5-雄烯-3,17-二酮 | 571-36-8

• 物质功能分类: 有机原料 - 酮类化合物
• 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-雄烯-3,17-二酮
• 中文别名: 5-雄烯二酮
• 英文名称: 5-androstenedione
• 英文别名: 5-androstene-3,17-dione；Δ⁵-androstene-3,17-dione；androstenedione；androst-5-ene-3,17-dione；5-androsten-3,17-dione；(8R,9S,10R,13S,14S)-10,13-dimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 571-36-8
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: SQGZFRITSMYKRH-QAGGRKNESA-N

物化性质

• 熔点：
  158 °C
• 沸点：
  423.7±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-雄烯-3,17-二酮 在 葡萄糖 、 glucose dehydrogenase (CDX-901)_ 、 ketoreductase from Sphingomonas wittichii 、 β-烟酰胺腺嘌呤二核苷酸 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 aq. phosphate buffer 、 乙酸乙酯 为溶剂， 反应 37.0h， 生成 醋酸去氢表雄酮
  参考文献：
  名称：

  醋酸脱氢表雄酮化学合成方法的开发

  摘要：

  脱氢表雄酮（DHEA，2）是哺乳动物中一种重要的内源性类固醇激素，可用于治疗男女健康中的各种功能障碍1，也是合成甾体药物（如醋酸阿比特龙）的中间体2-4。在本手稿中，我们描述了一种新颖，简洁且经济高效的途径，可从4-雄甾烯3,17-二酮（4-AD，4）转化为DHEA（2）和DHEA乙酸盐（3）。1）。成功的关键是从维氏鞘氨醇单胞菌中鉴定出一种酮还原酶，该酶可将5-雄甾烯-3,17-二酮（5）的C3-羰基高度区域和立体选择性还原为所需的3β醇（2，> 99％de）。该酶在高底物浓度（最高150 g / L）下显示出出色的鲁棒性和溶剂稳定性。

  DOI：

  10.1021/acs.oprd.6b00215
• 作为产物：
  描述：

  雄烯二醇 在 溴 、 溶剂黄146 作用下， 生成 5-雄烯-3,17-二酮
  参考文献：
  名称：

  GB501421

  摘要：

  公开号：
• 作为试剂：
  描述：

  还原型辅酶Ⅰ 在 human recombinant 3β-hydroxysteroid dehydrogenase/Delta 5->4 isomerase type 2 、 5-雄烯-3,17-二酮 作用下， 生成 β-烟酰胺腺嘌呤二核苷酸
  参考文献：
  名称：

  The functions of key residues in the inhibitor, substrate and cofactor sites of human 3β-hydroxysteroid dehydrogenase type 1 are validated by mutagenesis

  摘要：

  In postmenopausal women, human 3 beta-hydroxysteroid dehydrogenase type 1 (3 beta-HSD1) is a critical enzyme in the conversion of DHEA to estradiol in breast tumors, while 3 beta-HSD2 participates in the production of cortisol and aldosterone in the human adrenal gland. The goals of this project are to determine if Arg195 in 3 beta-HSD1 vs. Pro195 in 3 beta-HSD2 in the substrate/inhibitor binding site is a critical structural difference responsible for the higher affinity of 3 beta-HSD1 for inhibitor and substrate steroids compared to 3 beta-HSD2 and whether Asp61, Glu192 and Thr8 are fingerprint residues for cofactor and substrate binding using site-directed mutagenesis. The R195P-1 mutant of 3 beta-HSD1 and the P195R-2 mutant of 3 beta-HSD2 have been created, expressed, purified and characterized kinetically. Dixon analyses of the inhibition of the R195P-1 mutant, P195R-2 mutant, wild-type 3 beta-HSD1 and wild-type 3 beta-HSD2 by trilostane has produced kinetic profiles that show inhibition of 3 beta-HSD1 by trilostane (K-i = 0.10 mu M, competitive) with a 16-fold lower K-i and different mode than measured for 3 beta-HSD2 (K-i = 1.60 mu M, noncompetitive). The R195P-1 mutation shifts the high-affinity, competitive inhibition profile of 3 beta-HSD1 to a low-affinity (trilostane K-i = 2.56 mu M), noncompetitive inhibition profile similar to that of 3 beta-HSD2 containing Pro195. The P195R-2 mutation shifts the low-affinity, noncompetitive inhibition profile of 3 beta-HSD2 to a high-affinity (trilostane K-i = 0.19 mu M), competitive inhibition profile similar to that of 3 beta-HSD1 containing Arg195. Michaelis-Menten kinetics for DHEA, 16 beta-hydroxy-DHEA and 16 alpha-hydroxy-DHEA substrate utilization by the R195P-1 and P195R-2 enzymes provide further validation for higher affinity binding due to Arg195 in 3 beta-HSD1. Comparisons of the Michaelis-Menten values of cofactor and substrate for the targeted mutants of 3 beta-HSD1 (D61N, D61V, E192A, T8A) clarify the functions of these residues as well. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.jsbmb.2010.04.015

文献信息

• A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO
  作者：Marco Frigerio、Marco Santagostino

  DOI：10.1016/0040-4039(94)80038-3

  日期：1994.10

  o-Iodoxybenzoic acid (IBX) smoothly oxidizes primary and secondary alcohols to aldehydes and ketones, respectively. 1,2-Diols are converted to α-ketols or α-diketones without any oxidative cleavage of the glycol CC bond. IBX oxidations are easily conducted in DMSO solution at room temperature, with yields ranging from good to quantitative.

