β-sitosterol trimethylsilyl ether | 2625-46-9

• 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: β-sitosterol trimethylsilyl ether
• 英文别名: 24β-ethylcholest-5-en-3β-ol trimethylsilyl ether；β-sitosterol, trimethylsilyl ether；β-sitosteryl trimethylsilyl ether；TMS；24β-ethylcholesterol trimethylsilyl ether；trimethyl silylated β-sitosterol；[(3S,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]phenanthren-3-yl]oxy-trimethylsilane
• CAS: 2625-46-9；18880-69-8；25873-56-7
• 化学式: C₃₂H₅₈OSi
• 分子量: 486.897
• InChiKey: XEWVATFZTBNDCF-BBWXUVGCSA-N

物化性质

• 熔点：
  88-90 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  511.0±29.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.88
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  β-sitosterol trimethylsilyl ether 在 montmorillonite K-10 作用下， 以 甲醇 为溶剂， 反应 0.2h， 以98%的产率得到植物甾醇
  参考文献：
  名称：

  蒙脱石粘土催化 XI1：通过蒙脱石 K-10 催化的三甲基甲硅烷基醚的形成和裂解对羟基进行保护和脱保护

  摘要：

  摘要 以蒙脱石 K-10 为载体，在室温下以 1,1,1,3,3,3-六甲基二硅氮烷 (HMDS) 为原料制备了醇和酚的三甲基甲硅烷基醚，收率良好。三甲基甲硅烷基醚的脱甲硅烷基化反应在室温下由甲醇中的 K-10 以高产率催化。

  DOI：

  10.1080/00397919808004891
• 作为产物：
  描述：

  植物甾醇 、 六甲基二硅氮烷 在 montmorillonite K-10 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到β-sitosterol trimethylsilyl ether
  参考文献：
  名称：

  蒙脱石粘土催化 XI1：通过蒙脱石 K-10 催化的三甲基甲硅烷基醚的形成和裂解对羟基进行保护和脱保护

  摘要：

  摘要 以蒙脱石 K-10 为载体，在室温下以 1,1,1,3,3,3-六甲基二硅氮烷 (HMDS) 为原料制备了醇和酚的三甲基甲硅烷基醚，收率良好。三甲基甲硅烷基醚的脱甲硅烷基化反应在室温下由甲醇中的 K-10 以高产率催化。

  DOI：

  10.1080/00397919808004891

文献信息

• Separation of Δ5- and Δ7-Phytosterols by Adsorption Chromatography and Semipreparative Reversed Phase High-Performance Liquid Chromatography for Quantitative Analysis of Phytosterols in Foods
  作者：Xin Zhang、Amandine Cambrai、Michel Miesch、Stamatiki Roussi、Francis Raul、Dalal Aoude-Werner、Eric Marchioni

  DOI：10.1021/jf052761x

  日期：2006.2.1

  A method for the separation, isolation, and identification of phytosterols was developed. A commercial phytosterols mixture, Generol 95S, was fractionated first by adsorption silica gel column chromatography and then separated by means of a semipreparative reverse phase high-performance liquid chromatography fitted with a Polaris C8-A column (250 mm x 10 mm i.d., 5 microm) using isocratic acetonit

  开发了一种分离，分离和鉴定植物甾醇的方法。首先通过吸附硅胶柱色谱法分离市售的植物甾醇混合物Generol 95S，然后通过装有Polaris C8-A色谱柱（250 mm x 10 mm内径，5微米）的半制备反相高效液相色谱法进行分离。 ），使用等度乙腈：2-丙醇：水（2：1：1，v / v / v）作为流动相。获得了六种单独的植物甾醇的毫克级，其中包括香茅甾烯醇，菜油甾醇，β-谷甾醇，Delta7-菜甾醇，Delta7-菜甾醇和Delta7-谷甾醇。这些分离的甾醇的纯度为85-98％。计算这些植物甾醇相对于胆固醇的相对响应因子（RRF）作为真实的商业标准。
• Silica Sulfate, an Efficient Catalyst for the Trimethylsilylation of Alcohols
  作者：Tong‐Shou Jin、Ruo‐Fei Tian、Li‐Bin Liu、Ying Zhao、Tong‐Shuang Li

