A bioactive component of ginger
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.

6-Shogaol

Item No. 11901

Technical Information
Formal Name
1-(4-hydroxy-3-methoxyphenyl)-4-decen-3-one
CAS Number
555-66-8
Molecular Formula
C17H24O3
Formula Weight
Purity
≥95%
A solution in ethanol
DMF: 20 mg/mlDMSO: 20 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
λmax
203, 224, 281 nm
SMILES
O=C(/C=C/CCCCC)CCC1=CC(OC)=C(O)C=C1
InChi Code
InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
InChi Key
OQWKEEOHDMUXEO-BQYQJAHWSA-N
Origin
Plant/Zingiber officinalis
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.

    Add

    Add

    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

    6-Shogaol is a minor, bioactive component of ginger (Zingiber officinale Roscoe) with anti-inflammatory and anticancer properties. It is present in fresh ginger at low levels, but quantities of 6-shogaol are significantly increased in dried ginger. 6-Shogaol induces apoptosis in cancer cells through the production of reactive oxygen species and the activation of caspase, impairs tubulin polymerization, downregulates NF-κB signaling, inhibits the expression of inflammatory mediators, and suppresses Toll-like receptor signaling.1 6-Shogaol-rich extracts have been shown to enhance antioxidant defense mechanisms by inducing Nrf2/ARE-mediated gene expression in cell and animal models.2 It can also activate both TRPV1 and TRPA1 channels (EC50s = 0.32 and 16 µM, respectively).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ling, H., Yang, H., Tan, S.H., et al6-Shogaol, an active constituent of ginger, inhibits breast cancer cell invasion by reducing matrix metalloproteinase-9 expression via blockade of nuclear factor-κB activation. Br. J. Pharmacol. 161(8), 1763-1777 (2010).

    2. Bak, M.J., Ok, S., Jun, M., et al6-Shogaol-rich extract from ginger up-regulates the antioxidant defense systems in cells and mice. Molecules 17, 8037-8055 (2012).

    3. Morera, E., De Petrocellis, L., Morera, L., et alSynthesis and biological evaluation of [6]-gingerol analogues as transient receptor potential channel TRPV1 and TRPA1 modulators. Bioorg. Med. Chem. Lett. 22(4), 1674-1677 (2012).

    Product Citations

    Pázmándi, K., Ágics, B., Szöllősi, A.G., et alGinger-derived bioactive compounds attenuate the Toll-like receptor mediated responses of human dendritic cells. Eur. J. Pharmacol. 967, 176399 (2024).

    Moaddel, R., Rossi, M., Rodriguez, S., et alIdentification of gingerenone A as a novel senolytic compound. PLoS One 17(3), e0266135 (2022).