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7-Keto Cholesterol-[d7]

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Category	Cholesterol
Catalog NO.	BPG-3125
Product Name	7-Keto Cholesterol-[d7]
CAS	127684-08-6
Molecular Formula	C27H37D7O2
Molecular Weight	407.68

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Product Information

Description	7-Ketocholesterol-[25,26,26,26,27,27,27-d7] is a labelled analog of 7-Ketocholesterol, which is a metabolite of Cholesterol.
Synonyms	7-Ketocholesterol (25,26,26,26,27,27,27-D7); 7-Ketocholesterol-d7; 7-oxo-cholest-5-en-3beta-ol(d7)
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-7-one
Canonical SMILES	CC(C)CCCC(C)C1CCC2C1(CCC3C2C(=O)C=C4C3(CCC(C4)O)C)C
InChI	InChI=1S/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-23,25,28H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,25+,26+,27-/m1/s1/i1D3,2D3,17D
InChIKey	YIKKMWSQVKJCOP-KVZGVLACSA-N
Boiling Point	516.685°C at 760 mmHg
Melting Point	166-168°C
Purity	98% by CP; 99% atom D
Density	1.05 g/cm3
Solubility	Soluble in Chloroform, Methanol
Related CAS	566-28-9 (unlabelled)
Appearance	White to Off-white Solid
Application	A labelled metabolite of Cholesterol.
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	407.378
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 79.54%, H 12.61%, O 7.85%

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.

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