A derivative and metabolite of coumarin with diverse biological activities
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.

Umbelliferone

Item No. 24665

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-hydroxy-2H-1-benzopyran-2-one
CAS Number
93-35-6
Synonyms
  • 7-hydroxy Coumarin
  • NSC 19790
Molecular Formula
C9H6O3
Formula Weight
162.1
Purity
≥98%
Emission
460 nm
Excitation
330 and 370 nm
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlEthanol: 5 mg/mlMethanol: 5 mg/ml
λmax
326 nm
SMILES
OC1=CC=C(C=CC(O2)=O)C2=C1
InChi Code
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChi Key
ORHBXUUXSCNDEV-UHFFFAOYSA-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

    25 mg

    $60

    Add

    50 mg

    $108

    Add

    100 mg

    $204

    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

    Umbelliferone is a naturally occurring derivative and metabolite of coumarin that has diverse biological activities including antitumor and antidepressant-like properties.1,2,3 It inhibits the growth of a variety of human cell lines, including human ACHN renal, A549 lung, HCT15 colon, and LNCaP prostate carcinoma as well as Dakiki myeloma and HL-60 lymphoma cells, when used at concentrations ranging from 250 to 300 µg/ml.1 It also reversibly inhibits the production of prostate-specific androgen in LNCaP prostate cancer cells. Umbelliferone increases the production of reactive oxygen species (ROS), depolarizes the mitochondrial membrane, and halts the cell cycle at the G0/G1 phase in KB human oral carcinoma cells.2 In a rat model of depression induced by chronic unpredictable mild stress, umbelliferone (15 and 30 mg/kg) decreases immobility time in the forced swim test and increases sucrose consumption in the sucrose preference test, indicating antidepressant-like activity.3 Umbelliferone has been used as a ratiometric pH indicator that displays an emission maxima of 460 nm when solutions with a pH of less than six or greater than eight are excited at 330 and 370 nm, respectively.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Marshall, M.E., Kervin, K., Benefield, C., et al. Growth-inhibitory effects of coumarin (1,2-benzopyrone) and 7-hydroxycoumarin on human malignant cell lines in vitro. J. Cancer Res. Clin. Oncol. 120(Suppl.), S3-S10 (1994).

    2. Vijayalakshmi, A., and Sindhu, G. Umbelliferone arrest cell cycle at G0/G1 phase and induces apoptosis in human oral carcinoma (KB) cells possibly via oxidative DNA damage. Biomed. Pharmacother. 92, 661-671 (2017).

    3. Qin, T., Fang, F., Song, M., et al. Umbelliferone reverses depression-like behavior in chronic unpredictable mild stress-induced rats by attenuating neuronal apoptosis via regulating ROCK/Akt pathway. Behav. Brain Res. 317, 147-156 (2017).

    4. Fink, D.W., and Koehler, W.R. pH Effects on fluorescence of umbelliferone. Anal. Chem. 42(9), 990-993 (1970).