  DOI：10.1080/00397910600602495

  日期：2006.7

  An easy method for the preparation of trimethylsilyl ethers from alcohols and 1,1,1,3,3,3-hexamethyl-disilazane (HMDS) using silica sulfate as a catalyst under mild conditions in excellent yields is described.
• Antioxidant Constituents of Almond [<i>Prunus dulcis </i>(Mill.) D.A. Webb] Hulls
  作者：Gary R. Takeoka、Lan T. Dao

  DOI：10.1021/jf020660i

  日期：2003.1.1

  Almond hulls (Nonpareil variety) were extracted with methanol and analyzed by reversed phase HPLC with diode array detection. The extract contained 5-O-caffeoylquinic acid (chlorogenic acid), 4-O-caffeoylquinic acid (cryptochlorogenic acid), and 3-O-caffeoylquinic acid (neochlorogenic acid) in the ratio 79.5:14.8:5.7. The chlorogenic acid concentration of almond hulls was 42.52 +/- 4.50 mg/100 g of fresh weight (n = 4; moisture content = 11.39%). Extracts were tested for their ability to inhibit the oxidation of methyl linoleate at 40 degreesC. At an equivalent concentration (10 mug/1 g of methyl linoleate) almond hull extracts had higher antioxiclant activity than alpha-tocopherol. At higher concentrations (50 mug/1 g of methyl linoleate) almond hull extracts showed increased antioxidant activity that was similar to chlorogenic acid and morin [2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one] standards (at the same concentrations). These data indicate that almond hulls are a potential source of these dietary antioxidants. The sterols (3beta,22E)-stigmasta-5,22-dien-3-ol (stigmasterol) and (3beta)stigmast-5-en-3-ol (beta-sitosterol) (18.9 mg and 16.0 mg/100 g of almond hull, respectively) were identified by GC-MS of the silylated almond hull extract.
• Jin, Tong-Shou; Li, Yan-Wei; Sun, Guang, Journal of Chemical Research - Part S, 2002, # 9, p. 456 - 458
  作者：Jin, Tong-Shou、Li, Yan-Wei、Sun, Guang、Li, Tong-Shuang

  DOI：——

  日期：——
• Phytosterols in Sea Buckthorn (<i>Hippophaë rhamnoides</i> L.) Berries:  Identification and Effects of Different Origins and Harvesting Times
  作者：Baoru Yang、Riina M. Karlsson、Pentti H. Oksman、Heikki P. Kallio

  DOI：10.1021/jf010813m

  日期：2001.11.1

  Sterols in seeds, pulp/peel fractions, and whole berries of sea buckthorn (Hippophae rhamnoides L.) samples belonging to two major subspecies (sinensis and rhamnoides) from Finland and China were analyzed as TMS derivatives by gas chromatography-mass spectrometry after saponification of the oils. The total sterol contents, in the seeds, the fresh pulp/peel, and the whole berries were, 1200-1800, 240-400, and 340-520 mg/kg, respectively. The corresponding values in the extracted oils were 12-23, 10-29, and 13-33 g/kg. Sitosterol constituted 57-76 and 61-83%, respectively, of the seed and pulp/peel sterols. The sterol content and composition showed little variation between subspecies and collection sites. Different harvesting dates showed significant effects on the levels of some sterols both in the seeds and in the pulp/peel. The sterol profiles obtained are useful for characterizing sea buckthorn and detecting adulterations of the valuable oils. The information provided by the present investigation is also important for further chemical investigation of sea buckthorn sterols and industrial utilization of the berries as a raw material of functional foods.