Lanostane

Lanostane
Names
Other names
4,4,14-Trimethylcholestane
Identifiers
474-20-4 (5α) YesY
57496-02-3 (5β) YesY
3D model (Jmol) (5α): Interactive image
(5β): Interactive image
ChEBI CHEBI:20265 (5α) N
ChemSpider 7827588 (5α) N
PubChem 9548665 (5α)
Properties
C30H54
Molar mass 414.76 g·mol−1
Melting point 98 to 99 °C (208 to 210 °F; 371 to 372 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Lanostane or 4,4,14-trimethylcholestane is a chemical compound with formula C
30
H
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).[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. 1 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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