Lumisterol

Lumisterol
Names
	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 ;
3D model (JSmol)	Interactive image;
ChemSpider	4941479 ;
ECHA InfoCard	100.006.808
PubChem CID	6436872;
UNII	170D11Q82N ;
CompTox Dashboard (EPA)	DTXSID60878681 ;
	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 Key: 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/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
	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 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 has an analog based on 7-dehydrocholesterol, known as lumisterol 3.[3]

References

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.
Friedmann, Ernst (1989). Neurath, Hans (ed.). Vitamin D. Perspectives in Biochemistry. Volume 1. Washington, DC: American Chemical Society. ISBN 978-0-8412-1621-1.
National Center for Biotechnology Information. "Lumisterol 3 (CID=111049)". PubChem Compound Database. Retrieved 10 April 2018.

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[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. Volume 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.