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-[(2R,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]phenanthren-7-ol
Identifiers
CAS Number	474-69-1 Y
3D model (JSmol)	Interactive image
ChemSpider	4941479 Y
PubChem CID	6436872
UNII	170D11Q82N Y
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
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
Properties
Chemical formula	C28H44O
Molar mass	396.659 g·mol−1

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 [1,7] hydride shift.

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