7α-Hydroxy-4-cholesten-3-one-[d7]

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Category	Bile Acid Standards
Catalog NO.	BPG-3123
Product Name	7α-Hydroxy-4-cholesten-3-one-[d7]
CAS	2260669-17-6
Molecular Formula	C27H37D7O2
Molecular Weight	407.68

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Product Information

Description	7α-hydroxy-4-cholesten-3-one-[d7] is the labelled analogue of 7α-hydroxy-4-cholesten-3-one, a metabolite of Cholesterol.
Synonyms	7α-hydroxy-4-cholesten-3-one-d7; 25,26,26,26,27,27,27-heptadeuterio-7α-hydroxy-4-cholesten-3-one; (7α)-7-Hydroxycholest-4-en-3-one-d7; 7α-Hydroxycholest-4-en-3-one-d7; 7α-hydroxycholestenone-d7
IUPAC Name	(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2C(CC4=CC(=O)CCC34C)O)C
InChI	InChI=1S/C27H44O2/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/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1/i1D3,2D3,17D
InChIKey	IOIZWEJGGCZDOL-CTNVFXSSSA-N
Melting Point	178-180°C
Purity	>99%
Solubility	Soluble in Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Related CAS	3862-25-7 (unlabelled)
Appearance	White to Off-white Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	407.378
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 79.54%, H 12.61%, O 7.85%

References

1. Brydon WG, Culbert P, Kingstone K, Jarvie A, Iacucci M, Tenhage M, Ghosh S. An evaluation of the use of serum 7-alpha-hydroxycholestenone as a diagnostic test of bile acid malabsorption causing watery diarrhea. Can J Gastroenterol. 2011 Jun;25(6):319-23. doi: 10.1155/2011/701287. PMID: 21766092; PMCID: PMC3142604. PubMed ID: 21766092.
2. Russell DW. The enzymes, regulation, and genetics of bile acid synthesis. Annu Rev Biochem. 2003;72:137-74. doi: 10.1146/annurev.biochem.72.121801.161712. Epub 2003 Jan 16. PMID: 12543708. PubMed ID: 12543708.
3. Gälman C, Angelin B, Rudling M. Bile acid synthesis in humans has a rapid diurnal variation that is asynchronous with cholesterol synthesis. Gastroenterology. 2005 Nov;129(5):1445-53. doi: 10.1053/j.gastro.2005.09.009. PMID: 16285946. PubMed ID: 16285946.
4. Brydon WG, Nyhlin H, Eastwood MA, Merrick MV. Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Eur J Gastroenterol Hepatol. 1996 Feb;8(2):117-23. doi: 10.1097/00042737-199602000-00005. PMID: 8723414. PubMed ID: 8723414.
5. Hofmann AF, Mangelsdorf DJ, Kliewer SA. Chronic diarrhea due to excessive bile acid synthesis and not defective ileal transport: a new syndrome of defective fibroblast growth factor 19 release. Clin Gastroenterol Hepatol. 2009 Nov;7(11):1151-4. doi: 10.1016/j.cgh.2009.07.026. Epub 2009 Aug 7. PMID: 19665580; PMCID: PMC2850200. PubMed ID: 19665580.

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