CAS: 77-60-1; (2As,4S,5'R,6As,6Bs,8As,8Br,9S,10R,11As,12As,12Br)-5',6A,8A,9-Tetramethyldocosahydrospiro[naphtho[2',1':4,5]Indeno[2,1-B]Furan-10,2'-Pyran]-4-Ol

该化合物是一种自然产生的类固醇沙质素,主要来自各种植物来源,特别是原生二亚科拉,其特征是血清结构,其中包括一个环球阻塞的氢苯乙烷核心; 底生素一般是一种白色的脱白晶粉,在水中不溶解,但在乙醇和氯仿等有机溶剂中可溶解; 其分子配方为C27H44O, 其熔点因纯度和具体条件而异; 底生素在生物化学和药理领域很受关注,因为它在合成类固醇荷尔蒙和其他生物活性化合物中可能应用. 此外,还研究其可能的治疗效果,包括抗炎和抗癌特性. 与许多类固醇化合物一样,由于它的生物活动和可能对人类健康造成的影响,处理素需要谨慎.

结构式图片

上下游产品

CAS号512-04-9 薯蓣皂苷元 | CAS号915-35-5 乙酸龙舌兰皂苷酯 | CAS号690275-05-9 (E)-1-(tert-but... | CAS号110124-76-0 (25R)-5α-spiros... | CAS号35959-24-1 (25R)-5α-spiros... | CAS号17916-30-2 Pregn-5-en-20-o... | CAS号571-20-0 5α-雄烷二醇 | CAS号1169-20-6 (3S,5S,8R,9S,10... | CAS号1239-31-2 醋酸去氢表雄酮

合成工艺路线路线简述

  • 合成目标产物 Tigogenin 主要起始原料 Diosgenin
  • (文献来源)合成步骤主要原料 Diosgenin
薯蓣皂素置于palladium On Activated Charcoal 氢气,溶剂黄146体系中,用 乙醇,二氯甲烷 作为反应溶剂,20.0 °C,101.32 Kpa 条件下,反应 12.0H,以93%的收率获得产物剑麻皂素
参考文献:Synthesis Of The Cytotoxic Gitogenin 3β-O-[2-O-(α-L-Rhamnopyranosyl)-β-D-Galactopyranoside] And Its Congeners
标题:Synthesis Of The Cytotoxic Gitogenin 3β-O-[2-O-(α-L-Rhamnopyranosyl)-β-D-Galactopyranoside] And Its Congeners
摘要:(25R)-5A-螺甾-2A,3B-二醇 (Gitogenin) 3β-O-[2-O-(α-L-鼠李吡喃糖基)-β-D-半乳吡喃糖苷] (1),一种从长茎黄精(百合科)地下部分分离得到的细胞毒性螺甾皂苷,被简明地合成出来.在此过程中,其类似物2-4也被制备出来.所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力.
DOI:10.1055/s-2006-926316

专利信息


专利号:US-5807834-A
优先权日:1994-09-20
标 题 :Combination of a cholesterol absorption inhibitor and a cholesterol synthesis inhibitor
发明人:MOREHOUSE LEE A
权利人:PFIZER
摘要:PCT No. PCT/IB95/00447 Sec. 371 Date Mar. 18, 1997 Sec. 102(e) Date Mar. 18, 1997 PCT Filed Jun. 7, 1995 PCT Pub. No. WO96/09827 PCT Pub. Date Apr. 4, 1996Pharmaceutical combination compositions including certain cholesterol absorption inhibitors and cholesterol synthesis inhibitors. The compositions are useful for the treatment of hypercholesterolemia and atherosclerosis.

