27-Hydroxy Cholesterol-[d6]

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Category	Bile Acid Standards
Catalog NO.	BPG-3114
Product Name	27-Hydroxy Cholesterol-[d6]
CAS	1246302-95-3
Molecular Formula	C27H40D6O2
Molecular Weight	408.69

Scheme Design
Custom Synthesis
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Product Information
Application
References
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Product Information

Description	27-Hydroxy Cholesterol-[d6] is the labelled analogue of 27-Hydroxy Cholesterol, which is a metabolite of Cholesterol. It is a potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.
Synonyms	27-Hydroxy Cholesterol-d6; (3β)-Cholest-5-ene-25,26,26,27,27,27-d6-3,26-diol; 27-hydroxycholest-5-en-3-ol-d6; (3β)-(25,26,26,27,27,27-d6)Cholest-5-ene-3,26-diol
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-[dideuterio(hydroxy)methyl]heptan-2-yl]-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	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/i1D3,17D2,18D
InChIKey	FYHRJWMENCALJY-CDBHVEDQSA-N
Purity	>95%
Solubility	Soluble in Chloroform (Slightly, Heated), Methanol (Slightly, Heated, Sonicated)
Related CAS	20380-11-4 (unlabelled)
Appearance	Pale Brown Solid
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	408.387
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 79.35%, H 12.82%, O 7.83%

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. Anosov AA, Smirnova EY, Sharakshane AA, Nikolayeva EA, Zhdankina YS. Increase in the current variance in bilayer lipid membranes near phase transition as a result of the occurrence of hydrophobic defects. Biochim Biophys Acta Biomembr. 2020 Feb 1;1862(2):183147. doi: 10.1016/j.bbamem.2019.183147. Epub 2019 Dec 6. PMID: 31812627. PubMed ID: 31874216.
3. 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: 30910555.
4. 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.
5. Becares N, Gage MC, Voisin M, Shrestha E, Martin-Gutierrez L, Liang N, Louie R, Pourcet B, Pello OM, Luong TV, Goñi S, Pichardo-Almarza C, Røberg-Larsen H, Diaz-Zuccarini V, Steffensen KR, O'Brien A, Garabedian MJ, Rombouts K, Treuter E, Pineda-Torra I. Impaired LXRα Phosphorylation Attenuates Progression of Fatty Liver Disease. Cell Rep. 2019 Jan 22;26(4):984-995.e6. doi: 10.1016/j.celrep.2018.12.094. PubMed ID: 30673619.

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