CAS: 80-97-7; (5α)-Cholestan-3β-Ol

该化合物是一种固醇,具体地说是胆固醇的饱和衍生物,其特点是分子式C27H48O,其中包括一个附于类固骨的氢氧基(-OH)组.胆固醇是一种白色晶状固体,在水中不溶解,但在乙醇和氯仿等有机溶剂中可溶解.它有一个熔点,通常属于特定范围,表明其处于室温的固态.这种化合物在生物系统中,特别是在细胞膜的结构和功能中起着重要作用,它有助于膜的流动性和稳定性.胆固醇也是对脂质代谢研究的兴趣之一,并已被调查其在各种健康条件下的潜在影响,包括心血管疾病.生物样本中的存在可以作为某些代谢紊乱的生物标志.

结构式图片

物理性质

MSDS等安全信息

上下游产品

CAS号601-57-0 4-胆甾烯-3-酮 | CAS号57-88-5 胆固醇 | CAS号1255-88-5 CHOLESTANOL ACETATE | CAS号566-88-1 5alpha-Cholesta... | CAS号3381-52-0 CHOLESTANE, 3.B... | CAS号69483-57-4 5α-cholestan-3β... | CAS号313-04-2 链甾醇 | CAS号107584-99-6 sodium (20R)-5α... | CAS号20283-99-2 Cyclopenta[5,6]... | CAS号481-21-0 5α-胆甾烷 | CAS号10437-24-8 3β-formyloxy-5α... | CAS号566-88-1 5alpha-Cholesta... | CAS号516-95-0 Epidihydr°Chole... | CAS号1178-00-3 2,3-sec°Cholest... | CAS号571-31-3 3β-羟基-5β-雄甾烷-17-酮 | CAS号3381-51-9 (3S,5S,8R,9S,10... | CAS号3381-54-2 Cholest-5-en-3-...

合成工艺路线路线简述

  • 合成目标产物 Dihydrocholesterol 主要起始原料 Cholesterol
  • 1255-88-5 = 80-97-7 [标题:Reaction Conditions
    标题:Enzymatic Transesterification Of Steroid Esters In Organic Solvents
    作者:Njar,Vincent C. O.; Et Al
    参考文献:Tetrahedron Letters 日期:1987 卷标:28(52) 页码:6549-52]

    1256-86-6 = 80-97-7
    反应条件:1.1 Solvents: Ethanol
    标题:Steroid Sulfates. I. Some Solvolytic Reactions Of The Salts Of Steroid Sulfates
    作者:Mckenna,Jean; Et Al
    参考文献:Journal Of The Chemical Society 日期:1957 卷标:3889 页码:3889-93]

    21102-68-1 = 80-97-7
    反应条件:1.1 Reagents: Trimethylsilyl Triflate Solvents: Dichloromethane
    标题:Convenient Methods For The Direct Conversion Of Tetrahydropyranyl Ethers Into Silyl-Protected Alcohols And For The Removal Of Tetrahydropyranyl Group
    作者:Oriyama,Takeshi; Et Al
    参考文献:Synlett 日期:1996 卷标:(6) 页码:523-525]

    57-88-5 = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 5 D,50 °C
    标题:Ruthenium-Nhc Catalyzed α-Alkylation Of Methylene Ketones Provides Branched Products Through Borrowing Hydrogen Strategy
    作者:Schlepphorst,Christoph; Et Al
    参考文献:Acs Catalysis 日期:2016 卷标:6(7) 页码:4184-4188]

    = 80-97-7
    反应条件:1.1 Reagents: Alumina Solvents: Diethyl Ether,Benzene
    标题:The Hydrolysis Of 3,5-Dinitrobenzoates
    作者:Castells,J.; Et Al
    参考文献:Journal Of The Chemical Society 日期:1956 卷标:3245 页码:3245-6]

