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4-beta-Hydroxy Cholesterol

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Category	Cholesterol
Catalog NO.	BPG-3295
Product Name	4-beta-Hydroxy Cholesterol
CAS	17320-10-4
Molecular Formula	C27H46O2
Molecular Weight	402.65

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Description	4-beta-Hydroxy Cholesterol is a metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. It is also a potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.
Synonyms	(3β,4β)-Cholest-5-ene-3,4-diol; Cholest-5-ene-3β,4β-diol; 3β,4β-Dihydroxycholest-5-ene; cis-3,4-Dihydroxy-5-cholestene; cis-5-Cholestene-3,4-diol
IUPAC Name	(3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4O)O)C)C
InChI	InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)20-11-12-21-19-9-10-23-25(29)24(28)14-16-27(23,5)22(19)13-15-26(20,21)4/h10,17-22,24-25,28-29H,6-9,11-16H2,1-5H3/t18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
InChIKey	CZDKQKOAHAICSF-JSAMMMMSSA-N
Boiling Point	500.2±30.0 °C(Predicted)
Melting Point	172-174°C
Purity	> 95%
Density	1.03±0.1 g/cm3(Predicted)
Appearance	White Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	402.35
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 80.54%, H 11.51%, O 7.95%

References

1. Abrams ME, Johnson KA, Perelman SS, Zhang LS, Endapally S, Mar KB, Thompson BM, McDonald JG, Schoggins JW, Radhakrishnan A, Alto NM. Oxysterols provide innate immunity to bacterial infection by mobilizing cell surface accessible cholesterol. Nat Microbiol. 2020 Apr 13. doi: 10.1038/s41564-020-0701-5. Epub ahead of print. PMID: 32284563. PubMed ID: 32284563.
2. Miyazaki T, Sasaki SI, Toyoda A, Wei FY, Shirai M, Morishita Y, Ikegami T, Tomizawa K, Honda A. Impaired bile acid metabolism with defectives of mitochondrial-tRNA taurine modification and bile acid taurine conjugation in the taurine depleted cats. Sci Rep. 2020 Mar 18;10(1):4915. doi: 10.1038/s41598-020-61821-6. PMID: 32188916; PMCID: PMC7080809. PubMed ID: 32188916.

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