24-methylcholest-5-en-3β-yl acetate | 1900-53-4

• 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: 24-methylcholest-5-en-3β-yl acetate
• 英文别名: (24S)-β-methylcholesterol acetate；24α-Methylcholesterol acetate；24β-methylcholesterol acetate；22,23-dihydrobrassicasterol acetate；22-dihydrobrassicasterol acetate；Campesterol acetate；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1900-53-4；60536-89-2；73746-20-0；4651-52-9
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: JOBAYBRAHVTSSW-VDJOWXGMSA-N

物化性质

• 保留指数：
  3276

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24-methylcholest-5-en-3β-yl acetate 在 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以43%的产率得到ergost-5-en-7-on-3β-ol acetate
  参考文献：
  名称：

  Oxidized Derivatives of Dihydrobrassicasterol: Cytotoxic and Apoptotic Potential in U937 and HepG2 Cells

  摘要：

  The ability of phytosterol compounds to reduce plasma serum cholesterol levels in humans is well investigated. However, phytosterols are structurally similar to cholesterol with a double bond at the C5-6 position and are therefore susceptible to oxidation. Much research has been carried out on the biological effects of cholesterol oxidation products (COPs) in vitro. In contrast, there is less known about phytosterol oxidation products (POPs). From previous studies, it is apparent that oxidized derivatives of the phytosterols, beta-sitosterol and stigmasterol, are cytotoxic in vitro but are less potent than their COP counterparts. In the present study, the cytotoxic and apoptotic potential of oxidized derivatives of dihydrobrassicasterol (DHB) including 5 alpha,6 alpha-epoxyergostan-3 beta-ol (alpha-epoxide), 5 beta,6 beta-epoxyergostan-3 beta-ol (beta-epoxide), ergost-5-en-7-on-3 beta-ol (7-keto), ergost-5-ene-3 beta,7 beta-diol (7-beta-OH), and ergostane-3 beta,5 alpha,6 beta-triol (triol) were evaluated in the U937 and HepG2 cell lines. In general, 7-keto, 7-beta-OH, and triol derivatives had a significant cytotoxic impact on U937 and HepG2 cells. The oxides appear to be more toxic toward U937 cells. In line with previous findings, the POPs investigated in this study were less potent than the equivalent COPs. The results add to the body of data on the toxicity of individual POPs.

  DOI：

  10.1021/jf204737e
• 作为产物：
  描述：

  butanoic acid, 2,3-dimethyl-, methyl ester 在 palladium on activated charcoal lithium aluminium tetrahydride 、 四溴化碳 、 氢气 、 溴 、 sodium ethanolate 、 三苯基膦 、 mercury(II) oxide 作用下， 以 四氯化碳 、 乙醚 为溶剂， 生成 24-methylcholest-5-en-3β-yl acetate
  参考文献：
  名称：

  乙酸菜油酯 ((24R)-24-methyl-3β-acetoxycholesten-5-ene) 及其 24S-差向异构体的合成

  摘要：

  摘要 以光学活性的 3,4-二甲基戊基溴化镁和孕烯醇酮乙酸酯为原料，合成了乙酸菜油酯及其 24 S 差向异构体。两种差向异构体对黄斑皮螨幼虫的利用不同。

  DOI：

  10.1016/s0039-128x(70)80133-7

文献信息

• Kobayashi, Masaru; Hayashi, Takaaki; Hayashi, Koji, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 6, p. 1848 - 1855
  作者：Kobayashi, Masaru、Hayashi, Takaaki、Hayashi, Koji、Tanabe, Masato、Nakagawa, Takashi、et al.

  DOI：——

  日期：——
• 24β-methylcholesta-5,22E,25-trien-3β-ol and 24α-ethyl-5α-cholest-22E-en-3β-ol from Clerodendrum fragrans
  作者：Toshihiro Akihisa、Parthasarathi Ghosh、Swapnadip Thakur、Satoshi Oshikiri、Toshitake Tamura、Taro Matsumoto

  DOI：10.1016/0031-9422(88)80623-x

  日期：——
• Brassicasterol and 22,23-dihydrobrassicasterol from ergosterol via i-ergosterol
  作者：Malcolm J. Thompson、Charles F. Cohen、Stanton M. Lancaster

  DOI：10.1016/0039-128x(65)90168-6

  日期：1965.6
• Preparation of 22,23-Dihydrostigmasterol and 22,23-Dihydrobrassicasterol
  作者：Erhard Fernholz、William L. Ruigh

  DOI：10.1021/ja01869a022

  日期：1940.12
• Sterols of the siphonous marine alga Codium fragile
  作者：Ian Rubinstein、L. John Goad

  DOI：10.1016/s0031-9422(00)91238-x

  日期：1974.2