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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

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
149
PubMed

PubMed

TitleDatePubMed
Increased alpha1-fetoprotein production in rat liver injuries induced by various hepatotoxins.
1976 Apr
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds].
1995 Dec
High susceptibility to paraquat-driven lipid peroxidation of cultured hepatocytes loaded with linolenic acid.
1995 Jul
Role of reactive oxygen species in apoptosis induced by N-ethylmaleimide in HepG2 human hepatoblastoma cells.
2001 Dec 14
Cytotoxicity of natural hydroxyanthraquinones: role of oxidative stress.
2002 Sep-Oct
Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals.
2003 Feb 1
Oxidant-induced cell death in renal epithelial cells: differential effects of inorganic and organic hydroperoxides.
2003 Jan
Physical adsorption of N,N'-diphenyl-p-phenylenediamine onto carbon particles: application to the detection of sulfide.
2003 May
Voltammetric characterization of a N,N'-diphenyl-p-phenylenediamine-loaded screen-printed electrode: a disposable sensor for hydrogen sulfide.
2003 May 1
Pyruvate limits zinc-induced rat oligodendrocyte progenitor cell death.
2004 Jan
Inactivation of endoplasmic reticulum bound Ca2+-independent phospholipase A2 in renal cells during oxidative stress.
2004 Jun
Flavoenzyme-catalyzed redox cycling of hydroxylamino- and amino metabolites of 2,4,6-trinitrotoluene: implications for their cytotoxicity.
2004 May 15
Enzymatic redox properties of novel nitrotriazole explosives implications for their toxicity.
2004 May-Jun
Role of NAD(P)H:quinone oxidoreductase (NQO1) in apoptosis induction by aziridinylbenzoquinones RH1 and MeDZQ.
2005
Redox properties of novel antioxidant 5,8-Dihydroxycoumarin: implications for its prooxidant cytotoxicity.
2005 Nov-Dec
Quantitative structure-activity relationships in prooxidant cytotoxicity of polyphenols: role of potential of phenoxyl radical/phenol redox couple.
2005 Sep 15
Involvement of Raf-1/MEK/ERK1/2 signaling pathway in zinc-induced injury in rat renal cortical slices.
2006 Aug
Pyruvate and oxaloacetate limit zinc-induced oxidative HT-22 neuronal cell injury.
2006 Dec
Prooxidant cytotoxicity of chromate in mammalian cells: the opposite roles of DT-diaphorase and glutathione reductase.
2006 Nov-Dec
Phenolic-rich juice prevents DNA single-strand breakage and cytotoxicity caused by tert-butylhydroperoxide in U937 cells: the role of iron chelation.
2007 Jul
Neuroprotective effects of phenylenediamine derivatives independent of an antioxidant pathway in neuronal HT22 cells.
2007 May 11
Determination of ammonia based on the electrochemical oxidation of N,N'-diphenyl-1,4-phenylenediamine in propylene carbonate.
2007 Nov
Cytotoxicity of nitroaromatic explosives and their biodegradation products in mice splenocytes: implications for their immunotoxicity.
2008 Jul-Aug
Mechanistic aspects of 4-amino-2,6-dichlorophenol-induced in vitro nephrotoxicity.
2008 Mar 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 Apr
The effect of antioxidant on development of fibrosis by cisplatin in rats.
2009 Dec
The antioxidant activity of vitamin C, DPPD and L-cysteine against Cisplatin-induced testicular oxidative damage in rats.
2011 May
Patents

Patents

04910330
1
05929194
1
JPH02135218A
1
JPH04124192A
1
JPS54110261A
1
JPS55129468A
1
JPS62179569A
1
Name Type Language
N,N'-DIPHENYL-P-PHENYLENEDIAMINE
MI  
Common 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
NSC-5761
Code English
N,N'-DIPHENYL-PARA-PHENYLENEDIAMINE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 176.170
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
Code System Code Type Description
HSDB
2894
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
MERCK INDEX
m4633
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY Merck Index
FDA UNII
DD517SCM92
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-806-4
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
DAILYMED
DD517SCM92
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
EPA CompTox
DTXSID9020538
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
DRUG BANK
DB14192
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
CAS
74-31-7
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY Increased Histamine Release [PE]
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
SMS_ID
100000134271
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
NSC
5761
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
CHEBI
34860
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
PUBCHEM
6319
Created by admin on Fri Dec 15 15:36:37 GMT 2023 , Edited by admin on Fri Dec 15 15:36:37 GMT 2023
PRIMARY
NIH
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