7alpha-羟基孕烯诺龙 | 30626-96-1

• 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: 7alpha-羟基孕烯诺龙
• 英文名称: 3β,7α-dihydroxy-pregn-5-en-20-one
• 英文别名: 7α-hydroxypregnenolone；7-alpha-Hydroxypregnenolone；7alpha-Hydroxypregnenolone；1-[(3S,7S,8S,9S,10R,13S,14S,17S)-3,7-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 30626-96-1
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: UEWNVBNIVGLQPG-XXHSLLPRSA-N

物化性质

• 熔点：
  190 °C
• 沸点：
  486.1±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 碰撞截面：
  196.13 Ų [M+HCOO]-

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7alpha-羟基孕烯诺龙 、 N,O-双(三甲基硅烷基)三氟乙酰胺 反应 0.5h， 生成
  参考文献：
  名称：

  Studies of the enzyme complex responsible for pregnenolone and dehydroepiandrosterone 7α-hydroxylation in mouse tissues

  摘要：

  7 alpha-Hydroxylation of pregnenolone (PREG) and dehydroepiandrosterone (DHEA) is known to take place in numerous tissues of mouse and rat. The responsible cytochrome P450 species has not yet been identified Interest in the production of 7 alpha-hydroxylated steroid derivatives results from their ability to increase the immune response in mice. Using crystallizations to constant specific activity and gas chromatography-mass spectrometry, 7 alpha-hydroxy-PREG and 7 alpha-hydroxy-DHEA metabolites produced by microsomes of liver, brain, thymus, and spleen were identified. Study of the 7 alpha-hydroxylating enzyme in these tissues indicated that microsomes contained most of the activity, except for brain, where it was primarily mitochondrial. Production yields of 7 alpha-hydroxy-PREG and 7 alpha-hydroxy-DHEA by microsomes from heart, spleen, thymus, brain, and liver of 7-week-old mice were higher than those of 1-week-old and (except for liver) 41-week-old animals. Ar the optimal pH (7.4) and in all tested tissues bur liver, microsomal 7 alpha-hydroxylation was more extensive for PREG than for DHEA. With brain and thymus microsomes, K-M were lower for PREG than for DHEA and decreased when phosphate was used instead of Tris buffer. With brain microsomes, the use of 1 mM EDTA increased 7 alpha-hydroxylating activity. Complete inhibition was obtained with 0.1 mM Zn2+ or Cu2+ and with 1 mM Fe2+ or Fe3+. 7 alpha-Hydroxylation of PREG was activated only by 0.5 mM Ca2+ and that of DHEA only by 0.25 mM Mg2+. Since the production rates of 7 alpha-hydroxy-PREG and 7 alpha-hydroxy-DHEA in tissues may be a key to the triggering of immune defenses, and since both 7 alpha-hydroxylation and immunity decrease with aging, these data will prove to be useful in studies of the enzyme responsible and of the mechanisms that control its activity. (C) 1996 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(96)00122-5
• 作为产物：
  描述：

  孕烯醇酮醋酸酯 在 咪唑 、 3,5-二甲基吡唑 、 chromium(VI) oxide 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 76.5h， 生成 7alpha-羟基孕烯诺龙
  参考文献：
  名称：

  7α-羟基孕烯醇酮的化学合成，一种刺激运动活动的神经活性类固醇

  摘要：

  图形抽象图。没有可用的字幕。亮点报道了两种合成 7&agr;-羟基孕烯醇酮的简便方法。C7-酮还原立体选择性的解释。在 C7 氧化的其他类固醇类似物的潜在应用。摘要 7&agr;-Hydroxypregnenolone 是一种内源性神经活性类固醇，可刺激运动活动。描述了利用正交保护基策略从孕烯醇酮合成 7’-羟基孕烯醇酮。具体来说，C7 位被 CrO3 和 3,5-二甲基吡唑氧化，得到 7-酮类固醇中间体。得到的 7-酮被三仲丁基硼氢化锂立体选择性地还原为 7’-羟基。相比之下，用 NaBH4 还原相同的 7-酮中间体主要产生 7°-羟基差向异构体。此外，在目标化合物的另一种途径中，通过用 CuBr 和过苯甲酸叔丁酯直接 C-H 烯丙基苯甲酰氧基化孕烯醇酮-3-乙酸酯，然后皂化，成功地掺入了 7’-羟基。所公开的 7-氧化类固醇的合成有可能获得其他具有生物活性的甾醇和类固醇。

  DOI：

  10.1016/j.steroids.2017.10.004

文献信息

• Mammalian Cells Engineered To Produce New Steroids
  作者：Emma S. Spady、Thomas P. Wyche、Nathanael J. Rollins、Jon Clardy、Jeffrey C. Way、Pamela A. Silver

  DOI：10.1002/cbic.201800214

  日期：2018.9.4

  Biosynthesis on steroids: We expressed steroid‐modifying enzymes in mammalian cells to make new steroid products through regio‐ and stereospecific catalysis. The 7α‐hydroxylase CYP7B1 made three products from non‐native substrates, two of which were novel. CYP7B1 also demonstrated a previously unobserved ability to catalyze the hydroxylation of D‐ring‐substituted steroids at the 7β‐ and 11α‐positions.

