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27-Hydroxy Cholesterol-[d6]

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