|Creation Date||2006-05-22 14:17:33 UTC|
|Update Date||2013-02-09 00:11:17 UTC|
|Secondary Accession Numbers||None|
|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).|
- m-Cresylic acid
|Average Molecular Weight||108.1378|
|Monoisotopic Molecular Weight||108.057514878|
|Traditional IUPAC Name||M-cresol|
|CAS Registry Number||108-39-4|
|Super Class||Aromatic Homomonocyclic Compounds|
|Class||Phenols and Derivatives|
- Aromatic Homomonocyclic Compounds
- a methylphenol(Cyc)
|Direct Parent||Meta Cresols|
|Status||Detected and Quantified|
- Membrane (predicted from logP)
|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)|
- Membrane (predicted from logP)
|Tissue Location||Not Available|
|Blood||Expected but not Quantified||Not Applicable||Not Available||Not Available||Normal|
|Urine||Detected and Quantified||0.13 umol/mmol creatinine||Adult (>18 years old)||Both||Normal|
|Blood||Detected and Quantified||8849.0 (8877.0-9062.0) uM||Adult (>18 years old)||Both||Cresol poisoning|
|Blood||Detected and Quantified||2219.0 (2126.0-2496.0) uM||Adult (>18 years old)||Both||Cresol poisoning|
|Associated Disorders and Diseases|
|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.
|Associated OMIM IDs||None|
|DrugBank ID||DB01776 |
|DrugBank Metabolite ID||Not Available|
|Phenol Explorer Compound ID||Not Available|
|Phenol Explorer Metabolite ID||Not Available|
|FoodDB ID||FDB008788 |
|KNApSAcK ID||C00035128 |
|Chemspider ID||21105871 |
|KEGG Compound ID||C01467 |
|BioCyc ID||CPD-112 |
|BiGG ID||Not Available|
|Wikipedia Link||m-Cresol |
|NuGOwiki Link||HMDB02048 |
|Metagene Link||HMDB02048 |
|METLIN ID||Not Available|
|PubChem Compound||342 |
|PDB ID||CRS |
|ChEBI ID||17231 |
|Synthesis Reference||Not Available|
|Material Safety Data Sheet (MSDS)||Not Available|
- 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.
- 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.
- 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.
- 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.
- Hussain K, Campagnolo ER: Suspected cresol poisoning in cattle presented for slaughter. Vet Hum Toxicol. 2002 Feb;44(1):11-4.
- 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.
- Jorgensen JT: Improvement of patient convenience in treatment with growth hormone. J Pediatr Endocrinol. 1994 Apr-Jun;7(2):175-80.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
- McSherry TJ: Incompatibility between chlorpromazine and metacresol. Am J Hosp Pharm. 1987 Jul;44(7):1574.
- 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.
- 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.