6alpha-羟基-雄甾-4-烯-3,17-二酮 | 63-00-3

• 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: 6alpha-羟基-雄甾-4-烯-3,17-二酮
• 英文名称: 6β-hydroxy-4-androstene-3,17-dione
• 英文别名: 6beta-Hydroxyandrostenedione；6β-hydroxyandrost-4-ene-3,17-dione；6β-hydroxyandrostenedione；androst-4-en-6β-ol-3,17-dione；6β-hydroxyandrost-4-en-3,17-dione；(6R,8R,9S,10R,13S,14S)-6-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 63-00-3
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: WVAMBAWFDOYFOD-DQXCSHPPSA-N

物化性质

• 熔点：
  192-194 °C
• 沸点：
  479.1±45.0 °C(Predicted)
• 密度：
  1.19±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)：
  1.5
• 重原子数：
  22
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：2-8°C，密封，干燥，避光

反应信息

• 作为反应物：
  描述：

  6alpha-羟基-雄甾-4-烯-3,17-二酮 在 aluminum oxide 作用下， 以 苯 为溶剂， 反应 72.0h， 生成 5α-androst-3,6,17-trione
  参考文献：
  名称：

  Hydroxylation of androst-4-ene-3,17-dione byRhizopus Nigricans

  摘要：

  DOI：

  10.1007/bf00765613
• 作为产物：
  描述：

  去氢表雄酮 在 potassium permanganate 、 copper(II) sulfate 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 以45%的产率得到6alpha-羟基-雄甾-4-烯-3,17-二酮
  参考文献：
  名称：

  A One-Step Synthesis of 6β-Hydroxy-Δ⁴-3-ketones. Novel Oxidation of Homoallylic Sterols with Permanganate Ion

  摘要：

  DOI：

  10.1021/jo960402i

文献信息

• Microbial hydroxylation of steroids. 8. Incubation of Cn halo- and other substituted steroids with Cn hydroxylating fungi
  作者：Herbert L. Holland、Everton M. Thomas

  DOI：10.1139/v82-027

  日期：1982.1.15

  A series of C-21 substituted progesterone derivatives (R = F, Cl, Br, CH₃) has been prepared, and incubated the C-21 hydroxylating fungus A. niger. No biotransformation was observed where R = Cl, Br, or CH₃, but a minor amount of hydroxylation occurred at an unidentified site where R = F. Two C-11β substituted progesterone derivatives (R = F, OH) were converted to the corresponding C-11 ketone by the C-11α hydroxylator R. stolonifer, but a C-11β hydroxylator (C. lunata) was unable to perform a similar transformation with a C-11α hydroxy substrate. C. lunata hydroxylated a C-11β fluoro substrate at C-14α and C-21 in low yield. C-7α and -7β-hydroxy androst-4-ene-3,17-diones were prepared and incubated with C-7β hydroxylating (R. stolonifer) and C-7α hydroxylating (M. griseocyanus) fungi respectively. No ketone formation was observed. Similarly, the C-6β hydroxylator R. arrhizus was unable to transform a C-6α-hydroxy substrate or C-6α- or C-6β-hydroxy-B-norsteroids. No oxidation at halogen was observed for any of the substrates used. ¹³C–¹⁹F coupling constants for 11β-fluoroprogesterone suggest the presence of through space interactions between fluorine and both C-18 and C-19.

  一系列C-21取代孕酮衍生物（R = F、Cl、Br、CH3）已经制备，并与C-21羟化真菌A. niger培养。观察到当R = Cl、Br或 时未发生生物转化，但当R = F时，在未知位置发生了少量羟基化。两种C-11β取代孕酮衍生物（R = F、OH）被C-11α羟化酶R. stolonifer转化为相应的C-11酮，但C-11β羟化酶（C. lunata）无法使用C-11α羟基底物进行类似转化。C. lunata在低产率下将C-11β氟底物羟化为C-14α和C-21。制备了C-7α和-7β-羟基雄烯-4-烯-3,17-二酮，并分别与C-7β羟化（R. stolonifer）和C-7α羟化（M. griseocyanus）真菌培养。未观察到酮形成。同样，C-6β羟化酶R. arrhizus无法转化C-6α-羟基底物或C-6α-或C-6β-羟基B-诺甾醇。未观察到任何底物的卤素氧化。11β-氟孕酮的¹³C–¹⁹F偶合常数表明氟与C-18和C-19之间存在空间相互作用。
• [EN] CHEMILUMINESCENT ANDROSTENEDIONE CONJUGATES<br/>[FR] CONJUGUÉS D'ANDROSTÈNEDIONE CHIMIOLUMINESCENTS
  申请人：SIEMENS HEALTHCARE DIAGNOSTICS INC

  公开号：WO2018156925A1

  公开（公告）日：2018-08-30

  Chemiluminescent androstenedione conjugates are disclosed. These chemiluminescent androstenedione conjugates may be used as chemiluminescent tracers in immunoassays for the quantification and identification of certain analytes.

