dimethyl (E)-7-hexadecenylitaconate | 1093278-23-9

• 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: dimethyl (E)-7-hexadecenylitaconate
• 英文别名: ceriporic acid D dimethyl ester；dimethyl 2-[(E)-hexadec-7-enyl]-3-methylidenebutanedioate
• CAS: 1093278-23-9
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: JEKDHFZWOHLWDB-OUKQBFOZSA-N

物化性质

• 沸点：
  460.2±45.0 °C(predicted)
• 密度：
  0.941±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl (E)-7-hexadecenylitaconate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以94%的产率得到(E)-7-hexadecenylitaconic acid
  参考文献：
  名称：

  De novo synthesis of (Z)- and (E)-7-hexadecenylitaconic acids by a selective lignin-degrading fungus, Ceriporiopsis subvermispora

  摘要：

  Ceriporic acids are a class of alk(en)ylitaconic acids produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. Their structural units have similarity with biologically important lichen acids, such as chaetomellic and protolichesterinic acids. The unique function of alkylitaconic acid is the redox silencing of the Fenton reaction system by inhibiting reduction of Fe3+. As estimated by the catalytic function of Delta 9-desaturases, 7-hexadecenyl derivatives bearing a trans configuration have not been reported in the family of alk(en)ylitaconic acids, i.e. the structurally similar lichen acids-alk(en)ylcitraconic and paraconic acids. In this paper, we discuss the isolation of an itaconic acid derivative with an (E)-7-hexadecenyl chain from cultures of C. subvermispora. To identify the natural metabolite, (E)- and (Z)-7-hexadecenylitaconic acids were chemically synthesised. The isolated metabolite was identical to the synthetic (E)-hexadecenylitaconic acid and was designated as ceriporic acid D. Administration of C-13-[U]-glucose demonstrated that ceriporic acid C. and trans-7-hexadecenylitaconic acid (ceriporic acid D) were biosynthesised de novo by C. subvermispora. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.07.014
• 作为产物：
  描述：

  dimethyl α-bromomethyl fumarate 、 盐5-溴-3-铟杂氧杂基-β-D-葡萄糖酮酸环己基铵 在 三溴化磷 、 magnesium 、 Br₂Cu^(1-)*Li⁽¹⁺⁾ 作用下， 反应 16.0h， 生成 dimethyl (E)-7-hexadecenylitaconate 、 ceriporic acid C dimethyl ester
  参考文献：
  名称：

  De novo synthesis of (Z)- and (E)-7-hexadecenylitaconic acids by a selective lignin-degrading fungus, Ceriporiopsis subvermispora

  摘要：

  Ceriporic acids are a class of alk(en)ylitaconic acids produced by a selective lignin-degrading fungus, Ceriporiopsis subvermispora. Their structural units have similarity with biologically important lichen acids, such as chaetomellic and protolichesterinic acids. The unique function of alkylitaconic acid is the redox silencing of the Fenton reaction system by inhibiting reduction of Fe3+. As estimated by the catalytic function of Delta 9-desaturases, 7-hexadecenyl derivatives bearing a trans configuration have not been reported in the family of alk(en)ylitaconic acids, i.e. the structurally similar lichen acids-alk(en)ylcitraconic and paraconic acids. In this paper, we discuss the isolation of an itaconic acid derivative with an (E)-7-hexadecenyl chain from cultures of C. subvermispora. To identify the natural metabolite, (E)- and (Z)-7-hexadecenylitaconic acids were chemically synthesised. The isolated metabolite was identical to the synthetic (E)-hexadecenylitaconic acid and was designated as ceriporic acid D. Administration of C-13-[U]-glucose demonstrated that ceriporic acid C. and trans-7-hexadecenylitaconic acid (ceriporic acid D) were biosynthesised de novo by C. subvermispora. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.07.014