    1981-90-4 = 80-97-7
    反应条件:1.1 Reagents: Aluminum Chloride,Sodium Iodide Solvents: Acetonitrile
    标题:Hard Acid And Soft Nucleophile Systems. Part 13. Aluminum Chloride-Sodium Iodide-Acetonitrile System. A Very Mild Reagent For Selective Dealkylation
    作者:Node,Manabu; Et Al
    参考文献:Bulletin Of The Institute For Chemical Research 日期:1992 卷标:70(3) 页码:308-17]

    1981-90-4 = 80-97-7
    反应条件:1.1 Reagents: [(Trimethylsilyl)Thio]Benzene,Zinc Chloride Solvents: 1,2-Dichloroethane
    标题:Cleavage Of Methyl And Benzyl Ethers With Thiotrimethylsilanes
    作者:Hanessian,Stephen; Et Al
    参考文献:Tetrahedron Letters 日期:1980 卷标:21(24) 页码:2305-8]

    = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Dioxide Solvents: Ethyl Acetate
    标题:New Stereoselective Synthesis Of 20S And 20R Steroidal Side Chains. Remarkable Stereoselectivity Differences Between Saturated And α,β-Unsaturated Steroidal Esters
    作者:Ibuka,Toshiro; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(17) 页码:3947-52]

    23656-66-8 = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Isopropanol; 20 H,1 Atm,30 °C
    标题:Synthesis Of Plant-Derived Cholesterol From Bisnoralcohol
    作者:Li,Xing-Zi; Et Al
    参考文献:Steroids 日期:2022 卷标:178]

    = 80-97-7
    反应条件:1.1 Reagents: P-Toluenesulfonic Acid Solvents: Benzene
    标题:Reaction Of Steroidal Alcohols With Isobutene. Usefulness Of Tert-Butyl As A Hydroxy-Protecting Group In A Synthesis Of Testosterone
    作者:Beyerman,H. C.; Et Al
    参考文献:Recueil Des Travaux Chimiques Des Pays-Bas 日期:1965 卷标:84(2) 页码:203-12]

    566-88-1 = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Solvents: Cyclohexane; 2 H,0.1 Mpa,Rt
    标题:Facile Hydrogenation Of Ketones Catalyzed By Platinum On Carbon Under Ordinary Pressures And Temperatures
    作者:Fujiwara,Yuta; Et Al
    参考文献:Chemcatchem 日期:2011 卷标:3(10) 页码:1624-1628]

    313-04-2 = 80-97-7
    反应条件:1.1 Reagents: Ammonium Formate Catalysts: Palladium
    标题:Ammonium Formate
    作者:King,Anthony O.; Et Al
    参考文献:E-Eros Encyclopedia Of Reagents For Organic Synthesis 日期:2006 卷标:1 页码:1-6]

    = 80-97-7
    反应条件:1.1 Reagents: Sodium Bicarbonate,Periodic Acid,Osmium Tetroxide Solvents: Water
    标题:Tiglate Ester As An Alcohol Blocking Group In Organic Synthesis
    作者:Kupchan,S. Morris; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1962 卷标:27(9) 页码:3103-6]

    = 80-97-7
    反应条件:1.1 Reagents: Ammonium Persulfate,Oxygen Catalysts: Acridinium,10-Methyl-9-(2,4,6-Trimethylphenyl)-,Perchlorate (1:1) Solvents: Dichloromethane,Water; 5 H,20 - 30 °C1.2 Reagents: Sodium Bicarbonate Solvents: Water; 20 - 30 °C
    标题:Oxidative Deprotection Of P-Methoxybenzyl Ethers Via Metal-Free Photoredox Catalysis
    作者:Ahn,Deok Kyun; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2019 卷标:84(6) 页码:3612-3623]

    1255-88-5 = 80-97-7
    反应条件:1.1 Reagents: Methanol Solvents: Methanol
    标题:Unexpected Reaction Using Methanol Dried Over Molecular Sieves
    作者:Mizuno,Mamoru; Et Al
    参考文献:Synthetic Communications 日期:2002 卷标:32(11) 页码:1665-1670]

