campesteryl acetate | 1900-53-4

• 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: campesteryl acetate
• 英文别名: 24(R)-24-methyl-5-cholesten-3β-yl acetate；24-methylcholest-5-en-3β-yl acetate；[3β,24R]-ergost-5-en-3-ol acetate；24β-Methylcholesterol acetate；22-Dihydrobrassicasterol acetate；acetate of dihydrobrassicasterol；[(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 1900-53-4
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: JOBAYBRAHVTSSW-NTUCOQBPSA-N

物化性质

• 保留指数：
  3323;3278;3288.5;3282.5;3274.6

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 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：

  campesteryl acetate 在 air 、 mercury dibromide 作用下， 以 叔丁醇 为溶剂， 反应 2.0h， 以90%的产率得到7-oxo-24(R)-24-methyl-5-cholesten-3β-yl acetate
  参考文献：
  名称：

  胆汁酸。LXVIII。甾体的烯丙基和苄基光化学氧化。

  摘要：

  为了提供产率高于化学氧化获得的7-氧胆固醇的衍生物，研究了甾体烯丙基或苄基酮的制备。在溴化汞存在的情况下，使用高选择性低能量紫外灯研究了空气诱导的氧化。通过该程序，乙酸胆固醇，5-胆甾烯-3β，27-二醇二乙酸酯，24（R）-24-甲基-5-胆甾烯-2β-乙酸乙烯酯，24（R）-24-乙基-5-胆甾烯-将乙酸28-乙酸酯和24（R）-24-乙基-（22E）-胆甾-5,22-二烯-3β-乙酸乙酸酯氧化成烯丙基酮基衍生物，收率很高。类似地，雌二醇-17β二乙酸酯以提高的产率转化为6-氧代产物。该方法在合成乙酸7-氧胆固醇酯及其类似物和6-氧-雌甾烯中非常有用。

  DOI：

  10.1016/0039-128x(83)90034-x
• 作为产物：
  描述：

  butanoic acid, 2,3-dimethyl-, methyl ester 在 palladium on activated charcoal lithium aluminium tetrahydride 、 四溴化碳 、 氢气 、 溴 、 sodium ethanolate 、 三苯基膦 、 mercury(II) oxide 作用下， 以 乙醚 为溶剂， 生成 campesteryl acetate
  参考文献：
  名称：

  乙酸菜油酯 ((24R)-24-methyl-3β-acetoxycholesten-5-ene) 及其 24S-差向异构体的合成

  摘要：

  摘要 以光学活性的 3,4-二甲基戊基溴化镁和孕烯醇酮乙酸酯为原料，合成了乙酸菜油酯及其 24 S 差向异构体。两种差向异构体对黄斑皮螨幼虫的利用不同。

  DOI：

  10.1016/s0039-128x(70)80133-7

文献信息

• Stereoselective Synthesis and NMR Characterization of C-24 Epimeric Pairs of 24-Alkyl Oxysterols
  作者：Shoujiro Ogawa、Hiroaki Kawamoto、Takashi Mitsuma、Hiroki Fujimori、Tatsuya Higashi、Takashi Iida

  DOI：10.1007/s11745-012-3739-1

  日期：2013.2

  be effectively characterized by the aromatic solvent‐induced shift (ASIS) by C5D5N, particularly for the difference in the 13C resonances in the substituted cholestane side chain. A method for differentiating the 1H and 13C signal assignment of the terminal 26‐/27‐CH3 in the iso‐octane side chain was also discussed on the basis of a combined use of the preferred conformational analysis and HMQC and

  两对C-24差向异构体（24 - [R ）- /（24小号）-24羟基-24-甲基-5- α -胆甾3 β基乙酸酯和（24 - [R ） - /（24小号）-25-羟基-24-甲基-5- α -胆甾3 β基乙酸酯以及一些相关的24乙基氧固醇类似物立体选择性地直接从各自的父由远程合成24烷基固醇ö -insertion与2,6-反应催化量的（5,10,15,20-四甲叉基卟啉）钌（II）羰基络合物[Ru（TMP）CO]和HBr存在下的二氯吡啶N-氧化物（DCP）。1 H‐和13解释了用来区分两个差向异构对的C-NMR信号。发现C-24上的C-24烷基氧固醇是由C 5 D 5 N引起的芳族溶剂诱导的位移（ASIS）有效表征的，特别是对于取代的胆甾烷侧链中13 C共振的差异。在iso中区分端子26- / 27-CH 3的1 H和13 C信号分配的方法还结合了首选的构象分析和HMQC和HMBC技术
• 1.alpha.-Hydroxy-24-EPI-vitamin D.sub.4
  申请人：Bone Care International, Inc.

  公开号：US05756783A1

  公开（公告）日：1998-05-26

  1.alpha.-Hydroxy-24-epi-vitamin D.sub.4 and novel intermediates formed in a novel method of preparing this compound. The method includes campesterol as a starting material which is converted to 24-epi-vitamin D.sub.4 which is in turn hydroxylated to 1.alpha.-hydroxy-24-epi-vitamin D.sub.4 via tosylated and cyclic derivatives of 24-epi-vitamin D.sub.4. 1.alpha.-Hydroxy-24-epi-vitamin D.sub.4 has been found to be bioactive.

