Lanostane

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title: "Lanostane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["lanostanes", "triterpenes"] topic_path: "general/lanostanes" source: "https://en.wikipedia.org/wiki/Lanostane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424957756 | ImageFile = Lanostane.svg | ImageAlt = | ImageSize = 250 | IUPACName = | OtherNames = 4,4,14α-Trimethylcholestane |Section1={{Chembox Identifiers | CASNo = 474-20-4 | CASNo_Comment = (5α) | CASNo_Ref = | CASNo1 = 57496-02-3 | CASNo1_Comment = (5β) | CASNo1_Ref = | PubChem1 = 9548665 | PubChem1_Comment = (5α) | ChemSpiderID_Ref = | ChemSpiderID = 7827588 | ChemSpiderID_Comment = (5α) | ChEBI_Ref = | ChEBI = 20265 | ChEBI_Comment = (5α) | SMILES1 = CC@H[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 | SMILES1_Comment = (5α) | SMILES2 = CC@H[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 | 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 | StdInChI_Ref = | 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_Ref = | StdInChIKey = ZQIOPEXWVBIZAV-ZKYCIREVSA-N |Section2={{Chembox Properties | C=30 | H=54 | Appearance = | Density = | MeltingPtC = 98 to 99 | MeltingPt_ref = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Lanostane or 4,4,14α-trimethylcholestane is a tetracyclic chemical compound with formula . 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).

File:5alpha-lanostane.svg|5α-Lanostane File:5beta-lanostane.svg|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

References

  1. Voser, W.. (1950). "Zur Kenntnis der Triterpene. 156. Mitteilung. Zur Konstitution des Lanostadienols". Helvetica Chimica Acta.
  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.

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