6,6'-dimethoxy-gossypol | 1110-58-3

• 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
• 英文名称: 6,6'-dimethoxy-gossypol
• 英文别名: gossypol-6,6'-dimethyl ether；7-(8-formyl-1,7-dihydroxy-6-methoxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,8-dihydroxy-3-methoxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde
• CAS: 1110-58-3
• 化学式: C₃₂H₃₄O₈
• 分子量: 546.617
• InChiKey: OUHOXIPLBJIWEG-UHFFFAOYSA-N

物化性质

• 沸点：
  723.2±60.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6,6'-dimethoxy-gossypol 、 sodium ethanolamine sulphate 以 乙醇 为溶剂， 生成 monosodium mono((((1,1'-dihydroxy-5,5'-diisopropyl-6,6'-dimethoxy-3,3'-dimethyl-7,7'-dioxo-[2,2'-binaphthalene]-8,8'(7H,7'H)-diylidene)bis(methaneylylidene))bis(azanediyl))bis(ethane-2,1-diyl) bis(sulfate))
  参考文献：
  名称：

  棉酚醚的亚胺

  摘要：

  首次合成了棉酚甲醚亚胺，展示了它们的结构，并确定了它们的免疫调节活性。已经显示出二甲醚亚胺的醌型存在和棉酚甲醚亚胺的苯甲型存在。

  DOI：

  10.1007/bf00630315
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 、 溶剂黄146 作用下， 生成 6,6'-dimethoxy-gossypol
  参考文献：
  名称：

  Structure of Gossypol.¹ XIV. Apogossypolic Acid

  摘要：

  DOI：

  10.1021/ja01276a048

文献信息

• Stereoselective coupling of hemigossypol to form (+)-gossypol in moco cotton is mediated by a dirigent protein
  作者：Jinggao Liu、Robert D. Stipanovic、Alois A. Bell、Lorraine S. Puckhaber、Clint W. Magill

  DOI：10.1016/j.phytochem.2008.06.007

  日期：2008.12

  The terpenoid gossypol, a secondary metabolite found in the cotton plant, is synthesized by a free radical dimerization of hemigossypol. Gossypol exists as an atropisomeric mixture because of restricted rotation around the central binaphthyl bond. The dimerization of hemigossypol is regiospecific in cotton. In the case of some moco cotton, the dimerization also exhibits a high level of stereoselectivity. The mechanism that controls this stereoselective dimerization is poorly understood. In this paper, we demonstrate that a dirigent protein controls this stereoselective dimerization process. A partially purified protein preparation from cotton flower petals, which by itself is unable to convert hemigossypol to gossypol, converts hemigossypol with a 30% atropisomeric excess into (+)-gossypol when combined with an exogenous laccase, which by itself produces racemic gossypol. Published by Elsevier Ltd.
• Chander; Seshadri, Journal Of Scientific and Industrial Research, 1958, vol. 17 B, p. 279
  作者：Chander、Seshadri

  DOI：——

  日期：——
• Scheiffele; Shirley, Journal of Organic Chemistry, 1964, vol. 29, p. 3617,3619
  作者：Scheiffele、Shirley

  DOI：——

  日期：——
• Haas; Shirley, Journal of Organic Chemistry, 1965, vol. 30, p. 4111,41113
  作者：Haas、Shirley

  DOI：——

  日期：——
• SMALL MOLECULE ANTAGONISTS OF BCL-2 FAMILY PROTEINS
  申请人：Wang Shaomeng

  公开号：US20090082424A1

  公开（公告）日：2009-03-26

  The present invention relates to naturally occurring and chemically synthesized small molecule antagonists of Bcl-2 family proteins. In particular, the present invention provides gossypol compounds (e.g., isomers, enantiomers, racemic compounds, metabolites, derivatives, pharmaceutically acceptable salts, in combination with acids or bases, and the like) and methods of using these compounds as antagonists of the anti-apoptotic effects of Bcl-2 family member proteins (e.g., Bcl-2, Bcl-X L , and the like). The present invention also provides compositions comprising gossypol compounds and optionally one or more additional therapeutic agents (e.g., anticancer/chemotherapeutic agents). The present invention also provides methods for treating diseases and pathologies (e.g., neoplastic diseases) comprising administering a composition comprising gossypol compounds and optionally one or more additional therapeutic agents (e.g., anticancer/chemotherapeutic agents) and/or techniques (e.g., radiation therapies, surgical interventions, and the like) to a subject or in vitro cells, tissues, and organs.