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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8O
Molecular Weight 108.1378
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PARACRESOL

SMILES

CC1=CC=C(O)C=C1

InChI

InChIKey=IWDCLRJOBJJRNH-UHFFFAOYSA-N
InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3

HIDE SMILES / InChI

Molecular Formula C7H8O
Molecular Weight 108.1378
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

p-cresol, also known as also 4-methylphenol, is a unique bacterial metabolite from protein fermentation that is not produced by human enzymes, this metabolites has been frequently used to assess the degree of proteolytic fermentation. Recently investigation showed that p-cresol measurements might help to predict cardiovascular disease risk in renal patients over a wide range of residual renal function, beyond traditional markers of glomerular filtration. In addition, there were studies, which revealed, that urinary p-cresol was elevated in young French children with autism spectrum disorder.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major [Km 58.4 uM]
major
major
major
minor [Km 50.3 uM]
minor
minor
minor
minor
no
no
no
no
no
no
no
no
no
no
unlikely
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Laboratory tests of the effects of p-cresol and 4-methylcyclohexanol on oviposition by three species of Toxorhynchites mosquitoes.
1989 Oct
Age-dependent consequences of seizures and the development of temporal lobe epilepsy in the rat.
2001
Automated, microprocessor controlled short path thermal desorption system for analysis of volatiles in foods.
2001
The antioxidant activity of BHT and new phenolic compounds PYA and PPA measured by chemiluminescence.
2001
Subicular lesions cause dendritic atrophy in CA1 and CA3 pyramidal neurons of the rat hippocampus.
2001
Visual agnosia and Klüver-Bucy syndrome in marmosets (Callithrix jacchus) following ablation of inferotemporal cortex, with additional mnemonic effects of immunotoxic lesions of cholinergic projections to medial temporal areas.
2001 Apr 13
Butylated hydroxytoluene (BHT) induction of pulmonary inflammation: a role in tumor promotion.
2001 Apr-May
Antioxidant properties, autooxidation, and mutagenic activity of echinochrome a compared with its etherified derivative.
2001 Aug
Effect of the antioxidant ionol (BHT) on growth and development of etiolated wheat seedlings: control of apoptosis, cell division, organelle ultrastructure, and plastid differentiation.
2001 Aug
Adenovirus-mediated GDNF and CNTF pretreatment protects against striatal injury following transient middle cerebral artery occlusion in mice.
2001 Aug
Proteolytic activation of latent Paraguaya peach PPO. Characterization of monophenolase activity.
2001 Feb
Protein-bound uremic solutes: the forgotten toxins.
2001 Feb
Reduction of inflammatory response in the mouse brain with adenoviral-mediated transforming growth factor-ss1 expression.
2001 Feb
Effects of noncovalent and covalent FAD binding on the redox and catalytic properties of p-cresol methylhydroxylase.
2001 Feb 20
Advanced analytical determination of volatile organic compounds (VOC) and other major contaminants in water samples using GC-ion trap MS.
2001 Jan
Oxidative insult in sheep red blood cells induced by T-butyl hydroperoxide: the roles of glutathione and glutathione peroxidase.
2001 Jan
A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides.
2001 Jan 25
Generation of 8-epi-prostaglandin F(2alpha) in isolated rat kidney glomeruli by a radical-independent mechanism.
2001 Jul
Carbetapentane attenuates kainate-induced seizures via sigma-1 receptor modulation.
2001 Jul 13
A highly efficient synthetic strategy for polymeric support synthesis of Le(x), Le(y), and H-type 2 oligosaccharides.
2001 Jun 1
Characteristic aroma components of British Farmhouse Cheddar cheese.
2001 Mar
Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity.
2001 Mar
Pilot studies evaluating the lung tumor yield in cigarette smoke-exposed mice.
2001 Mar
Aggravation of brain injury after transient focal ischemia in p53-deficient mice.
2001 Mar 31
Effects of the butylated hydroxyanisole and butylated hydroxytoluene on the DNA adduct formation and arylamines N-acetyltransferase activity in human colon tumor cells.
2001 Mar-Apr
Fused heterocyclic antioxidants: antioxidative activities of hydrocoumarins in a homogeneous solution.
2001 May
Status epilepticus causes necrotic damage in the mediodorsal nucleus of the thalamus in immature rats.
2001 May 15
Oxidation of albumin is enhanced in the presence of uremic toxins.
2001 May-Jul
Neuroprotective effect of melatonin on brain damage induced by acute global cerebral ischemia in cats.
2001 May-Jun
Anterior cingulate cortex pathology in schizophrenia and bipolar disorder.
2001 Oct
Degradation products of cyanidin glycosides from tart cherries and their bioactivities.
2001 Oct
Cellular model for induction of drip loss in meat.
2001 Oct
Butylhydroxytoluene (BHT) increases susceptibility of transgenic rasH2 mice to lung carcinogenesis.
2001 Oct
Phosphorylation of cyclic adenosine monophosphate response element binding protein in oligodendrocytes in the corpus callosum after focal cerebral ischemia in the rat.
2001 Oct
Protective effects of glial cell line-derived neurotrophic factor on hippocampal neurons after traumatic brain injury in rats.
2001 Oct
Artificially induced unusual shape of erythrocytes: an atomic force microscopy study.
2001 Oct
Lipid peroxidation associated protein damage in rat brain crude synaptosomal fraction mediated by iron and ascorbate.
2001 Oct
Cortical devascularization: quantitative diffusion weighted magnetic resonance imaging and histological findings.
2001 Oct 12
Lithium-pilocarpine-induced status epilepticus in immature rats result in long-term deficits in spatial learning and hippocampal cell loss.
2001 Oct 19
Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica.
2001 Oct 5
Electroantennogram and behavioural responses of the malaria vector Anopheles gambiae to human-specific sweat components.
2001 Sep
Antioxidant properties of evening primrose seed extracts.
2001 Sep
Use of selective inhibitors and chromogenic substrates to differentiate bacteria based on toluene oxygenase activity.
2001 Sep
Effect of antioxidants on preservation of motility,viability and acrosomal integrity of equine spermatozoa during storage at 5 degrees C.
2001 Sep 1
Morphological and functional analysis of an incomplete CNS fiber tract lesion: graded crush of the rat optic nerve.
2001 Sep 30
Urinary p-cresol is elevated in young French children with autism spectrum disorder: a replication study.
2014 Sep
Patents

