O-acetyl 3-(8'(Z)-pentadecenyl)phenol | 111047-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: O-acetyl 3-(8'(Z)-pentadecenyl)phenol
• 英文别名: [3-[(Z)-Pentadec-8-enyl]phenyl] acetate
• CAS: 111047-34-8
• 化学式: C₂₃H₃₆O₂
• 分子量: 344.538
• InChiKey: HKFPRUPOVWQOCH-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  M-[(Z)-8-十五碳烯基]苯酚 、 乙酸酐 在 吡啶 作用下， 生成 O-acetyl 3-(8'(Z)-pentadecenyl)phenol
  参考文献：
  名称：

  Phospholipase Cγ1 Inhibitory Principles from the Sarcotestas of Ginkgo biloba

  摘要：

  Ten phenolic compounds were isolated from the CHCl3 extract of Ginkgo biloba sarcotestas (Ginkgoaceae) as a new class of phosphatidylinositol-specific phospholipase C gamma 1 (PI-PLC gamma 1) inhibitors. The substances without the long chain were ineffective. On the other hand, the activities of these compounds were dramatically decreased by acetylation of aromatic hydroxyl groups of cardanol, phenolic acid, and bilobol and by methylation of the aromatic carboxyl group of phenolic acid. The unsaturated long chain as well as the aromatic hydroxyl and carboxyl groups might play a key role for the PI-PLC gamma 1 inhibitory activity. These compounds also inhibited the growth of a number of human cancer cell lines, but were less cytotoxic against a human normal colon cell line.

  DOI：

  10.1021/np970367q

文献信息

• Antitumor principles from Ginkgo biloba L.
  作者：HIDER ITOKAWA、NOBUO TOTSUKA、KEISUKE NAKAHARA、KOICHI TAKEYA、JEAN-PIERRE LEPOITTEVIN、YOSHINORI ASAKAWA

  DOI：10.1248/cpb.35.3016

  日期：——

  Seven long-chain phenols were isolated from Ginkgo biloba L. Three of them, anacardic acid (Ib), bilobol (IIa), and cardanol (IIIa), showed antitumor activity against Sarcoma 180 ascites in mice. The antitumor effectiveness was rated (+ +) for Ib, (+ + +) for IIa, and (+ + +) for IIIa at 40 mg/kg/d by the total packed cell volume method.

  从银杏叶中分离出了七种长链酚，其中的三种，即银杏酸（Ib）、双叶酚（IIa）和贲门醇（IIIa），对小鼠肉瘤 180 腹水具有抗肿瘤活性。按照总包装细胞体积法，在 40 mg/kg/d 的剂量下，Ib、IIa 和 IIIa 的抗肿瘤效果分别为 (+ +)、(+ + +)和 (+ + +)。