An internal standard for the quantification of 7-keto cholesterol
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Unlabeled Version(s)
163397-keto Cholesterol
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7-keto Cholesterol-d7

Item No. 25972

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-hydroxy-cholest-5-en-7-one-25,26,26,26,27,27,27-d7
CAS Number
127684-08-6
Synonyms
  • Δ5-Cholesterol-3β-ol-7-one-d7
  • 7-oxo Cholesterol-d7
Molecular Formula
C27H37D7O2
Formula Weight
407.7
Purity
≥99% deuterated forms (d1-d7)
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 0.1 mg/mlEthanol: 20 mg/ml
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CC([C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@@H](CCCC(C([2H])([2H])[2H])([2H])C([2H])([2H])[2H])C)=O
InChi Code
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
InChi Key
YIKKMWSQVKJCOP-KVZGVLACSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    7-keto Cholesterol-d7 is intended for use as an internal standard for the quantification of 7-keto cholesterol (Item No. 16339) by GC- or LC-MS. 7-keto Cholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL.1,2 It is produced by oxidation of cholesterol via ethanol-mediated lipid peroxidation or photodamage as well as oxidation of 7-dehydro cholesterol (Item No. 14612) by the cytochrome P450 (CYP) isoform CYP7A1.3,4,5 7-keto Cholesterol inhibits CYP7A1 (IC50 = ~1 μM).4 It induces activation and chemotaxis of retinal microglia as well as polarization to a pro-inflammatory state via NLRP3 inflammasome activation in vitro.6 Intraocular implantation of 7-keto cholesterol-coated wafers increases ocular levels of VEGF, IL-1β, and GRO/KC, macrophage infiltration, and neovascularization in rat eye.7 Levels of 7-keto cholesterol in lipid deposits are increased in a variety of chronic diseases, including atherosclerosis, Alzheimer's disease, and age-related macular degeneration.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shentu, T.P., Titushkin, I., Singh, D.K., et al. oxLDL-induced decrease in lipid order of membrane domains is inversely correlated with endothelial stiffness and network formation. Am. J. Physiol. Cell Physiol. 299(2), C218-C229 (2010).

    2. Brown, A.J., Leong, S.l., Dean, R.T., et al. 7-Hydroperoxycholesterol and its products in oxidized low density lipoprotein and human atherosclerotic plaque. J. Lipid Res. 38, 1730-1745 (1997).

    3. Rodriguez, I.R., and Fliesler, S.J. Photodamage generates 7-keto- and 7-hydroxycholesterol in the rat retina via a free radical-mediated mechanism. Photochem. Photobiol. 85(5), 1116-1125 (2009).

    4. Shinkyo, R., Xu, L., Tallman, K.A., et al. Conversion of 7-dehydrocholesterol to 7-ketocholesterol is catalyzed by human cytochrome P450 7A1 and occurs by direct oxidation without an epoxide intermediate. The Journal of Biological Chemisty 286(38), 33021-33028 (2011).

    5. Mitic, T., Shave, S., Semjonous, N., et al. 11β-Hydroxysteroid dehydrogenase type 1 contributes to the balance between 7-keto- and 7-hydroxy-oxysterols in vivo. Biochem. Pharmacol. 86(1), 146-153 (2013).

    6. Indaram, M., Ma, W., Zhao, L., et al. 7-Ketocholesterol increases retinal microglial migration, activation, and angiogenicity: A potential pathogenic mechanism underlying age-related macular degeneration. Sci. Rep. 5:9144, (2015).

    7. Amaral, J., Lee, J.W., Chou, J., et al. 7-Ketocholesterol induces inflammation and angiogenesis in vivo: A novel rat model. PLoS One 8(2), e56099 (2013).