Lanostane

Lanostane
Other names

4,4,14-Trimethylcholestane
Identifiers
CAS number 474-20-4 (5α) Y, 57496-02-3 (5β) Y
Jmol-3D images
Image 3
Properties
Molecular formula C30H54
Molar mass 414.75 g mol−1
Melting point

98-99 °C[1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lanostane or 4,4,14-trimethylcholestane is a chemical compound with formula C30H54. 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).[2]

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.[2]

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. ^ a b 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