7-氧代-beta-谷甾醇 | 2034-74-4

• 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: 7-氧代-beta-谷甾醇
• 英文名称: 3β-hydroxystigmast-5-en-7-one
• 英文别名: 7-oxo-β-sitosterol；7-ketositosterol；7-oxositosterol；stigmast-5-en-3β-ol-7-one；(24R)-3β-hydroxystigmast-5-en-7-one；3β-hydroxystigmast-5-ene-7-one；3β-hydroxystigmatol-5-en-7-one；7-keto-β-sitosterol；3-Hydroxystigmast-5-en-7-one；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
• CAS: 2034-74-4
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: ICFXJOAKQGDRCT-ZIHMWMKCSA-N

物化性质

• 熔点：
  120-123 °C
• 沸点：
  536.1±29.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：12mg/mL，乙醇：3mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-氧代-beta-谷甾醇 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以57%的产率得到5-stigmasten-3β,7β-diol
  参考文献：
  名称：

  Oxyphytosterols as Active Ingredients in Wheat Bran Suppress Human Colon Cancer Cell Growth: Identification, Chemical Synthesis, and Biological Evaluation

  摘要：

  Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 23) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 18 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.

  DOI：

  10.1021/jf506361r
• 作为产物：
  描述：

  植物甾醇 在 叔丁基过氧化氢 、 di-μ-hydroxo-bis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)] chloride 作用下， 以 甲醇 、 癸烷 、 二氯甲烷 为溶剂， 反应 40.0h， 以52%的产率得到7-氧代-beta-谷甾醇
  参考文献：
  名称：

  迅速合成菠菜甾醇和舒腾醇，坚果油和仙人掌梨子籽油中存在的两种植物甾醇，并评估它们对中枢神经系统细胞的生物学活性。

  摘要：

  菠菜甾醇和叔丁醇，存在于摩洛哥坚果油和仙人掌梨种子油中的两种植物甾醇，是通过四步反应从市售的豆甾醇中合成的。此外，分别用结晶紫试验和MTT试验评价了158N鼠少突胶质细胞，C6大鼠神经胶质瘤细胞和SK-N-BE人神经元细胞对这些植物甾醇对细胞生长和线粒体活性的影响。比较了Spinasterol和schottenol与7-ketocholesterol（7KC）和阿魏酸的作用，阿甘和仙人掌梨种子油中也存在阿魏酸。无论考虑哪种细胞，均观察到了7KC的剂量依赖性细胞毒性作用，而未发现或仅存在阿魏酸的轻微作用。用菠菜甾醇和舒腾醇，未检测到或对细胞生长有轻微影响。与菠菜甾醇，在158N和C6细胞上发现线粒体活性降低（30-50％）；没有发现对SK-N-BE有影响。使用舒腾醇后，在158N（50％）和C6（10-20％）细胞上线粒体活性降低。没有发现对SK-N-BE有影响。总而言之，这些数据表明，菠菜

  DOI：

  10.1016/j.steroids.2015.01.005

文献信息

• Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples
  作者：Adam Zmysłowski、Jerzy Sitkowski、Katarzyna Bus、Karol Ofiara、Arkadiusz Szterk

  DOI：10.1016/j.foodchem.2020.127132

  日期：2020.11

  sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid

  已经证明，在升高的温度下，固醇会经历各种化学反应，例如氧化，脱氢，脱水和聚合。这项研究的目的是证明二聚体的存在并定量分析二聚体（3β，3'β-二硬脂基醚）。将富含甾醇的样品在180°C，200°C和220°C下加热1至5小时。使用液相萃取，固相萃取和气相色谱-质谱联用技术对3β，3'β-二十二烷基醚进行了定量分析。另外，为了进行分析，从天然甾醇中合成了合适的标准品。为了确定高温下3β，3'β-二叔丁基醚形成的机理，尝试使用提出的合成方法。另外，
• An environmentally benign catalytic oxidation of cholesteryl acetate with molecular oxygen by using N-hydroxyphthalimide
  作者：Zhen Yao、Xingbang Hu、Jianyong Mao、Haoran Li

  DOI：10.1039/b915737a

  日期：——

  A green and effective method is reported for the oxidation of cholesteryl acetate to 7-keto-cholesteryl acetate with O2 in the presence of catalytic amounts of N-hydroxyphthalimide (NHPI) under mild conditions. It was found that Co(OAc)2 could cooperate with Mn(OAc)2 to enhance the catalytic ability of NHPI resulting in better yields. This economical and environmentally-friendly method provides a potentially

  报道了一种绿色有效的氧化方法。 胆固醇胆固醇 到 7-酮-胆固醇乙酸酯带O 2在催化量的存在N-羟基邻苯二甲酰亚胺（NHPI）在温和的条件下。发现Co（OAc）2可以与Mn（OAc）2协同作用以增强NHPI的催化能力，从而获得更好的收率。这种经济环保的方法为合成中间体中间体提供了潜在的新途径。维生素D 3 在工业上，这消除了在当前途径中使用大量的溴，并克服了已知的氧化方法的缺点。
• A metal-free approach to access ketones, amides, and nitriles employing TBAI/TBHP oxidative system in water
  作者：Suzane Quintana Gomes、Airton G. Salles

  DOI：10.1080/00397911.2019.1669183

  日期：2019.12.2

  and heteroaromatic-bearing amines have been efficiently employed as substrates in allylic and benzylic oxidations via C(sp3)–H bond activation by TBAI/TBHP in water. This operationally simple method allows access to ketones, nitriles, and amides in moderate to high yields and a regio- and chemoselective late-stage functionalization. GRAPHICAL ABSTRACT

  摘要 碳氢化合物、苄胺和含杂芳烃的胺已被有效地用作烯丙基和苄基氧化反应的底物，通过 TBAI/TBHP 在水中的 C(sp3)-H 键活化。这种操作简单的方法允许以中等至高产率获得酮、腈和酰胺，以及区域和化学选择性的后期功能化。图形概要
• Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
  作者：Florence O. McCarthy、Jay Chopra、Alan Ford、Sean A. Hogan、Joe P. Kerry、Nora M. O'Brien、Eileen Ryan、Anita R. Maguire

  DOI：10.1039/b505069c

  日期：——

  β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides.

  δ-谷甾醇是最常见的植物胆固醇衍生物（植物甾醇），可发生与胆固醇类似的氧化作用，生成δ-谷甾醇氧化物。植物固醇氧化物的生物影响只在植物固醇混合物（通常包括δ-谷甾醇、坎贝酯醇、豆甾醇和二氢巴西甾醇）中进行过评估。由于缺乏纯植物甾醇（包括δ-谷甾醇），因此无法收集有关单个δ-谷甾醇氧化物的重要毒性数据。本文介绍了多克纯δ-谷甾醇的高效合成路线，以及纯δ-谷甾醇氧化物的首次合成和表征。
• 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。