Sample Use Guides

in rats: It was investigated the kinetic behavior of intravenously injected p-cresol (10 mg/kg) in rats with normal and decreased renal function, and compared the results with those obtained for creatinine (60 mg/kg) under similar conditions. Over a 4-hour period, p-cresol serum concentration showed only a minimal decline in rats with decreased renal function (t1/2 = 11.7 +/- 0.4 hours), compared to rats with normal renal function (t1/2 = 1.4 +/- 0.7 hours). The volume of distribution of p-cresol was approximately 4 times larger than that of creatinine, but was not significantly affected by renal failure. Not only renal, but also non-renal and total clearance, were much lower in rats with decreased renal function.
Route of Administration: Intravenous
It was investigated the in vitro impact p-cresol (PC) and p-cresyl sulfate (PCS) on monocyte chemoattractant protein-1 (MCP-1) expression via NF-kappa B (NF-κB) p65 in human vascular smooth muscle cells (VSMC). There was no significant difference in cell viability after toxins treatment for all concentrations tested. There was a significant increase in MCP-1 expression in cells treated with PCu and PCm (p < 0.001) and PCSn, PCSu and PCSm (p < 0.001), compared with the control. When VSMC were treated with the NF-κB p65 inhibitor plus PCu and PCm, there was a significant decrease in MCP-1 production (p < 0.005). This effect was not observed with PCS.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:35 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:35 GMT 2025
Record UNII
1MXY2UM8NV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
P-CRESOL
FHFI   HSDB   INCI   MI  
INCI  
Preferred Name English
PARACRESOL
Common Name English
P-TOLUOL
Common Name English
P-TOLYL ALCOHOL
Common Name English
P-HYDROXYTOLUENE
Common Name English
NSC-3696
Code English
PARA-CRESOL
Systematic Name English
P-CRESOL [MI]
Common Name English
P-CRESYLIC ACID
Common Name English
1-METHYL-4-HYDROXYBENZENE
Systematic Name English
PHENOL, 4-METHYL-
Systematic Name English
CRESOL, P-
Common Name English
P-METHYLHYDROXYBENZENE
Common Name English
1-HYDROXY-4-METHYLBENZENE
Systematic Name English
AMYLMETACRESOL IMPURITY D [EP IMPURITY]
Common Name English
METACRESOL IMPURITY C [EP IMPURITY]
Common Name English
P-CRESOL [FHFI]
Common Name English
PARACRESOL [USP IMPURITY]
Common Name English
P-METHYLPHENOL
Common Name English
P-OXYTOLUENE
Common Name English
4-CRESOL
Systematic Name English
FEMA NO. 2337
Code English
P-CRESOL [HSDB]
Common Name English
4-METHYLPHENOL
Systematic Name English
4-HYDROXYTOLUENE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
NCI_THESAURUS C45494
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
LOINC 79507-0
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
JECFA EVALUATION P-CRESOL
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
Code System Code Type Description
CAS
106-44-5
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
EPA CompTox
DTXSID7021869
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-398-6
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
DRUG BANK
DB01688
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
RXCUI
2467144
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
PUBCHEM
2879
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
MERCK INDEX
m3834
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY Merck Index
JECFA MONOGRAPH
573
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
FDA UNII
1MXY2UM8NV
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
CHEBI
1895
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
EVMPD
SUB128340
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
MESH
C032538
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
HSDB
1814
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
DAILYMED
1MXY2UM8NV
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
NCI_THESAURUS
C61880
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
SMS_ID
100000153965
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
CHEBI
17847
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
NSC
3696
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
WIKIPEDIA
P-CRESOL
Created by admin on Mon Mar 31 17:33:35 GMT 2025 , Edited by admin on Mon Mar 31 17:33:35 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (GC)
EP