Lumisterol

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 an electrocyclic ring opening and subsequent sigmatropic [1,7] hydride shift.

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.808
UNII
  • 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 checkY
    Key: DNVPQKQSNYMLRS-YAPGYIAOSA-N checkY
  • 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
  • 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
C28H44O
Molar mass 396.659 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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