Human Metabolome Database Version 3.5

Showing metabocard for m-Cresol (HMDB02048)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:33 -0600
Update Date 2013-02-08 17:11:17 -0700
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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  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 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
InChI Identifier InChI=1S/C7H8O/c1-6-3-2-4-7(8)5-6/h2-5,8H,1H3
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)
  • Toluene
Direct Parent Meta Cresols
Status Detected and Quantified
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
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
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)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Comment Normal
  • Not Applicable
Urine Detected and Quantified
0.13 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 8849.0 (8877.0-9062.0) uM Adult (>18 years old) Both Comment Cresol poisoning
Blood Detected and Quantified 2219.0 (2126.0-2496.0) uM Adult (>18 years old) Both Comment 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 Link_out
      Associated OMIM IDs None
      DrugBank ID DB01776 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB008788
      KNApSAcK ID C00035128 Link_out
      Chemspider ID 21105871 Link_out
      KEGG Compound ID C01467 Link_out
      BioCyc ID CPD-112 Link_out
      BiGG ID Not Available
      Wikipedia Link m-Cresol Link_out
      NuGOwiki Link HMDB02048 Link_out
      Metagene Link HMDB02048 Link_out
      METLIN ID Not Available
      PubChem Compound 342 Link_out
      PDB ID CRS Link_out
      ChEBI ID 17231 Link_out
      Synthesis Reference Not 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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      5. Hussain K, Campagnolo ER: Suspected cresol poisoning in cattle presented for slaughter. Vet Hum Toxicol. 2002 Feb;44(1):11-4. Pubmed: 11824764 Link_out
      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 Link_out
      7. Jorgensen JT: Improvement of patient convenience in treatment with growth hormone. J Pediatr Endocrinol. 1994 Apr-Jun;7(2):175-80. Pubmed: 8061763 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      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 Link_out
      15. McSherry TJ: Incompatibility between chlorpromazine and metacresol. Am J Hosp Pharm. 1987 Jul;44(7):1574. Pubmed: 3631086 Link_out
      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 Link_out
      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 Link_out