5-Dehydroepisterol

5-Dehydroepisterol
Ball-and-stick model of 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
23582-83-4 YesY
3D model (Jmol) Interactive image
ChemSpider 9069833 N
KEGG C15780 YesY
PubChem 10894570
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).
N verify (what is YesYN ?)
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 127026Freely accessible. PMID 11796362.


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