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Lumisterol

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Lumisterol
Lumisterol
Names
IUPAC name (22E)-9β,10α-Ergosta-5,7,22-trien-3β-ol
Systematic IUPAC name (1R,3aR,7S,9aS,9bR,11aR)-1--9a,11a-dimethyl-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopentaphenanthren-7-ol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.808 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26+,27+,28+/m0/s1Key: DNVPQKQSNYMLRS-YAPGYIAOSA-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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/b8-7+/t19-,20+,22-,24+,25-,26+,27+,28+/m0/s1Key: DNVPQKQSNYMLRS-YAPGYIAOBK
SMILES
  • O4C/C3=C/C=C1\(CC2(1CC2(/C=C/(C)C(C)C)C)C)3(C)CC4
Properties
Chemical formula C28H44O
Molar mass 396.659 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Lumisterol is a compound that is part of the vitamin D family of steroid compounds. It is the (9β,10α) stereoisomer of ergosterol and was produced as a photochemical by-product in the preparation of vitamin D1, which was a mixture of vitamin D2 and lumisterol. Vitamin D2 can be formed from lumisterol by an electrocyclic ring opening and subsequent sigmatropic hydride shift.

Lumisterol has an analog based on 7-dehydrocholesterol, known as lumisterol 3.

References

  1. Dewick, Paul M. (2002). Medicinal Natural Products. A Biosynthetic Approach (PDF) (Second ed.). New York: John Wiley & Sons. p. 259. ISBN 0-471-49640-5.
  2. Friedmann, Ernst (1989). Neurath, Hans (ed.). Vitamin D. Perspectives in Biochemistry. Vol. 1. Washington, DC: American Chemical Society. ISBN 978-0-8412-1621-1.
  3. National Center for Biotechnology Information. "Lumisterol 3 (CID=111049)". PubChem Compound Database. Retrieved 10 April 2018.


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