Human Metabolome Database Version 3.5

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Showing metabocard for m-Cresol (HMDB02048)

Blood
Urine

Record Information

Version

3.5

Creation Date

2006-05-22 08:17:33 -0600

Update Date

2013-02-08 17:11:17 -0700

HMDB ID

HMDB02048

Secondary Accession Numbers

None

Metabolite Identification

Common Name

m-Cresol

Description

m-Cresol is an isomer of p-cresol and o-cresol. Cresols are organic compounds which are methylphenols. They are a widely occurring natural and manufactured group of aromatic organic compounds which are categorized as phenols (sometimes called phenolics). Depending on the temperature, cresols can be solid or liquid because they have melting points not far from room temperature. Like other types of phenols, they are slowly oxidized by long exposure to air and the impurities often give cresols a yellowish to brownish red tint. Cresols have an odor characteristic to that of other simple phenols, reminiscent to some of a "medicine" smell. Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. In the past, cresol solutions have been used as antiseptics in surgery, but they have been largely displaced in this role by less toxic compounds. Lysol was also advertised as a disinfecting vaginal douche in mid-twentieth century America. Cresols are found in many foods and in wood and tobacco smoke, crude oil, coal tar, and in brown mixtures such as creosote and cresylic acids, which are wood preservatives. Small organisms in soil and water produce cresols when they break down materials in the environment. Most exposures to cresols are at very low levels that are not harmful. When cresols are breathed, ingested, or applied to the skin at very high levels, they can be very harmful. Effects observed in people include irritation and burning of skin, eyes, mouth, and throat; abdominal pain and vomiting; heart damage; anemia; liver and kidney damage; facial paralysis; coma; and death. Breathing high levels of cresols for a short time results in irritation of the nose and throat. Aside from these effects, very little is known about the effects of breathing cresols, for example, at lower levels over longer times. Ingesting high levels results in kidney problems, mouth and throat burns, abdominal pain, vomiting, 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, brain, and lungs. (wikipedia).

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

1-Hydroxy-3-methylbenzene
3-Hydroxytoluene
3-Methylphenol
m-Cresylic acid
m-Hydroxytoluene
m-Kresol
m-Methylphenol
m-Oxytoluene
m-Toluol
Meta-Cresol

Chemical Formula

C₇H₈O

Average Molecular Weight

108.1378

Monoisotopic Molecular Weight

108.057514878

IUPAC Name

3-methylphenol

Traditional IUPAC Name

M-cresol

CAS Registry Number

108-39-4

SMILES

CC1=CC(O)=CC=C1

InChI Identifier

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

InChI Key

RLSSMJSEOOYNOY-UHFFFAOYSA-N

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Aromatic Homomonocyclic Compounds

Class

Phenols and Derivatives

Sub Class

Cresols

Other Descriptors

Aromatic Homomonocyclic Compounds
a methylphenol(Cyc)
cresol(ChEBI)

Substituents

Toluene

Direct Parent

Meta Cresols

Ontology

Status

Detected and Quantified

Origin

Endogenous

Microbial

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	11.8 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	22.7 mg/mL at 25 °C	Not Available
LogP	1.96	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	25.1 g/L	ALOGPS
LogP	1.93	ALOGPS
LogP	2.18	ChemAxon
LogS	-0.63	ALOGPS
pKa (strongest acidic)	10.13	ChemAxon
pKa (strongest basic)	-5.5	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 A²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	33.08	ChemAxon
Polarizability	11.91	ChemAxon
Formal Charge	0	ChemAxon
Physiological Charge	0	ChemAxon

Spectra

1H NMR Spectrum

MS/MS Spectrum Quattro_QQQ 10

MS/MS Spectrum Quattro_QQQ 25

MS/MS Spectrum Quattro_QQQ 40

MS/MS Spectrum EI-B (VARIAN MAT-44)

MS/MS Spectrum EI-B (HITACHI RMU-6L)

MS/MS Spectrum EI-B (HITACHI RMU-7M)

[1H,13C] 2D NMR Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status		Value	Age	Sex	Condition	Comments
Blood	Expected and not Quantified		Not Applicable	Not Available	Not Available	Normal	Inferred from detection in urine
Urine	Detected and Quantified		0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Not Available

Abnormal Concentrations

Biofluid	Status		Value	Age	Sex	Condition	Comments
Blood	Detected and Quantified		8849.0 (8877.0-9062.0) uM	Adult (>18 years old)	Both	Cresol poisoning	Fatal level
Blood	Detected and Quantified		2219.0 (2126.0-2496.0) uM	Adult (>18 years old)	Both	Cresol poisoning	Conjugated form of m-Cresol after cresol poisoning

Associated Disorders and Diseases

Disease References

Cresol poisoning IBS

Monma-Ohtaki J, Maeno Y, Nagao M, Iwasa M, Koyama H, Isobe I, Seko-Nakamura Y, Tsuchimochi T, Matsumoto T: An autopsy case of poisoning by massive absorption of cresol a short time before death. Forensic Sci Int. 2002 Mar 28;126(1):77-81. Pubmed: 11955837

Associated OMIM IDs

None

External Links

DrugBank ID

DB01776