5-Dehydroepisterol

5-Dehydroepisterol is a sterol and an intermediate in steroid biosynthesis, particularly synthesis of brassinosteroids.[1] It is formed from episterol through action of ERG3, the C-5 sterol desaturase in the yeast[2] and is then converted into 24-methylenecholesterol by 7-dehydrocholesterol reductase.[3]

5-Dehydroepisterol
Ball-and-stick model of 5-dehydroepisterol
Names
IUPAC name
Campesta-5,7,24(241)-trien-3β-ol
Systematic IUPAC name
(1R,3aR,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-7-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
3D model (JSmol)
ChemSpider
KEGG
  • 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 ☒N
    Key: ZEPNVCGPJXYABB-LOIOQLKMSA-N ☒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
  • 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
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

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.
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