3β-acetoxy-5α-ergost-8(14)-ene | 4042-95-9

• 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: 3β-acetoxy-5α-ergost-8(14)-ene
• 英文别名: (24S)-β-methyl-5α-cholest-8(14)-en-3β-ol acetate；(10S)-3c-Acetoxy-10r.13c-dimethyl-17c-((1R:4S)-1.4.5-trimethyl-hexyl)-(5tH.9tH)-Δ⁸⁽¹⁴⁾-tetradecahydro-1H-cyclopenta[a]phenanthren；3β-Acetoxy-24β_F-methyl-5α-cholesten-(8(14))；3β-Acetoxy-5α-Δ⁸⁽¹⁴⁾-ergosten；Essigsaeure-[5α-ergosten-(8(14))-yl-(3β)-ester]；5α-Ergosten-(8(14))-yl-(3β)-acetat；Δ⁸⁽¹⁴⁾-Ergostenol-3-acetat；3β-Acetoxy-5α-ergost-8(14)-en；3β-Acetoxy-5α-ergosten-8(14)；Ergost-8(14)en-3β-yl-acetat；Δ8(14)-Ergosterol-O-acetat；3β-Acetoxy-ergost-8(14)-en；3β-Acetoxyergost-8(14)-ene；3β-Acetoxy-ergosten-8(14)；Ergost-8(14)-en-3-yl-acetat；alpha-Ergostenol acetate；[(3S,5S,9R,10S,13R,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 4042-95-9
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: LALAQRGFSWBMHR-VHEPHSCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5α-ergost-8(14)-ene 在 对甲苯磺酸 作用下， 以 甲醇 、 氯仿 为溶剂， 以87%的产率得到菜油甾醇
  参考文献：
  名称：

  海洋和半合成羟基类固醇作为孕烷 X 受体调节的新支架。

  摘要：

  近年来，已从海洋来源中鉴定出许多具有不寻常结构和有希望的生物特征的甾醇。在这里，我们报告了从软珊瑚 Sinularia kavarattiensis 中分离出一系列 24-烷基化羟基类固醇，作为孕烷 X 受体 (PXR) 调节剂。从该支架开始，制备了许多衍生物，并通过评估反式激活和量化基因表达来评估它们激活 PXR 的能力。我们的研究表明，ergost-5-en-3β-ol (4) 在 HepG2 细胞中诱导 PXR 反式激活并刺激 PXR 靶基因 CYP3A4 的表达。为了阐明这些配体与 PXR 之间相互作用的分子基础，我们通过对接模拟研究了该系列中最有效的化合物 4 与 PXR 的结合机制。

  DOI：

  10.3390/md12063091
• 作为产物：
  描述：

  麦角固醇 在 吡啶 、 platinum(IV) oxide 、 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 20.0 ℃ 、303.99 kPa 条件下， 反应 51.0h， 生成 3β-acetoxy-5α-ergost-8(14)-ene
  参考文献：
  名称：

  海洋和半合成羟基类固醇作为孕烷 X 受体调节的新支架。

  摘要：

  近年来，已从海洋来源中鉴定出许多具有不寻常结构和有希望的生物特征的甾醇。在这里，我们报告了从软珊瑚 Sinularia kavarattiensis 中分离出一系列 24-烷基化羟基类固醇，作为孕烷 X 受体 (PXR) 调节剂。从该支架开始，制备了许多衍生物，并通过评估反式激活和量化基因表达来评估它们激活 PXR 的能力。我们的研究表明，ergost-5-en-3β-ol (4) 在 HepG2 细胞中诱导 PXR 反式激活并刺激 PXR 靶基因 CYP3A4 的表达。为了阐明这些配体与 PXR 之间相互作用的分子基础，我们通过对接模拟研究了该系列中最有效的化合物 4 与 PXR 的结合机制。

  DOI：

  10.3390/md12063091

文献信息

• XANES Analysis of Used Engine Oils and Relationship to Wear
  作者：E. S. Yamaguchi、D. M. Wilson、M. Kasrai、G. M. Bancroft

  DOI：10.1080/10402000208982571

  日期：2002.1

  of the zinc dithiophosphates in used oils. Comparison of this XANES technique with a more traditional technique, 31P nuclear magnetic resonance (NMR) spectroscopy, showed that XANES spectroscopy gave data consistent with NMR. Since these were diesel engine oils, the authors were also able to examine, by solid-state NMR, the soot from two fully formulated engine oils, one a high wear and one a low wear

  多年来，已经开发了许多分析工具来测量发动机油配方中二硫代磷酸锌的消耗。其中许多工具都是显而易见的，例如红外光谱和薄层色谱；然而，在本文中，我们报告了我们使用 X 射线吸收近边结构 (XANES) 光谱检查油中二硫代磷酸锌消耗的研究。因此，XANES 加入了添加剂化学家可用的一系列技术，用于研究废油中二硫代磷酸锌的状态。将此 XANES 技术与更传统的 31P 核磁共振 (NMR) 光谱技术进行比较，表明 XANES 光谱提供与 NMR 一致的数据。由于这些是柴油发动机油，作者还能够通过固态核磁共振检查，来自两种全配方发动机油的烟灰，一种是高磨损油，一种是低磨损油。通过这项研究，作者能够证明 Rounds 的二硫代磷酸锌消耗和磨损的假设似乎是无效的。2002 年 10 月 27-30 日在墨西哥坎昆举行的 ASME/STLE 摩擦学会议上作为摩擦学家和润滑工程师协会的论文发表
• Forecasting Peak Daily Ozone Levels—I. A Regression with Time Series Errors Model Having a Principal Component Trigger to Fit 1991 Ozone Levels
  作者：Pao-Wen Grace Liu、Richard Johnson

