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Cholesterol-[25,26,26,26,27,27,27-d7]

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Category	Bile Acid Standards
Catalog NO.	BPG-3120
Product Name	Cholesterol-[25,26,26,26,27,27,27-d7]
CAS	83199-47-7
Molecular Formula	C27H39D7O
Molecular Weight	393.71

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Product Information

Description	Cholesterol-[25,26,26,26,27,27,27-d7] is the labelled analogue of Cholesterol. Cholesterol is the principal sterol of the higher animals. Cholesterol was found in all body tissues, especially in the brain, spinal cord, and in animal fats or oils. Cholesterol is the main constituent of gallstones.
Synonyms	Cholesterol-25,26,26,26,27,27,27-d7; Cholesterol-d7; (3β)-Cholest-5-en-3-ol-d7; (-)-Cholesterol-d7; 3β-Hydroxycholest-5-ene-d7; 5:6-Cholesten-3β-ol-d7; Cholest-5-en-3β-ol-d7; Cholesterin-d7; Cholesteryl-d7 alcohol-d7; Dythol-d7; Lidinit-d7; NSC 8798-d7; Provitamin D-d7; 5-Cholesten-3β-ol-d7
IUPAC Name	(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)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(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI	InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1/i1D3,2D3,18D
InChIKey	HVYWMOMLDIMFJA-IFAPJKRJSA-N
Melting Point	147-149°C
Purity	98% by CP; 97% atom D
Solubility	Soluble in Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
Related CAS	57-88-5 (unlabelled)
Appearance	White to Off-White Solid
Shelf Life	1 Year
Storage	Store at 2-8°C
Exact Mass	393.399
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 82.37%, H 13.57%, O 4.06%

References

1. Shon JC, Lee SM, Jung JH, Wu Z, Kwon YS, Sim HJ, Seo JS. Integrated metabolomics and lipidomics reveals high accumulation of polyunsaturated lysoglycerophospholipids in human lung fibroblasts exposed to fine particulate matter. Ecotoxicol Environ Saf. 2020 Jul 1;202:110896. doi: 10.1016/j.ecoenv.2020.110896. Epub ahead of print. PMID: 32622306. PubMed ID: 32622306.
2. Henze LJ, Koehl NJ, Jansen R, Holm R, Vertzoni M, Whitfield PD, Griffin BT. Development and evaluation of a biorelevant medium simulating porcine gastrointestinal fluids. Eur J Pharm Biopharm. 2020 Jun 21:S0939-6411(20)30177-6. doi: 10.1016/j.ejpb.2020.06.009. Epub ahead of print. PMID: 32580049. PubMed ID: 32580049.
3. Vazquez MM, Gutierrez MV, Salvatore SR, Puiatti M, Dato VA, Chiabrando GA, Freeman BA, Schopfer FJ, Bonacci G. Nitro-oleic acid, a ligand of CD36, reduces cholesterol accumulation by modulating oxidized-LDL uptake and cholesterol efflux in RAW264.7 macrophages. Redox Biol. 2020 Jun 2;36:101591. doi: 10.1016/j.redox.2020.101591. Epub ahead of print. PMID: 32531545; PMCID: PMC7287307. PubMed ID: 32531545.
4. Iaea DB, Spahr ZR, Singh RK, Chan RB, Zhou B, Bareja R, Elemento O, Di Paolo G, Zhang X, Maxfield FR. Stable reduction of STARD4 alters cholesterol regulation and lipid homeostasis. Biochim Biophys Acta Mol Cell Biol Lipids. 2020 Apr;1865(4):158609. doi: 10.1016/j.bbalip.2020.158609. Epub 2020 Jan 7. PMID: 31917335; PMCID: PMC6996790. PubMed ID: 31917335.
5. Yan B, Zou Z, Chu H, Chan G, Tsang JO, Lai PM, Yuan S, Yip CC, Yin F, Kao RY, Sze KH, Lau SK, Chan JF, Yuen KY. Lipidomic Profiling Reveals Significant Perturbations of Intracellular Lipid Homeostasis in Enterovirus-Infected Cells. Int J Mol Sci. 2019 Nov 26;20(23). pii: E5952. doi: 10.3390/ijms20235952. PubMed ID: 31779252.
6. Cucchi D, Camacho-Muñoz D, Certo M, Niven J, Smith J, Nicolaou A, Mauro C. Omega-3 polyunsaturated fatty acids impinge on CD4+ T cell motility and adipose tissue distribution via direct and lipid mediator-dependent effects. Cardiovasc Res. 2019 Aug 10. pii: cvz208. doi: 10.1093/cvr/cvz208. [Epub ahead of print]...PubMed ID: 31399738.
7. Chung KP, Hsu CL, Fan LC, Huang Z, Bhatia D, Chen YJ, Hisata S, Cho SJ, Nakahira K, Imamura M, Choi ME, Yu CJ, Cloonan SM, Choi AMK. Mitofusins regulate lipid metabolism to mediate the development of lung fibrosis. Nat Commun. 2019 Jul 29;10(1):3390. doi: 10.1038/s41467-019-11327-1. PubMed ID: 31358769.
8. Wang C, Siriwardane DA, Jiang W, Mudalige T. Quantitative analysis of cholesterol oxidation products and desmosterol in parenteral liposomal pharmaceutical formulations. Int J Pharm. 2019 Oct 5;569:118576. doi: 10.1016/j.ijpharm.2019.118576. Epub 2019 Jul 27. PubMed ID: 31362094.
9. Herron JM, Hines KM, Tomita H, Seguin RP, Cui JY, Xu L. Multi-omics investigation reveals benzalkonium chloride disinfectants alter sterol and lipid homeostasis in the mouse neonatal brain. Toxicol Sci. 2019 Jun 14. pii: kfz139. doi: 10.1093/toxsci/kfz139. [Epub ahead of print]...PubMed ID: 31199489.
10. Honsho M, Dorninger F, Abe Y, Setoyama D, Ohgi R, Uchiumi T, Kang D, Berger J, Fujiki Y. Impaired plasmalogen synthesis dysregulates liver X receptor-dependent transcription in cerebellum. J Biochem. 2019 May 28. pii: mvz043. doi: 10.1093/jb/mvz043. [Epub ahead of print]...PubMed ID: 31135054.

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