A toxicant and an agonist of AhR
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.

2,3,7,8-Tetrachlorodibenzo-p-dioxin

Item No. 38392

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3,7,8-tetrachloro-dibenzo[b,e][1,4]dioxin
CAS Number
1746-01-6
Synonyms
  • TCDBD
  • TCDD
  • 2,3,7,8-Tetrachlorodibenzodioxin
  • 2,3,7,8-Tetrachlorodibenzo-1,4-dioxin
Molecular Formula
C12H4Cl4O2
Formula Weight
322.0
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly soluble
SMILES
ClC1=C(Cl)C=C2OC3=CC(Cl)=C(Cl)C=C3OC2=C1
InChi Code
InChI=1S/C12H4Cl4O2/c13-5-1-9-10(2-6(5)14)18-12-4-8(16)7(15)3-11(12)17-9/h1-4H
InChi Key
HGUFODBRKLSHSI-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

    1 mg

    $303

    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

    2,3,7,8-Tetrachlorodibenzo-p-dioxin is a toxicant and an agonist of the aryl hydrocarbon receptor (AhR; ED50 = 0.2 nmol/kg in a reporter assay using chicken embryos).1 It also induces AhR ubiquitination and degradation in Hepa-1c1c7 hepatic cells when used at a concentration of 1 nM.2 Oral administration of 2,3,7,8-tetrachlorodibenzo-p-dioxin (0.1 mg/kg) increases mortality and induces severe liver necrosis, thymic atrophy, and cell depletion in lymphoid organs in rats.3 It does not induce hepatomegaly or reduce thymus weight and lymphocyte number but does increase immune cell infiltration into the lungs in AhR knockout mice when administered at a dose of 2 mg/kg.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Poland, A., Glover, E., and Kende, A.S. Stereospecific, high affinity binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin by hepatic cytosol. Evidence that the binding species is receptor for induction of aryl hydrocarbon hydroxylase. The Journal of Biological Chemisty 251(16), 4936-4946 (1976).

    2. Ma, Q., and Baldwin, K.T. 2,3,7,8-Tetrachlorodibenzo-p-dioxin-induced degradation of aryl hydrocarbon receptor (AhR) by the ubiquitin-proteasome pathway. Role of the transcription activaton and DNA binding of AhR. The Journal of Biological Chemisty 275(12), 8432-8438 (2000).

    3. Gupta, B.N., Vos, J.G., Moore, J.A., et al. Pathologic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin in laboratory animals. Environ. Health Perspect. 5, 125-140 (1973).

    4. Fernandez-Salguero, P.M., Hilbert, D.M., Rudikoff, S., et al. Aryl-hydrocarbon receptor-deficient mice are resistant to 2,3,7,8-tetrachlorodibenzo-p-dioxin-induced toxicity. Toxicol. Appl. Pharmacol. 140(1), 173-179 (1996).