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7α-Hydroxycholesterol-[25,26,26,26,27,27,27-d7]

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Category	Standards
Catalog NO.	BPG-3129
Product Name	7α-Hydroxycholesterol-[25,26,26,26,27,27,27-d7]
CAS	349553-94-2
Molecular Formula	C27H39D7O2
Molecular Weight	409.70

7α-Hydroxycholesterol-[25,26,26,26,27,27,27-d7]

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Product Information

Description	7α-Hydroxycholesterol-[25,26,26,26,27,27,27-d7] is the labelled analogue of 7a-Hydroxycholesterol, which is an oxysterol and a precursor in the biosynthesis of the bile acids, cholic acids and chenodeoxycholic acids. It is also a secondary metabolite of Cholesterol.
Synonyms	7a-Hydroxycholesterol-25,26,26,26,27,27,27-D7; 7α-Hydroxycholesterol-d7; 7alpha-hydroxycholesterol-d7; cholest-5-en-3beta,7alpha-diol-d7; (3β,7α)-(25,26,26,26,27,27,27-d7)Cholest-5-ene-3,7-diol
IUPAC Name	(3S,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)O)C
InChI	InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24-,25+,26+,27-/m1/s1/i1D3,2D3,17D
InChIKey	OYXZMSRRJOYLLO-WCYTWDCFSA-N
Purity	≥95%; 98% atom D
Solubility	Soluble in Methanol, DMF, DMSO, Ethanol
Related CAS	566-26-7 (unlabelled)
Appearance	Off-white Solid
Shelf Life	1 Year
Storage	Store at 2-8°C under inert atmosphere
Exact Mass	409.394
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 79.15%, H 13.04%, O 7.81%

References

1. Ménégaut L, Thomas C, Jalil A, Julla JB, Magnani C, Ceroi A, Basmaciyan L, Dumont A, Le Goff W, Mathew MJ, Rébé C, Dérangère V, Laubriet A, Crespy V, Pais de Barros JP, Steinmetz E, Venteclef N, Saas P, Lagrost L, Masson D. Interplay between Liver X Receptor and Hypoxia Inducible Factor 1α Potentiates Interleukin-1β Production in Human Macrophages. Cell Rep. 2020 May 19;31(7):107665. doi: 10.1016/j.celrep.2020.107665. PMID: 32433974. PubMed ID: 32433974.
2. Kloudova-Spalenkova A, Ueng YF, Wei S, Kopeckova K, Peter Guengerich F, Soucek P. Plasma oxysterol levels in luminal subtype breast cancer patients are associated with clinical data. J Steroid Biochem Mol Biol. 2019 Dec 23;197:105566. doi: 10.1016/j.jsbmb.2019.105566. [Epub ahead of print]. PMID: 31874216. PubMed ID: 31874216.
3. Aires V, Labbé J, Deckert V, Pais de Barros JP, Boidot R, Haumont M, Maquart G, Le Guern N, Masson D, Prost-Camus E, Prost M, Lagrost L. Healthy adiposity and extended lifespan in obese mice fed a diet supplemented with a polyphenol-rich plant extract. Sci Rep. 2019 Jun 24;9(1):9134. doi: 10.1038/s41598-019-45600-6. PubMed ID: 31235831.

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