3-epi-5,6-dihydroergosterol | 5035-32-5

• 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: 3-epi-5,6-dihydroergosterol
• 英文别名: 24β_F-methyl-5α-cholestadien-(7.22t)-ol-(3α)；3α-Hydroxy-10.13-dimethyl-17β-((1R:4R)-1.4.5-trimethyl-hexen-(2t)-yl)-5α-gonen-(7)；(10S)-3t-Hydroxy-10r.13c-dimethyl-17c-((1R:4R)-1.4.5-trimethyl-hexen-2t-yl)-(5tH.9tH.14tH)-Δ⁷-tetradecahydro-1H-cyclopenta[a]phenanthren；(24R)-24-Methyl-5α-cholestadien-(7.22t)-ol-(3α)；(3R,5S,9R,10S,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 5035-32-5
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: QOXPZVASXWSKKU-DLONVHBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-epi-5,6-dihydroergosterol 在 mercury(II) diacetate 、 溶剂黄146 作用下， 生成 5α.14β-ergostatrien-(7.9(11).22t)-ol-(3β)
  参考文献：
  名称：

  Windaus et al., Justus Liebigs Annalen der Chemie, 1931, vol. 488, p. 91,107

  摘要：

  DOI：
• 作为产物：
  描述：

  麦角固醇 在 乙醚 、 戊醇 、 sodium 、 钯 作用下， 生成 3-epi-5,6-dihydroergosterol
  参考文献：
  名称：

  Film Formation in EHL Point Contacts under Zero Entraining Velocity Conditions

  摘要：

  The contacts of adjacent bulls in a retainerless bearing are subjected to the zero entrainment velocity (ZEV). The existence of an effective elastohydrodynamic lubrication (EHL) film between contacts running tinder ZEV conditions has long been proven experimentally. However, the classical EHL theory predicts a Zero film thickness under ZEV conditions. Mechanisms, such as the thermal viscosity wedge effect and immobile film theory, have been proposed to tentatively explain the phenomenon. However, detailed numerical results are needed to provide theoretical evidence for such film formations. This paper aims to simulate, based on the viscosity wedge mechanism, the film formation of EHL point contacts tinder ZEV conditions. Complete numerical solutions have been successfully obtained. The results show, that the thermal viscosity wedge induces a concave film profile, instead of a parallel film (Hertzian) as postulated by sonic previous researchers. By the simulation solver developed, the variation of film thickness with loads, oil supply conditions and ellipticity, parameters have been investigated. Some unique lubrication behaviors tinder ZEV conditions are demonstrated. Furthermore, preliminary quantitative comparisons with the latest optical EHL experiments are finished. Both results are in good correlation.

  DOI：

  10.1080/10402000208982583

文献信息

• Comparative Study of the Effect of 5,6-Dihydroergosterol and 3-epi-5,6-dihydroergosterol on Chemokine Expression in Human Keratinocytes
  作者：Ye Seul Park、Hye Jin Moon、Kwang Hyun Ahn、Tae Hoon Lee、Hakwon Kim

  DOI：10.3390/molecules25030522

  日期：——

  5,6-Dihydroergosterol-glucose is an organic synthetic derivative of spinasterol-glucose, which has potent anti-inflammatory activity. We previously synthesized alpha and beta anomers of DHE-glycosides and compared their inhibitory activity on CCL17 and CCL22 mRNA expression induced by TNF-α/IFN-γ in activated HaCaTs. Recently, we synthesized a new type of DHE-glycosides, 3-epi-5,6-dihydroergosterol(3-epi-DHE)-glycosides, and compared its inhibitory activity on mRNA expression levels of CCL17 and CCL22 in TNF-α/IFN-γ-induced HaCaT. DHE-Xly did not affect TNF-α/IFN-γ induced CCL17 and CCL22 mRNA expression in HaCaTs, however, 3-epi-DHE-Xly strongly inhibited TNF-α/IFN-γ induced CCL17 and CCL22 mRNA expression levels in human keratinocytes. These results provide important clues for development of chronic dermatitis treatment via inhibition of chemokine expression using DHE derivatives.

  5,6-双氢麦角固醇葡萄糖是自旋固醇葡萄糖的有机合成衍生物，具有强效的抗炎活性。我们之前合成了DHE-糖苷的α和β异构体，并比较了它们对由TNF-α/IFN-γ在激活的HaCaTs中诱导的CCL17和CCL22 mRNA表达的抑制活性。最近，我们合成了一种新型的DHE-糖苷，3-epi-5,6-双氢麦角固醇（3-epi-DHE）-糖苷，并比较了它对TNF-α/IFN-γ诱导的HaCaT中CCL17和CCL22 mRNA表达水平的抑制活性。DHE-Xly不影响TNF-α/IFN-γ诱导的HaCaTs中CCL17和CCL22 mRNA表达，然而，3-epi-DHE-Xly强烈抑制了人角质细胞中TNF-α/IFN-γ诱导的CCL17和CCL22 mRNA表达水平。这些结果为使用DHE衍生物抑制趋化因子表达开发慢性皮炎治疗提供了重要线索。
• Windaus et al., Justus Liebigs Annalen der Chemie, 1930, vol. 477, p. 268,278
  作者：Windaus et al.

  DOI：——

  日期：——
• Lettre, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1930, vol. 189, p. 1
  作者：Lettre

  DOI：——

  日期：——
• de Boe, 1930, p. 336,359
  作者：de Boe

  DOI：——

  日期：——
• Douglas et al., Journal of the Chemical Society, 1959, p. 1720,1723
  作者：Douglas et al.

  DOI：——

  日期：——