湿地松酸 | 2761-77-5

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 湿地松酸
• 英文名称: communic acid
• 英文别名: Communsaeure；(+)-Communic acid；(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(3-methylpenta-2,4-dienyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 2761-77-5
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: YGBZFOQXPOGACY-CUDHKJQZSA-N

物化性质

• 熔点：
  121 °C
• 沸点：
  414.0±34.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	methyl communate ester	1235-39-8	C21H32O2	316.484
  ——	Communol	1156-07-6	C20H32O	288.473
  ——	methyl labda-8(17),13(E)-dien-19-oate	10267-39-7	C21H34O2	318.5
  ——	Isodihydrocommunol	10380-71-9	C20H34O	290.489

反应信息

• 作为反应物：
  描述：

  湿地松酸 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 dimethyl 8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioate
  参考文献：
  名称：

  自然顺序杯状化学—41：Communic acid的结构和立体化学

  摘要：

  从普通杜松（Juniperus communis L）的树皮中分离出一种新的二萜酸，其酸为钠盐。该酸的结构和构型（1a）来源于与甲苯酚和与邻苯二酚二羧酸的直接相关性。根据降解实验的结果。

  DOI：

  10.1016/0040-4020(61)80076-8

文献信息

• First Enantiospecific Syntheses of Marine Merosesquiterpenes Neopetrosiquinones A and B: Evaluation of Biological Activity
  作者：Ikram Chayboun、Ettahir Boulifa、Ahmed Ibn Mansour、Fernando Rodriguez-Serrano、Esther Carrasco、Pablo Juan Alvarez、Rachid Chahboun、Enrique Alvarez-Manzaneda

  DOI：10.1021/np500975b

  日期：2015.5.22

  The first enantiospecific syntheses of neopetrosiquinones A (6) and)3 (7), two merosesquiterpenes isolated from the deep-water sponge Neopetrosia cf proxima, from the labdane diterpene trans-communic acid (10) have been achieved. A key step of the synthetic sequence is the simultaneous aromatization of the C ring and the benzylic oxidation on C-7 of an advanced intermediate, mediated by the oxygen-DDQ system. The in vitro antiproliferative activities of neopetrosiquinone B (7) and of the synthetic intermediates 8 and 9 against human breast (MCF-7), lung (A-549), and colon (T-84) tumor cell lines have been assayed. The most potent was compound 9 (IC50 = 4.1 mu M), which was twice as active as natural compound 7 (IC50 = 8.3 mu M) against A-549 cells. In addition, the treatment with these compounds resulted in an induction of apoptosis. These findings indicate that the terpene benzoquinones reported here might be potentially useful as anticancer agents.
• Mangoni,L.; Belardini,M., Gazzetta Chimica Italiana, 1964, vol. 94, p. 1108 - 1121
  作者：Mangoni,L.、Belardini,M.

  DOI：——

  日期：——
• Chemistry of the natural order cupressales—41
  作者：V.P. Arya、H. Erdtman、T. Kubota

  DOI：10.1016/0040-4020(61)80076-8

  日期：1961.1

  A new diterpene acid, communic acid, has been isolated as its sodium salt from the bark of the common juniper, Juniperus communis L. The structure and configuration (1a) of this acid follows from direct correlations with torulosol and with agathene dicarboxylic acid as well as from the results of degradation experiments.

  从普通杜松（Juniperus communis L）的树皮中分离出一种新的二萜酸，其酸为钠盐。该酸的结构和构型（1a）来源于与甲苯酚和与邻苯二酚二羧酸的直接相关性。根据降解实验的结果。