testolic acid

• 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
• 英文名称: testolic acid
• 英文别名: 3-[(1S,2S,4aS,4bR,10aR)-2-hydroxy-2,4b-dimethyl-7-oxo-3,4,4a,5,6,9,10,10a-octahydro-1H-phenanthren-1-yl]propanoic acid
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: KMUJXIPRPXRPTP-DZBHQSCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  testolic acid 以 aq. buffer 为溶剂， 反应 24.0h， 以387.7 mg的产率得到睾内酯
  参考文献：
  名称：

  Biotransformations of steroids to testololactone by a multifunctional strain Penicillium simplicissimum WY134-2

  摘要：

  The biotransformations of a range of steroidal compounds, including 17 alpha-hydroxy progesterone, progesterone, testosterone, androst-4-ene-3,17-dione (AD), pregnenolone, and dehydroepiandrosterone (DHEA), by Penicillium simplicissimum WY134-2 have been investigated. In all the cases, testolic acid and testololactone were detected, and the acid was converted to the lactone when pH was adjusted to 1, leading to isolation of testololactone in 25%-96% yields. Especially for progesterone and testosterone, the isolated yields were 93% and 96% with substrate concentration being 3 g/L, suggesting that P. simplicissimum WY134-2 may be used for the synthesis of testololactone. The results revealed the multi-functional catalytic activity of P. simplicissimum WY134-2 toward steroids for the first time. The possible reaction pathways of steroids promoted by this strain were discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.039
• 作为产物：
  描述：

  睾酮 在 Penicillium simplicissimum WY₁₃₄-2 、 Tween 80 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 testolic acid
  参考文献：
  名称：

  Biotransformations of steroids to testololactone by a multifunctional strain Penicillium simplicissimum WY134-2

  摘要：

  The biotransformations of a range of steroidal compounds, including 17 alpha-hydroxy progesterone, progesterone, testosterone, androst-4-ene-3,17-dione (AD), pregnenolone, and dehydroepiandrosterone (DHEA), by Penicillium simplicissimum WY134-2 have been investigated. In all the cases, testolic acid and testololactone were detected, and the acid was converted to the lactone when pH was adjusted to 1, leading to isolation of testololactone in 25%-96% yields. Especially for progesterone and testosterone, the isolated yields were 93% and 96% with substrate concentration being 3 g/L, suggesting that P. simplicissimum WY134-2 may be used for the synthesis of testololactone. The results revealed the multi-functional catalytic activity of P. simplicissimum WY134-2 toward steroids for the first time. The possible reaction pathways of steroids promoted by this strain were discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.039