  邻碘氧苯甲酸（IBX）分别将伯醇和仲醇平滑氧化为醛和酮。1,2-二醇可转化为α-酮醇或α-二酮，而乙二醇CC键没有任何氧化裂解。IBX氧化很容易在室温下的DMSO溶液中进行，收率范围从良好到定量。
• Phylloerythrin: Mechanisms for cellular uptake and location, photosensitisation and spectroscopic evaluation
  作者：E Scheie、A Flåøyen、J Moan、K Berg

  DOI：10.1080/00480169.2002.36291

  日期：2002.6

  AIM To elucidate the photobiological behaviour of phylloerythrin by studying the cellular uptake and intracellular localisation pattern of phylloerythrin and its spectral properties in Chinese hamster lung fibroblast cells (V79). METHODS Phylloerythrin was diluted in dimethylsulfoxide (DMSO). Fluorescence emission and excitation spectra were measured using a luminescence spectrometer equipped with

  目的通过研究叶绿素的细胞吸收和细胞内定位模式及其在中国仓鼠肺成纤维细胞（V79）中的光谱特性，阐明叶绿素的光生物学行为。方法将菊红素稀释在二甲基亚砜（DMSO）中。使用配备有红敏光电倍增管的发光光谱仪测量荧光发射光谱和激发光谱。将V79细胞单层培养，并用0.25 microg / ml叶绿素标记，以用于摄取，细胞存活和细胞内定位研究。为了进行细胞存活和细胞内定位研究，随后将细胞以9.0 mW / cm2的通量率暴露于蓝光下。结果叶绿素在DMSO中的荧光激发光谱的特征是Soret谱带在418 nm处有最大峰。荧光发射光谱在643和706nm处具有峰。细胞中相应的光谱分别红移至422、650和712 nm。温育约10小时后，叶绿素的细胞吸收完成。摄取，活化能以及使用叶绿素在37摄氏度和0摄氏度下使用荧光显微镜观察的细胞分析表明，染料是通过扩散介导的途径吸收到细胞中的。叶绿素处理过的细胞曝光后，
• A novel oxidation of homoallylic alcohols under sonochemical conditions
  作者：M.J.S. Miranda Moreno、M.L. Sá e Melo、A.S. Campos Neves

  DOI：10.1016/s0040-4039(00)79722-x

  日期：1991.7

  The oxidation of 3β-hydroxy-Δ5-cholestenes, -pregnenes and -androstenes to the corresponding Δ4-3,6-diones has been achieved in high yields by a new one-step process, using tetra-n-propylammonium perruthenate with 4-methylmorpholine N-oxide as co-oxidant, under sonochemical conditions.

  3β羟基Δ的氧化5 -cholestenes，-pregnenes和-androstenes到相应Δ4-3,6二酮已经由新的一步法以高产率来实现，使用四- Ñ -propylammonium丙基过钌酸铵与4- -甲基吗啉N-氧化物作为助氧化剂，在声化学条件下。
• Studies on Steroidal Compounds. XI. Reaction of 5-Ene Steroids with Sulfuryl Chloride in Pyridine.
  作者：Hiromu Mori、Joji Yamada

  DOI：10.1248/cpb.11.1418

  日期：——

  Some 3β-acetoxy-5-ene steroids were reacted with sulfuryl chloride in pyridine and the corresponding 3β-acetoxy-5α, 6β-dichloro steroids were obtained. Dehydroepiandrosterone acetate (VII) was transformed into 5α, 6β, 16, 16-tetrachloro compound (VI) on treatment with sulfuryl chloride in chloroform. The reaction of androst-5-ene-3, 17-dione (IX) with sulfuryl chloride in pyridine gave 6α-chloroandrost-4-ene-3, 17-dione (X), whereas the same reaction on pregn-5-ene-3, 20-dione (V) afforded the corresponding 5α, 6β-dichloro compound (IIIa). Some transformations of compounds above-mentioned were also written.

  一些3β-乙酰氧基-5-烯类类固醇与氯化亚砜在吡啶中反应，获得了相应的3β-乙酰氧基-5α, 6β-二氯类固醇。脱氢表雄酮醋酸酯（VII）在氯仿中与氯化亚砜反应后转化为5α, 6β, 16, 16-四氯化合物（VI）。而甾-5-烯-3, 17-二酮（IX）与氯化亚砜在吡啶中的反应则生成了6α-氯甾-4-烯-3, 17-二酮（X），而同样的反应在孕-5-烯-3, 20-二酮（V）中则获得了相应的5α, 6β-二氯化合物（IIIa）。上述化合物的一些转化反应也有所描述。
• Chromium(VI) based oxidants-1
  作者：H. Firouzabadi、N. Iranpoor、F. Kiaeezadeh、J. Toofan

  DOI：10.1016/s0040-4020(01)87476-7

  日期：1986.1

  2'-bipyridylchromium peroxide, pyridinechromium peroxide, and chromium peroxide etherate is described. 2,2'-Bipyridylchromium peroxide converts different classes of alcohols to the carbonyl compounds. In 1,2-diols C—C bond cleavage occurs extensively. α-Hydroxy acids are decarboxylated quantitatively. Oximes are converted to their carbonyl compounds and thiols to their disulfides, dihydroxy phenolic compounds to quinones

  描述了2，2′-联吡啶基过氧化铬，吡啶过氧化铬和过氧化铬醚化物的制备。2,2'-联吡啶基过氧化铬将不同种类的醇转化为羰基化合物。在1,2-二醇中，CC键断裂广泛发生。α-羟基酸被定量地脱羧。肟转化为羰基化合物，硫醇转化为二硫化物，二羟基酚化合物转化为醌，苄胺转化为苯甲醛，芳族胺转化为偶氮化合物，蒽和菲转化为醌。过氧化吡啶铬有效地将不同种类的醇有效地转化为羰基化合物，硫醇转化为其二硫化物，蒽转化为蒽醌。扁桃酸和苯甲酸非常有效地脱羧。