CAS: 83-45-4; Stigmastanol

该化合物是植物衍生的活性醇,植物衍生的活性醇,在结构上与胆固醇相似;是水中不溶解但溶解于乙醇和氯仿等有机溶剂中的白白离白结晶粉;Sitostanol主要存在于各种植物油,坚果和种子中,以其胆固醇低效特性而闻名;它的作用是抑制胆固醇在肠胃中的吸收,使其有利于心血管健康;Sitostanol经常用作饮食补充剂,并被纳入诸如人造黄和酸奶等功能性食物,以帮助管理胆固醇水平;其安全性特征一般是有利的,尽管过度消费可能导致胃肠道不适.此外,对锡stanol进行了研究,研究其潜在的抗氟化和抗氧化剂影响,有助于其促进整体健康.

结构式图片

上下游产品

24-Ethyl-Coprostanol 5060-24-2
(24S)-5α-Stigmast-22(E)-En-3β-Ol 4736-56-5
3β-Acetoxy-5α-Stigmastane 2364-21-8

合成工艺路线路线简述

  • 83-48-7 = 83-45-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Tetrahydrofuran; 3 H,Rt
    标题:An Assay For Dna Polymerase β Lyase Inhibitors That Engage The Catalytic Nucleophile For Binding
    作者:Daskalova,Sasha M.; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2020 卷标:28(17)]

    83-46-5 = 83-45-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol,Dichloromethane; 4 H,Rt
    标题:Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction Of 1,3-Dimesylates For The Synthesis Of Alkylcyclopropanes
    作者:Sanford,Amberly B.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:2020 卷标:142(11) 页码:5017-5023]

    115587-24-1 = 83-45-4
    反应条件:1.1 Catalysts: Sodium Methoxide
    标题:Isolation Of Ovulatory-Active Substances From Crops Of Job'S Tears (Coix Lacryma-Jobi L. Var. Ma-Yuen Stapf.)
    作者:Kondo,Yoshikazu; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1988 卷标:36(8) 页码:3147-52]

    5060-25-3 = 83-45-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Solvents: 1-Propanol; 30 Min,4 Bar,80 °C
    标题:Integrated Modelling Of Reaction And Catalyst Deactivation Kinetics-Hydrogenation Of Sitosterol To Sitostanol Over A Palladium Catalyst
    作者:Salmi,Tapio; Et Al
    参考文献:Chemical Engineering Science 日期:2013 卷标:104 页码:156-165]

    83-46-5 = 83-45-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 24 H,Rt
    标题:Novel Human Umbilical Vein Endothelial Cells (Huvec)-Apoptosis Inhibitory Phytosterol Analogues: Insight Into Their Structure-Activity Relationships
    作者:Lee,Sujin; Et Al
    参考文献:Archives Of Pharmacal Research 日期:2012 卷标:35(3) 页码:455-460]

    83-46-5 = 83-45-4
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl Acetate; 0.5 Mpa,50 °C
    标题:Novel Approach To Determining The Absolute Configurations At The C3-Positions Of Various Types Of Sterols Based On An Induced Circular Dichroism
    作者:Fujiwara,Toshio; Et Al
    参考文献:Steroids 日期:2012 卷标:77(12) 页码:1198-1204]

    115587-25-2 = 83-45-4
    反应条件:1.1 Reagents: Sodium Borohydride2.1 Catalysts: Sodium Methoxide
    标题:Isolation Of Ovulatory-Active Substances From Crops Of Job'S Tears (Coix Lacryma-Jobi L. Var. Ma-Yuen Stapf.)
    作者:Kondo,Yoshikazu; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1988 卷标:36(8) 页码:3147-52]

    83-46-5 = 83-45-4 + 5060-25-3
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: 1-Propanol; 1 H,4 Bar,80 °C
    标题:Catalyst Deactivation In Selective Hydrogenation Of β-Sitosterol To β-Sitostanol Over Palladium
    作者:Lindroos,Minna; Et Al
    参考文献:Chemical Industries (Dekker) 日期:2003 卷标:89 页码:587-594]

    4651-51-8 + 83-48-7 + 83-46-5 = 83-45-4 + 6538-02-9
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Isopropanol; 1 H,85 - 90 °C
    标题:Stanol Synthesis From Palm Oil Distillate
    作者:Chuanphongpanich,Sarunya; Et Al
    参考文献:Chiang Mai Journal Of Science 日期:2006 卷标:33(1) 页码:109-116]

    83-48-7 + 474-67-9 + 474-62-4 + 83-46-5 = 83-45-4 + 474-60-2
    反应条件:1.1 Catalysts: Palladium1.2 Solvents: 1-Propanol1.3 Reagents: Hydrogen
    标题:Modeling And Scale-Up Of Sitosterol Hydrogenation Process: From Laboratory Slurry Reactor To Plant Scale
    作者:Waern,Johan; Et Al
    参考文献:Industrial & Engineering Chemistry Research 日期:2006 卷标:45(21) 页码:7067-7076
📜豆甾醇置于5% Pd/c,氢气体系中,用 乙酸乙酯 作为反应溶剂,50.0 °C,500.01 Kpa 条件下,以77%的收率获得产物豆甾烷醇
参考文献:基于诱导圆二色性确定各种甾醇 C3 位绝对构型的新方法
标题:基于诱导圆二色性确定各种甾醇 C3 位绝对构型的新方法
摘要:源自 δ(5)-甾醇的 2,2'-联萘酯的圆二色性 (Cd) 光谱显示不是双信号 Cd,而是在 210 和 240 Nm 附近的诊断 Cd 带.这些带可能归因于烯烃发色团和联萘发色团之间的相互作用.各种类型的不饱和甾醇被衍生化,然后完全氢化,得到饱和甾醇.结果,饱和甾醇的联萘衍生物的 Cd 光谱显示出以 240 Nm 为中心的双信号曲线(3S(β):正手性;3R(α):负手性).这提出了一种基于诱导 Cd 区分甾醇 C-3 位置的绝对立体中心的简单实用的方法.这一发现将对各种甾醇代谢物的分析做出重大贡献.
DOI:10.1016/j.Steroids.2012.07.006

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✅ COA系统入驻 | 共享模式

主要参考文献


1: Matysik S, Elger T, Huss M, Liebisch G, Höring M, Loibl J, Kandulski A, Müller M, Tews HC, Buechler C. Unique sterol metabolite shifts in inflammatory bowel disease and primary sclerosing cholangitis. J Steroid Biochem Mol Biol. 2024 Sep 16;245:106621. doi: 10.1016/j.jsbmb.2024.106621. Epub ahead of print. 72(28):15672-15679. doi: 10.1021/acs.jafc.4c02109. Epub 2024 Jul 1.
4: Garrido-Sanchez L, Leiva-Badosa E, Llop-Talaveron J, Pintó-Sala X, Lozano- Andreu T, Corbella-Inglés E, Alia-Ramos P, Arias-Barquet L, Ramon-Torrel JM, Badía-Tahull MB. Blood Phytosterol Concentration and Genetic Variant Associations in a Sample Population. Nutrients. 2024 Apr 5;16(7):1067. doi: 10.3390/nu16071067.
5: Stanasila L, Lütjohann D, Popp J, Marques-Vidal P. Association between Serum Phytosterols and Lipid Levels in a Population-Based Study. Nutrients. 2024 Mar 8;16(6):775. doi: 10.3390/nu16060775.
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