    57-88-5 = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 5 D,60 °C
    标题:Ruthenium Nanoparticles Ligated By Cholesterol-Derived Nhcs And Their Application In The Hydrogenation Of Arenes
    作者:Rakers,Lena; Et Al
    参考文献:Chemical Communications (Cambridge 日期:2018 卷标:54(51) 页码:7070-7073]

    601-53-6 = 80-97-7
    反应条件:1.1 Solvents: Diethyl Ether
    标题:Stereochemistry Of Reduction Of Ketones With Grignard Reagents.
    作者:Wheeler,Owen H.; Et Al
    参考文献:Rev. Col. Quim. Puerto Rico 日期:1962 卷标:20 页码:24-5]

    570-74-1 = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol; 5 H,1 Atm,60 °C
    标题:Addressable Cholesterol Analogs For Live Imaging Of Cellular Membranes
    作者:Rakers,Lena; Et Al
    参考文献:Cell Chemical Biology 日期:2018 卷标:25(8) 页码:952-961]

    1981-90-4 = 80-97-7
    反应条件:1.1 Reagents: Ethanethiol,Aluminum Bromide
    标题:Aluminum Halide-Thiol System: A Useful Reagent For Demethylation Of Aliphatic And Aromatic Methyl Ethers And Demethylenation Of Methylenedioxy Compounds
    作者:Node,Manabu; Et Al
    参考文献:Chemistry Letters 日期:1979 卷标:(1) 页码:97-8]

    = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Dioxide Solvents: Ethyl Acetate
    标题:A New Stereoselective Synthesis Of (20R)- And (20S)-Steroidal Side Chains
    作者:Ibuka,Toshiro; Et Al
    参考文献:Journal Of The Chemical Society 日期:1988 卷标:(5) 页码:342-4]

    3381-52-0 = 80-97-7
    反应条件:1.1 Reagents: 1,5-Dimethoxynaphthalene,Sodium Borohydride Solvents: Acetonitrile,Water
    标题:Extremely Mild And Selective Method For Hydrolysis Of Tosyl Esters By Photosensitized Single Electron Transfer Reactions
    作者:Nishida,Atsushi; Et Al
    参考文献:Chemical & Pharmaceutical Bulletin 日期:1990 卷标:38(11) 页码:2977-80]

    3381-52-0 = 80-97-7
    反应条件:1.1 Reagents: 1,5-Dimethoxynaphthalene,Sodium Borohydride Solvents: Acetonitrile
    标题:Hydrolysis Of Tosyl Esters Initiated By An Electron Transfer From Photoexcited Electron-Rich Aromatic Compounds
    作者:Nishida,Atsushi; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(14) 页码:3386-7]

    107584-99-6 = 80-97-7
    反应条件:1.1 Reagents: P-Toluenesulfonic Acid Solvents: 1,4-Dioxane1.2 Reagents: Sodium Bicarbonate Solvents: Water1.3 Solvents: Ethyl Acetate
    标题:A New Mild Ptsa-Catalyzed Method For Sulfate Ester Hydrolysis And Acid-Catalyzed Rearrangement Of 12-Acetyl-Diene-11-Ol Tetracyclic Triterpenoids Involving An Angular Methyl Migration
    作者:Singh,S. B.
    参考文献:Tetrahedron Letters 日期:2000 卷标:41(36) 页码:6973-6976]

    566-88-1 = 80-97-7
    反应条件:1.1 Reagents: Aluminum Chloride,Lithium Aluminum Hydride Solvents: Diethyl Ether
    标题:Reduction Of 3-Cholestanone With Lithium Aluminum Hydride-Aluminum Chloride
    作者:Richer,Jean Claude; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1961 卷标:26 页码:972-3]

