3beta,7alpha-二羟基豆甾-5-烯 | 34427-61-7

• 物质功能分类: 天然产物 - 甾体化合物
• 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
• 中文名称: 3beta,7alpha-二羟基豆甾-5-烯
• 中文别名: 3Β,7Α-二羟-豆甾-5-烯
• 英文名称: 7α-hydroxysitosterol
• 英文别名: (24R)-24-ethyl-cholest-5-en-3β,7α-diol；(24R)-stigmasta-5-en-3β,7α-diol；(3β,7α)-stigmast-5-ene-3,7-diol；3β,7α-dihydroxy-stigmast-5-en；sitosterol-5-en-3β,7α-diol；stigmast-5-ene-3β,7α-diol；Ikshusterol；(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• CAS: 34427-61-7
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: SXJVFYZNUGGHRG-GDDJFQTCSA-N

物化性质

• 熔点：
  202-204 °C(Solv: acetone (67-64-1))
• 沸点：
  535.0±38.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3beta,7alpha-二羟基豆甾-5-烯 在 磷酸 作用下， 以 正丁醇 为溶剂， 反应 1.0h， 生成 24-ethyl-cholest-2,4,6-triene
  参考文献：
  名称：

  Identification of New Steroidal Hydrocarbons in Refined Oils and the Role of Hydroxy Sterols as Possible Precursors

  摘要：

  The dehydration of sterols during the refining process of vegetable oils results in the formation of steroidal hydrocarbons (sterenes or steradienes) with two double bonds in the ring system. Other steroidal hydrocarbons whose structures were in agreement with the presence of three double bonds in the ring system were detected in the sterene fractions of refined vegetable oils. The 5 alpha-, 7 alpha-, and 7 beta-hydroxy derivatives of cholesterol and phytosterols have been dehydrated in n-butanol/H3PO4 to form steroidal hydrocarbons with three double bonds at the 2, 4, and 6 positions in the ring system. These hydrocarbons had the same relative retention time and mass spectra as those present in the sterene fractions of refined oils. The dehydration of the hydroxy sterols dissolved in extra virgin olive oil and in the presence of 1% bleaching earths at 80 degrees C for 1 h results in the formation of the same steroidal hydrocarbons found in the refined oils.

  DOI：

  10.1021/jf9912147
• 作为产物：
  描述：

  豆甾醇 在 sodium tetrahydroborate 、 氧气 、 hematoporphyrin 作用下， 以 吡啶 、 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 125.0h， 生成 3beta,7alpha-二羟基豆甾-5-烯
  参考文献：
  名称：

  β-谷甾醇，菜油甾醇，豆甾醇和芸苔甾醇的5alpha-，7alpha-和7beta-羟基衍生物的质谱表征。

  摘要：

  β-谷甾醇，菜油甾醇，豆甾醇和芸苔甾醇的5α-氢过氧化物是通过在吡啶并以血卟啉为敏化剂的条件下将各甾醇在吡啶中进行光氧化而获得的。氢过氧化物的还原得到相应的5α-羟基衍生物。通过使等分的5α-氢过氧化物异构化为7α-氢过氧化物而获得固醇的7α-氢过氧化物和7β-氢过氧化物，其继而异构化为7β-氢过氧化物。还原得到相应的7α-和7β-羟基衍生物。通过比较薄层色谱的迁移率，特定的颜色反应，确定了β-谷甾醇，菜油甾醇，豆甾醇和芸苔甾醇的5α-，7α-和7β-羟基衍生物。质谱数据与相应的胆固醇羟基衍生物的质谱数据相同。植物甾醇对光氧化的行为与胆固醇相同，而且，不同的植物甾醇以大约相同的速率光氧化。研究的植物甾醇的羟基衍生物的三甲基甲硅烷基醚和胆固醇的相应羟基衍生物的质谱具有相同的裂解模式和相似的相对离子丰度。

