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Chemical Compound Review

Metacresol     3-methylphenol

Synonyms: m-cresol, m-kresol, m-toluol, m-Cresole, m-cresylic, ...
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Disease relevance of m-cresol


Psychiatry related information on m-cresol

  • Data from these techniques as well as organoleptic evaluation of both the SMC and the chromatographic eluant indicated that the volatile sulfur compounds and cresol were important odorous components in SMC; cresol was reported as a musty, cattle-feces aroma [6].

High impact information on m-cresol

  • These results demonstrate that both preservatives impaired leukocyte function, but m-cresol was the most noxious in this respect.(ABSTRACT TRUNCATED AT 250 WORDS)[7]
  • The T(onset) value (140 degrees C) of aniline in the TGA is higher than those of phenol and the higher-boiling cresol guests (T(onset)=90-110 degrees C) because the former structure has more O-H...N/N-H...O hydrogen bonds than the clathrate of 1 with phenol which has O-H...O hydrogen bonds [8].
  • We also report the application of 2DCOR-GC to probe the mechanism of the alkylation of m-cresol with isopropyl alcohol in scCO(2) using Nafion SAC-13 as the catalyst [9].
  • Two structures of B28 Asp insulin have been determined from crystals grown in the presence of phenol and m-cresol [10].
  • 4-Chloro-m-cresol (cresol) and caffeine have been shown to be potent activators of the Ca(2+) release mediated by the ryanodine-sensitive Ca(2+) release channel and therefore increase the cytosolic free calcium concentration in skeletal muscles [11].

Chemical compound and disease context of m-cresol


Biological context of m-cresol


Anatomical context of m-cresol

  • The levels in the heart muscle, liver and spleen tissues were also extremely high, and there was 250 ml of cresol-odor-emitting fluid in the stomach [20].
  • Concentrations of butanoic, pentanoic, and 3-methylbutanoic acid were greater (P < 0.05) and concentrations of 3-methylphenol, 4-methylphenol, indole, and decane were less (P < 0.05) in feces from pigs fed feather meal [21].
  • Cresol, a commonly used disinfectant, may cause gastrointestinal corrosive injury, central nervous system and cardiovascular disturbances, and renal and hepatic injury following intoxication [22].
  • Three cresol isomers at 15 mumol/mg protein each induced the swelling in the absence of Ca2+ in medium and accelerated the swelling of liver mitochondria in the presence of Ca2+ in medium [23].
  • The identification of four further major constituents of the pedal gland exudate of the bontebok, Damaliscus dorcas dorcas, viz. alpha-terpineol, 2-n-heptylpyridine, m-cresol and (A)-6-dodecen-4-olide and the investigation of the stereochemistry of the double bond in (Z)-6-dodecen-4-olide by means of iterative computer analysis are described [24].

Associations of m-cresol with other chemical compounds

  • For m-cresol, m-aminophenol, and aniline intermediate rates of biodegradation and a linear increase in the percent mineralized with time were observed [25].
  • Phenethyl alcohol, m-cresol, and related compounds cause inhibition of germ tube formation in conidia of Neurospora crassa [26].
  • The anaerobic biodegradation of m-cresol was observed in anoxic aquifer slurries kept under both sulfate-reducing and nitrate-reducing but not methanogenic conditions [27].
  • The useful lifetime of the biosensor was 27 days and it was useful to determine monophenolics compounds (e.g. cresol, chlorophenol) and diphenolics compounds (e.g. catechol and dopamine) by amperometric measurements at -100mV (versus SCE) in a batch system [28].
  • Energy-resolved, competitive threshold collision-induced dissociation (TCID) methods are used to measure the gas-phase acidities of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid relative to hydrogen cyanide, hydrogen sulfide, and the hydroperoxyl radical using guided ion beam tandem mass spectrometry [29].

Gene context of m-cresol

  • A TP II analogue, [1-Nal3] TP II, was synthesized by a conventional solution method, followed by deprotection with 1M TFMSA-thioanisole (molar ratio 1:1) in TFA in the presence of Me2Se and m-cresol as scavengers [30].
  • A two-step deprotection methodology, consisting of a combination of a first-step reagent [0.3 M BSTFA-TBAI in CH(2)Cl(2), BF(3).Et(2)O] followed by a second-step reagent [1 M TMSOTf-thioanisole in TFA, m-cresol, EDT] was developed for use in solid-phase protocols [31].
  • Third, pressure measurements indicate that tyrosinase-coated chitosan films only react with cresol vapors if the oxygen cosubstrate is present [32].
  • After therapy for diabetic coma with insulin (containing the preservative cresol) and electrolyte solutions was started, the patient complained of increasing myalgia, developed a high fever and respiratory and metabolic acidosis and lost consciousness [33].
  • The zinc and m-cresol environments are described and the nature of the protamine binding site is outlined [34].

