(22E,24R)-5-hydroxy-5α-ergosta-7,22-diene-3,6-dione | 38774-65-1

• 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
• 英文名称: (22E,24R)-5-hydroxy-5α-ergosta-7,22-diene-3,6-dione
• 英文别名: (22e,24r)-5-Hydroxy-5alpha-ergosta-7,22-diene-3,6-dione；(5R,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-5-hydroxy-10,13-dimethyl-1,2,4,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,6-dione
• CAS: 38774-65-1
• 化学式: C₂₈H₄₂O₃
• 分子量: 426.64
• InChiKey: AKHIQQYDROLRJV-PUTWEWQSSA-N

物化性质

• 沸点：
  548.9±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (22E,24R)-5-hydroxy-5α-ergosta-7,22-diene-3,6-dione 在 吡啶 、 正丁基锂 、 偶氮二异丁腈 、 溴 、 三正丁基氢锡 、 臭氧 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 20.58h， 生成 (22E)-5α-hydroxycampesta-7,22-diene-3,6-dione
  参考文献：
  名称：

  Fortisterol和Herbarulide的所谓结构的合成以及Herbarulide的结构修订。

  摘要：

  所谓的5,6-环氧-5,6-secosteroids fortisterol和herbarulide的结构仅在C24的立体构型上有所不同。运用此类天然产物的假设生物合成的见解，我们设计了一个短的合成途径（分别为四个步骤和八个步骤），从商业麦角甾醇开始，并具有烷氧基自由基重排的功能。核磁共振波谱数据的比较显示了具有所提出的fortisterol结构的herbarulide，而另外两种非对映异构体的合成不能最终证明fortisterol的真实结构。一路走来，开发了一种不需要铬（VI）试剂的臭名昭著的Burawoy酮的高产可扩展方法。

  DOI：

  10.1021/acs.orglett.0c00180
• 作为产物：
  描述：

  6-epicerevisterol 在 chromium(VI) oxide 、 溶剂黄146 作用下， 生成 (22E,24R)-5-hydroxy-5α-ergosta-7,22-diene-3,6-dione
  参考文献：
  名称：

  85.固醇类的研究。第十七部分。麦角固醇中的不饱和中心

  摘要：

  DOI：

  10.1039/jr9330000302

文献信息

• Synthesis, characterisation, crystal structure and antimicrobial evaluation of novel 6-alkoxyergosta-4,6,8(14),22-tetraen-3-one derived from natural ergosta-5,7,22-trien-3β-ol
  作者：Mitchell Bacho、Vania Artigas、Tiare Araya-Contreras、Mauricio Bittner、Carlos A. Escobar、Mauricio Fuentealba、José Becerra、Victor Fajardo、Aurelio San-Martín

  DOI：10.1080/14786419.2021.1946534

  日期：2023.1.2

  Abstract In this study, we report a facile transformation starting from 5α-hydroxyergosta-7,22-dien-3,6-dione (1) to afford two novel compounds: 6-methoxyergosta-4,6,8(14),22-tetraen-3-one (2) and 6-ethoxyergosta-4,6,8(14),22-tetraen-3-one (3) using alcoholic acid catalysis. Their structures were elucidated using NMR experiments, FT-IR, MS and X-ray analysis. These compounds were evaluated for antibacterial

