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27-Hydroxycholesterol

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Category	Cholesteryl Esters
Catalog NO.	BPG-3281
Product Name	27-Hydroxycholesterol
CAS	20380-11-4
Molecular Formula	C27H46O2
Molecular Weight	402.65

Scheme Design
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Product Information
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References
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Product Information

Description	27-Hydroxycholesterol, a desmosterol metabolite found in the brain , activates LXRα (EC50= 85 nM)and LXRβ (EC50= 71 nM) in vitro. 27-HC is also an estrogen receptor partial agonist. It suppresses β-estradiol-mediated breast cancer cell proliferation in vitro.
Synonyms	cholest-(25R)-5-ene-3β,27-diol; (25R)-Cholest-5-ene-3β,26-diol; 27-OHC; 5,25R-Cholesten-3beta,26-diol; (25R)-26-Hydroxycholesterol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,6R)-7-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)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C)CO
InChI	1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChIKey	FYHRJWMENCALJY-YSQMORBQSA-N
Boiling Point	517.1±23.0°C (Predicted)
Melting Point	171-173°C
Purity	>99%
Density	1.03±0.1 g/cm3 (Predicted)
Solubility	Soluble in Chloroform (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
Related CAS	13095-61-9 (rac-isomer)
Appearance	White to Pale Brown 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. Olżyńska A, Kulig W, Mikkolainen H, Czerniak T, Jurkiewicz P, Cwiklik L, Rog T, Hof M, Jungwirth P, Vattulainen I. Tail-Oxidized Cholesterol Enhances Membrane Permeability for Small Solutes. Langmuir. 2020 Aug 28. doi: 10.1021/acs.langmuir.0c01590. Epub ahead of print. PMID: 32804507. PubMed ID: 32804507.
2. Germano A, Rossin D, Leoni V, Iaia N, Saba L, Basile V, Puglisi S, Caccia C, Poli G, Biasi F, Terzolo M. Involvement of 27-Hydroxycholesterol in Mitotane Action on Adrenocortical Carcinoma. Cells. 2020 Apr 4;9(4):885. doi: 10.3390/cells9040885. PMID: 32260362; PMCID: PMC7226725. PubMed ID: 32260362.
3. 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.
4. Xiao L, Luo G, Guo X, Jiang C, Zeng H, Zhou F, Li Y, Yu J, Yao P. Macrophage iron retention aggravates atherosclerosis: Evidence for the role of autocrine formation of hepcidin in plaque macrophages. Biochim Biophys Acta Mol Cell Biol Lipids. 2019 Oct 27:158531. doi: 10.1016/j.bbalip.2019.158531. [Epub ahead of print]...PubMed ID: 31666189.
5. Stottrup BL, TigreLazo J, Bagonza VB, Kunz JC, Zasadzinski JA. Comparison of Line Tension Measurement Methods for Lipid Monolayers at Liquid-Liquid Coexistence. Langmuir. 2019 Aug 7. doi: 10.1021/acs.langmuir.9b01696. [Epub ahead of print]...PubMed ID: 31343892.
6. Hutchinson SA, Lianto P, Moore JB, Hughes TA, Thorne JL. Phytosterols Inhibit Side-Chain Oxysterol Mediated Activation of LXR in Breast Cancer Cells. Int J Mol Sci. 2019 Jul 2;20(13). pii: E3241. doi: 10.3390/ijms20133241. PubMed ID: 31269628.
7. Kunz S, Matysik S. A comprehensive method to determine sterol species in human faeces by GC-triple quadrupole MS. J Steroid Biochem Mol Biol. 2019 Mar 25;190:99-103. doi: 10.1016/j.jsbmb.2019.03.014. [Epub ahead of print]...PubMed ID: 30923016.
8. 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: 30797576.
9. Solheim S, Hutchinson SA, Lundanes E, Wilson SR, Thorne JL, Roberg-Larsen H. Fast liquid chromatography-mass spectrometry reveals side chain oxysterol heterogeneity in breast cancer tumour samples. J Steroid Biochem Mol Biol. 2019 Feb 16. pii: S0960-0760(18)30754-4. doi: 10.1016/j.jsbmb.2019.02.004. [Epub ahead of print]...PubMed ID: 30779932.
10. Kim, S.M., B.Y. Kim, S.A. Lee, S.K. Eo, Y. Yun, C.D. Kim, and K. Kim. (2014). 27-Hydroxycholesterol and 7alpha-hydroxycholesterol trigger a sequence of events leading to migration of CCR5-expressing Th1 lymphocytes. Toxicol Appl Pharmacol 274:462-70. [PubMed] ...PubMed ID: 24370436.

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