An oxidized derivative of DTPD
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DTPD-Q

Item No. 40612

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,5-bis[(2-methylphenyl)amino]-2,5-cyclohexadiene-1,4-dione
CAS Number
252950-56-4
Synonyms
  • 2,5-Bis(o-tolylamino)cyclohexa-2,5-diene-1,4-dione
  • DTPD-quinone
Molecular Formula
C20H18N2O2
Formula Weight
318.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly soluble: 0.1-1mg/mlEthanol: Slightly soluble: 0.1-1mg/mlPBS (pH 7.2): Slightly soluble: 0.1-1mg/ml
SMILES
O=C(C(NC1=CC=CC=C1C)=C2)C=C(NC3=CC=CC=C3C)C2=O
InChi Code
InChI=1S/C20H18N2O2/c1-13-7-3-5-9-15(13)21-17-11-20(24)18(12-19(17)23)22-16-10-6-4-8-14(16)2/h3-12,21-22H,1-2H3
InChi Key
QJOYQAODZKIBDH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    DTPD-Q is an oxidized derivative of the antioxidant and methylphenyl substituted p-phenylenediamine DTPD.1 It is an inhibitor of dynamin 1 (IC50 = 273 µM) and reduces clathrin-mediated endocytosis in serum-starved U2OS cells (IC50 = 120 µM). DTPD-Q is less toxic to the aquatic bacterium V. fischeri than DTPD (EC50 = 1.98 mg/L).2 It increases intestinal permeability of, and production of reactive oxygen species (ROS) in, C. elegans when used at concentrations of 1 or 10 µg/ml.3 DTPD-Q has been found in roadway runoff water and roadside soils, indoor dust, as well as consumer products made from recycled tire rubber.4,5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. MacGregor, K.A., Abdel-Hamid, M.K., Odell, L.R., et al. Development of quinone analogues as dynamin GTPase inhibitors. Eur. J. Med. Chem. 85, 191-206 (2014).

    2. Wang, W., Chen, Y., Fang, J., et al. Toxicity of substituted p-phenylenediamine antioxidants and their derived novel quinones on aquatic bacterium: Acute effects and mechanistic insights. J. Hazard. Mater. 469:133900, (2024).

    3. Wang, Y., Liang, G., Chao, J., et al. Comparison of intestinal toxicity in enhancing intestinal permeability and in causing ROS production of six PPD quinones in Caenorhabditis elegans. Sci. Total Environ. 927, 172306 (2024).

    4. Cao, G., Wang, W., Zhang, J., et al. New evidence of rubber-derived quinones in water, air, and soil. Environ. Sci. Technol. 56(7), 4142-4150 (2022).

    5. Zhu, J., Guo, R., Jiang, S., et al. Occurrence of p-phenylenediamine antioxidants (PPDs) and PPDs-derived quinones in indoor dust. Sci. Total Environ. 912, 169325 (2024).

    6. Zhao, H.N., Hu, X., Gonzalez, M., et al. Screening p-phenylenediamine antioxidants, their transformation products, and industrial chemical additives in crumb rubber and elastomeric consumer products. Environ. Sci. Technol. 57(7), 2779-2791 (2023).