stigmastanol | 55529-51-6

• 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: stigmastanol
• 英文别名: Fucostanol；(3S,5S,8R,9S,10S,13R,14S,17R)-17-[(2R,5S)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 55529-51-6
• 化学式: C₂₉H₅₂O
• 分子量: 416.731
• InChiKey: LGJMUZUPVCAVPU-GJAZBXDESA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  471.9±13.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  stigmastanol 在 chromium(VI) oxide 、 硫酸 作用下， 生成 5α.24α_FH-stigmastanone-(3)
  参考文献：
  名称：

  Ochromonas malhamensis 将钝叶醇转化为多孔甾醇过程中 C-4 去甲基化的立体化学

  摘要：

  摘要 Obtusifoliol-[2,2,4- 3 H 3 ] 被合成并与金藻藻Ochromonas malhamensis 孵育，将其转化为poriferasterol。应用于 poriferasterol 的反应序列表明，保留在 C-4 的氚占据了 4α 位。这表明 O. malhamensis 对 4α-甲基甾醇前体的生物 C-4 去甲基化导致轴向 4β-氢转化为 4-去甲基甾醇产物的赤道 4α-位置。

  DOI：

  10.1016/0031-9422(71)85069-0
• 作为产物：
  描述：

  Stigmast-8(14)-en-3β-ylacetat 在 氯仿 作用下， 生成 stigmastanol
  参考文献：
  名称：

  对水产品研究的贡献；软骨甾醇。

  摘要：

  DOI：

  10.1021/jo01163a020

文献信息

• 5α-Poriferast-9(11)-en-3β-ol from the marine red alga, Gracilaria edulis
  作者：B. Das、Y. Venkateswarlu、K.V.N.S. Srinivas、A.V.Rama Rao

  DOI：10.1016/0031-9422(92)80074-o

  日期：1992.3

  Abstract A new sterol isolated from the marine red alga, Gracilaria edulis , has been characterized as 5α-poriferast-9(11)-en-3β-ol from its spectral data and chemical reactions.

  摘要 从海洋红藻Gracilaria edulis 中分离出一种新的甾醇，其光谱数据和化学反应被鉴定为5α-poriferast-9(11​​)-en-3β-ol。
• Fatty Acid Steryl, Stanyl, and Steroid Esters by Esterification and Transesterification in Vacuo Using <i>Candida rugosa</i> Lipase as Catalyst
  作者：Nikolaus Weber、Petra Weitkamp、Kumar D. Mukherjee

  DOI：10.1021/jf000830w

  日期：2001.1.1

  Sterols (sitosterol, cholesterol, stigmasterol, ergosterol, and 7-dehydrocholesterol) and sitostanol have been converted in high to near-quantitative yields to the corresponding long-chain acyl esters via esterification with fatty acids or transesterification with methyl esters of fatty acids or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20-40 mbar) at 40 degreesC. Neither organic solvent nor water is added in these reactions. Under similar conditions, cholesterol has been converted to cholesteryl butyrate and steroids (5 alpha -pregnan-3 beta -ol-20-one or 5-pregnen-3 beta -ol-20-one) have been converted to their propionic acid esters, both in moderate to high yields, via transesterification with tributyrin and tripropionin, respectively. Reaction parameters studied in esterification include the temperature and the molar ratio of the substrates as well as the amount and reuse properties of the C, rugosa lipase. Lipases from porcine pancreas, Rhizopus arrhizus, and Chromobacterium viscosum are quite ineffective as biocatalysts for the esterification of cholesterol with oleic acid under the above conditions.
• Die Synthese von 5α‐Stigmasta‐22,25‐dien‐3β‐ol, 5α‐Stigmast‐22‐en‐3β‐ol und 5α‐Stigmastan‐3β‐ol und ihren 24‐Epimeren
  作者：Wolfgang Sucrow、Marion Slopianka、Penelope Polyzou Caldeira

  DOI：10.1002/cber.19751080415

  日期：1975.4
• CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. X. CLIONASTEROL
  作者：C. ALBERT KIND、WERNER BERGMANN

  DOI：10.1021/jo01198a007

  日期：1942.7
• CONTRIBUTIONS TO THE STUDY OF MARINE PRODUCTS. VIII. THE STEROL OF SPONGES: CLIONASTEROL AND PORIFERASTEROL
  作者：FRANK R. VALENTINE、WERNER BERGMANN

  DOI：10.1021/jo01203a011

  日期：1941.5