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
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
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
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/25010144 |
Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator​
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 18.2 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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 |
PubMed
Title | Date | PubMed |
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Laboratory tests of the effects of p-cresol and 4-methylcyclohexanol on oviposition by three species of Toxorhynchites mosquitoes. | 1989 Oct |
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Age-dependent consequences of seizures and the development of temporal lobe epilepsy in the rat. | 2001 |
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Automated, microprocessor controlled short path thermal desorption system for analysis of volatiles in foods. | 2001 |
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The antioxidant activity of BHT and new phenolic compounds PYA and PPA measured by chemiluminescence. | 2001 |
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Subicular lesions cause dendritic atrophy in CA1 and CA3 pyramidal neurons of the rat hippocampus. | 2001 |
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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 |
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Butylated hydroxytoluene (BHT) induction of pulmonary inflammation: a role in tumor promotion. | 2001 Apr-May |
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Antioxidant properties, autooxidation, and mutagenic activity of echinochrome a compared with its etherified derivative. | 2001 Aug |
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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 |
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Adenovirus-mediated GDNF and CNTF pretreatment protects against striatal injury following transient middle cerebral artery occlusion in mice. | 2001 Aug |
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Proteolytic activation of latent Paraguaya peach PPO. Characterization of monophenolase activity. | 2001 Feb |
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Protein-bound uremic solutes: the forgotten toxins. | 2001 Feb |
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Reduction of inflammatory response in the mouse brain with adenoviral-mediated transforming growth factor-ss1 expression. | 2001 Feb |
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Effects of noncovalent and covalent FAD binding on the redox and catalytic properties of p-cresol methylhydroxylase. | 2001 Feb 20 |
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Advanced analytical determination of volatile organic compounds (VOC) and other major contaminants in water samples using GC-ion trap MS. | 2001 Jan |
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Oxidative insult in sheep red blood cells induced by T-butyl hydroperoxide: the roles of glutathione and glutathione peroxidase. | 2001 Jan |
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A solid phase reagent for the capture phosphorylation of carbohydrates and nucleosides. | 2001 Jan 25 |
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Generation of 8-epi-prostaglandin F(2alpha) in isolated rat kidney glomeruli by a radical-independent mechanism. | 2001 Jul |
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Carbetapentane attenuates kainate-induced seizures via sigma-1 receptor modulation. | 2001 Jul 13 |
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A highly efficient synthetic strategy for polymeric support synthesis of Le(x), Le(y), and H-type 2 oligosaccharides. | 2001 Jun 1 |
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Characteristic aroma components of British Farmhouse Cheddar cheese. | 2001 Mar |
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Chemoprotective potentials of homoisoflavonoids and chalcones of Dracaena cinnabari: modulations of drug-metabolizing enzymes and antioxidant activity. | 2001 Mar |
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Pilot studies evaluating the lung tumor yield in cigarette smoke-exposed mice. | 2001 Mar |
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Aggravation of brain injury after transient focal ischemia in p53-deficient mice. | 2001 Mar 31 |
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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 |
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Fused heterocyclic antioxidants: antioxidative activities of hydrocoumarins in a homogeneous solution. | 2001 May |
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Status epilepticus causes necrotic damage in the mediodorsal nucleus of the thalamus in immature rats. | 2001 May 15 |
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Oxidation of albumin is enhanced in the presence of uremic toxins. | 2001 May-Jul |
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Neuroprotective effect of melatonin on brain damage induced by acute global cerebral ischemia in cats. | 2001 May-Jun |
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Anterior cingulate cortex pathology in schizophrenia and bipolar disorder. | 2001 Oct |
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Degradation products of cyanidin glycosides from tart cherries and their bioactivities. | 2001 Oct |
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Cellular model for induction of drip loss in meat. | 2001 Oct |
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Butylhydroxytoluene (BHT) increases susceptibility of transgenic rasH2 mice to lung carcinogenesis. | 2001 Oct |
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Phosphorylation of cyclic adenosine monophosphate response element binding protein in oligodendrocytes in the corpus callosum after focal cerebral ischemia in the rat. | 2001 Oct |
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Protective effects of glial cell line-derived neurotrophic factor on hippocampal neurons after traumatic brain injury in rats. | 2001 Oct |
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Artificially induced unusual shape of erythrocytes: an atomic force microscopy study. | 2001 Oct |
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Lipid peroxidation associated protein damage in rat brain crude synaptosomal fraction mediated by iron and ascorbate. | 2001 Oct |
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Cortical devascularization: quantitative diffusion weighted magnetic resonance imaging and histological findings. | 2001 Oct 12 |
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Lithium-pilocarpine-induced status epilepticus in immature rats result in long-term deficits in spatial learning and hippocampal cell loss. | 2001 Oct 19 |
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Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica. | 2001 Oct 5 |
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Electroantennogram and behavioural responses of the malaria vector Anopheles gambiae to human-specific sweat components. | 2001 Sep |
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Antioxidant properties of evening primrose seed extracts. | 2001 Sep |
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Use of selective inhibitors and chromogenic substrates to differentiate bacteria based on toluene oxygenase activity. | 2001 Sep |
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Effect of antioxidants on preservation of motility,viability and acrosomal integrity of equine spermatozoa during storage at 5 degrees C. | 2001 Sep 1 |
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Morphological and functional analysis of an incomplete CNS fiber tract lesion: graded crush of the rat optic nerve. | 2001 Sep 30 |
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Urinary p-cresol is elevated in young French children with autism spectrum disorder: a replication study. | 2014 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12969155
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27438970
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
Edited
Mon Mar 31 17:33:35 GMT 2025
by
admin
on
Mon Mar 31 17:33:35 GMT 2025
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Record UNII |
1MXY2UM8NV
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 172.515
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NCI_THESAURUS |
C45494
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LOINC |
79507-0
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JECFA EVALUATION |
P-CRESOL
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106-44-5
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DTXSID7021869
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203-398-6
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DB01688
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2467144
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2879
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m3834
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573
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1MXY2UM8NV
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1895
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SUB128340
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C032538
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1814
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1MXY2UM8NV
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C61880
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100000153965
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17847
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3696
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P-CRESOL
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