5-Dehydroepisterol

5-Dehydroepisterol

Names
IUPAC name (3S,10R,13R)-17-[(1R)-1,5-dimethyl-4-methylenehexyl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Other names 24-Methylcholesta-5,7,24(28)-trienol, ergosta-5,7,24(28)-trien-3β-ol, campesta-7,24(28)-dien-3β-ol
Identifiers
CAS Number	23582-83-4
3D model (Jmol)	Interactive image
ChemSpider	9069833
KEGG	C15780
PubChem	10894570
InChI InChI=1S/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1 Key: ZEPNVCGPJXYABB-LOIOQLKMSA-N InChI=1/C28H44O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9-10,18,20,22,24-26,29H,3,7-8,11-17H2,1-2,4-6H3/t20-,22+,24-,25+,26+,27+,28-/m1/s1 Key: ZEPNVCGPJXYABB-LOIOQLKMBD
SMILES O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCC(=C)/C(C)C)C)[C@@]3(C)CC4
Properties
Chemical formula	C28H44O
Molar mass	396.648 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

5-Dehydroepisterol is a sterol and an intermediate in steroid biosynthesis, particularly synthesis of brassinosteroids.^[1] It is formed from episterol through action of the enzyme lathosterol oxidase,^[2] and is then converted into 24-methylenecholesterol by 7-dehydrocholesterol reductase.^[3]

Episterol and 5-dehydroepisterol are found in Leishmania.^[4][5]

References

1. Pathway ko00100 at KEGG Pathway Database.
2. Reaction R07491 at KEGG Pathway Database.
3. Reaction R07492 at KEGG Pathway Database.
4. Goad LJ, Holz GG, Beach DH (June 1985). "Sterols of ketoconazole-inhibited Leishmania mexicana mexicana promastigotes". Mol Biochem Parasitol. 15 (3): 257–79. doi:10.1016/0166-6851(85)90089-1. PMID 4033689.
5. Rodrigues JC, Attias M, Rodriguez C, Urbina JA, Souza W (February 2002). "Ultrastructural and Biochemical Alterations Induced by 22,26-Azasterol, a Δ24(25)-Sterol Methyltransferase Inhibitor, on Promastigote and Amastigote Forms of Leishmania amazonensis". Antimicrob Agents Chemother. 46 (2): 487–99. doi:10.1128/AAC.46.2.487-499.2002. PMC 127026. PMID 11796362.