2-hydroxy-6-(12'-hydroxyheptadec-13'(E)-en-1-yl)benzoic acid | 1616593-67-9

• 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: 2-hydroxy-6-(12'-hydroxyheptadec-13'(E)-en-1-yl)benzoic acid
• 英文别名: 2-hydroxy-6-[(E)-12-hydroxyheptadec-13-enyl]benzoic acid
• CAS: 1616593-67-9
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: BZJXJFVIGRMNAE-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  P-(2-ethoxycarbonyl-3-methoxybenzyl)-O,O-diethylphosphonate 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 cerium(III) chloride 、 草酰氯 、 potassium tert-butylate 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 tin(ll) chloride 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙酸乙酯 、 乙硫醇 为溶剂， 反应 40.5h， 生成 2-hydroxy-6-(12'-hydroxyheptadec-13'(E)-en-1-yl)benzoic acid
  参考文献：
  名称：

  Four new ginkgolic acids from Ginkgo biloba

  摘要：

  Four new compounds, 2-hydroxy-6-(12'-hydroxyheptadec-13'(E)-en-1-yl)benzoic acid (1), 2-hydroxy-6-(13'-hydroxyheptadec-1 1'(E)-en-1-yl)benzoic acid (2), 2-hydroxy-6-(10'-hydroxypentadec-11'(E)-en-1 -yl)benzoic acid (3), and 2-hydroxy-6-(11'-hydroxypentadec-9'(E)-en-1-yl)benzoic acid (4) were isolated from the leaves of Ginkgo biloba and the structures of new ginkgolic acids were deduced on the basis of spectroscopic methods and chemical means. Compounds 1 and 2, and 3 and 4 examined as an inseparable mixture of hydroxyl and double bond positional isomers, were ultimately defined by total synthesis. Compounds 1-4 showed moderate lipid droplets accumulation inhibitory activity on mouse pre-adipocyte cell line, MC3T3-G2/PA6. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.076

文献信息

• Four new ginkgolic acids from Ginkgo biloba
  作者：Jun Deguchi、Yuki Hasegawa、Ayana Takagi、Shihoko Kutsukake、Mizue Kono、Yusuke Hirasawa、Chin Piow Wong、Toshio Kaneda、Hiroshi Morita

  DOI：10.1016/j.tetlet.2014.05.076

  日期：2014.7

  Four new compounds, 2-hydroxy-6-(12'-hydroxyheptadec-13'(E)-en-1-yl)benzoic acid (1), 2-hydroxy-6-(13'-hydroxyheptadec-1 1'(E)-en-1-yl)benzoic acid (2), 2-hydroxy-6-(10'-hydroxypentadec-11'(E)-en-1 -yl)benzoic acid (3), and 2-hydroxy-6-(11'-hydroxypentadec-9'(E)-en-1-yl)benzoic acid (4) were isolated from the leaves of Ginkgo biloba and the structures of new ginkgolic acids were deduced on the basis of spectroscopic methods and chemical means. Compounds 1 and 2, and 3 and 4 examined as an inseparable mixture of hydroxyl and double bond positional isomers, were ultimately defined by total synthesis. Compounds 1-4 showed moderate lipid droplets accumulation inhibitory activity on mouse pre-adipocyte cell line, MC3T3-G2/PA6. (C) 2014 Elsevier Ltd. All rights reserved.