18,20-环-20,21-二羟基-4-孕烯-3-酮 | 10385-97-4

• 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: 18,20-环-20,21-二羟基-4-孕烯-3-酮
• 英文名称: 18,21-dihydroxy-4-pregnen-3,20-dione
• 英文别名: 18-hydroxy-11-deoxycorticosterone；18-hydroxydeoxycorticosterone；(1R,2S,5S,9R,12S,13R)-6-hydroxy-6-(hydroxymethyl)-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-17-en-16-one
• CAS: 10385-97-4
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: GPYDBMQOMJCWRO-IHMLDWSPSA-N

物化性质

• 熔点：
  191-195 °C
• 沸点：
  543.1±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  18,20-环-20,21-二羟基-4-孕烯-3-酮 在 sodium periodate 作用下， 生成 (3aS,11aR,13aR)-11a-Methyl-4,5,5a,5b,6,7,10,11,11a,11b,12,13-dodecahydro-3aH-2-oxa-pentaleno[1,6a-a]phenanthrene-3,9-dione
  参考文献：
  名称：

  减少18-羟基-11-脱氧皮质酮的代谢物

  摘要：

  描述了使用副纯化梭状芽胞杆菌和化学方法通过微生物转化制备18-羟基-11-脱氧氢化可的松（1a）的二氢（2和6）和四氢衍生物（3、5和7）的条件。产物被充分表征并降解为它们各自的20→18乙内酯。微生物和Δ的化学削减4 -3- ketolactone 8被呈现。

  DOI：

  10.1016/0040-4020(82)80055-0
• 作为产物：
  描述：

  醋酸去氧皮质酮 在 chromium(VI) oxide 、 lead(IV) acetate 、 manganese(IV) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 、 水 、 碘 、 silver(I) acetate 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 环己烷 、 水 、 苯 为溶剂， 反应 8.5h， 生成 18,20-环-20,21-二羟基-4-孕烯-3-酮
  参考文献：
  名称：

  通过20-羟基类固醇的立体定向次碘化反应方便地合成18-羟基皮质酮和18-羟基-11-脱氧皮质酮

  摘要：

  通过20-羟基衍生物的亚碘化获得18-羟基皮质酮和18-羟基-11-脱氧皮质酮。C-20的绝对构型通过X射线确定，只有20S醇在低碘化条件下反应。

  DOI：

  10.1016/s0040-4020(99)00187-8

文献信息

• Identification of 19-hydroxydeoxycorticosterone in regenerating rat adrenal incubations
  作者：S.L. Dale、M.M. Holbrook、J.C. Melby

  DOI：10.1016/0039-128x(80)90082-3

  日期：1980.11

  19-Hydroxydeoxycorticosterone (19-OH-DOC) was isolated from the incubation medium of enucleated rat adrenal glands during the early sodium retaining phase. Identification included comparison of chromatographic mobility of parent and derivatized compound with standard prepared by the 21-hydroxylation of 19-hydroxyprogesterone and mass spectrometry. The possible role of 19-OH-DOC as a precursor is discussed.
• Differences between adrenal adenoma causing primary aldosteronism and other adrenal tissues in the incorporation of labeled steroid precursors into their products
  作者：Toshitaka Usa、Arunabha Ganguly、Myron H. Weinberger

  DOI：10.1016/0039-128x(80)90076-8

  日期：1980.11

  The incorporation and conversion of several labeled steroid precursors into their products were examined in slices of adrenal tissue from two patients with primary aldosteronism and compared with that in "normal" adrenal tissue and adrenal tissues from a patient with Cushing's syndrome. The products of the incorporation were separated by Sephadex LH-20 column chromatography. The major products of conversion in the adenomatous tissue of primary aldosteronism were 18-hydroxycorticosterone and lesser amounts of aldosterone. Smaller amounts of 18-hydroxycorticosterone were isolated from all other adrenal tissues studied. No aldosterone could be recovered after incubating any of the adrenal tissue studied with labeled 18-hydroxy-11-deoxycorticosterone or 18-hydroxycorticosterone as precursor steroid. These in vitro results seem to suggest that there is increased 18-hydroxylation in the adenoma of primary aldosteronism compared with other tissues and that relatively more 18-hydroxycorticosterone is produced in such tissue than aldosterone.
• Mineralocorticoid properties of potential metabolites of 18-hydroxydeoxycorticosterone and 18-hydroxyprogesterone
  作者：John F. Weet、George R. Lenz

  DOI：10.1021/jm00380a014

  日期：1985.2

  The high secretion rate of 18-hydroxydeoxycorticosterone in hypertensives and the steroids implication as a mineralocorticoid has led to the synthesis of potential di-, tetra-, and hexahydro metabolites of it and 18-hydroxy-progesterone. These potential metabolites have been synthesized by reduction of the double bond and the 3- and 20-ketones, singly or in combination. They have been evaluated for pro- and antimineralocorticoid activity and their affinity for the renal aldosterone receptor. All except one of the potential metabolites either lack or have reduced mineralocorticoid activity and aldosterone receptor binding affinity. The exception is the 3-ketopregn-4-ene-18,20-diol which has high receptor affinity but functions as an aldosterone antagonist.