6β-chloro-5α-stigmastane-3β,5-diol | 108923-56-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 6β-chloro-5α-stigmastane-3β,5-diol
• 英文别名: 6β-Chlor-5α-stigmastan-3β,5-diol
• CAS: 108923-56-4
• 化学式: C₂₉H₅₁ClO₂
• 分子量: 467.176
• InChiKey: ANBWOXALEHBGDJ-METNKUIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.44
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6β-chloro-5α-stigmastane-3β,5-diol 在 盐酸 、 4-二甲氨基吡啶 、 jones reagent 、 sodium methylate 、 二异丁基氢化铝 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 38.5h， 生成 6α-Chloro-5β-stigmastane-3β,5-diol
  参考文献：
  名称：

  Mori, Kenji; Fukamatsu, Kunio; Kido, Masaru, Liebigs Annalen der Chemie, 1993, # 6, p. 665 - 670

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6-epoxy-β-sitosterol 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 6β-chloro-5α-stigmastane-3β,5-diol
  参考文献：
  名称：

  Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach

  摘要：

  Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5 beta-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5 beta-cholestane skeleton, 1b with the 5 beta-androstane skeleton, Ic with a fluorine substituent instead of the chlorine and Id with a beta-D-galactopyranose instead of the beta-D-glucopyranose of the original pheromone. Their bioassay shows that la and Ic are active, while Ib and Id are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00018-1

文献信息

• Kssenofontowa; Chalezki, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2565,2567
  作者：Kssenofontowa、Chalezki

  DOI：——

  日期：——
• On the cytotoxity of oxidized phytosterols isolated from photoautotrophic cell cultures of Chenopodium rubrum tested on meal-worms Tenebrio molitor
  作者：Werner Meyer、Harald Jungnickel、Markus Jandke、Konrad Dettner、Gerhard Spiteller

  DOI：10.1016/s0031-9422(97)00622-5

  日期：1998.3

  Cell injury-as evoked by oxidative stress, insect attack or ageing-causes lipid peroxidation of polyunsaturated acids, e.g. linoleic acid. Hydroperoxides (LOOH) so produced transform fatty acids, terpenes and sterols to epoxides. We describe a bioassay to determine the cytotoxity of sterol oxidation products by measuring the mortality of meal-worms (Tenebrio molitor) after injection of diluted test compounds. LOOH was tested in concentrations from 10(-5) M up to 10(-3) M and developed recognizable mortality (25%, 10(-2) M, 23 hr). A direct relation between activity and concentration was observed. 5,6-Epoxides of phytosterols and derived 3,5,6-trihydroxysteranes have been isolated from Chenopodium rubrum cell cultures. Using 5,6-epoxycholesterol and 3,5,6-trihydroxycholestane as standards of known bioactivity, the toxicity of epoxides of sitosterol and stigmasterol, as well as the trihydroxy compounds thereof, was checked. The phytosterol derivatives are by a factor of five less active than the corresponding cholesterol oxidation products. 5,6-Epoxides and 5.6-chlorohydrins showed half of the activity of the corresponding 3,5,6-trihydroxyphytosterols. These developed highest cytotoxity (40% mortality in 5 x 10(-3) M solution after 23 hr). The activity of 5,6 alpha- and 5,6 beta-epoxides was found to be equal. Metabolism and proposed biological function of oxidized phytosterols is discussed. (C) 1998 Elsevier Science Ltd. All rights Reserved.