  DOI：10.1080/10473289.2002.10470841

  日期：2002.9

  model for the peak daily 1-hr ozone level is proposed. A Regression with Time Series Errors (RTSE) model, which includes a principal component (PC) trigger, is the basis for forecasting the peak daily 1-hr ozone level. The RTSE model, with a PC trigger, is first employed to estimate daily peak ozone measured at the University of Wisconsin, Milwaukee-North (UWM-N), during the 1991 ozone season. The RTSE

  这项研究的动机是需要在高臭氧日警告威斯康星州密尔沃基的人口。提出了每天1小时臭氧峰值水平的统计模型。具有时间序列误差的回归（RTSE）模型（包括一个主要成分（PC）触发器）是预测每天1小时峰值臭氧水平的基础。带有PC触发器的RTSE模型首先用于估算1991年臭氧季节在密尔沃基北部的威斯康星大学（UWM-N）测得的每日峰值臭氧。RTSE模型使用每日峰值温度，早晨矢量平均风向和PC触发作为预测变量。PC触发器旨在总结臭氧峰值大于十亿分之100（ppb）时的大气情况。经验证，带有PC触发器的RTSE模型，大大改善了每日峰值臭氧的预测，特别是峰值臭氧大于100 ppb的预测。与没有PC触发的RTSE模型相比，带有PC触发的RTSE模型将R2从0.680提升到0.809。建议使用PC触发的RTSE模型是适当的统计模型，具有实时臭氧预报的潜力。
• Jereisterol A and B : Two 3β-methoxy-secosteroids from the pacific sponge Jereicopsis graphidiophora.
  作者：M. Valeria D'Auria、Luigi Gomez Paloma、Luigi Minale、Raffaele Riccio、Cecile Debitus

  DOI：10.1016/s0040-4039(00)71261-5

  日期：1991.5

  Two 3 β - methoxy secosteroids, named jereisterol A and B were isolated from the pacific sponge Jereicopsis graphidiophora Lévi & Lévi. Their structures, which combine rare 3 β-methoxy and seco features, were determined as (24 R) 24-methyl-3β-methoxy-8α,9α-oxido-8,9-secocholesta-7,9(11)-diene (1) and (24R) 24-methyl-3β-methoxy-8,14-secocholesta-8,14-dione (2).

  从太平洋海棉Jereicopsis graphidiophoraLévi＆Lévi中分离了两种名为jereisterol A和B的3β-甲氧基类固醇。它们的结构结合了稀有的3个β-甲氧基和癸二酮特征，被确定为（24 R）24-甲基-3β-甲氧基-8α，9α-氧化-8,9-仲胆固醇7,9（11）-二烯（ 1）和（24R）24-甲基-3β-甲氧基-8,14-仲胆甾醇-8,14-二酮（2）。
• EHL Film Thickness Limitation Theory Under a Limiting Shear Stress
  作者：Yongbin Zhang、Shizhu Wen

  DOI：10.1080/10402000208982584

  日期：2002.1

  It is numerically shown that the elastohydrodynamic lubrication (EHL) film thickness has a limit under an assumed limiting shear stress of the contact-lubricant interface in isothermal Pure rolling line contacts. The prediction of the central film thickness limit is made, and well matches experiments. The present theory shows that, in elastohydrodynamic line contacts, the central film thickness is of molecular scale and part of the contact area is in non-continuum film lubrication when the equivalent cylinder curvature radius is less than the critical one. This critical radius depends on the load and the contact-lubricant interfacial limiting shear stress at low pressures.
• Antiwear Tribofilm Formation on Steel Surfaces Lubricated With Gear Oil Containing Borate, Phosphorus, and Sulfur Additives
  作者：K. Komvopoulos、V. Chiaro、B. Pakter、E. S. Yamaguchi、P. R. Ryason

  DOI：10.1080/10402000208982589

  日期：2002.1

  The formation of antiwear tribofilms plays a critical role in the longevity of automotive gears. The focus of this experimental study was on the lubrication efficacy of gear oils with different contents of borate-, phosphorus-, and sulfur-containing additives leading to the formation of protective tribofilms. Experiments were performed with AISI 52100 steel balls sliding against AISI 52100 steel disks in baths of different oils at ambient (similar to32degreesC) and elevated (similar to100degreesC) temperatures under load and speed conditions favoring sliding in the boundary lubrication regime. Friction coefficient responses accompanied by electrical contact voltage measurements provided real-time information about the formation and durability of the antiwear tribofilms. The wear resistance of the tribochemical films was quantified by wear rate data obtained from surface profilometry measurements of wear tracks on the disk specimens and sliding tests performed at ambient temperatures after the formation of the tribofilms during elevated-temperature sliding. Results indicate a strong dependence of tribofilm formation on temperature and type of additives. The slightly lower friction and higher wear resistance obtained at elevated temperatures with blended oils is attributed to the increased chemical reactivity of additives containing borate, phosphorus, and sulfur, leading to the formation of durable tribofilms. Relatively higher wear resistance and faster tribofilm formation were obtained with the borate-enriched gear oil formulations.