A phenol
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.

Purpurogallin

Item No. 29689

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3,4,6-tetrahydroxy-5H-benzocyclohepten-5-one
CAS Number
569-77-7
Synonyms
  • NCI 35676
  • NSC 35676
  • NSC 646653
Molecular Formula
C11H8O5
Formula Weight
220.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): Partially soluble
λmax
243, 280, 304 nm
SMILES
OC1=C(O)C=C(C=CC=C(O)C2=O)C2=C1O
InChi Code
InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)
InChi Key
WDGFFVCWBZVLCE-UHFFFAOYSA-N
Origin
Synthetic
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

    50 mg

    $42

    Add

    100 mg

    $74

    Add

    500 mg

    $183

    Add

    1 g

    $322

    Add
    Kinase Resource Center
    Discover Products & Resources for Kinase Research
    • Kinase inhibitors, screening libraries, assay kits, & more
    • Tools to study kinase signaling pathways:
      • Growth factor signaling
      • PI3K/Akt/mTOR
      • MAPKs (ERK, p38, & JNK)
      • JAK/STAT signaling
    • Articles, resources, & advice
    EXPLORE NOW
    Product Description

    Purpurogallin is a phenol that has been found in D. divisa and a derivative of pyrogallol (Item No. 20347) that has diverse biological activities, including antimicrobial, antioxidant, and enzyme inhibitory properties.1,2,3,4,5,6 It is active against the Gram-positive bacteria S. aureus, methicillin-resistant S. aureus (MRSA), S. epidermidis, and B. subtilis (MICs = 11-110 µg/ml), the Gram-negative bacteria S. marcescens, P. vulgaris, K. pneumoniae, E. coli, S. typhi, and E. cloacae (MIC = 110 µg/ml for all), as well as P. falciparum strain FCB1 clone NC-1 (IC50 = 55 µM).1,3 Purpurogallin (2, 5, and 10 µM) scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay and reduces hydrogen peroxide- and radiation-induced production of reactive oxygen species (ROS) in HaCaT keratinocytes.2 It inhibits the activity of EGFR, glutathione-S-transferase (GST), prolyl endopeptidase, and glyoxalase I (IC50s = 27.5, 8, 16, and 50 µM, respectively), as well as catechol O-methyltransferase (COMT; Ki = 0.074 µM), in cell-free assays.1,3,4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Inamori, Y., Muro, C., Sajima, E., et al. Biological activity of purpurogallin. Biosci. Biotechnol. Biochem. 61(5), 890-892 (1997).

    2. Zhen, A.X., Piao, M.J., Hyun, Y.J., et al. Purpurogallin protects keratinocytes from damage and apoptosis induced by ultraviolet B radiation and particulate matter 2.5. Biomol. Ther. (Seoul) 27(4), 395-403 (2019).

    3. Barnard, J.F., Vander Jagt, D.L., and Honek, J.F. Small molecule probes of glyoxalase I and glyoxalase II. Biochim. Biophys. Acta 1208(1), 127-135 (1994).

    4. Abou-Karam, M., and Shier, W.T. Inhibition of oncogene product enzyme activity as an approach to cancer chemoprevention. Tyrosine-specific protein kinase inhibition by purpurogallin from Quercus sp. nutgall. Phytother. Res. 13(4), 337-340 (1999).

    5. Das, M., Bickers, D.R., and Mukhtar, H. Plant phenols as in vitro inhibitors of glutathione S-transferase(s). Biochem. Biophys. Res. Commun. 120(2), 427-433 (1984).

    6. Veser, J. Kinetics and inhibition studies of catechol O-methyltransferase from the yeast Candida tropicalis. J. Bacteriol. 169(8), 3696-3700 (1987).