  DOI：

  10.1021/jf9812580

文献信息

• Inhibitory Effect of Some Oxygenated Stigmastane-Type Sterols on 12-O-Tetradecanoylphorbol-13-acetate-Induced Inflammation in Mice.
  作者：Yumiko KIMURA、Ken YASUKAWA、Michio TAKIDO、Toshihiro AKIHISA、Toshitake TAMURA

  DOI：10.1248/bpb.18.1617

  日期：——

  The oxygenated stigmastane-type sterols stigmastane-3β, 6α-diol, stigmastane-3β, 6β-diol, 7α-hydroxysitosterol and its diacetyl derivative, 7β-hydroxysitosterol and its diacetyl derivative, 7-oxositosterol, 4β-hydroxysitosterol, and stigmast-4-ene-3β, 6β-diol were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the sterols, with the exception of 7α-hydroxysitosterol and its diacetyl derivative, were found to possess marked inhibitory activity. The 50% inhibitory dose of these compounds for TPA-inflammation (1 μg) was 0.5-1.0 mg/ear.

  氧化的甾烷型固醇（stigmastane-3β, 6α-diol、stigmastane-3β, 6β-diol、7α-羟基甾醇及其二乙酰衍生物、7β-羟基甾醇及其二乙酰衍生物、7-氧代甾醇、4β-羟基甾醇和stigmast-4-ene-3β, 6β-diol）对小鼠体内12-O-十四烷酰基-13-乙酰基-7-羟基-4-甲基-10-羟基-1-磷酰基-5-胆甾烯酸（TPA）引起的炎症的抗炎活性进行了评估。除7α-羟基甾醇及其二乙酰衍生物外，所有固醇均具有明显的抑制活性。这些化合物对TPA炎症的50%抑制剂量（1微克）为0.5-1.0毫克/耳。
• Gram-scale chromatographic purification of β-sitosterolSynthesis and characterization of β-sitosterol oxides
  作者：X ZHANG、P GEOFFROY、M MIESCH、D JULIENDAVID、F RAUL、D AOUDEWERNER、E MARCHIONI

  DOI：10.1016/j.steroids.2005.06.003

  日期：2005.12.1

  An effective purification method for P-sitosterol was developed starting from a commercial source of a phytosterol mixture using preparative adsorption column chromatography. P-Sitosterol (>= 95% purity) was obtained on a gram-scale. Thus, the synthesis of six P-sitosterol oxides, including 7 alpha-hydroxy, 7 beta-hydroxy, 5,6 alpha-epoxy, 5,6 beta-epoxy, 7-keto, and 5 alpha,6 beta-dihydroxysitosterol, were successfully carried out. The spectral characteristics of all the synthetic intermediates and target compounds (similar to 95% purity) were well-documented. (c) 2005 Elsevier Inc. All rights reserved.
• Non-cannabinoid constituents from a high potency Cannabis sativa variety
  作者：Mohamed M. Radwan、Mahmoud A. ElSohly、Desmond Slade、Safwat A. Ahmed、Lisa Wilson、Abir T. El-Alfy、Ikhlas A. Khan、Samir A. Ross

  DOI：10.1016/j.phytochem.2008.07.010

  日期：2008.10

  Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L. variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and beta-sitosteryl-3-O-beta-D-glucopyranoside-2'-O-palmitate (6). In addition, five known compounds, alpha-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and beta-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and anti-oxidant activities. Compounds 2-4 were inactive as analgesics. (C) 2008 Elsevier Ltd. All rights reserved.
• Chinese traditional medicines for psoriasis
  申请人：——

  公开号：US20030152588A1

  公开（公告）日：2003-08-14

  The invention relates to disclose some Chinese formula for psoriasis. Whether treatment for psoriasis is targeted at both the hyperproliferative and inflammatory aspect of the topical therapy. Specially, the administration dosage is soft gel, cream, tincture and aerosol etc. topical dosages.