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Record Information
Version3.6
Creation Date2006-05-22 14:17:33 UTC
Update Date2014-10-09 20:53:49 UTC
HMDB IDHMDB02048
Secondary Accession NumbersNone
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
  1. 1-Hydroxy-3-methylbenzene
  2. 3-Hydroxytoluene
  3. 3-Methylphenol
  4. m-Cresylic acid
  5. m-Hydroxytoluene
  6. m-Kresol
  7. m-Methylphenol
  8. m-Oxytoluene
  9. m-Toluol
  10. Meta-Cresol
Chemical FormulaC7H8O
Average Molecular Weight108.1378
Monoisotopic Molecular Weight108.057514878
IUPAC Name3-methylphenol
Traditional NameM-cresol
CAS Registry Number108-39-4
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 KeyRLSSMJSEOOYNOY-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassCresols
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • a methylphenol(Cyc)
  • cresol(ChEBI)
Substituents
  • Toluene
Direct ParentMeta Cresols
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
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 Solubility25.1ALOGPS
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
Spectra
SpectraMS/MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Dame, ZT. et al. ...
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
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 LinkHMDB02048
Metagene LinkHMDB02048
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(1):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