5-Dehydroepisterol

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5-Dehydroepisterol
220px
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
ChemSpider 9069833 N
Jmol 3D model Interactive image
KEGG C15780 YesY
PubChem 10894570
  • 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
Vapor pressure {{{value}}}
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.
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