ceriporic acid C dimethyl ester | 150177-85-8

• 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: ceriporic acid C dimethyl ester
• 英文别名: dimethyl (Z)-7-hexadecenylitaconate；dimethyl 2-[(Z)-hexadec-7-enyl]-3-methylidenebutanedioate
• CAS: 150177-85-8
• 化学式: C₂₃H₄₀O₄
• 分子量: 380.568
• InChiKey: JEKDHFZWOHLWDB-SEYXRHQNSA-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：

  ceriporic acid C dimethyl ester 在 四氧化锇 、 sodium sulfite 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora

  摘要：

  A lignin-degrading basidiomycete, Ceriporiopsis subvermispora produces a series of alkyl- and alkenylitaconates (ceriporic acids). Previously, two alkylitaconic acids with tetradecyl and hexadecyl side chains were isolated and identified as 1-heptadecene-2,3-dicarboxylic acid (ceriporic acid A)and 1-nonadecene-2,3-dicarboxylic acid (ceriporic acid B). In the present study, one hexadecenylitaconate (ceriporic acid Q was isolated and its chemical structure was analyzed by glycolation and subsequent (1) trimethylsilation, or (2) acetalation with acetone and acetone-d(6). Analyses of the isolated metabolite demonstrated that the hexadecenylitaconic acid was (Z)-1,10-nonadecadiene-2,3-dicarboxylic acid. The structure of the side chain in ceriporic acid C was the same as that of hexadecenylcitraconate, chaetomellic acid B. Thus, it was found that ceriporic acids share close structural similarity with alk(en)yl citraconate derivatives, chaetomellic acids and other lichen lactones, protolichesterinic, lichesterinic, and murolic acids. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00098-7
• 作为产物：
  描述：

  三甲基硅烷化重氮甲烷 、 (Z)-1,10-nonadecadiene-2,3-dicarboxylic acid 以 正己烷 为溶剂， 反应 0.5h， 生成 ceriporic acid C dimethyl ester
  参考文献：
  名称：

  Ceriporic acid C, a hexadecenylitaconate produced by a lignin-degrading fungus, Ceriporiopsis subvermispora

  摘要：

  A lignin-degrading basidiomycete, Ceriporiopsis subvermispora produces a series of alkyl- and alkenylitaconates (ceriporic acids). Previously, two alkylitaconic acids with tetradecyl and hexadecyl side chains were isolated and identified as 1-heptadecene-2,3-dicarboxylic acid (ceriporic acid A)and 1-nonadecene-2,3-dicarboxylic acid (ceriporic acid B). In the present study, one hexadecenylitaconate (ceriporic acid Q was isolated and its chemical structure was analyzed by glycolation and subsequent (1) trimethylsilation, or (2) acetalation with acetone and acetone-d(6). Analyses of the isolated metabolite demonstrated that the hexadecenylitaconic acid was (Z)-1,10-nonadecadiene-2,3-dicarboxylic acid. The structure of the side chain in ceriporic acid C was the same as that of hexadecenylcitraconate, chaetomellic acid B. Thus, it was found that ceriporic acids share close structural similarity with alk(en)yl citraconate derivatives, chaetomellic acids and other lichen lactones, protolichesterinic, lichesterinic, and murolic acids. (C) 2003 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(03)00098-7

文献信息

• De novo synthesis of (Z)- and (E)-7-hexadecenylitaconic acids by a selective lignin-degrading fungus, Ceriporiopsis subvermispora
  作者：Hiroshi Nishimura、Saeko Tsuda、Hitoe Shimizu、Yasunori Ohashi、Takahito Watanabe、Yoichi Honda、Takashi Watanabe

  DOI：10.1016/j.phytochem.2008.07.014

  日期：2008.10

  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.