(R,Z)-2-(hexadec-7-enyl)-itaconic acid | 717103-46-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,Z)-2-(hexadec-7-enyl)-itaconic acid
• 英文别名: (R)-3-[(Z)-hexadec-7-enyl]-itaconic acid；ceriporic acid C；(R,Z)-7-hexadecenylitaconic acid；1,10Z-heptadecadiene-2,3R-dicarboxylic acid；(2R)-2-[(Z)-hexadec-7-enyl]-3-methylidenebutanedioic acid
• CAS: 717103-46-3
• 化学式: C₂₁H₃₆O₄
• 分子量: 352.514
• InChiKey: BQGIGMHUCMNPDK-OEIFXAAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  25
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,Z)-2-(hexadec-7-enyl)-itaconic acid 在 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-3-(7,8-epoxy-hexadecyl)-itaconic acid
  参考文献：
  名称：

  Epoxy ceriporic acid produced by selective lignin-degrading fungus Ceriporiopsis subvermispora

  摘要：

  Ceriporiopsis subvermispora is a selective white rot basidiomycete which degrades lignin in wood at a distance far from enzymes. Low molecular mass metabolites play a central role in the oxidative degradation of lignin. To understand the unique wood-decaying mechanism, we surveyed the oxidized derivatives of ceriporic acids (alk(en)ylitaconic acids) produced by C. subvermispora using high-resolution liquid chromatography multiple-stage mass spectrometry (HR-LC/MSn). The analysis of the precursor and product ions from the extract suggested that an epoxidized derivative of ceriporic acid is produced by the fungus. To identify the new metabolite, an authentic compound of ceriporic acid epoxide was synthesized in vitro by reacting (R)-3-[(Z)-hexadec-7-enyl]-itaconic acid (ceriporic acid C) with m-chloroperbenzoic acid. The precursor and product ions from the natural metabolite and authentic epoxide were identical and distinguishable from those of hydroxy and hydroperoxy derivatives after reduction with NaBD4. Feeding experiments with [U-C-13]-glucose, 99% and the subsequent analyses of the first and second generation product ions demonstrated that the oxidized ceriporic acid was (R)-3-(7,8-epoxy-hexadecyl)-itaconic acid. To our knowledge, this study is the first to report that natural alkylitaconic acid bears an epoxy group on its side chain. (C) 2011 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2011.07.005