(19E)-3β-acetoxy-5-androstene-7,17,19-trione-19-O-(methoxycarbonylmethyl)oxime | 943231-21-8

• 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: (19E)-3β-acetoxy-5-androstene-7,17,19-trione-19-O-(methoxycarbonylmethyl)oxime
• CAS: 943231-21-8
• 化学式: C₂₄H₃₁NO₇
• 分子量: 445.513
• InChiKey: IOHWVGCNPVGXTQ-IOVYIVQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  108.33
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (19E)-3β-acetoxy-5-androstene-7,17,19-trione-19-O-(methoxycarbonylmethyl)oxime 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.58h， 生成 (19E)-3β-hydroxy-5-androstene-7,17,19-trione-19-O-(carboxymethyl)oxime
  参考文献：
  名称：

  A novel radioimmunoassay of 7-oxo-DHEA and its physiological levels

  摘要：

  A novel radioimmunoassay (RIA) of unconjugated 7-oxo-dehydroepiandrosterone (7-oxo-DHEA) in human serum was developed for the first time. This steroid is an intermediate in the biosynthesis of immunomodulatory 7-hydroxylated DHEA metabolites, and has been shown to possess thermogenic properties. The method employs polyclonal rabbit antiserum to (19E)-3 beta-hydroxy-7,17,19-trione-19-O-(carboxymethyloxime):BSA conjugate and a homologous radioiodinated derivative with tyrosine methyl ester. The cross reactivity of the antiserum with structurally closest 7-hydroxyepimers of DHEA was lower than 1.7%, with DHEA 0.4%, with all other related steroid less than 0.4%. The method includes ether extraction of serum (0.5 ml), followed by RIA. Its detection limit was 0.06 pmol (18 pg)/tube, the average intra- and inter-assay coefficients of variation were 4.1% and 8.3%, respectively Mean recovery of serum spiked with 7-oxo-DHEA varied between 78.8% and 112%. Its levels in three serum pools were compared with a low-resolution gas chromatography-mass spectrometry method with satisfactory results. The method has been used for determination of 7-oxo-DHEA in serum samples of 215 subjects (91 males and 124 females) without overt endocrine disorders, aged 5-71 years. The over-all mean +/- S.D. was 0.280 +/- 0.227, the median 0.239 nmol/l. No significant sex differences were recorded. The only group which differed significantly from all other ones were males below 10 years, significantly lower values than in other age groups were found also in the first two age groups of females. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.12.005
• 作为产物：
  描述：

  (19E)-17,19-dioxoandrost-5-en-3β-yl acetate 19-{O-[(methoxycarbonyl)methyl]oxime} 在 3,5-二甲基吡唑 、 chromium(VI) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以62%的产率得到(19E)-3β-acetoxy-5-androstene-7,17,19-trione-19-O-(methoxycarbonylmethyl)oxime
  参考文献：
  名称：

  A novel radioimmunoassay of 7-oxo-DHEA and its physiological levels

  摘要：

  A novel radioimmunoassay (RIA) of unconjugated 7-oxo-dehydroepiandrosterone (7-oxo-DHEA) in human serum was developed for the first time. This steroid is an intermediate in the biosynthesis of immunomodulatory 7-hydroxylated DHEA metabolites, and has been shown to possess thermogenic properties. The method employs polyclonal rabbit antiserum to (19E)-3 beta-hydroxy-7,17,19-trione-19-O-(carboxymethyloxime):BSA conjugate and a homologous radioiodinated derivative with tyrosine methyl ester. The cross reactivity of the antiserum with structurally closest 7-hydroxyepimers of DHEA was lower than 1.7%, with DHEA 0.4%, with all other related steroid less than 0.4%. The method includes ether extraction of serum (0.5 ml), followed by RIA. Its detection limit was 0.06 pmol (18 pg)/tube, the average intra- and inter-assay coefficients of variation were 4.1% and 8.3%, respectively Mean recovery of serum spiked with 7-oxo-DHEA varied between 78.8% and 112%. Its levels in three serum pools were compared with a low-resolution gas chromatography-mass spectrometry method with satisfactory results. The method has been used for determination of 7-oxo-DHEA in serum samples of 215 subjects (91 males and 124 females) without overt endocrine disorders, aged 5-71 years. The over-all mean +/- S.D. was 0.280 +/- 0.227, the median 0.239 nmol/l. No significant sex differences were recorded. The only group which differed significantly from all other ones were males below 10 years, significantly lower values than in other age groups were found also in the first two age groups of females. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.12.005