  摘要 在这项研究中，我们报告了从 5α-hydroxyergosta-7,22-dien-3,6-dione (1)开始的简单转化，得到两种新型化合物：6-methoxyergosta-4,6,8(14),22- tetraen-3-one (2)和 6-ethoxyergosta-4,6,8(14),22-tetraen-3-one ( 3)使用醇酸催化。使用 NMR 实验、FT-IR、MS 和 X 射线分析阐明了它们的结构。使用纸片和肉汤扩散试验评估这些化合物的抗菌活性。在那些测试中，发现化合物3是最重要的抗菌剂。一般来说，化合物1-3对金黄色葡萄球菌和变形链球菌的抑菌圈在 7.00-12.3 mm 范围内，同时对于革兰氏阴性细菌大肠杆菌和假单胞菌属。被发现在 7.00-8.00 毫米的范围内。对于活性最强的化合物3，MIC 显着低于麦角甾醇的 MIC，值为 160 µg/mL。总的来说，这些化合物比它们的天然前体更活跃。
• The constituents of Gymnopilus spectabilis.
  作者：GENJIRO KUSANO、YUTAKA KOIKE、HIDEO INOUE、SHIGEO NOZOE

  DOI：10.1248/cpb.34.3465

  日期：——

  Cerevisterol (1) and a new acetylenic compound, 4, 6-decadiyne-1, 3, 8-triol (2) were isolated and characterized from a hallucinogenic mushroom, Gymnopilus spectabilis (FR.) A. H. SMITH, along with ergosterol, ergosteryl peroxide and choline.Psychoactive compounds such as psilocybin and related compounds have not been detected in our collections of this mushroom, though some psilocybin has been found in several other Japanese mushrooms.

  从迷幻蘑菇Gymnopilus spectabilis (FR.) A. H. SMITH中分离并鉴定了Cerevisterol (1)和一种新的炔烃化合物4, 6-decadiyne-1, 3, 8-triol (2)，同时还分离了麦角甾醇、麦角甾醇过氧化物和胆碱。尽管在我们对这种蘑菇的采集样本中未检测到迷幻成分如裸盖菇素及相关化合物，但在其他一些日本蘑菇中发现了部分裸盖菇素。
• Permanganate Oxidation of Ergosterol
  作者：Mary Fieser、Adolfo Quilico、Alex Nickon、William E. Rosen、E. James Tarlton、Louis F. Fieser

  DOI：10.1021/ja01112a057

  日期：1953.8
• Synthesis of 24-epiteasterone
  作者：N. V. Kovganko、S. K. Ananich

  DOI：10.1007/bf00630173

  日期：——
• Seasonal variations in the community structure of aquatic organisms in a paddy field under a long-term fertilizer trial
  作者：Masatsugu Yamazaki、Yukihiro Hamada、Takeo Ibuka、Takashi Momii、Makoto Kimura

  DOI：10.1080/00380768.2001.10408422

  日期：2001.9

  To estimate the effect of fertilizers on aquatic organisms ranging in size from 30 mum to 2 cm in a Japanese paddy field under a long-term fertilizer trial (the plots without fertilizers, with chemical fertilizers only, and with chemical fertilizers as well as two levels (7.5 and 22.5 tons ha(-1)) of rice straw compost), we collected the floodwater samples once every 10 d during the cropping season throughout 3 y and mainly classified aquatic organisms in the floodwater at the order level. The frequency of the presence of Chlorococcales, Lemanaceae, Euglenida, Oligotrichida, Pharyngophorida, Sessilida, Turbellaria, Podocopida, and Cyclopoida was significantly different among the plots, while the maximum population density was significantly different for Cladocera and Cyclopoida among the plots. The effects of the sampling year on the frequency of presence and the maximum population density were also observed. The floodwater samples after midseason drainage in three plots with fertilizer application differed from the samples in the plot without fertilizer application in the community structure of aquatic organisms. Principal component analysis showed that Lemanaceae, Pharyngophorida, and Turbellaria were important components in the floodwater samples after midseason drainage in the three plots with fertilizer application. Although Cladocera appeared more abundantly after midseason drainage in the plot without fertilizers and the plot with chemical fertilizers only, it appeared more abundantly before midseason drainage in the two plots with composts. Shannon-Weaver's index of diversity (H') was higher in the three plots with fertilizers than in the plot without fertilizers. The effect of fertilizer application on the community structure and the diversity of aquatic organisms was more conspicuous than that of the sampling year.