Lanostane

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

Lanostane
Names
Other names
4,4,14α-Trimethylcholestane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26+,28-,29-,30+/m1/s1 ☒N
    Key: ZQIOPEXWVBIZAV-ZKYCIREVSA-N ☒N
  • (5α): InChI=1/C30H54/c1-21(2)11-9-12-22(3)23-15-19-30(8)25-13-14-26-27(4,5)17-10-18-28(26,6)24(25)16-20-29(23,30)7/h21-26H,9-20H2,1-8H3/t22-,23-,24+,25-,26+,28-,29-,30+/m1/s1
    Key: ZQIOPEXWVBIZAV-ZKYCIREVBA
  • (5α): C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)CCC[C@]4(C)[C@@]3([H])CC[C@@]21C
  • (5β): C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2(C)[C@]3([H])CC[C@]4([H])C(C)(C)CCC[C@]4(C)[C@@]3([H])CC[C@@]21C
Properties
C30H54
Molar mass 414.762 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).
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Infobox references

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]

  • 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.[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 (6): 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 Journal of Biochemistry. 10 (1): 1–19. doi:10.1111/j.1432-1033.1969.tb00650.x.
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