    566-88-1 = 80-97-7
    反应条件:1.1 Reagents: Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(Oh)2O10.Xh2O) Catalysts: Potassium Hydroxide Solvents: Isopropanol
    标题:Hydrogen Transfer Reduction Of Ketones Catalyzed By Fluka K-10 Montmorillonite
    作者:Dolmazon,David; Et Al
    参考文献:Journal Of Molecular Catalysis A: Chemical 日期:1998 卷标:136(2) 页码:147-151]

    15600-08-5 = 80-97-7
    反应条件:1.1 Reagents: Tetrabutylammonium Cyanoborohydride Solvents: Hexamethylphosphoramide
    标题:Tetrabutylammonium Cyanoborohydride. New,Exceptionally Selective Reducing Reagent
    作者:Hutchins,Robert O.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:1973 卷标:95(18) 页码:6131-3]

    15600-08-5 = 80-97-7
    反应条件:1.1 Reagents: Sodium Borohydride Solvents: Ethanol
    标题:Configuration Of Steroid Bromo Ketones. Ii. 4β-Bromotestan-17β-Ol-3-One Acetate And 2β-Bromocholestan-3-One
    作者:Fieser,Louis F.; Et Al
    参考文献:Journal Of The American Chemical Society 日期:1953 卷标:75 页码:1704-7]

    112399-95-8 = 80-97-7
    反应条件:1.1 Reagents: Hydrogen Catalysts: Platinum Dioxide Solvents: Methanol,Tetrahydrofuran
    标题:P,P'-Dinitrobenzhydryl Ethers,Acid And Base Stable Protecting Groups,Which Are Readily Removable In The Presence Of Benzyl And Monomethoxytrityl Functions
    作者:Just,George; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1988 卷标:53(5) 页码:1030-3]

    = 80-97-7
    反应条件:1.1 Reagents: Sodium Hydroxide,Sodium Bisulfite Solvents: Water
    标题:Tiglate Ester As An Alcohol Blocking Group In Organic Synthesis
    作者:Kupchan,S. Morris; Et Al
    参考文献:Journal Of Organic Chemistry 日期:1962 卷标:27(9) 页码:3103-6
📜Cholesterol置于乙醚,溶剂黄146,铂体系中,化学反应生成 3β-胆甾烷醇
参考文献:Bruce; Ralls,Organic Syntheses,1943,Vol. Coll. Vol. Ii,P. 191
标题:Bruce; Ralls,Organic Syntheses,1943,Vol. Coll. Vol. Ii,P. 191

海关参考信息

专利信息


专利号:US-2024294462-A1
优先权日:2023-02-15
标题:Method for the Synthesis of Ionizable Lipids Using a Doubly Alkylated Intermediate
发明人：SAADATI FARIBA; TRAN HUY; CIUFOLINI MARCO; ATMURI N D PRASAD
权利人:NANOVATION THERAPEUTICS INC
摘要:Provided herein is a method for the preparation of ionizable, cationic amino lipids using a doubly alkylated nucleophilic intermediate to produce a ketone. The ketone, or a corresponding alcohol, is subjected to one or more synthesis steps to add an ionizable moiety thereto. The method can be advantageously employed for the synthesis of unsymmetrical analogues of the above lipids that would be considerably more difficult to make by alternative strategies. The method can also be used to prepare symmetrical ionizable, cationic amino lipids with fewer steps and/or with the use of fewer hazardous chemicals than known synthesis methods.

专利号:US-2008300418-A1
优先权日:2004-11-08
标 题:Synthesis of Cardiolipin Analogues and Uses Thereof
发明人：AHMAD MOGHIS U; UKKALAM MURALI K; ALI SHOUKATH M; AHMAD IMRAN
权利人:AHMAD MOGHIS U; UKKALAM MURALI K; ALI SHOUKATH M; AHMAD IMRAN
摘要:The invention provides novel synthetic methodologies for preparing cardiolipin, migrated caridiolipin (1,2-positional isomer of cardiolipin) and their analogues having varying fatty acids and/or alkyl chains with varying length and degrees of saturation/unsaturation. The method comprises (a) reacting an optically pure 1,2-O-dialkyl-sn-glycerol or 1,2-O-dialkyl-sn-glycerol with one or more phosphoramidite reagent(s), wherein a phosphite triester is produced; (b) coupling the product of (a) with glycerol, wherein a protected cardiolipin is produced; and (c) deprotecting the protected cardiolipin, such that cardiolipin is prepared. The cardiolipins and analogues thereof, prepared by the present methods, can be incorporated into liposomes, which can also include active agents such as hydrophobic or hydrophilic drugs, antisense nucleotides or diagnostic agents. Such liposomes can be used to treat diseases or can be used in diagnostic and/or analytical assays.

