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Revision as of 20:24, 21 March 2013 editAddbot (talk | contribs)Bots2,838,809 editsm Bot: Migrating 1 interwiki links, now provided by Wikidata on d:q3915037← Previous edit Revision as of 14:13, 15 April 2014 edit undoWildCation (talk | contribs)Extended confirmed users2,163 edits Added CSID, InChIs, ChEMBL ID for 5-alpha stereoisomer.Next edit →
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| CASNo1_Comment = (5β) | CASNo1_Comment = (5β)
| CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1_Ref = {{cascite|correct|CAS}}
| PubChem = | PubChem1 = 9548665
| PubChem1_Comment = (5α)
| ChemSpiderID = 7827588
| ChemSpiderID_Comment = (5α)
| ChEBI = 20265
| ChEBI_Comment = (5α)
| SMILES1 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C | SMILES1 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
| SMILES1_Comment = (5α) | SMILES1_Comment = (5α)
| SMILES2 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C | SMILES2 = C(CCCC(C)C)1()CC2(C)3()CC4()C(C)(C)CCC4(C)3()CC21C
| SMILES2_Comment = (5β) | SMILES2_Comment = (5β)
| 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
| InChI_Comment = (5α)
| InChIKey = ZQIOPEXWVBIZAV-ZKYCIREVBA
| InChIKey_Comment = (5α)
| StdInChI = 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
| StdInChI_Comment = (5α)
| StdInChIKey = ZQIOPEXWVBIZAV-ZKYCIREVSA-N
| StdInChIKey = (5α)
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties

Revision as of 14:13, 15 April 2014

Lanostane
Names
Other names 4,4,14-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: (5α)
  • (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 98-99 °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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