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Record Information
Version4.0
Creation Date2006-05-22 14:17:33 UTC
Update Date2017-09-25 17:15:56 UTC
HMDB IDHMDB0002048
Secondary Accession Numbers
  • HMDB02048
StatusDetected and Quantified
Metabolite Identification
Common Namem-Cresol
Descriptionm-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
Thumb
Synonyms
ValueSource
1-Hydroxy-3-methylbenzeneChEBI
3-CresolChEBI
3-HydroxytolueneChEBI
3-PhenylphenolChEBI
m-KresolChEBI
m-MethylphenolChEBI
Meta-cresolChEBI
MetacresolChEBI
3-MethylphenolHMDB
m-Cresylic acidHMDB
m-HydroxytolueneHMDB
m-OxytolueneHMDB
m-ToluolHMDB
3-Cresol, sodium saltMeSH
3-Cresol, calcium salt(1:2)MeSH
Chemical FormulaC7H8O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
IUPAC Name3-methylphenol
Traditional NameM-cresol
CAS Registry Number108-39-4
SMILES
CC1=CC=CC(O)=C1
InChI Identifier
InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
InChI KeyRLSSMJSEOOYNOY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as meta cresols. These are aromatic compounds containing a meta-cresol moiety, which consists of a benzene ring bearing a methyl group and a hydroxyl group at ring positions 1 and 3, respectively.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentMeta cresols
Alternative Parents
Substituents
  • M-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition
Biological Location:
Source:
Subcellular:
Biofluid and excreta:
Role
Industrial application:
Pharmaceutical industry:
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point11.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility22.7 mg/mL at 25 °CNot Available
LogP1.96HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility25.1 mg/mLALOGPS
logP1.93ALOGPS
logP2.18ChemAxon
logS-0.63ALOGPS
pKa (Strongest Acidic)10.13ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m3·mol-1ChemAxon
Polarizability11.91 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4i-6900000000-f2082b2d78602454887cView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4i-9700000000-987a7fd82a03c828f2f6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0a4i-5900000000-80356192ec6d2f2cce17View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014l-3900000000-5be628cfaed43892ecb6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-4900000000-ff165ee98ef540125c4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9000000000-606fcb6bc90a29dd8728View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-dcdf60701ebd4f253affView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-6900000000-8a57217dc9acf65664ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-0a4i-9700000000-987a7fd82a03c828f2f6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-80356192ec6d2f2cce17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4i-9800000000-f9433af649d30cc0e317View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Both
    Normal
      • Zerihun T. Dame, ...
    details
    UrineDetected and Quantified0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified8849.0 (8877.0-9062.0) uMAdult (>18 years old)Both
    Cresol poisoning
    details
    BloodDetected and Quantified2219.0 (2126.0-2496.0) uMAdult (>18 years old)Both
    Cresol poisoning
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Nonalcoholic fatty liver disease (NAFLD)
    details
    Associated Disorders and Diseases
    Disease References
    Cresol poisoning IBS
    1. 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 IDsNone
    DrugBank IDDB01776
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB008788
    KNApSAcK IDC00035128
    Chemspider ID21105871
    KEGG Compound IDC01467
    BioCyc IDCPD-112
    BiGG IDNot Available
    Wikipedia Linkm-Cresol
