四膜虫醇

四膜虫醇英語:,或称作伽马蜡烷-3β-醇,Gammaceran-3β-ol)是一种五环三萜醇,最早发现于海洋纤毛虫四膜蟲Tetrahymena pyriformis)的细胞膜[1],之后在其它纤毛虫、真菌蕨类细菌中都有发现[2]。经过数百万年的成岩作用,海洋沉积物中的四膜虫醇会转化为对应的饱和伽马蜡烷[2],可用于分析古代的海洋环境[3]

胆固醇(A)、四膜虫醇(B)、藿烯醇B(C)的化学结构
Tetrahymanol
Chemical structure of tetrahymanol
IUPAC名
(3S,4aR,6aR,6aR,6bR,8aS,12aS,14aR,14bR)-4,4,6a,6b,9,9,12a,14b-Octamethyl-1,2,3,4a,5,6,6a,7,8,8a,10,11,12,13,14,14a-hexadecahydropicen-3-ol
系统名
(1R,2R,5R,7S,10R,11R,14R,15S,20S)-1,2,6,6,10,15,19,19-octamethylpentacyclo[12.8.0.02,11.05,10.015,20]docosan-7-ol
(1R,2R,5R,7S,10R,11R,14R,15S,20S)-1,2,6,6,10,15,19,19-八甲基五环[12.8.0.02,11.05,10.015,20]-7-二十二醇
别名 Gammaceran-3β-ol
识别
CAS号 2130-17-8  checkY
PubChem 168951
ChemSpider 147779
SMILES
 
  • C[C@]12CCCC([C@@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)C)(C)C
InChI
 
  • 1S/C30H52O/c1-25(2)15-9-16-27(5)20(25)12-18-29(7)22(27)10-11-23-28(6)17-14-24(31)26(3,4)21(28)13-19-30(23,29)8/h20-24,31H,9-19H2,1-8H3/t20-,21-,22+,23+,24-,27-,28-,29+,30+/m0/s1
InChIKey BFNSRKHIVITRJP-VJBYBJRLSA-N
ChEBI 9493
KEGG C06083
性质
化学式 C30H52O
摩尔质量 428.73 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

另见

参考文献

  1. Mallory FB, Gordon JT, Conner RL. . Journal of the American Chemical Society. June 1963, 85 (9): 1362–1363. doi:10.1021/ja00892a042.
  2. Ten Haven HL, Rohmer M, Rullkötter J, Bisseret P. . Geochimica et Cosmochimica Acta. November 1989, 53 (11): 3073–3079. Bibcode:1989GeCoA..53.3073T. doi:10.1016/0016-7037(89)90186-5.
  3. Sinninghe Damste JS, Kenig F, Koopmans MP, Koster J, Schouten S, Hayes JM, de Leeuw JW. . Geochimica et Cosmochimica Acta. May 1995, 59 (9): 1895–900. Bibcode:1995GeCoA..59.1895S. PMID 11540109. doi:10.1016/0016-7037(95)00073-9. hdl:1874/4297.
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