationship of OA and for metabolic and immunological studies.
• Pigments of Fungi. LXIX. Total Synthesis of (R)-Ochratoxin α and the Formal Total Synthesis of Ochratoxin
  作者：C. Donner、M. Gill

  DOI：10.1071/ch02014

  日期：——

  (R)-Ochratoxin α, the monochiral carboxylic acid component of the biologically active dipeptide ochratoxin A, is synthesized for the first time over nine steps from (R)-propylene oxide. The method constitutes a versatile and general route to functionalized dihydroisocoumarins.

  (R)-赭曲霉毒素 α 是具有生物活性的二肽赭曲霉毒素 A 的单手性羧酸成分，首次由 (R)-环氧丙烷通过九个步骤合成。该方法构成了功能化二氢异香豆素的通用和通用途径。