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'''Lanostane''' or '''4,4,14α-trimethylcholestane''' is a ] with formula {{chem|C|30|H|54}}. It is a ], specifically a ]. It is an isomer of ]. '''Lanostane''' or '''4,4,14α-trimethylcholestane''' is a ] ] with formula {{chem|C|30|H|54}}. It is a ], specifically a ]. It is an isomer of ].


The name is applied to two ]s, distinguished by the prefixes '''5α-''' and '''5β-''', which differ by the handedness of the bonds at a particular ] atom (number 5 in the standard steroid numbering scheme).<ref name=iupac69/> The name is applied to two ]s, distinguished by the prefixes '''5α-''' and '''5β-''', which differ by the handedness of the bonds at a particular ] atom (number 5 in the standard steroid numbering scheme).<ref name=iupac69/>
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{{Saponins}} {{Saponins}}
{{Tetracyclics}}


] ]

Revision as of 07:25, 19 March 2023

Lanostane
Names
Other names 4,4,14α-Trimethylcholestane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: ZQIOPEXWVBIZAV-ZKYCIREVSA-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/s1Key: ZQIOPEXWVBIZAV-ZKYCIREVBA
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 to 99 °C (208 to 210 °F; 371 to 372 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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 (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.
Saponin Glycosides
Sapogenin (aglycone)
Steroidal
(C27 skeleton)
Triterpene
(C30 skeleton)
Tetracyclic
Pentacyclic
Glycone
Tetracyclics
Classes

Steroids

Antibiotics
Antidepressants
(TeCAs)
Steroids
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