    NuGOwiki LinkHMDB0002048
    METLIN IDNot Available
    PubChem Compound342
    PDB IDCRS
    ChEBI ID17231
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Oxford JS, Lambkin R, Gibb I, Balasingam S, Chan C, Catchpole A: A throat lozenge containing amyl meta cresol and dichlorobenzyl alcohol has a direct virucidal effect on respiratory syncytial virus, influenza A and SARS-CoV. Antivir Chem Chemother. 2005;16(2):129-34. [PubMed:15889535 ]
    2. Koetsawang A, Koetsawang S: The use of a condensation product of metacresol sulfonic acid with methanal in the treatment of cervical erosion. J Med Assoc Thai. 1980 Nov;63(11):608-10. [PubMed:7205102 ]
    3. Malaise J, Leonet J, Goffin E, Lefebvre C, Tennstedt D, Vandeleene B, Buysschaert M, Squifflet JP: Pancreas transplantation for treatment of generalized allergy to human insulin in type 1 diabetes. Transplant Proc. 2005 Jul-Aug;37(6):2839. [PubMed:16182826 ]
    4. Perez de Salazar JL, Diaz Loya FJ, Garcia Mendoza M: [The trichomonacidal, fungicidal and bactericidal effects of metacresol sulfonic acid polymer with methanal in cervico-vaginitis]. Ginecol Obstet Mex. 1983 Feb;51(310):43-8. [PubMed:6681370 ]
    5. Hussain K, Campagnolo ER: Suspected cresol poisoning in cattle presented for slaughter. Vet Hum Toxicol. 2002 Feb;44(1):11-4. [PubMed:11824764 ]
    6. Wang G, Jing F, Su S: [An experimental study of metacresol burn]. Zhonghua Zheng Xing Shao Shang Wai Ke Za Zhi. 1999 Jul;15(4):305-8. [PubMed:11593614 ]
    7. Jorgensen JT: Improvement of patient convenience in treatment with growth hormone. J Pediatr Endocrinol. 1994 Apr-Jun;7(2):175-80. [PubMed:8061763 ]
    8. Rasmussen LH, Zachmann M, Nilsson P: Authentic recombinant human growth hormone. Results of a multicenter clinical trial in patients with growth hormone deficiency. Helv Paediatr Acta. 1989 Jun;43(5-6):443-8. [PubMed:2663792 ]
    9. Wheeler BJ, Taylor BJ: Successful management of allergy to the insulin excipient metacresol in a child with type 1 diabetes: a case report. J Med Case Rep. 2012 Aug 31;6:263. doi: 10.1186/1752-1947-6-263. [PubMed:22937994 ]
    10. Morfin de Madrigal A, Lopez Amado G: [500 cases of cervicitis treated with metacresol sulfonic acid]. Ginecol Obstet Mex. 1972 Jan;31(183):83-9. [PubMed:5007546 ]
    11. Phares KR, Weiser WE, Miller SP, Myers MA, Wade M: Stability and preservative effectiveness of treprostinil sodium after dilution in common intravenous diluents. Am J Health Syst Pharm. 2003 May 1;60(9):916-22. [PubMed:12756943 ]
    12. Leonet J, Malaise J, Goffin E, Lefebvre C, Tennstedt D, Vandeleene B, Buysschaert M, Squifflet JP: Solitary pancreas transplantation for life-threatening allergy to human insulin. Transpl Int. 2006 Jun;19(6):474-7. [PubMed:16771868 ]
    13. Clerx V, Van Den Keybus C, Kochuyt A, Goossens A: Drug intolerance reaction to insulin therapy caused by metacresol. Contact Dermatitis. 2003 Mar;48(3):162-3. [PubMed:12755733 ]
    14. Plantin P, Sassolas B, Guillet MH, Tater D, Guillet G: [Cutaneous allergic accidents caused by insulin. Current aspects apropos of 2 cases]. Ann Dermatol Venereol. 1988;115(8):813-7. [PubMed:2974269 ]
    15. McSherry TJ: Incompatibility between chlorpromazine and metacresol. Am J Hosp Pharm. 1987 Jul;44(7):1574. [PubMed:3631086 ]
    16. Gloge A, Langer B, Poppe L, Retey J: The behavior of substrate analogues and secondary deuterium isotope effects in the phenylalanine ammonia-lyase reaction. Arch Biochem Biophys. 1998 Nov 1;359(1):1-7. [PubMed:9799553 ]
    17. Das Gupta V: Quantitation of meperidine hydrochloride in pharmaceutical dosage forms by high-performance liquid chromatography. J Pharm Sci. 1983 Jun;72(6):695-7. [PubMed:6875832 ]