25-Hydroxy-Cholesterol

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Category	Glycosylated Sterols
Catalog NO.	BPG-3287
Product Name	25-Hydroxy-Cholesterol
CAS	2140-46-7
Molecular Formula	C27H46O2
Molecular Weight	402.65

Scheme Design
Custom Synthesis
cGMP Manufacturing
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Product Information
References
Documents
Reviews

Product Information

Description	25-hydroxycholesterol is an inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as in CEM cells associated with negative regulation of c-Myc.
Synonyms	(3β)-Cholest-5-ene-3,25-diol; Cholest-5-ene-3β,25-diol; 25-Hydroxy-5-cholestene-3β-ol; 5-Cholesten-3β,25-diol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-6-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Canonical SMILES	CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI	InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1
InChIKey	INBGSXNNRGWLJU-ZHHJOTBYSA-N
Boiling Point	513.1±23.0°C (Predicted)
Melting Point	164-169°C
Purity	>98%
Density	1.03±0.1 g/cm3 (Predicted)
Solubility	Soluble in Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly, Sonicated)
Appearance	White to Off-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. 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.
2. Wnętrzak A, Chachaj-Brekiesz A, Kobierski J, Karwowska K, Petelska AD, Dynarowicz-Latka P. Unusual Behavior of the Bipolar Molecule 25-Hydroxycholesterol at the Air/Water Interface-Langmuir Monolayer Approach Complemented with Theoretical Calculations. J Phys Chem B. 2020 Feb 13;124(6):1104-1114. doi: 10.1021/acs.jpcb.9b10938. Epub 2020 Feb 3. PMID: 31972080. PubMed ID: 31972080.
3. Yalcinkaya M, Kerksiek A, Gebert K, Annema W, Sibler R, Radosavljevic S, Luetjohann D, Rohrer L, von Eckardstein A. HDL inhibits endoplasmic reticulum stress-induced apoptosis of pancreatic β-cells in vitro by activation of Smoothened. J Lipid Res. 2020 Jan 6:jlr.RA119000509. doi: 10.1194/jlr.RA119000509. Epub ahead of print. PMID: 31907205. PubMed ID: 31907205.
4. Hutchinson SA, Lianto P, Roberg-Larsen H, Battaglia S, Hughes TA, Thorne JL. ER-Negative Breast Cancer Is Highly Responsive to Cholesterol Metabolite Signalling. Nutrients. 2019 Nov 1;11(11). pii: E2618. doi: 10.3390/nu11112618. PubMed ID: 31683867.
5. Petersen D, Reinholdt P, Szomek M, Hansen SK, Poongavanam V, Dupont A, Heegaard CW, Krishnan K, Fujiwara H, Covey DF, Ory DS, Kongsted J, Wüstner D. Binding and intracellular transport of 25-hydroxycholesterol by Niemann-Pick C2 protein. Biochim Biophys Acta Biomembr. 2019 Sep 12:183063. doi: 10.1016/j.bbamem.2019.183063. [Epub ahead of print]...PubMed ID: 31521631.
6. Patrick He, Aaron Smith, Ingrid C. Gelissen, Alaina J. Ammit. The effect of statins and the synthetic LXR agonist T0901317 on expression of ABCA1 transporter protein in human lung epithelial cell lines in vitro. Pharmacological Reports. 2019 August 17. doi: 10.1016/j.pharep.2019.08.006...PubMed ID: 31136842.
7. Tajima N, Xiaoyan L, Taniguchi M, Kato N. 24S-hydroxycholesterol alters activity of large-conductance Ca2+-dependent K+ (slo1 BK) channel through intercalation into plasma membrane. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 May 25. pii: S1388-1981(19)30085-X. doi: 10.1016/j.bbalip.2019.05.010. [Epub ahead of print]...PubMed ID: 30910555.
8. Rossin D, Dias IHK, Solej M, Milic I, Pitt AR, Iaia N, Scoppapietra L, Devitt A, Nano M, Degiuli M, Volante M, Caccia C, Leoni V, Griffiths HR, Spickett CM, Poli G, Biasi F. Increased production of 27-hydroxycholesterol in human colorectal cancer advanced stage: Possible contribution to cancer cell survival and infiltration. Free Radic Biol Med. 2019 Mar 23;136:35-44. doi: 10.1016/j.freeradbiomed.2019.03.020. [Epub ahead of print]...PubMed ID: 30785396.
9. Jo Y, Hamilton JS, Hwang S, Garland K, Smith GA, Su S, Fuentes I, Neelam S, Thompson BM, McDonald JG, DeBose-Boyd RA. Schnyder corneal dystrophy-associated UBIAD1 inhibits ER-associated degradation of HMG CoA reductase in mice. Elife. 2019 Feb 20;8. pii: e44396. doi: 10.7554/eLife.44396. PubMed ID: 30797576.
10. Wang X, Sun J, Zhao XE, Xu Y, Sun L, Zhu S, You J, Wang X. Stable isotope labeling derivatization coupled with magnetic dispersive solid phase extraction for the determination of hydroxyl-containing cholesterol and metabolites by in vivo microdialysis and ultra-high performance liquid chromatography tandem mass spectrometry. J Chromatogr A. 2019 Feb 14. pii: S0021-9673(19)30151-7. doi: 10.1016/j.chroma.2019.02.021. [Epub ahead of print]...PubMed ID: 30779932.

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