methyl (Z)-[6-(5-hydroxypent-2-enyl)-1,4-dioxaspiro[4.4]non-7-yl]acetate | 1154438-02-4

• 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: methyl (Z)-[6-(5-hydroxypent-2-enyl)-1,4-dioxaspiro[4.4]non-7-yl]acetate
• 英文别名: [6-(5-hydroxy-pent-2-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-acetic acid methyl ester
• CAS: 1154438-02-4
• 化学式: C₁₅H₂₄O₅
• 分子量: 284.353
• InChiKey: MPQGMQXXRRHLFG-LLGAQUFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-[6-(5-hydroxypent-2-enyl)-1,4-dioxaspiro[4.4]non-7-yl]acetate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以10%的产率得到[6-(5-oxo-pent-2-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-acetic acid methyl ester
  参考文献：
  名称：

  Purification and cDNA cloning of a wound inducible glucosyltransferase active toward 12-hydroxy jasmonic acid

  摘要：

  Tuberonic acid (12-hydroxy epi-jasmonic acid, TA) and its glucoside (TAG) were isolated from potato leaflets (Solanum tuberosum L.) and shown to have tuber-inducing properties. The metabolism of jasmonic acid (JA) to TAG in plant leaflets, and translocation of the resulting TAG to the distal parts, was demonstrated in a previous study. It is thought that TAG generated from JA transmits a signal from the damaged parts to the undamaged parts by this mechanism. In this report, the metabolism of TA in higher plants was demonstrated using [12-(3) H]TA, and a glucosyltransferase active toward TA was purified from the rice cell cultures. The purified protein was shown to be a putative salicylic acid (SA) glucosyltransferase (OsSGT) by MALDI-TOF-MS analysis. Recombinant OsSGT obtained by overexpression in Escherichia coli was active not only toward TA but also toward SA. The OsSGT characterized in this research was not specific, but this is the first report of a glucosyltransferase active toward TA. mRNA expressional analysis of OsSGT and quantification of TA, TAG, SA and SAG after mechanical wounding indicated that OsSGT is involved in the wounding response. These results demonstrated a crucial role for TAG not only in potato tuber formation, but also in the stress response in plants and that the SA glucosyltransferase can work for TA glucosylation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2009.01.004
• 作为产物：
  描述：

  Prop-2-enyl 2-oxo-1-prop-2-enylcyclopentane-1-carboxylate 在 Grubbs catalyst first generation 甲醇 、 palladium diacetate 、 sodium 、 4-甲基苯磺酸吡啶 、 三苯基膦 、 sodium chloride 作用下， 以 二氯甲烷 、 二甲基亚砜 、 丙酮 、 乙腈 为溶剂， 反应 35.17h， 生成 methyl (Z)-[6-(5-hydroxypent-2-enyl)-1,4-dioxaspiro[4.4]non-7-yl]acetate 、 methyl (E)-[6-(5-hydroxypent-2-enyl)-1,4-dioxaspiro[4.4]non-7-yl]acetate
  参考文献：
  名称：

  Bruemmer, Oliver; Rueckert, Anke; Blechert, Siegfried, Chemistry - A European Journal, 1997, vol. 3, # 3, p. 441 - 446

  摘要：

  DOI：