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 ;
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). verify (what is ?) Infobox references

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.

References

This article uses material from the Wikipedia English article Lumisterol, which is released under the Creative Commons Attribution-ShareAlike 3.0 license ("CC BY-SA 3.0"); additional terms may apply (view authors). Content is available under CC BY-SA 4.0 unless otherwise noted. Images, videos and audio are available under their respective licenses.
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Lumisterol

References

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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
ECHA InfoCard	100.006.808
PubChem CID	6436872
UNII	170D11Q82N^Y
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^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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references