ContaminantDB: o-Cresol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:15 UTC

Update Date

2026-03-26 21:20:28 UTC

Accession Number

CHEM000175

Identification

Common Name

o-Cresol

Class

Small Molecule

Description

o-Cresol is a minor urinary metabolite of toluene, a widely used chemical with neurotoxicological properties. (4). o-Cresol is used commercially as a disinfectant. Exposure may occur by inhalation, by cutaneous adsorption or by oral ingestion. o-Cresol denature and precipitate cellular proteins and thus may rapidly cause poisoning. o-Cresol is metabolized by conjugation and oxidation. Ingestion of o-Cresol cause intense burning of mouth and throat, followed by marked abdominal pain and distress. The minimum lethal dose of cresol by mouth is about 2 g. (3).

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HMDB Contaminants - Urine
HPV EPA Chemicals
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
Sludge Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Disinfectant
Food Toxin
Household Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Pollutant
Solvent

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hydroxy-2-methylbenzene	ChEBI
2-Cresol	ChEBI
2-Hydroxy-1-methylbenzene	ChEBI
2-Hydroxytoluene	ChEBI
O-Cresylic acid	ChEBI
O-Kresol	ChEBI
O-Methylphenol	ChEBI
Ortho-cresol	ChEBI
Orthocresol	ChEBI
O-Cresylate	Generator
1-Methyl-2-hydroxybenzene	HMDB
2-Methylphenol	HMDB, MeSH
O-Hydroxytoluene	HMDB
O-Methylphenylol	HMDB
O-Oxytoluene	HMDB
O-Toluol	HMDB
2-Cresol, potassium salt	MeSH, HMDB
2-Cresol, ammonium salt	MeSH, HMDB
2-Cresol, sodium salt	MeSH, HMDB

Chemical Formula

C₇H₈O

Average Molecular Mass

108.138 g/mol

Monoisotopic Mass

108.058 g/mol

CAS Registry Number

95-48-7

IUPAC Name

2-methylphenol

Traditional Name

o-cresol

SMILES

CC1=CC=CC=C1O

InChI Identifier

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

InChI Key

QWVGKYWNOKOFNN-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ortho cresols. These are organic compounds containing an ortho-cresol moiety, which consists of a benzene bearing one hydroxyl group at ring positions 1 and 2, respectively.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

cresol (CHEBI:28054 )
a methylphenol (CPD-109 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

human xenobiotic metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Colorless solids or liquids.

Experimental Properties

Property	Value
Melting Point	29.8°C
Boiling Point	191.5°C (376.7°F)
Solubility	25.9 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	27.5 g/L	ALOGPS
logP	1.89	ALOGPS
logP	2.18	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	10.37	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.08 m³·mol⁻¹	ChemAxon
Polarizability	11.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9600000000-5a01d451557a1b35332a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-5900000000-cef3087dea0c431cce4b	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a6r-9600000000-5a01d451557a1b35332a	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0a4i-7900000000-c8eb63e9fe9da99fda0f	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00ko-5900000000-cef3087dea0c431cce4b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6900000000-7ba7c816e0edce6b772f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-06di-7900000000-db9d20fae81c588496fe	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0a4i-5900000000-c7d0037b6de77737b7e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-151af99851311002a3fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03y3-9000000000-260e2bcf6f7dca1a3c9c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	splash10-0a6r-9600000000-ac87a40c538d227b6915	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positive	splash10-0pbi-9200000000-be9e6e56af8374e66beb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0a4i-7900000000-1a7cfac9452c2b14f977	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-5d6424b7db2e7e40d6d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-2900000000-e468ad1b8f28b32d7276	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-9000000000-2629c90f57b18d57c59d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8feea1e7288d5bc80ea5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-22006f43be347c915292	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-9300000000-d3ec19098100f79d4ebd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-3f09649991cc4cfcf1ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0i03-9100000000-267c04454ade05650a34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-2900000000-c580eec1345db0ab9045	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-9000000000-923877cbbb5c2a1edb9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016u-9000000000-09eba92f6442b1a88ad5	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9800000000-c390212681445a7e2727	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (7) ; inhalation (7) ; dermal (7)

Mechanism of Toxicity

Target organs of ingested cresols in humans are the blood, kidneys, lungs, liver, heart, and central nervous system. Cresols impair the stratum corneum and produce coagulation necrosis by denaturating and precipitating proteins. They may also induce changes in neurotransmitter levels, affect the activities of some enzymes, increase lipid peroxidation, and change membrane fluidity in the brain. (7)

Metabolism

Cresols can be absorbed following inhalation, oral, and dermal exposure. Once in the body they can distribute rapidly into many organs and tissues. Cresols undergo oxidative metabolism in the liver and are rapidly eliminated, mostly in the urine, as sulfate or glucuronide conjugates. The activation of cresols by oxidation involves tyrosinase and thyroid peroxidase, forming a reactive quinone methide. Experiments with recombinant P-450s demonstrated cresol metabolism was mediated by several P-450s including CYP2D6, 2C19, 1A2, 1A1, and 2E1. (7, 1, 8, 2)

Toxicity Values

LD50: 344 mg/kg (Oral, Mouse) (9) LD50: 179 mg/m3 (Inhalation, Mouse) (9) LD50: 620 mg/kg (Dermal, Mouse) (9)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Cresols are used to as solvents, disinfectants and deodorizers, as well as to make other chemicals. They may be formed normally in the body from other compounds. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in chemical mixtures used as wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment. Breathing air containing cresols is the primary source of exposure. Exposure may also result from drinking contaminated water, eating contaminated food and coming into contact with liquids containing cresols. (7)

Minimum Risk Level

Intermediate Oral: 0.1 mg/kg/day (5) Chronic Oral: 0.1 mg/kg/day (5)

Health Effects

Cresols breathed, ingested, or applied to the skin at very high levels can be very harmful because they are corrosive substances. Ingestion of high levels results in mouth and throat burns, abdominal pain, vomiting, kidney problems, and effects on the blood and nervous system. Skin contact with high levels of cresols can burn the skin and damage the kidneys, liver, blood, lungs, and brain. Tachycardia, respiratory failure, unconsciousness and death may occur in both cases. Many of these effects may not by caused directly by cresols, but may be a result of secondary reactions to shock caused by external and internal burns. (6, 7)

Symptoms

Ingestion of cresols results in burning of the mouth and throat, abdominal pain, and vomiting. Inhalation or dermal exposure to cresols can produce irritation and corrosion at the site of contact. (6)

Treatment

Following oral exposure, immediately dilute with 4 to 8 ounces (120 to 240 mL) of water or milk (not to exceed 4 ounces/120 mL in a child). Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury. In case of hypotension, infuse isotonic fluid. If hypotension persists, administer dopamine or norepinephrine. In case of hypertension, monitor vital signs regularly. For mild/moderate asymptomatic hypertension (no end organ damage), pharmacologic treatment is generally not necessary. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of acute lung injury, maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Early use of PEEP and mechanical ventilation may be needed. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines. (10)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0002055

FooDB ID

FDB008785

Phenol Explorer ID

Not Available

KNApSAcK ID