5-Alpha-二氢可的松 | 1482-51-5

• 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: 5-Alpha-二氢可的松
• 中文别名: 4,5-Α-二氫皮甾醇；4,5-Α-二氫可體醇
• 英文名称: 17,21-dihydroxy-5α-pregnane-3,11,20-trione
• 英文别名: 5α-dihydrocortisone；17,21-Dihydroxy-5α-pregnan-3,11,20-trion；17.21.Dihydroxy-5α-pregnantrion-(3.11.20)；4,5alpha-Dihydrocortisone；(5S,8S,9S,10S,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,4,5,6,7,8,9,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,11-dione
• CAS: 1482-51-5
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: YCLWEYIBFOLMEM-FZPGBCFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Alpha-二氢可的松 在 吡啶 、 乙醚 、 二氯甲烷 、 氢溴酸 、 溴 、 乙酸酐 、 对甲苯磺酸 、 溶剂黄146 作用下， 生成 21-acetoxy-20,20-ethanediyldioxy-4α-bromo-17-hydroxy-5α-pregnane-3,11-dione
  参考文献：
  名称：

  Evans et al., Journal of the Chemical Society, 1958, p. 1529,1536

  摘要：

  DOI：
• 作为产物：
  描述：

  可的松 以 乙醇 为溶剂， 反应 96.0h， 以40%的产率得到5-Alpha-二氢可的松
  参考文献：
  名称：

  Biotransformation of corticosteroids by Penicillium decumbens ATCC 10436

  摘要：

  The biotransformation of a series of corticosteroids by the fungus Penicillium decumbens ATCC 10436 has been investigated. Conversion to the corresponding 5 alpha-dihydrosteroid was observed for all the Delta(4)-3-ketosteroids studied with the exception of deoxycorticosterone, which was converted to a Delta(1,4)-diene. Deoxycorticosterone acetate was, however, converted to a 5 alpha-dihydro product concomitant with ester hydrolysis. Other substrates carrying a C-21 acetoxy group were also hydrolyzed to the alcohol. In two cases (resulting from deoxycorticosterone acetate and 11-deoxycortisone) the 5 alpha-3-keto product was further reduced to the 3 beta-alcohol. No reduction of Delta(1,4)-dienes was observed.

  DOI：

  10.1016/0039-128x(95)00071-w

文献信息

• [EN] METHODS FOR STEREOSELECTIVE REDUCTION<br/>[FR] PROCÉDÉS DE RÉDUCTION STÉRÉOSÉLECTIVE
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2009086451A1

  公开（公告）日：2009-07-09

  The invention is directed to a method to reduce a C-C double bond of an enone of a steroidal compound to produce a mixture of β ketone product and α ketone product, comprising treating a solution or suspension of the steroidal compound in a solvent with hydrogen gas in the presence of a catalyst and a substituted pyridine.

  本发明涉及一种方法，用于还原类固醇化合物的烯酮的C-C双键，以产生β酮产物和α酮产物的混合物，包括在催化剂和取代吡啶的存在下，用氢气处理类固醇化合物在溶剂中的溶液或悬浮液。
• USE OF EQUOL FOR TREATING SKIN DISEASES
  申请人：Lephart Edwin Douglas

  公开号：US20100076071A1

  公开（公告）日：2010-03-25

  Equol (7-hydroxy-3(4′hydroxyphenyl)-chroman), the major metabolite of the phytoestrogen daidzein, specifically binds and blocks the hormonal action of 5α-dihydrotestosterone (DHT) in vitro and in vivo. Equol can bind circulating free DHT and sequester it from the androgen receptor, thus altering growth and physiological hormone responses that are regulated by androgens. These data suggest a novel model to explain equol's biological properties. The significance of equol's ability to specifically bind and sequester DHT from the androgen receptor have important ramifications in health and disease and may indicate a broad and important usage for equol in the treatment and prevention of androgen-mediated pathologies of skin and hair. Thus, equol can specifically bind DHT and prevent DHT's biological actions in physiological and pathophysiological processes affecting skin and hair.

  Equol（7-羟基-3（4'-羟基苯基）-色苷）是植物雌激素黄豆异黄酮的主要代谢产物，在体内和体外特异性结合并阻断5α-二氢睾酮（DHT）的激素作用。Equol可以结合循环游离的DHT并将其与雄激素受体分离，从而改变由雄激素调节的生长和生理激素反应。这些数据表明了解释Equol生物特性的新模型。Equol特异性结合和分离DHT对雄激素介导的皮肤和头发病理的治疗和预防具有重要意义，可能表明Equol在健康和疾病中具有广泛和重要的用途。因此，Equol可以特异性结合DHT并防止DHT在影响皮肤和头发的生理和病理生理过程中的生物作用。
• Use of equol for treating skin diseases
  申请人：Brigham Young University

  公开号：EP2305272A1

  公开（公告）日：2011-04-06

  Equol (7-hydroxy-3(4'hydroxyphenyl)-chroman), the major metabolite of the phytoestrogen daidzein, specifically binds and blocks the hormonal action of 5adihydrotestosterone (DHT) in vitro and in vivo. Equol can bind circulating free DHT and sequester it from the androgen receptor, thus altering growth and physiological hormone responses that are regulated by androgens. These data suggest a novel model to explain equol's biological properties. The significance of equol's ability to specifically bind and sequester DHT from the androgen receptor have important ramifications in health and disease and may indicate a broad and important usage for equol in the treatment and prevention of androgen-mediated pathologies of skin and hair. Thus, equol can specifically bind DHT and prevent DHT's biological actions in physiological and pathophysiological processes affecting skin and hair.

  Equol（7-羟基-3(4'羟基苯基)-色满）是植物雌激素黛泽素的主要代谢产物，在体外和体内能特异性地结合并阻断 5-二氢睾酮（DHT）的荷尔蒙作用。Equol能与循环中的游离DHT结合，并将其从雄激素受体中分离出来，从而改变受雄激素调节的生长和生理激素反应。这些数据为解释 Equol 的生物特性提供了一个新的模型。马郁兰能够特异性地与雄激素受体结合并从雄激素受体中螯合 DHT，这在健康和疾病方面具有重要意义，可能预示着马郁兰在治疗和预防雄激素介导的皮肤和毛发病变方面具有广泛而重要的用途。因此，在影响皮肤和头发的生理和病理生理过程中，马郁兰可以特异性地结合 DHT 并阻止 DHT 的生物作用。
• Action of Some Steroids on the Central Nervous System of the Mouse. I. Synthetic Methods
  作者：J. D. Cocker、J. Elks、P. J. May、F. A. Nice、G. H. Phillipps、W. F. Wall

  DOI：10.1021/jm00328a003

  日期：1965.7
• Steroids. LXXXVI.¹ Synthesis of Monofunctional 11-Ketones
  作者：FRANZ SONDHEIMER、E. BATRES、G. ROSENKRANZ

  DOI：10.1021/jo01360a026

  日期：1957.9

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