A bioactive oxysterol
Technical Support & Resources

Information provided in the product description is from published literature. Due to the nature of scientific experimentation, your results (e.g., selectivity and effective concentrations) or specific application for this product may differ. If you have questions about how this product fits your application, please contact our technical support staff.

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

7-keto Cholesterol

Item No. 16339

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-hydroxy-cholest-5-en-7-one
CAS Number
566-28-9
Synonyms
  • Δ5-Cholesterol-3β-ol-7-one
  • 7-oxo Cholesterol
  • SC-4722
Molecular Formula
C27H44O2
Formula Weight
400.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlDMSO: 0.1 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2)(1:2): 0.3 mg/ml
λmax
238 nm
SMILES
CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C(C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=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
InChi Key
YIKKMWSQVKJCOP-ABXCMAEBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    5 mg

    $63

    Add

    10 mg

    $118

    Add

    50 mg

    $454

    Add

    100 mg

    $783

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    Product Description

    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).

    Product Citations

    Radhakrishnan, K., Zhang, Y., Mustapha, O., et al. 7-ketocholesterol contributes to microglia-driven increases in astrocyte reactive oxygen species in Alzheimer’s disease. bioRxiv [Preprint] (2025).

    Balamurugan, K., Medishetti, R., Kotha, J., et al. PHLPP1 promotes neutral lipid accumulation through AMPK/ChREBP-dependent lipid uptake and fatty acid synthesis pathways. iScience 25, 103766 (2022).