stigmasterol trimethylsilyl ether | 14030-29-6

• 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: stigmasterol trimethylsilyl ether
• 英文别名: Stigmasterol TMS ether；[(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-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: 14030-29-6
• 化学式: C₃₂H₅₆OSi
• 分子量: 484.882
• InChiKey: SZLWSWKRZSAHBC-MZXORBNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.66
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  stigmasterol trimethylsilyl ether 在 1% Pd on activated carbon 、 ammonium acetate 、 氢气 、 臭氧 、 三苯基氧化膦 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， -70.0~50.0 ℃ 、303.99 kPa 条件下， 反应 24.5h， 生成 胆固醇
  参考文献：
  名称：

  一种合成胆固醇的新方法

  摘要：

  本发明公开了一种合成胆固醇的新方法，包括步骤：（1）豆甾醇02溶于有机溶剂I中，在催化剂的作用下与三甲基氯硅烷进行硅醚化反应，经水洗、浓缩得化合物03；（2）化合物03溶解在有机溶剂II中进行臭氧氧化反应，再加锌粉和冰醋酸进行还原，反应完成后，过滤，洗涤，浓缩，得化合物04；（3）三苯基膦与1‑卤代‑3‑甲基丁烷反应得3‑甲基丁基三苯基卤化膦；将所述3‑甲基丁基三苯基卤化膦加入非质子溶剂中，加入强碱，然后与化合物04进行wittig反应，经中和、浓缩、过滤，得化合物05；（4）化合物05在催化剂和钝化剂的作用下在溶剂III中进行选择性氢化反应，经过滤、浓缩、结晶，得胆固醇01。该方法工艺简单，原料成本低廉，经济环保，便于工业化生产。

  公开号：

  CN106632565A
• 作为产物：
  描述：

  三甲基氯硅烷 、 豆甾醇 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以97.36%的产率得到stigmasterol trimethylsilyl ether
  参考文献：
  名称：

  一种合成胆固醇的新方法

  摘要：

  本发明公开了一种合成胆固醇的新方法，包括步骤：（1）豆甾醇02溶于有机溶剂I中，在催化剂的作用下与三甲基氯硅烷进行硅醚化反应，经水洗、浓缩得化合物03；（2）化合物03溶解在有机溶剂II中进行臭氧氧化反应，再加锌粉和冰醋酸进行还原，反应完成后，过滤，洗涤，浓缩，得化合物04；（3）三苯基膦与1‑卤代‑3‑甲基丁烷反应得3‑甲基丁基三苯基卤化膦；将所述3‑甲基丁基三苯基卤化膦加入非质子溶剂中，加入强碱，然后与化合物04进行wittig反应，经中和、浓缩、过滤，得化合物05；（4）化合物05在催化剂和钝化剂的作用下在溶剂III中进行选择性氢化反应，经过滤、浓缩、结晶，得胆固醇01。该方法工艺简单，原料成本低廉，经济环保，便于工业化生产。

  公开号：

  CN106632565A

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。
• 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.
• 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.
• Nutritional Traits of Bean (Phaseolus vulgaris) Seeds from Plants Chronically Exposed to Ozone Pollution
  作者：Marcello Iriti、Antimo Di Maro、Silvana Bernasconi、Nedda Burlini、Paolo Simonetti、Valentina Picchi、Cinzia Panigada、Giacomo Gerosa、Augusto Parente、Franco Faoro

  DOI：10.1021/jf802819m

  日期：2009.1.14

  The effect of chronic exposure to ozone pollution on nutritional traits of bean (Phaseolus vulgaris L. cv. Borlotto Nano Lingua di Fuoco) seeds from plants grown in filtered and nonfiltered open-top chambers (OTCs) has been investigated. Results showed that, among seed macronutrients, ozone significantly raised total lipids, crude proteins, and dietary fiber and slightly decreased total free amino acid content, although with a significant reduction of asparagine, lysine, valine, methionine, and glycine, compensated by a conspicuous augmentation of ornithine and tryptophan. Phytosterol analysis showed a marked increase of P-sitosterol, stigmasterol, and campesterol in seeds collected from nonfiltered OTCs. With regard to secondary metabolites, ozone exposure induced a slight increase of total polyphenol content, although causing a significant reduction of some flavonols (aglycone kaempferol and its 3-glucoside derivative) and hydroxycinnamates (caffeic, p-coumaric, and sinapic acids). Total anthocyanins decreased significantly, too. Nevertheless, ozone-exposed seeds showed higher antioxidant activity, with higher Trolox equivalent antioxidant capacity (TEAC) values than those measured in seeds collected from filtered air.