专利号:US-2008188429-A1
优先权日:2002-12-27
标题 :Synthetic siRNA compounds and methods for the downregulation of gene expression
发明人：IYER RADHAKRISHNAN P
权利人:IYER RADHAKRISHNAN P
摘要:This invention relates to the design and synthesis of chemically modified short interfering nucleic acid (siNA) compounds capable of mediating RNA interference (RNAi) against target genes.

专利号:US-7417142-B2
优先权日:2002-03-28
标 题:Chiral porphyrins, chiral metalloporphyrins, and methods for synthesis of the same
发明人：ZHANG X PETER; CHEN YING; GAO GUANG-YAO
权利人:UNIV TENNESSEE RES FOUNDATION
摘要:Novel methods of synthesizing heteroatom-containing chiral porphyrins and chiral metalloporphyrins and the novel chiral porphyrins and chiral metalloporphyrins themselves are disclosed. Metal complexes of the chiral porphyrins are prepared in high yields and shown to be active catalysts for highly enantioselective and diastereoselective cyclopropanation, aziridination, and epoxidation of alkenes under a practical one-pot protocol.

专利号:WO-2018005963-A1
优先权日:2016-07-01
标 题:Synthesis of new methylumbelliferone prodrugs and their incorporation into lipid-based drug delivery formulations
发明人：SZOKA FRANCIS C JR; DAI ZHIPENG
权利人:ZONEONE PHARMA INC
摘要:Lipophilic prodrugs of 4-methylumbelliferone are incorporated into lipid based drug delivery systems (e.g., emulsions, micelles, liposomes and lipid particles). The formulations protect 4-methylumbelliferone from first pass hepatic metabolism to 4-MUG. Exemplary formulations are oral and parenteral formulations. Methods of treating proliferative diseases, e.g., cancer by administering the formulation to a subject in need thereof are provided.

专利号:US-9650407-B2
优先权日:2011-11-02
标 题 :Reprogramming of cellular adhesion
发明人：GARTNER ZEV JORDAN; SELDEN NICHOLAS SCOTT; TODHUNTER MICHAEL E; LIANG SAMANTHA ISABEL; WEBER ROBERT JOSEPH; JEE NOEL YOUNGHO; LIU JENNIFER S
权利人:UNIV CALIFORNIA
摘要:Disclosed are membrane-anchored polynucleotides, and compositions comprising the membrane-anchored polynucleotides. Also disclosed are the processes for the synthesis of these compounds, compositions comprising such compounds, and the use of such compounds and compositions in research and therapeutic applications.

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合成参考文献


摘要:André-Joyaux, E.; Gnägi, L.; Meléndez, C.; Soulard, V.; Renaud, P., Science of Synthesis, (2021) , 439.
摘要:S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118
摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
摘要:de Figueiredo, R. M., Science of Synthesis: Knowledge Updates, (2024) 2, 265.
参考文献:10.1099/vir.0.032391-0
摘要:Yamamoto M, Aizaki H, Fukasawa M, Teraoka T, Miyamura T, Wakita T, Suzuki T. Structural requirements of virion-associated cholesterol for infectivity, buoyant density and apolipoprotein association of hepatitis C virus. J Gen Virol. 2011 Sep;92(Pt 9):2082–7. doi: 10.1099/vir.0.032391-0.
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