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Lanostane

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Lanostane
Names

Other names 4,4,14α-Trimethylcholestane
Identifiers
CAS Number	474-20-4 (5α)^Y 57496-02-3 (5β)^Y
3D model (JSmol)	(5α): Interactive image (5β): Interactive image
ChEBI	CHEBI:20265 (5α)^N
ChemSpider	7827588 (5α)^N
PubChem CID	9548665 (5α)
CompTox Dashboard (EPA)	DTXSID60963824
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/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
SMILES (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
Chemical formula	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). N verify (what is ^YN ?) Infobox references

Lanostaneor4,4,14α-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).^[2]

5α-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[edit]

^ 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.

^ ^a ^b 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

v t e Tetracyclics
Classes	Polyketides Tetracenes Steroids
Antibiotics	Tetracyclines Tetracycline Chlortetracycline Demeclocycline Doxycycline Eravacycline Lymecycline Minocycline Omadacycline Oxytetracycline Rolitetracycline Sarecycline Glycylcycline Tigecycline Triterpenes Fusidanes Fusidic acid Helvolic acid Cephalosporin P₁
Antidepressants (TeCAs)	Azipramine Ciclopramine Esmirtazapine Mianserin Mirtazapine Naranol Oxaprotiline Setiptiline (teciptiline)
Steroids	Sex hormones Progestogens Acetomepregenol Chlormadinone acetate Danazol Delmadinone acetate Etonogestrel Gestodene Hydroxyprogesterone caproate Levonorgestrel Norethisterone Norgestrel Progesterone Segesterone acetate Tibolone Sterane Cholane Cholestane Ergostane Gonanes Androstane Estrane Pregnane Allopregnane Norpregnane Retropregnane Triterpenes Cycloartane Cucurbitacins Cucurbitane Dammarane Euphane Lanostane Protostane Sterols Phytosterols Campesterol beta-Sitosterol Cholesterol Stanol esters

Retrieved from "https://en.wikipedia.org/w/index.php?title=Lanostane&oldid=1188983161" Categories: ●Lanostanes ●Triterpenes Hidden categories: ●Chemical articles with multiple compound IDs ●Multiple chemicals in an infobox that need indexing ●Chemical articles with multiple CAS registry numbers ●Articles without KEGG source ●Articles without UNII source ●Articles with changed EBI identifier ●Articles with changed ChemSpider identifier ●Articles with changed InChI identifier ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description matches Wikidata ●This page was last edited on 8 December 2023, at 23:07 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view