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Lanostane

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Lanostane
Names
Other names 4,4,14-Trimethylcholestane
Identifiers
CAS Number
3D model (JSmol)
CompTox Dashboard (EPA)
SMILES
  • (5α): C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
  • (5β): C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
Properties
Chemical formula C30H54
Molar mass 414.762 g·mol
Melting point 98-99 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Lanostane or 4,4,14-trimethylcholestane is a chemical compound with formula C
30H
54. It is a polycyclic hydrocarbon, specifically a triterpene. It is an isomer of cucurbitane.

The name is applied to two stereoisomers, distinguished by the prefixes 5α- and 5β-, which differ by the handedness of the bonds at a particular carbon atom (number 5 in the standard steroid numbering scheme).

  • 5α-Lanostane 5α-Lanostane
  • 5β-Lanostane 5β-Lanostane

Replacement of a hydrogen atom attached to carbon number 3 in the 5α isomer with a hydroxyl group results in lanosterol, the biogenetic precursor of the steroids in animals.

References

  1. Voser, W.; Montavon, M.; Günthard, Hs. H.; Jeger, O.; Ruzicka, L. (1950). "Zur Kenntnis der Triterpene. 156. Mitteilung. Zur Konstitution des Lanostadienols". Helvetica Chimica Acta. 33: 1893–1910. doi:10.1002/hlca.19500330658.
  2. ^ IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature (1969), The Nomenclature of Steroids - Revised Tentative Rules. European J. of Biochemistry, volume 10, 1-19
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