专利号:EP-3002290-B1
优先权日:2007-06-19
标 题:Synthesis of deoxycholic acid (dca)
发明人:MORIARTY ROBERT M; DAVID NATHANIEL E; MAHMOOD NADIR AHMEDUDDIN; PRASAD ACHAMPETA RATHAN; SWARINGEN ROY A JR; REID JOHN GREGORY; SAHOO AKHILA KUMAR
权利人:ALLERGAN SALES LLC

专利号:US-5606041-A
优先权日:1992-06-26
标题:Process for steroidal peracyl glycosides
发明人:BUSCH FRANK R; GOGGIN KATHLEEN D; LAMBERT JOHN F; SHINE RUSSELL J; WALINSKY STANLEY W
权利人:PFIZER
摘要:Processes for the synthesis of tigogenin beta-O-cellobioside heptaalkanoate which is an intermediate for the known hypo-cholesterolemic agent tigogenin beta-cellobioside. The process comprises reacting α-cellobiosyl bromide heptaalkanoate and β-tigogenin in the presence of zinc fluoride or zinc cyanide under conditions capable of forming said tigogenyl β-O-cellobioside heptaalkanoate. The analogous preparations of hecogenin β-O-cellobioside heptaalkanoate 11-ketotigogenin β-O-cellobioside heptaalkanoate, and diosgenin β-O-cellobioside heptaalkanoate are also disclosed. The process provides both high β-anomeric selectivity and high yields.

专利号:EP-3002290-A2
优先权日:2007-06-19
标 题 :Synthesis of deoxycholic acid (dca)

专利号:CN-1401658-A
优先权日:2002-09-13
标题 :Process for synthesis of 2,4-O-di-alpha-L-pyranorhamnosyl-beta-D-pyranoglucosyldioscin

专利号:US-5530107-A
优先权日:1992-10-15
标 题:Method for making steroidal peracyl glycosides
发明人:ALLAN DOUGLAS J M; BUSCH FRANK R; LAMBERT JOHN F; SHINE RUSSELL J; WALINSKY STANLEY W
权利人:PFIZER
摘要:Processes for the synthesis of tigogenin beta-O-cellobioside heptaalkanoate which is an intermediate for the known hypocholesterolemic agent tigogenin beta-cellobioside. The process comprises reacting α-cellobiosyl bromide heptaalkanoate and β-tigogenin in the presence of zinc fluoride or zinc cyanide under conditions capable of forming said tigogenyl β-O-cellobioside heptaalkanoate. The analogous preparations of hecogenin β-O-cellobioside heptaalkanoate, 11-ketotigogenin β-O-cellobioside heptaalkanoate, and diosgenin β-O-cellobioside heptaalkanoate are also disclosed. The process provides both high β-anomeric selectivity and high yields.
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主要参考文献

参考标题:Synthesis Of 5α-Androstan-3β,17β-Diol From Tigogenin
作者:M. I. Merlani,L. Sh. Amiranashvili,N. I. Men'Shova,E. P. Kemertelidze |发布日期:2007.1
摘要:Abstract5α-Androstan-3β,17β-Diol (3B-Adiol), A Known Inhibitor Of Prostate Cancer Cell Growth, Was Synthesized From Tigogenin. Its Structure Was Confirmed By Nmr And Ir Spectroscopy And Mass Spectroscopy.

合成参考文献


摘要:Toxins of Animal and Plant Origin, Proceedings International Symposium, 2nd, 1970, de Vries A., and E. Kochva, eds., 3 vols., New York, Gordon and Breach Science Pub., 1971-73, 2(597), 1972
摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
参考文献:10.1007/bf02976370
摘要:Kim SY, Son KH, Chang HW, Kang SS, Kim HP. Inhibition of mouse ear edema by steroidal and triterpenoid saponins. Arch Pharm Res. 1999 Jun;22(3):313–6. doi: 10.1007/bf02976370.
参考文献:10.1007/s13659-014-0011-9
摘要:Kumar V, Desai D, Shriram V. Hairy Root Induction in Helicteres isora L. and Production of Diosgenin in Hairy Roots. Natural Products and Bioprospecting. 2014 Apr 09;4(2):107–12. doi: 10.1007/s13659-014-0011-9.
参考文献:10.1007/s11356-022-19733-7
摘要:Rauf A, Akram M, Anwar H, Daniyal M, Munir N, Bawazeer S, Bawazeer S, Rebezov M, Bouyahya A, Shariati MA, Thiruvengadam M, Sarsembenova O, Mabkhot YN, Islam MN, Emran TB, Hodak S, Zengin G, Khan H. Therapeutic potential of herbal medicine for the management of hyperlipidemia: latest updates. Environmental Science and Pollution Research. 2022 Mar 22;29(27):40281–301. doi: 10.1007/s11356-022-19733-7.
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