[4-14C]-dehydroepiandrosterone | 5976-88-5

• 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
• 英文名称: [4-14C]-dehydroepiandrosterone
• 英文别名: <4-(14)C>dehydroepiandrosterone；[¹⁴C]DHEA；(3S,8R,9S,10R,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one
• CAS: 5976-88-5
• 化学式: C₁₉H₂₈O₂
• 分子量: 290.419
• InChiKey: FMGSKLZLMKYGDP-QRLMTXJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [4-14C]-dehydroepiandrosterone 、 <1,2-(3)H>dehydroepiandrosterone 在 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Preparation of (1,2-3H,4-14C)16.ALPHA.-hydroxyandrostenedione and its use for radiometric determination of human placental aromatase activity.

  摘要：

  [1, 2-3H, 4-14C] 16α-Hydroxyandrostenedione (4) (3H, 3.20 mCi/mmol; 3H/14C = 222) was synthesized from commercially available [1, 2-3H, 4-14C] dehydroepiandrosterone (1) through bromination at C-16α of the 17-ketone 1 and controlled alkaline hydrolysis of the 16α-bromoketone 3, obtained from the brominated product 2 by 8 N CrO3 oxidation followed by p-toluenesulfonic acid treatment, as key reactions. The tritium distribution of the labeled 16α-ketol 4 was determined by chemical and biochemical methods to be 47% at C-1α, 18% at C-2α, and 35% at the β-side of C-1 and C-2. When the labeled ketol 4 was incubated with human placental microsomes and reduced nicotinamide adenine dinucleotide phosphate, the rate of 3H2O release into the medium was dependent upon protein concentration and incubation time. Aromatase activity obtained by the radiometric assay was comparable to that determined by the high-performance liquid chromatographic method.

  DOI：

  10.1248/cpb.35.2448

文献信息

• Use of bioconversion for the preparation of [4-14C]-labeled 7α- and 7β-hydroxylated derivatives of dehydroepiandrosterone and epiandrosterone
  作者：Sonia Chalbot、Catherine Trap、Jean-Paul Monin、Robert Morfin

  DOI：10.1016/s0039-128x(02)00072-7

  日期：2002.12

  testosteroni . The 7α- and 7β-hydroxylated derivatives of [ 4- 14 C ]-EPIA produced were prepared after incubation with mycelium of Rhizopus nigricans . Each labeled steroid was purified by chromatography and identified by crystallization to constant specific activity after isotopic dilution with each authentic steroid carrier. Production yields and radio-purity measurements allowed the use of such procedures

  摘要 利用酵母表达的人细胞色素P4507B1制备了[ 4- 14 C]-脱氢表雄酮的7α-和7β-羟基化衍生物。表雄酮 (EPIA)、5α-雄甾烷-3β,17β-二醇和 5α-雄甾烷-3,17-二酮是在 [4- 14 C ]-5α-二氢睾酮与表达的大肠杆菌 (3β,17β) 孵育后获得的-来自睾丸假单胞菌的羟基类固醇脱氢酶。产生的[ 4- 14 C]-EPIA的7α-和7β-羟基化衍生物是在与黑根霉菌丝体孵育后制备的。每种标记的类固醇通过色谱法纯化，并在用每种真正的类固醇载体进行同位素稀释后通过结晶鉴定到恒定的比活性。