Analytical, diagnostic and therapeutic context of m-cresol

  • After a 60-min baseline period, insulin (20 IU H-Insulin 100 Hoechst) or vehicle (2.7 mg/ml m-Cresol) was intranasally administered every 15 min to 18 healthy subjects according to a double-blind within-subject crossover design [35].
  • The killing percentage in insulin with m-cresol reduced compared with insulin without preservative (mean +/- SE 95.4 +/- 0.8%) and the control without insulin (95.8 +/- 0.8%), both before and after 1 and 4 days perfusion (74.8 +/- 0.7, 80.2 +/- 2.8, and 80.6 +/- 1.6%, respectively; P less than 0.01) [7].
  • A new method of capillary electrophoresis was established to separate the three cresol isomers [36].
  • The TyrD./TyrD FTIR spectrum is compared to a cresol./cresol FTIR difference spectrum obtained by UV irradiation at 10 K of cresol at pH 8 [37].
  • Phenol/cresol degradation by the thermophilic Bacillus thermoglucosidasius A7: cloning and sequence analysis of five genes involved in the pathway [38].


  1. Stability of insulin lispro in insulin infusion systems. Lougheed, W.D., Zinman, B., Strack, T.R., Janis, L.J., Weymouth, A.B., Bernstein, E.A., Korbas, A.M., Frank, B.H. Diabetes Care (1997) [Pubmed]
  2. 4-Hydroxyphenylacetate decarboxylases: properties of a novel subclass of glycyl radical enzyme systems. Yu, L., Blaser, M., Andrei, P.I., Pierik, A.J., Selmer, T. Biochemistry (2006) [Pubmed]
  3. Complete nucleotide sequence of tbuD, the gene encoding phenol/cresol hydroxylase from Pseudomonas pickettii PKO1, and functional analysis of the encoded enzyme. Kukor, J.J., Olsen, R.H. J. Bacteriol. (1992) [Pubmed]
  4. Myalgia and elevated creatine kinase activity associated with subcutaneous injections of diluent. Bach, M.A., Blum, D.M., Rose, S.R., Charnas, L.R. J. Pediatr. (1992) [Pubmed]
  5. TOM, a new aromatic degradative plasmid from Burkholderia (Pseudomonas) cepacia G4. Shields, M.S., Reagin, M.J., Gerger, R.R., Campbell, R., Somerville, C. Appl. Environ. Microbiol. (1995) [Pubmed]
  6. Amelioration of odorous components in spent mushroom compost. Bazemore, R., Wysocki, C.J., Murray, S., Lawley, H.J., Preti, G. J. Agric. Food Chem. (2000) [Pubmed]
  7. Preservatives in insulin preparations impair leukocyte function. In vitro study. van Faassen, I., Verweij-van Vught, A.M., Lomecky-Janousek, M.Z., Razenberg, P.P., van der Veen, E.A. Diabetes Care (1990) [Pubmed]
  8. Guest-induced supramolecular isomerism in inclusion complexes of T-shaped host 4,4-bis(4'-hydroxyphenyl)cyclohexanone. Aitipamula, S., Nangia, A. Chemistry (Weinheim an der Bergstrasse, Germany) (2005) [Pubmed]
  9. 2DCOR-GC: an application of the generalized two-dimensional correlation analysis as a route to optimization of continuous flow supercritical fluid reactions. Hyde, J.R., Bourne, R.A., Noda, I., Stephenson, P., Poliakoff, M. Anal. Chem. (2004) [Pubmed]
  10. Interactions of phenol and m-cresol in the insulin hexamer, and their effect on the association properties of B28 pro --> Asp insulin analogues. Whittingham, J.L., Edwards, D.J., Antson, A.A., Clarkson, J.M., Dodson, G.G. Biochemistry (1998) [Pubmed]
  11. Can 4-chloro-m-cresol be substituted for caffeine as an activator of calcium oscillation in bullfrog sympathetic ganglion cells? Higure, Y., Shimazaki, Y., Nohmi, M. Cell Calcium (2006) [Pubmed]
  12. Evidence for isofunctional enzymes used in m-cresol and 2,5-xylenol degradation via the gentisate pathway in Pseudomonas alcaligenes. Poh, C.L., Bayly, R.C. J. Bacteriol. (1980) [Pubmed]
  13. Quinone methide formation from para isomers of methylphenol (cresol), ethylphenol, and isopropylphenol: relationship to toxicity. Thompson, D.C., Perera, K., London, R. Chem. Res. Toxicol. (1995) [Pubmed]
  14. Cresol isomers: comparison of toxic potency in rat liver slices. Thompson, D.C., Perera, K., Fisher, R., Brendel, K. Toxicol. Appl. Pharmacol. (1994) [Pubmed]
  15. Inhibition of cyclooxygenase activity, platelet aggregation and thromboxane B2 production by two environmental toxicants: m- and o-cresol. Chan, C.P., Yuan-Soon, H., Wang, Y.J., Lan, W.H., Chen, L.I., Chen, Y.J., Lin, B.R., Chang, M.C., Jeng, J.H. Toxicology (2005) [Pubmed]
  16. Effect of some uremic toxins on oxygen consumption of rats in vivo and in vitro. Hohenegger, M., Vermes, M., Esposito, R., Giordano, C. Nephron (1988) [Pubmed]
