A plant metabolite 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.

Indole-3-carboxylic Acid

Item No. 31166

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1H-indole-3-carboxylic acid
CAS Number
771-50-6
Synonyms
  • I3CA
  • ICOOH
  • Indole-β-carboxylic Acid
  • β-Indolylcarboxylic Acid
Molecular Formula
C9H7NO2
Formula Weight
161.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:8): 0.11 mg/mlEthanol: 1 mg/ml
λmax
213, 281 nm
SMILES
O=C(O)C1=CNC2=CC=CC=C21
InChi Code
InChI=1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
InChi Key
KMAKOBLIOCQGJP-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

    25 g

    $49

    Add

    50 g

    $86

    Add

    100 g

    $160

    Add

    250 g

    $329

    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

    Indole-3-carboxylic acid is a plant metabolite derived from tryptophan that has been found in Arabidopsis and has diverse biological activities.1,2,3,4 It induces resistance in Arabidopsis against the plant necrotrophic fungus P. cucumerina when applied as a soil-drenching solution at a concentration of 150 µM prior to infection.2 Indole-3-carboxylic acid is cytotoxic to A549 human lung and MCF-7 human breast cancer cells (EC50s = 4.6 and 12.9 µg/ml, respectively) and inhibits HIV replication in infected H9 lymphocytes (IC50 = 16.4 µg/ml).3 Indole-3-carboxylic acid has also been used as a precursor in the synthesis of substituted thiadiazoles with anticancer activity.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Iven, T., König, S., Singh, S., et al. Transcriptional activation and production of tryptophan-derived secondary metabolites in Arabidopsis roots contributes to the defense against the fungal vascular pathogen Verticillium longisporum. Mol. Plant 5(6), 1389-1402 (2012).

    2. Gamir, J., Pastor, V., Sánchez-Bel, P., et al. Starch degradation, abscisic acid and vesicular trafficking are important elements in callose priming by indole-3-carboxylic acid in response to Plectosphaerella cucumerina infection. Plant J. 96(3), 518-531 (2018).

    3. Wu, P.-L., Lin, F.-W., Wu, T.-S., et al. Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis. Chem. Pharm. Bull. (Tokyo) 52(3), 345-349 (2004).

    4. Kumar, D., Kumar, N.M., Chang, K.-A., et al. Synthesis and anticancer activity of 5-(3-indolyl)-1,3,4-thiadiazoles. Eur. J. Med. Chem. 45(10), 4664-4668 (2010).