An active metabolite of isotretinoin
Related Products
Isomer(s)
358194-oxo Retinoic Acid
Parent Compound(s)
21648Isotretinoin
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.

4-oxo Isotretinoin

Item No. 34388

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13-cis-4-oxo-retinoic acid
CAS Number
71748-58-8
Synonyms
  • Ro 22-6595
Molecular Formula
C20H26O3
Formula Weight
314.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:4): 0.2 mg/mlEthanol: 15 mg/ml
λmax
285, 364 nm
SMILES
OC(/C=C(C)\C=C\C=C(C)\C=C\C(C(C)(CC1)C)=C(C)C1=O)=O
InChi Code
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13-
InChi Key
GGCUJPCCTQNTJF-FAOQNJJDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice 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

    500 µg

    $44

    Add

    1 mg

    $84

    Add

    5 mg

    $264

    Add

    10 mg

    $484

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    4-oxo Isotretinoin is an active metabolite of the retinoid isotretinoin (Item No. 21648).1 It is formed from isotretinoin by several cytochrome P450 (CYP450) isoforms, including CYP3A, CYP2B6, and CYP2C19.2 4-oxo Isotretinoin (10 µM) increases protein expression of cytokeratin 7 (CK7) and CK19 in normal human epidermal keratinocytes.3 It inhibits proliferation of retinoid-sensitive UM-SCC-22A and UM-SCC-35 head and neck squamous cell carcinoma (HNSCC) cells in a concentration-dependent manner.4 4-oxo Isotretinoin has been found in influent and effluent wastewater.5 It is teratogenic to mouse embryos when administered to pregnant dams at a dose of 100 mg/kg on day 11 of gestation.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Colburn, W.A., Vane, F.M., and Shorter, H.J. Pharmacokinetics of isotretinoin and its major blood metabolite following a single oral dose to man. Eur. J. Clin. Pharmacol. 24(5), 689-694 (1983).

    2. Sonawane, P., Cho, H.E., Tagde, A., et al. Metabolic characteristics of 13-cis-retinoic acid (isotretinoin) and anti-tumour activity of the 13-cis-retinoic acid metabolite 4-oxo-13-cis-retinoic acid in neuroblastoma. Br. J. Pharmacol. 171(23), 5330-5344 (2014).

    3. Baron, J.M., Heise, R., Blaner, W.S., et al. Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro. J. Invest. Dermatol. 125(1), 143-153 (2005).

    4. Klaassen, I., Brakenhoff, R.H., Smeets, S.J., et al. Metabolism and growth inhibition of four retinoids in head and neck squamous normal and malignant cells. Br. J. Cancer 85(4), 630-635 (2001).

    5. Yeung, K.W.Y., Zhou, G.-J., Hilscherová, K., et al. Current understanding of potential ecological risks of retinoic acids and their metabolites in aquatic environments. Environ. Int. 136, 105464 (2020).

    6. Kochhar, D.M., and Penner, J.D. Developmental effects of isotretinoin and 4-oxo-isotretinoin: The role of metabolism in teratogenicity. Teratology 36(1), 67-75 (1987).