2,3-Oxidosqualene

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2,3-Oxidosqualene

IUPAC name 2,2-Dimethyl-3-[(3E,7E,11E,15E)- 3,7,12,16,20-pentamethylhenicosa- 3,7,11,15,19-pentaenyl]oxirane
Other names Squalene oxide 2,3-Squalene oxide Squalene epoxide
Identifiers
CAS number	7200-26-2
PubChem	5366020
ChemSpider	4517951^Y
MeSH	2,3-oxidosqualene
Jmol-3D images	Image 1 Image 2
SMILES O1C(C)(C)C1CC/C(=C/CC/C(=C/CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C)C CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CCC1C(O1)(C)C)/C)/C)C
InChI InChI=1S/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+^Y Key: QYIMSPSDBYKPPY-BANQPHDMSA-N^Y InChI=1/C30H50O/c1-24(2)14-11-17-27(5)20-12-18-25(3)15-9-10-16-26(4)19-13-21-28(6)22-23-29-30(7,8)31-29/h14-16,20-21,29H,9-13,17-19,22-23H2,1-8H3/b25-15+,26-16+,27-20+,28-21+ Key: QYIMSPSDBYKPPY-BANQPHDMBU
Properties
Molecular formula	C₃₀H₅₀O
Molar mass	426.717 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

(S)-2,3-Oxidosqualene ((S)-2,3-epoxysqualene) is an intermediate in the synthesis of the cell membrane sterol precursors lanosterol and cycloartenol, as well as saponins. It is formed when squalene is oxidized by the enzyme squalene monooxygenase. 2,3-Oxidosqualene is the substrate of various oxidosqualene cyclases, including lanosterol synthase, which produces lanosterol, a precursor to cholesterol.^[1]

The stereoisomer 2,3-(R)-oxidosqualene is an inhibitor of lanosterol synthase.

References

↑ Abe I. (2007). "Enzymatic synthesis of cyclic triterpenes". Natural Products Reports 24 (6): 1311–31. doi:10.1039/b616857b. PMID 18033581.

to HMG-CoA	Acetyl-CoA Acetoacetyl-CoA HMG-CoA

Ketone bodies	Acetone Acetoacetic acid beta-Hydroxybutyric acid

to DMAPP	Mevalonic acid Phosphomevalonic acid 5-Diphosphomevalonic acid Isopentenyl pyrophosphate Dimethylallyl pyrophosphate

Geranyl-	Geranyl pyrophosphate Geranylgeranyl pyrophosphate

Carotenoid	Prephytoene diphosphate Phytoene

Mineralocorticoids	Pregnenolone Progesterone Cortodoxone Corticosterone Aldosterone

Glucocorticoids	Pregnenolone 17-Hydroxypregnenolone 17-Hydroxyprogesterone Cortisol Cortisol Cortisone

Androgens (C19 androstane)	DHEA Androstenedione/5-Androstenediol Testosterone Dihydrotestosterone DHEA sulfate Epitestosterone

Estrogens (C18 estrane)	Estetrol Estrone Estradiol Estriol

Nonhuman

Phytosterols	Stigmasterol Brassicasterol

Ergosterols	Ergosterol Ergocalciferol

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

anat/phys/devp/horm

noco (d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

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