Tetrahymanol

Tetrahymanol
Chemical structure of tetrahymanol
Names
IUPAC name
Gammaceran-3β-ol
Systematic IUPAC name
(3S,4aR,6aR,6bR,8aS,12aS,12bR,14aR,14bR)-4,4,6a,6b,9,9,12a,14b-Octamethyldocosahydropicen-3-ol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
  • 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 checkY
    Key: BFNSRKHIVITRJP-VJBYBJRLSA-N checkY
  • 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
    Key: BFNSRKHIVITRJP-VJBYBJRLSA-N
  • 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
Properties
C30H52O
Molar mass 428.745 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetrahymanol is a gammacerane-type membrane lipid first found in the marine ciliate Tetrahymena pyriformis.[1] It was later found in other ciliates, fungi, ferns, and bacteria.[2] After being deposited in sediments that compress into sedimentary rocks over millions of years, tetrahymanol is dehydroxylated into gammacerane.[2] Gammacerane has been interpreted as a proxy for ancient water column stratification.[3]

  1. ^ Mallory FB, Gordon JT, Conner RL (June 1963). "The Isolation of a Pentacyclic Triterpenoid Alcohol from a Protozoan". Journal of the American Chemical Society. 85 (9): 1362–1363. doi:10.1021/ja00892a042.
  2. ^ a b Ten Haven HL, Rohmer M, Rullkötter J, Bisseret P (November 1989). "Tetrahymanol, the most likely precursor of gammacerane, occurs ubiquitously in marine sediments". Geochimica et Cosmochimica Acta. 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 (May 1995). "Evidence for gammacerane as an indicator of water column stratification". Geochimica et Cosmochimica Acta. 59 (9): 1895–900. Bibcode:1995GeCoA..59.1895S. doi:10.1016/0016-7037(95)00073-9. hdl:1874/4297. PMID 11540109.