  发光雄烯二酮共轭物被披露。这些发光雄烯二酮共轭物可用作化学发光示踪剂，用于定量和鉴定特定分析物的免疫分析。
• Method and product for increasing fertility in sheep using milk protein
  申请人：The Director General of the Ministry of Agriculture and Fisheries

  公开号：US04749567A1

  公开（公告）日：1988-06-07

  A product and method for increasing fertility in sheep. By "increasing felity" is meant increasing the potential of a flock of sheep to multiply by increasing ovulation in ewes. The product is an immunogenic conjugate of 4-androstene-3, 17-dione and a soluble milk protein (SMP): 6-hydroxyandrost-4-ene-3, 17-dione 6-hemisuccinyl: SMP. The method comprises immunizing the ewes in a flock of sheep against 4-androstene-3, 17-dione by administering 6-hydroxyandrost-4-ene-3, 17-dione 6-hemisuccinyl SMP at the rate of 3 to 5 mg per ewe. In previously untreated ewes, two administrations are required at between 8 to 9 and 4 to 5 weeks before the planned commencement of mating. Subsequent administrations are annually and are recommended at 5 weeks before the commencement of mating.

  一种用于增加绵羊生育能力的产品和方法。所谓的“增加生育能力”是指通过增加母羊排卵来增加整个羊群繁殖的潜力。该产品是4-雄烯-3,17-二酮和可溶性乳蛋白（SMP）的免疫原性结合物：6-羟基雄烯-4-烯-3,17-二酮6-半琥珀酰基：SMP。该方法包括通过给母羊群注射6-羟基雄烯-4-烯-3,17-二酮6-半琥珀酰基SMP，以每只母羊3至5毫克的剂量，对羊群中的母羊进行免疫。对于之前未接受治疗的母羊，需要在计划交配开始前8至9周和4至5周之间进行两次注射。随后的注射每年进行一次，建议在交配开始前5周进行。
• In‐depth gas chromatography/tandem mass spectrometry fragmentation analysis of formestane and evaluation of mass spectral discrimination of isomeric 3‐keto‐4‐ene hydroxy steroids
  作者：Annette Sophie Kollmeier、Xavier Torre、Christian Müller、Francesco Botrè、Maria Kristina Parr

  DOI：10.1002/rcm.8937

  日期：2020.12.30

  The aromatase inhibitor formestane (4‐hydroxyandrost‐4‐ene‐3,17‐dione) is included in the World Anti‐Doping Agency’s List of Prohibited Substances in Sport. However, it also occurs endogenously as do its 2‐, 6‐ and 11‐hydroxy isomers. The aim of this study is to distinguish the different isomers using GC/EI‐MS for enhanced confidence in detection and selectivity for determination.

  芳香酶抑制剂福尔马坦（4-羟基雄烷-4-烯-3,17-二酮）被列入世界反兴奋剂机构的《运动中禁用物质清单》。但是，它也像2-，6-和11-羟基异构体一样内源性地发生。这项研究的目的是使用GC / EI-MS区分不同的异构体，以增强检测的信心和测定的选择性。
• Substratspezifische Hydroxylierungen von Steroiden mittels Pilz-Stämmen der Gattung<i>Gibberella</i>. Mikrobiologische Reaktionen, 9. Mitteilung
  作者：J. Urech、E. Vischer、A. Wettstein

  DOI：10.1002/hlca.19600430417

  日期：——

  Continning our earlier work on the action of fungi of the genus Gibberella on steroids we have shown that G. saubinetti (MONT. SACC. has the ability of hydroxylating steroids in the 6β- or the 15α-position. On the other hand, the steroid transforming properties of G. baccata (WALLR. SACC. seem to be limited to 15α-hydroxylation. Some interesting substrate specificity has been observed in this connection

  继续我们对赤霉菌属真菌对类固醇的作用的早期研究，我们表明G. SAubinetti（MONT。SACC。具有在6β-或15α-位羟基化类固醇的能力。另一方面，类固醇转化的性质G.山定子（WALLR。SACC。似乎仅限于15α羟基化。一些有趣的底物特异性已在这方面，已观察到。15α羟基Δ 4雄甾烯3，已对所得到的17二酮这些实验过程中的第一次。