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Details

Stereochemistry ACHIRAL
Molecular Formula C18H16N2
Molecular Weight 260.333
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of N,N'-DIPHENYL-P-PHENYLENEDIAMINE

SMILES

N(C1=CC=CC=C1)C2=CC=C(NC3=CC=CC=C3)C=C2

InChI

InChIKey=UTGQNNCQYDRXCH-UHFFFAOYSA-N
InChI=1S/C18H16N2/c1-3-7-15(8-4-1)19-17-11-13-18(14-12-17)20-16-9-5-2-6-10-16/h1-14,19-20H

HIDE SMILES / InChI
Molecular Formula C18H16N2
Molecular Weight 260.333
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

N,N'-Diphenyl-p-phenylenediamine is used as an antioxidant and/or stabilizer for rubber, petroleum oils and feedstuffs. It is also used as a polymerization inhibitor and a retardant against copper degradation. It is a chemical intermediate to make dyes, drugs, plastics and detergent additives.

Approval Year

1994
152
PubMed

PubMed

TitleDatePubMed
The antioxidant activity of vitamin C, DPPD and L-cysteine against Cisplatin-induced testicular oxidative damage in rats.
2011-05
The effect of antioxidant on development of fibrosis by cisplatin in rats.
2009-12
Skin sensitization potency and cross-reactivity of p-phenylenediamine and its derivatives evaluated by non-radioactive murine local lymph node assay and guinea-pig maximization test.
2009-04
Enzymatic redox properties of novel nitrotriazole explosives implications for their toxicity.
2008-11-13
Cytotoxicity of nitroaromatic explosives and their biodegradation products in mice splenocytes: implications for their immunotoxicity.
2008-09-25
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008-04
Mechanistic aspects of 4-amino-2,6-dichlorophenol-induced in vitro nephrotoxicity.
2008-03-12
Determination of ammonia based on the electrochemical oxidation of N,N'-diphenyl-1,4-phenylenediamine in propylene carbonate.
2007-11
Phenolic-rich juice prevents DNA single-strand breakage and cytotoxicity caused by tert-butylhydroperoxide in U937 cells: the role of iron chelation.
2007-07
Neuroprotective effects of phenylenediamine derivatives independent of an antioxidant pathway in neuronal HT22 cells.
2007-05-11
Prooxidant cytotoxicity of chromate in mammalian cells: the opposite roles of DT-diaphorase and glutathione reductase.
2007-02-14
Pyruvate and oxaloacetate limit zinc-induced oxidative HT-22 neuronal cell injury.
2006-12
Involvement of Raf-1/MEK/ERK1/2 signaling pathway in zinc-induced injury in rat renal cortical slices.
2006-08
Redox properties of novel antioxidant 5,8-Dihydroxycoumarin: implications for its prooxidant cytotoxicity.
2006-01-13
Quantitative structure-activity relationships in prooxidant cytotoxicity of polyphenols: role of potential of phenoxyl radical/phenol redox couple.
2005-09-15
Role of NAD(P)H:quinone oxidoreductase (NQO1) in apoptosis induction by aziridinylbenzoquinones RH1 and MeDZQ.
2005
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.
2004-06
Flavoenzyme-catalyzed redox cycling of hydroxylamino- and amino metabolites of 2,4,6-trinitrotoluene: implications for their cytotoxicity.
2004-05-15
Pyruvate limits zinc-induced rat oligodendrocyte progenitor cell death.
2004-01
Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
2003-09-09
Cytotoxicity of RH1 and related aziridinylbenzoquinones: involvement of activation by NAD(P)H:quinone oxidoreductase (NQO1) and oxidative stress.
2003-08-01
Voltammetric characterization of a N,N'-diphenyl-p-phenylenediamine-loaded screen-printed electrode: a disposable sensor for hydrogen sulfide.
2003-05-01
Physical adsorption of N,N'-diphenyl-p-phenylenediamine onto carbon particles: application to the detection of sulfide.
2003-05
Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals.
2003-02-01
Oxidant-induced cell death in renal epithelial cells: differential effects of inorganic and organic hydroperoxides.
2003-01
Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress.
2002-11-21
Effects of Juglans sinensis Dode extract and antioxidant on mercury chloride-induced acute renal failure in rabbits.
2002-09
A comparative study of intermolecular interactions in the crystal structures of phenyl/phenyl end-capped oligoanilines.
2002-07
Differential role of reactive oxygen species in chemical hypoxia-induced cell injury in opossum kidney cells and rabbit renal cortical slices.
2002
Role of reactive oxygen species in apoptosis induced by N-ethylmaleimide in HepG2 human hepatoblastoma cells.
2001-12-14
Quantitative structure-activity relationships in enzymatic single-electron reduction of nitroaromatic explosives: implications for their cytotoxicity.
2001-09-03
Role of reactive oxygen species generated by NADPH oxidase in the mechanism of activation of K(+)-Cl(-)-cotransport by N-ethylmaleimide in HepG2 human hepatoma cells.
2001-07
H2O2-induced cell death in human glioma cells: role of lipid peroxidation and PARP activation.
2001-04
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].
1995-12
High susceptibility to paraquat-driven lipid peroxidation of cultured hepatocytes loaded with linolenic acid.
1995-07
Increased alpha1-fetoprotein production in rat liver injuries induced by various hepatotoxins.
1976-04
Patents

Patents

04910330
1
05929194
1
JPH02135218A
1
JPH04124192A
1
JPS54110261A
1
JPS55129468A
1
JPS62179569A
1
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:02:47 GMT 2025
Edited
by admin
on Mon Mar 31 18:02:47 GMT 2025
Record UNII
DD517SCM92
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
N,N'-DIPHENYL-P-PHENYLENEDIAMINE
MI  
Common Name English
NSC-5761
Preferred Name English
N,N'-DIPHENYL-P-PHENYLENEDIAMINE [MI]
Common Name English
1,4-DIANILINOBENZENE
Systematic Name English
N, N'-DIPHENYL PARAPHENYLENEDIAMINE
Systematic Name English
N,N'-DIPHENYL-1,4-PHENYLENEDIAMINE
Systematic Name English
DPPD
Common Name English
P-PHENYLENEDIAMINE, N,N'-DIPHENYL- [HSDB]
Common Name English
N,N'-DIPHENYL PARAPHENYLENEDIAMINE
Systematic Name English
BIS(PHENYLAMINO)BENZENE
Systematic Name English
DIPHENYL-P-PHENYLENEDIAMINE
Common Name English
N,N'-DIPHENYL 4-PHENYLENEDIAMINE
Common Name English
N,N'-DIPHENYL-PARA-PHENYLENEDIAMINE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 176.170
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
NDF-RT N0000185508
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
Code System Code Type Description
HSDB
2894
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PRIMARY
MERCK INDEX
m4633
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PRIMARY Merck Index
FDA UNII
DD517SCM92
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-806-4
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
DAILYMED
DD517SCM92
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
NDF-RT
N0000171131
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY Allergens [Chemical/Ingredient]
EPA CompTox
DTXSID9020538
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
DRUG BANK
DB14192
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
CAS
74-31-7
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
NDF-RT
N0000175629
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY Increased Histamine Release [PE]
NDF-RT
N0000184306
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY Cell-mediated Immunity [PE]
SMS_ID
100000134271
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
NSC
5761
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
CHEBI
34860
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
PUBCHEM
6319
Created by admin on Mon Mar 31 18:02:47 GMT 2025 , Edited by admin on Mon Mar 31 18:02:47 GMT 2025
PRIMARY
NIH
NCATS
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