  17. Mutants of Pseudomonas cepacia G4 defective in catabolism of aromatic compounds and trichloroethylene. Shields, M.S., Montgomery, S.O., Cuskey, S.M., Chapman, P.J., Pritchard, P.H. Appl. Environ. Microbiol. (1991) [Pubmed]
  18. Molecular cloning, characterization, and regulation of a Pseudomonas pickettii PKO1 gene encoding phenol hydroxylase and expression of the gene in Pseudomonas aeruginosa PAO1c. Kukor, J.J., Olsen, R.H. J. Bacteriol. (1990) [Pubmed]
  19. Measurement of aquatic biodegradation rates by determining heterotrophic uptake of radiolabeled pollutants. Pfaender, F.K., Bartholomew, G.W. Appl. Environ. Microbiol. (1982) [Pubmed]
  20. An autopsy case of poisoning by massive absorption of cresol a short time before death. Monma-Ohtaki, J., Maeno, Y., Nagao, M., Iwasa, M., Koyama, H., Isobe, I., Seko-Nakamura, Y., Tsuchimochi, T., Matsumoto, T. Forensic Sci. Int. (2002) [Pubmed]
  21. Growth performance, carcass characteristics, nutrient digestibility and fecal odorous compounds in growing-finishing pigs fed diets containing hydrolyzed feather meal. van Heugten, E., van Kempen, T.A. J. Anim. Sci. (2002) [Pubmed]
  22. Concentrated cresol intoxication. Wu, M.L., Tsai, W.J., Yang, C.C., Deng, J.F. Veterinary and human toxicology. (1998) [Pubmed]
  23. Effects of cresols (o-, m-, and p-isomers) on the bioenergetic system in isolated rat liver mitochondria. Kitagawa, A. Drug and chemical toxicology. (2001) [Pubmed]
  24. Further compounds from the pedal gland of the bontebok (Damaliscus dorcas dorcas). Burger, B.V., le Roux, M., Garbers, C.F., Spies, H.S., Bigalke, R.C., Pachler, K.G., Wessels, P.L., Christ, V., Maurer, K.H. Z. Naturforsch., C, Biosci. (1977) [Pubmed]
  25. Adaptation to and biodegradation of xenobiotic compounds by microbial communities from a pristine aquifer. Aelion, C.M., Swindoll, C.M., Pfaender, F.K. Appl. Environ. Microbiol. (1987) [Pubmed]
  26. Inhibition of germ tube formation in Neurospora. Eberhart, B.M. J. Bacteriol. (1977) [Pubmed]
  27. Anaerobic degradation of m-cresol in anoxic aquifer slurries: carboxylation reactions in a sulfate-reducing bacterial enrichment. Ramanand, K., Suflita, J.M. Appl. Environ. Microbiol. (1991) [Pubmed]
  28. Amperometric tyrosinase biosensor based on polyacrylamide microgels. Hervás Pérez, J.P., Sánchez-Paniagua López, M., López-Cabarcos, E., López-Ruiz, B. Biosensors & bioelectronics. (2006) [Pubmed]
  29. Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid. Angel, L.A., Ervin, K.M. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
  30. Synthesis of [I-NaI3]] thymopoietin II and examination of its immunological effect on the uremic T-lymphocytes. Abiko, T., Nakatsubo, S. Mediators of inflammation. (2000) [Pubmed]
  31. Stereoselective synthesis of CF(2)-substituted phosphothreonine mimetics and their incorporation into peptides using newly developed deprotection procedures. Otaka, A., Mitsuyama, E., Kinoshita, T., Tamamura, H., Fujii, N. J. Org. Chem. (2000) [Pubmed]
  32. Enzymatic coupling of phenol vapors onto chitosan. Wu, L.Q., Chen, T., Wallace, K.K., Vazquez-Duhalt, R., Payne, G.F. Biotechnol. Bioeng. (2001) [Pubmed]
  33. Fulminant malignant hyperthermia associated with ketoacidotic diabetic coma. Wappler, F., Roewer, N., Köchling, A., Braune, H., Reissinger, T., Schulte am Esch, J. Intensive care medicine. (1996) [Pubmed]
  34. Structure of porcine insulin cocrystallized with clupeine Z. Balschmidt, P., Hansen, F.B., Dodson, E.J., Dodson, G.G., Korber, F. Acta Crystallogr., B (1991) [Pubmed]
  35. Central nervous system effects of intranasally administered insulin during euglycemia in men. Kern, W., Born, J., Schreiber, H., Fehm, H.L. Diabetes (1999) [Pubmed]
  36. Separation of cresols using coelectroosmotic capillary electrophoresis. Masselter, S.M., Zemann, A.J., Bobleter, O. Electrophoresis (1993) [Pubmed]
  37. Fourier transform infrared difference study of tyrosineD oxidation and plastoquinone QA reduction in photosystem II. Hienerwadel, R., Boussac, A., Breton, J., Berthomieu, C. Biochemistry (1996) [Pubmed]
  38. Phenol/cresol degradation by the thermophilic Bacillus thermoglucosidasius A7: cloning and sequence analysis of five genes involved in the pathway. Duffner, F.M., Kirchner, U., Bauer, M.P., Müller, R. Gene (2000) [Pubmed]
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