Gammacerane

Gammacerane
Names
IUPAC name
Gammacerane[1]
Systematic IUPAC name
(4aS,6aR,6bR,8aS,12aS,12bR,14aR,14bS)-4,4,6a,6b,9,9,12a,14b-Octamethyldocosahydropicene
Identifiers
3D model (JSmol)
2562711
ChEBI
ChemSpider
  • InChI=1S/C30H52/c1-25(2)15-9-17-27(5)21(25)13-19-29(7)23(27)11-12-24-28(6)18-10-16-26(3,4)22(28)14-20-30(24,29)8/h21-24H,9-20H2,1-8H3/t21-,22-,23+,24+,27-,28-,29+,30+/m0/s1
    Key: QDUDLLAGYKHBNK-QPYQYMOUSA-N
  • InChI=1S/C30H52/c1-25(2)15-9-17-27(5)21(25)13-19-29(7)23(27)11-12-24-28(6)18-10-16-26(3,4)22(28)14-20-30(24,29)8/h21-24H,9-20H2,1-8H3/t21-,22-,23+,24+,27-,28-,29+,30+/m0/s1
    Key: QDUDLLAGYKHBNK-QPYQYMOUSA-N
  • [H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@]5(C)CCCC(C)(C)[C@]5([H])CC[C@@]34C)[C@@]1(C)CCCC2(C)C
Properties
C30H52
Molar mass 412.746 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Gammacerane is a pentacyclic triterpene compound with the formula C30H52 and five six-membered rings. Its derivatives include tetrahymanol（gammaceran-3β-ol）and so on. After millions of years of diagenesis, these derivatives became gammacerane can be used as biomarkers in petroleum to study the origin of petroleum.[2]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1535. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ 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.