(22E)-3β-acetoxy-5α-ergosta-6,8(14),22-triene | 5226-38-0

• 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)-3β-acetoxy-5α-ergosta-6,8(14),22-triene
• 英文别名: 5α-ergostatrien-(6.8(14).22t)-yl-(3β)-acetate；(10S)-3c-Acetoxy-10r.13c-dimethyl-17c-((1R:4R)-1.4.5-trimethyl-hexen-(2t)-yl)-(5tH.9tH)-Δ^6.8(14)-dodecahydro-1H-cyclopenta[a]phenanthren；3β-Acetoxy-24β_F-methyl-5α-cholestatrien-(6.8(14).22t)；Essigsaeure-[5α-ergostatrien-(6.8(14).22t)-yl-(3β)-ester]；5α-Ergostatrien-(6.8(14).22t)-yl-(3β)-acetat；3β-Acetoxy-5α-ergostatrien-(6.8(14).22t)；[(3S,5R,9R,10S,13R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 5226-38-0
• 化学式: C₃₀H₄₆O₂
• 分子量: 438.694
• InChiKey: HXAOBWJHBHAGGJ-CDTVXXSZSA-N

物化性质

• 沸点：
  511.6±49.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (22E)-3β-acetoxy-5α-ergosta-6,8(14),22-triene 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以48%的产率得到3β-acetoxy-14-hydroxy-5α-ergosta-7,22-dien-6-one
  参考文献：
  名称：

  Synthesis of potential ecdysteroid precursors from Δ7,22 sterols

  摘要：

  DOI：

  10.1016/s0040-4020(01)90337-0
• 作为产物：
  描述：

  (3b,22E)-麦角甾-5,7,22-三烯-3b-醇 3-乙酸酯 在 氯仿 作用下， 生成 (22E)-3β-acetoxy-5α-ergosta-6,8(14),22-triene
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Novel side chain modified Δ8(14)-15-ketosterols
  作者：Alexander Yu. Misharin、Vitali S. Ivanov、Arif R. Mehtiev、Galina E. Morozevich、Yaroslav V. Tkachev、Vladimir P. Timofeev

  DOI：10.1016/j.steroids.2006.12.002

  日期：2007.3

  23-oxido-5alpha-ergost-8(14)-en-15-one, (22R,23R)-3beta-hydroxy-22,23-oxido-5alpha-ergost-8(14)-en-15-one, (22R,23R)-5alpha-ergost-8(14)-en-15-on-3beta,22,23-triol and (22R,23R)-3beta-hydroxy-22,23-isopropylidenedioxy-5alpha-ergost-8(14)-en-15-one. New Delta8(14)-15-ketosterols were evaluated for their cytotoxicity and effects on sterol biosynthesis in human hepatoma Hep G2 cells in comparison with known

  描述了从麦角固醇开始的五种新颖的包含修饰的侧链的Delta8（14）-15-酮固醇的合成。通过三个阶段将乙酸麦角甾醇酯转化为（22E）-3β-乙酰氧基-5α-麦角甾醇8（14），22-dien-15-一，总产率为32％；获得的产物的进一步转化导致产生（22E）-3β-羟基-5α-麦角8（14），22-dien-15-一，（22S，23S）-3β-羟基-22,23-氧化-5α -ergost-8（14）-en-15-one，（22R，23R）-3beta-hydroxy-22,23-oxido-5alpha-ergost-8（14）-en-15-one，（22R，23R） -5alpha-ergost-8（14）-en-15-on-3beta，22,23-triol和（22R，23R）-3beta-hydroxy-22,23-isopropylidenedioxy-5alpha-ergost-8（14）-en
• Bills, Cox, Journal of Biological Chemistry, 1929, vol. 84, p. 455,457
  作者：Bills, Cox

  DOI：——

  日期：——
• CCCLXXIX.—Studies in the sterol group. Part VIII. The reactions of isoergosterol
  作者：Isidor Morris Heilbron、Frank Stuart Spring

  DOI：10.1039/jr9290002807

  日期：——
• The Role of Radial Clearance on the Performance of Foil Air Bearings
  作者：Kevin Radil、Samuel Howard、Brian Dykas

  DOI：10.1080/10402000208982578

  日期：2002.1

  Load capacity tests were conducted to determine how radial clearance variations affect the load capacity coefficient of foil air bearings. Two Generation III foil air bearings with the same design but possessing different initial radial clearances were tested at room temperature against an as-ground PS304 coated journal operating at 30000 rpm. Increases in radial clearance were accomplished by reducing the journal's outside diameter via an in-place grinding system. Front each load capacity test the bearing load capacity coefficient was calculated from the rule-of-thumb (ROT) model developed for foil air bearings.The test results indicate that, in terms of the load capacity coefficient, radial clearance has a direct impact on the performance of the foil air bearing. Each test bearing exhibited an optimum radial clearance that resulted in a maximum load capacity coefficient. Relative to this optimum value are two separate operating regimes that are governed by different modes of failure. Bearings operating with radial clearances less than the optimum exhibit load capacity coefficients that are a strong function of radial clearance and are prone to a thermal runaway failure mechanism and bearing seizure. Conversely, a bearing operating with a radial clearance m,ice the optimum suffered only a 20% decline in its maximum load capacity coefficient and did not experience any thermal management problems. However, it is unknown to what degree these changes in radial clearance had on other performance parameters, such (is the stiffness and damping properties of the bearings.
• Effects of Monounsaturated Enriched Sunflower Oil on CHD Risk Factors Including LDL Size and Copper-Induced LDL Oxidation
  作者：Emma L. Ashton、James D. Best、Madeleine J. Ball

  DOI：10.1080/07315724.2001.10719052

  日期：2001.8

  Objective: To compare the effects of a diet high in monounsaturated enriched sunflower oil and a low fat diet on CHD risk factors including in vitro Cu-induced LDL oxidation and LDL size, lipids, lipoproteins, glucose and insulin.Design: A randomized crossover dietary intervention.Setting: Free living individuals.Subjects: Fourteen healthy males 35 to 55 years of age and 14 healthy postmenopausal women 50 to 60 years of age completed the dietary intervention. Two subjects did not complete the study, and their data were not included.Interventions: A low fat, high carbohydrate diet (22% to 25% of energy from total fat, 7% to 8% of energy from monounsaturated fat and 55% to 60% of energy from carbohydrate) was compared to a monounsaturated enriched sunflower oil (MO) diet (40% to 42% of energy from fat, with 26% to 28% from monounsaturated fat and 40% to 45% of energy from carbohydrate) in an isocaloric substitution. Each dietary period was one month.Results: Total cholesterol, LDL cholesterol, triglycerides and glucose were not significantly different between the two diets. HDL cholesterol, HDL3 cholesterol and insulin were significantly higher on the MO diet, mean 7%, 7% and 17% higher respectively. Copper-induced LDL oxidation lag phase was significantly longer (mean 18%) after the MO diet compared to the low fat, high carbohydrate diet. LDL particle size was not significantly different.Conclusions: The significant increase in LDL oxidation lag phase and the significantly higher HDL cholesterol on the MO diet would be expected to be associated with a decrease in CHD risk.