  1.alpha.-羟基-24-epi-维生素D.sub.4和在制备该化合物的新方法中形成的新中间体。该方法以甾醇为起始材料，将其转化为24-epi-维生素D.sub.4，然后通过24-epi-维生素D.sub.4的tosylated和环状衍生物进行羟基化，形成1.alpha.-羟基-24-epi-维生素D.sub.4。已发现1.alpha.-羟基-24-epi-维生素D.sub.4具有生物活性。
• [EN] 1 alpha -HYDROXY-24-EPI-VITAMIN D4
  申请人：LUNAR CORPORATION

  公开号：WO1993014763A1

  公开（公告）日：1993-08-05

  (EN) 1$g(a)-Hydroxy-24-$i(epi)-vitamin D4 and novel intermediates formed in a novel method of preparing this compound. The method includes campesterol as a starting material which is converted to 24-$i(epi)-vitamin D4 which is in turn hydroxylated to 1$g(a)-hydroxy-24-$i(epi)-vitamin D4 via tosylated and cyclic derivatives of 24-$i(epi)-vitamin D4. 1$g(a)-Hydroxy-24-$i(epi)-vitamin D4 has been found to be bioactive.(FR) 1$g(a)-hydroxy-24-$i(epi)-vitamine D4 et nouveaux intermédiaires obtenus par un nouveau procédé de préparation de ce composé. Le procédé fait appel au campestérol comme matière de départ qui est convertie en 24-$i(epi)-vitamine D4 qui est à son tour hydroxylée en 1$g(a)-hydroxy-24-$i(epi)-vitamine D4 par l'intermédiaire de dérivés tosylés et cycliques de 24-$i(epi)-vitamine D4. 1$g(a)-hydroxy-24-$i(epi)-vitamine D4 s'est révélée bioactive.

  1$g(a)-羟基-24-$i(epi)-维生素D4及其 novel中间体，这通过一种 novel方法制备。该方法使用了起点为卡门内龙（campesterol），然后将其转化为24-$i(epi)-维生素D4。随后，通过tosyl化和环状衍生物，将24-$i(epi)-维生素D4转化为1$g(a)-羟基-24-$i(epi)-维生素D4。1$g(a)-羟基-24-$i(epi)-维生素D4已被证明具有生物活性。
• Tsuda,K.; Sakai,K., Chemical and pharmaceutical bulletin, 1960, vol. 8, p. 554 - 558
  作者：Tsuda,K.、Sakai,K.

  DOI：——

  日期：——
• Roadside Particulate Air Pollution in Bangkok
  作者：Wanida Jinsart、Kenji Tamura、Samarnchai Loetkamonwit、Sarawut Thepanondh、Kanae Karita、Eiji Yano

  DOI：10.1080/10473289.2002.10470845

  日期：2002.9

  Airborne fine particles of PM2.5-10 and PM2.5 in Bangkok, Nonthaburi, and Ayutthaya were measured from December 22, 1998, to March 26, 1999, and from November 30, 1999, to December 2, 1999. Almost all the PM10 values in the high-polluted (H) area exceeded the Thailand National Ambient Air Quality Standards (NAAQS) of 120 mug/m(3). The low-polluted (L) area showed low PM10 (34-74 mug/m(3) in the daytime and 54-89 mug/m(3) at night). PM2.5 in the H area varied between 82 and 143 mug/m(3) in the daytime and between 45 and 146 mug/m(3) at night. In the L area, PM2.5 was quite low both day and night and varied between 24 and 54 mug/m(3), lower than the U.S. Environmental Protection Agency (EPA) standard (65 mug/m(3)). The personal exposure results showed a significantly higher proportion of PM2.5 to PM10 in the H area than in the L area (H = 0.80 +/- 0.08 and L = 0.65 +/- 0.04).Roadside PM10 was measured simultaneously with the Thailand Pollution Control Department (PCD) monitoring station at the same site and at the intersections where police work. The result from dual simultaneous measurements of PM10 showed a good correlation (correlation coefficient: r = 0.93); however, PM levels near the roadside at the intersections were higher than the concentrations at the monitoring station. The relationship between ambient PM level and actual personal exposures was examined. Correlation coefficients between the general ambient outdoors and personal exposure levels were 0.92 for both PM2.5 and PM10.Bangkok air quality data for 1997-2000, including 24-hr average PM10, NO2, SO2, and O-3 from eight PCD monitoring stations, were analyzed and validated. The annual arithmetic mean PM10 of the PCD data at the roadside monitoring stations for the last 3 years decreased from 130 to 73 mug/m(3), whereas the corresponding levels at the general monitoring stations decreased from 90 to 49 mug/m(3). The proportion of days when the level of the 24-hr average PM10 exceeded the NAAQS was between 13 and 26% at roadside stations. PCD data showed PM10 was well correlated with NO2 but not with SO2, suggesting that automobile exhaust is the main source of the particulate air pollution. The results obtained from the simultaneous measurement of PM2.5 and PM10 indicate the potential environmental health hazard of fine particles. In conclusion, Bangkok traffic police were exposed to high levels of automobile-derived particulate air pollution.