A transformation product of 6-PPD
Related Products
Parent Compound(s)
24250Diphenylamine
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4-Hydroxydiphenylamine

Item No. 40730

Technical Information
Formal Name
4-(phenylamino)-phenol
CAS Number
122-37-2
Synonyms
  • 4-HDPA
  • p-Hydroxydiphenylamine
  • para-Hydroxydiphenylamine
  • NSC 1543
Molecular Formula
C12H11NO
Formula Weight
Purity
≥98%
A solid
Ethanol: Soluble: ≥10 mg/mlPBS (pH 7.2): Soluble: ≥10 mg/ml
SMILES
OC1=CC=C(NC2=CC=CC=C2)C=C1
InChi Code
InChI=1S/C12H11NO/c14-12-8-6-11(7-9-12)13-10-4-2-1-3-5-10/h1-9,13-14H
InChi Key
JTTMYKSFKOOQLP-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    4-Hydroxydiphenylamine (4-HDPA) is an aqueous transformation product of the substituted p-phenylenediamine and antiozonant 6-PPD (Item No. 38246).1 It is also a biotransformation product of 6-PPD in zebrafish embryos and an active metabolite of the antioxidant and pesticide diphenylamine (Item No. 24250).2,3 4-HDPA scavenges carbon radicals in an AIBN-induced methyl methacrylate polymerization assay in a concentration-dependent manner.4 It has been found in tire wear particles, roadway runoff, and roadway-impacted creeks.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, H.N., Hu, X., Tian, Z., et alTransformation products of tire rubber antioxidant 6PPD in heterogeneous gas-phase ozonation: Identification and environmental occurrence. Environ. Sci. Technol. 57(14), 5621-5632 (2023).

    2. Grasse, N., Seiwert, B., Massei, R., et alUptake and biotransformation of the tire rubber-derived contaminants 6-PPD and 6-PPD quinone in the zebrafish embryo (Danio rerio). Environ. Sci. Technol. 57(41), 15598-15607 (2023).

    3. Alexander, W.E., Ryan, A.J., and Wright, S.E. Metabolism of diphenylamine in the rat, rabbit and man. Food Cosmet. Toxicol. 3(4), 571-579 (1965).

    4. Fujisawa, S., Ishihara, M., and Kadoma, Y. Antioxidant activity of diphenylamine–related compounds as scavengers of carbon radicals. J. Mol. Des. 4, 711-720 (2005).