Cerevisterol

Cerevisterol
Names
IUPAC name
5α-Ergosta-7,22-diene-3β,5,6β-triol
Systematic IUPAC name
(1R,3aR,5R,5aR,7S,9aR,9bS,11aR)-1-[(3E,5R)-5,6-Dimethylhept-3-en-2-yl]-9a,11a-dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthrene-5,5a,7(5H)-triol
Other names
(22E)-Ergosta-7,22-diene-3β,5α,6β-triol; (22E)-5α-Ergosta-7,22-diene-3β,5,6β-triol; (22E,24R)-Ergosta-7,22-diene-3β,5α,6β-triol; (22E,24R)-5α-Ergosta-7,22-diene-3β,5,6β-triol; (22E,24R)-24-Methyl-5α-cholesta-7,22-diene-3β,5,6β-triol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C28H46O3/c1-17(2)18(3)7-8-19(4)22-9-10-23-21-15-25(30)28(31)16-20(29)11-14-27(28,6)24(21)12-13-26(22,23)5/h7-8,15,17-20,22-25,29-31H,9-14,16H2,1-6H3/b8-7+/t18-,19+,20-,22+,23-,24-,25+,26+,27+,28-/m0/s1
    Key: ARXHRTZAVQOQEU-BRVLHLJYSA-N
  • O[C@@H]1C=C2[C@]3([H])CC[C@]([C@]3(CC[C@]2([H])[C@@]4(C)CC[C@@H](C[C@]14O)O)C)([H])[C@H](C)/C=C/[C@@H](C(C)C)C
Properties
C28H46O3
Molar mass 430.673 g·mol−1
Density 1.086 g/ml
Melting point 265.3 °C (509.5 °F; 538.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a sterol. Originally described in the 1930s from the yeast Saccharomyces cerevisiae, it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some in vitro bioactive properties, including cytotoxicity to some mammalian cell lines.