An anthraquinone with diverse biological activities
Related Products
Isomer(s)
11676Alizarin
Technical Support & Resources

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.

Anthraflavic Acid

Item No. 39246

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,6-dihydroxy-9,10-anthracenedione
CAS Number
84-60-6
Synonyms
  • 2,6-Dihydroxyanthraquinone
  • 2,6-DHAQ
  • NSC 33531
Molecular Formula
C14H8O4
Formula Weight
240.2
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly solubleWater: Slightly soluble
SMILES
O=C1C2=CC=C(C=C2C(C3=CC=C(C=C13)O)=O)O
InChi Code
InChI=1S/C14H8O4/c15-7-1-3-9-11(5-7)14(18)10-4-2-8(16)6-12(10)13(9)17/h1-6,15-16H
InChi Key
APAJFZPFBHMFQR-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

    1 g

    $32

    Add

    5 g

    $128

    Add

    10 g

    $240

    Add
    Cayman Chemical
    Visit Our Environmental Toxicology Resource Center

    Explore additional resources to study natural toxins, pollutants including PFAS and 6-PPD-Q, and their biological effects.

    ENVIRONMENTAL TOXICOLOGY TOOLS & SERVICES
    Product Description

    Anthraflavic acid is a polyketide synthase-derived anthraquinone that has been found in Rhei Rhizoma and has diverse biological activities.1,2,3,4,5,6 It inhibits α-amylase in a cell-free assay (IC50 = 198.3 nM) and cytochrome P450 activity induced by a mixture of polychlorinated biphenyls (PCBs) in rat hepatic microsomes.3,4 Anthraflavic acid binds to estrogen receptor α (ERα) and ERβ (Kis = 0.31 and 0.69 µM, respectively).5 It is cytotoxic against a panel of six breast cancer cell lines (IC50s = 156-241 µg/ml).3 Anthraflavic acid (50 µM) inhibits mutagenicity induced by the carcinogen 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1) in the Ames test using S. typhimurium.4 Topical application of anthraflavic acid (3 µmol/animal) reduces the number of tumors per mouse and the number of mice with tumors in a model of two-stage carcinogenesis initiated by 7,12-dimethylbenz[a]anthracene (DMBA; Item No. 30383) and promoted by 12-O-tetradecanoylphorbol-13-acetate (TPA; Item No. 10008014).6 Anthraflavic acid has been used as an anolyte in redox flow batteries.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ho, X.Y., Katermeran, N.P., Deignan, L.K., et al. Assessing the diversity and biomedical potential of microbes associated with the Neptune’s Cup sponge, Cliona patera. Front. Microbiol. 12, 631445 (2021).

    2. Weng, W.-C., and Sheu, S.-J. Separation of anthraquinones by capillary electrophoresis and high-performance liquid chromatography. J. High Resol. Chromatogr. 23(2), 143-148 (2000).

    3. Zhao, G., Chinnathambi, A., Alahmadi, T.A., et al. Introducing a novel chemotherapeutic drug formulated with anthraflavic acid for treating human breast carcinoma and type 2 diabetes mellitus. Arch. Med. Sci. 19(6), 1850-1858 (2021).

    4. Ayrton, A.D., Lewis, D.F., Ioannides, C., et al. Anthraflavic acid is a potent and specific inhibitor of cytochrome P-448 activity. Biochim. Biophys. Acta 916(3), 328-331 (1987).

    5. Matsuda, H., Shimoda, H., Morikawa, T., et al. Phytoestrogens from the roots of Polygonum cuspidatum (Polygonaceae): Structure-requirement of hydroxyanthraquinones for estrogenic activity. Bioorg. Med. Chem. Lett. 11(14), 1839-1842 (2001).

    6. Mukhtar, H., Das, M., Khan, W.A., et al. Exceptional activity of tannic acid among naturally occurring plant phenols in protecting against 7,12-dimethylbenz(α)anthracene-, benzo(α)pyrene-, 3-methylcholanthrene-, and N-methyl-N-nitrosourea-induced skin tumorigenesis in mice. Cancer Res. 48(9), 2361-2365 (1988).

    7. Zhao, E.W., Shellard, J.K., Klusener, P.A.A., et al. In situ bulk magnetization measurements reveal the state of charge of redox flow batteries. Chem. Commun. (Camb.) 58(9), 1342-1345 (2022).