  类固醇的生物合成：我们在哺乳动物细胞中表达了类固醇修饰酶，从而通过区域和立体定向催化来生产新的类固醇产品。7α-羟化酶CYP7B1从非天然底物制得了三种产物，其中两种是新颖的。CYP7B1还显示了以前无法观察到的在7β和11α位催化D环取代的类固醇羟化反应的能力。
• Biotransformation of Some Steroids by <i>Mucor Hiemalis</i> MRC 70325
  作者：Kudret Yildirim、Hilal Saran、Omer Faruk Dolu、Ali Kuru

  DOI：10.3184/174751913x13745069090242

  日期：2013.9

  In this work, incubations of testosterone, dehydroepiandrosterone and pregnenolone with Mucor hiemalis MRC 70325 have been reported. Incubation of testosterone afforded androst-4-en-3,17-dione (3%), 14α-hydroxyandrost-4-en-3,17-dione (9%), 6β-hydroxyandrost-4-en-3,17-dione (2%) and 14α,17β-dihydroxyandrost-4-en-3-one (62%). Incubation of dehy droepiandrosterone afforded 3β,17β-dihydroxyandrost-5-ene (6%) and 3β,7α-dihydroxyandrost-5-en-17-one (72%). Incubation of pregnenolone afforded 3β,14α-dihydroxypregn-5-en-7,20-dione (3%), 3β,7α-dihydroxy-pregn-5-en-20-one (64%) and 3β,7α,11α-trihydroxypregn-5-en-20-one (11%). 3β,14α-Dihydroxypregn-5-en-7,20-dione was identified as a new metabolite.

  在这项工作中，报告了睾酮、脱氢表雄酮和孕烯醇酮与 Mucor hiemalis MRC 70325 的孵育情况。睾酮孵育产生雄甾-4-烯-3,17-二酮（3%）、14α-羟基雄甾-4-烯-3,17-二酮（9%）、6β-羟基雄甾-4-烯-3,17-二酮（2%）和 14α,17β-二羟基雄甾-4-烯-3-酮（62%）。孵育去氢表雄酮可得到 3β,17β-二羟基雄甾-5-烯（6%）和 3β,7α-二羟基雄甾-5-烯-17-酮（72%）。孕烯醇酮孵育可得到 3β,14α-二羟基孕甾-5-烯-7,20-二酮（3%）、3β,7α-二羟基孕甾-5-烯-20-酮（64%）和 3β,7α,11α-三羟基孕甾-5-烯-20-酮（11%）。3β,14α-二羟基孕甾-5-烯-7,20-二酮被鉴定为一种新的代谢物。
• Biotransformation of 5-en-3β-ol steroids by<i>Mucor circinelloides lusitanicus</i>
  作者：Lihong Shan、Kai Jiao、Minghui Yin、Jiajia Huang、Yanjie Chen、Shangshang Qin、Hongmin Liu

  DOI：10.3109/10242422.2015.1089865

  日期：2016.5.3

  2, 3β, 7α, 11α-trihydroxypregna-5-en-20-one (2b) was obtained as the final product in good yield (46.4%). All the metabolites were determined by infrared spectra, high-resolution mass spectrometry, proton nuclear magnetic resonance, and carbon-13 nuclear magnetic resonance.

  摘要 在这项工作中，我们首次报道了使用 Mucor circinelloides lusitanicus 生物转化 5-en-3β-ol 类固醇的模式。在这里，我们选择了七种 5-en-3β-ol 类固醇作为底物。该真菌的主要特征是将 7α-羟基引入底物 1--5。使用底物 2, 3β, 7α, 11α-trihydroxypregna-5-en-20-one (2b) 作为最终产物以良好的产率 (46.4%) 获得。所有代谢物均通过红外光谱、高分辨率质谱、质子核磁共振和碳 13 核磁共振测定。
• Biotransformation of 3β-hydroxy-5-en-steroids by<i>Mucor silvaticus</i>
  作者：Yanjie Wang、Dongmei Sun、Zhibao Chen、Hongsheng Ruan、Wenzhong Ge

  DOI：10.3109/10242422.2013.813490

  日期：2013.8

  the examined substrates were transformed, mainly by 7α-hydroxylation. Studies carried out with M. silvaticus demonstrated the versatility of this organism in introducing hydroxyl groups at the 7α-, 9α-, 11α-, and 14α-positions in 3-ol-5-ene steroids. The relationships between the substrate structures and hydroxylated positions are also discussed.

  摘要 研究了 Mucor silvaticus 对 C-16 或/和 C-17 处具有不同取代基的四种 3β-羟基-5-en-类固醇的生物转化。通过 IR、MS、1H NMR、13C NMR 和 2-D NMR 对代谢物进行表征。所有检查的底物都被转化，主要是通过 7α-羟基化。对 M. silvaticus 进行的研究证明了这种生物在 3-ol-5-ene 类固醇的 7α-、9α-、11α-和 14α-位引入羟基的多功能性。还讨论了底物结构和羟基化位置之间的关系。
• Cholesterol transformations during heat treatment
  作者：D. Derewiaka、E. Molińska (née Sosińska)

  DOI：10.1016/j.foodchem.2014.08.117

  日期：2015.3

  the increase of temperature. Treatment of cholesterol at higher temperatures i.e. 180 °C and 220 °C led to the formation of polymers and other products e.g. cholestadienes and fragmented cholesterol molecules. Further studies are required to identify the structure of cholesterol oligomers and to establish volatile compounds, which are markers of cholesterol transformations, mainly oxidation.

  该研究的目的是表征热处理过程中胆固醇标准品变化的产物。将胆固醇在120°C，150°C，180°C和220°C下加热30至180分钟。在220°C的热处理过程中，发现胆固醇含量的损失最高，而在150°C的温度下，胆固醇氧化产物的含量最高。温度的升高会刺激挥发性化合物的产生。在较高的温度（即180°C和220°C）下处理胆固醇会导致形成聚合物和其他产物，例如胆甾二烯和胆固醇碎片分子。需要进一步的研究来鉴定胆固醇低聚物的结构并建立挥发性化合物，这些化合物是胆固醇转化（主要是氧化）的标志。