Lumisterol

Lumisterol

IUPAC name (3S,9R,10S,13R,14R,17R) -17-[(E,2R,5R)-5,6-Dimethylhept-3-en-2-yl] -10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro -1H-cyclopenta[a]phenanthren-3-ol
Identifiers
CAS number	474-69-1
PubChem	6436872
ChemSpider	4941479^Y
Jmol-3D images	Image 1
SMILES O[C@@H]4C/C3=C/C=C1\[C@@H](CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C)C(C)C)C)C)[C@]3(C)CC4
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/s1^Y Key: DNVPQKQSNYMLRS-YAPGYIAOSA-N^Y 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/s1 Key: DNVPQKQSNYMLRS-YAPGYIAOBK
Properties
Molecular formula	C₂₈H₄₄O
Molar mass	396.65 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[1]^[2] Vitamin D₂ can be formed from lumisterol by a electrocyclic ring opening and subsequent sigmatropic [1,7] hydride shift.

References

^ Dewick, Paul M. (2002). Medicinal Natural Products. A Biosynthetic Approach, second edition, p. 259. New York: John Wiley & Sons. ISBN 0471496405. View PDF file at WordPress.com. Accessed 31 July 2010.
^ Friedmann, Ernst "Vitamin D" in Neurath, Hans, editor (1989). Perspectives in Biochemistry, volume 1. Washington, DC: American Chemical Society. ISBN 9780841216211. Partial view at Google Books.