Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.


Record Information
Version2.0
Creation Date2012-07-30 14:55:23 -0600
Update Date2015-09-13 12:56:15 -0600
Secondary Accession Numbers
  • ECMDB21349
Identification
Name:p-Cresol
Descriptionp-Cresol, also known as 4-methylphenol or 4-hydroxytoluene, is a positional isomer of cresol. The other two isomers are m-cresol and o-cresol. (Wikipedia) p-Cresol is one of the metabolites of the amino acid tyrosine, and to a certain extent also of phenylalanine, which are converted to 4-hydroxyphenylacetic acid by intestinal bacteria, before being decarboxylated to p-cresol (putrefaction). The main contributing bacteria are aerobes (mainly enterobacteria), but to a certain extent also anaerobes play a role (mainly Clostridium perfringens). p-Cresol has been reported to affect several biochemical, biological and physiological functions: for example, it alters cell membrane permeability in bacteria. (HMDB, PMID 10570076) In E. coli, p-Cresol can be produced as a by-product of thiazole biosynthesis. (EcoCyc)
Structure
Thumb
Synonyms:
  • 1-Hydroxy-4-methylbenzene
  • 1-Methyl-4-hydroxybenzene
  • 4-(Pentafluorosulfanyl)phenol
  • 4-(Pentafluorosulphanyl)phenol
  • 4-Cresol
  • 4-Hydroxytoluene
  • 4-methyl phenol
  • 4-Methyl-Phenol
  • 4-Methylphenol
  • 4-Methylphenol ( p-cresol)
  • p-cresol
  • Cresol, para
  • P-Cresol
  • P-Cresol (4-methylphenol)
  • P-Cresol 98+ %
  • P-Cresol for synthesis
  • P-Cresol Hydrate 90 %
  • P-Cresol Hydric acid 90 %
  • P-Cresylate
  • P-Cresylic acid
  • P-Hydroxytoluene
  • P-Kresol
  • P-Methyl phenol
  • P-Methylhydroxybenzene
  • P-Methylphenol
  • P-Oxytoluene
  • P-Toluol
  • P-Tolyl alcohol
  • Paracresol
  • Paramethyl phenol
  • Phenol, 4-methyI
Chemical Formula:C7H8O
Weight:Average: 108.1378
Monoisotopic: 108.057514878
InChI Key:IWDCLRJOBJJRNH-UHFFFAOYSA-N
InChI:InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
CAS number:106-44-5
IUPAC Name:4-methylphenol
Traditional IUPAC Name:P-cresol
SMILES:CC1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as para cresols. Para cresols are compounds containing a para cresol moiety, which consists of a benzene ring bearing one hydroxyl group at ring positions 1 and 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassCresols
Direct ParentPara cresols
Alternative Parents
Substituents
  • P-cresol
  • 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
Physical Properties
State:Solid
Charge:0
Melting point:35.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:21.5 mg/mL at 25 deg CPhysProp
LogP:1.94; 1.94 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility23.1 g/LALOGPS
logP1.95ALOGPS
logP2.18ChemAxon
logS-0.67ALOGPS
pKa (Strongest Acidic)10.36ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity33.08 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
tyrosine biosynthesisPW000806 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-1d2bdfde621a5af9be73View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-b76093f53701327ab25fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-7d25deb1e39c6ef4866fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7900000000-15d473146e11e4b049b2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-4900000000-14fef90a661a09457976View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-1d2bdfde621a5af9be73View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-5900000000-b76093f53701327ab25fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-4900000000-7d25deb1e39c6ef4866fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7900000000-15d473146e11e4b049b2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-4900000000-14fef90a661a09457976View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6900000000-27534de20ade11dd5454View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06fr-9700000000-f41dd95ca553de6bafffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-ab55ada5cae0538f383eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-385a7a99e0409c7f060dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02tl-9000000000-205f4e5245868e9debccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-5900000000-fd438231ac0ed75fdf09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-b76093f53701327ab25fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-4900000000-7d25deb1e39c6ef4866fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4i-7900000000-0cdab17a1a95f3e65f45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - NA 35V, negativesplash10-0a6u-9600000000-276b44cbbdb079cac718View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-cf0bed2b3a203309d9aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-4f20c8bd2dde845b499cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-393b5f734646352622f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-0c45920f40546c2d8944View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-417774c01b748db1609dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-5583b6dc3ae583b8dab0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-6eb0884733967edc9e6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-621936189d60e194cefdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056u-9100000000-2740c99af64b11309dfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-1c2034d922354f5d6682View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0a4i-6900000000-729e6f5bdb0da3ed9dedView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Akasaka K, Ohrui H, Meguro H, Tamura M: Determination of triacylglycerol and cholesterol ester hydroperoxides in human plasma by high-performance liquid chromatography with fluorometric postcolumn detection. J Chromatogr. 1993 Aug 11;617(2):205-11. Pubmed: 8408385
  • Bammens B, Verbeke K, Vanrenterghem Y, Evenepoel P: Evidence for impaired assimilation of protein in chronic renal failure. Kidney Int. 2003 Dec;64(6):2196-203. Pubmed: 14633143
  • Bone E, Tamm A, Hill M: The production of urinary phenols by gut bacteria and their possible role in the causation of large bowel cancer. Am J Clin Nutr. 1976 Dec;29(12):1448-54. Pubmed: 826152
  • Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. Pubmed: 14681860
  • Buhlmann P, Hayakawa M, Ohshiro T, Amemiya S, Umezawa Y: Influence of natural, electrically neutral lipids on the potentiometric responses of cation-selective polymeric membrane electrodes. Anal Chem. 2001 Jul 15;73(14):3199-205. Pubmed: 11476216
  • Cork A, Park KC: Identification of electrophysiologically-active compounds for the malaria mosquito, Anopheles gambiae, in human sweat extracts. Med Vet Entomol. 1996 Jul;10(3):269-76. Pubmed: 8887339
  • Dills RL, Bellamy GM, Kalman DA: Quantitation of o-, m- and p-cresol and deuterated analogs in human urine by gas chromatography with electron capture detection. J Chromatogr B Biomed Sci Appl. 1997 Dec 5;703(1-2):105-13. Pubmed: 9448067
  • Geyer H, Scheunert I, Korte F: Bioconcentration potential of organic environmental chemicals in humans. Regul Toxicol Pharmacol. 1986 Dec;6(4):313-47. Pubmed: 3101145
  • Gostner A, Blaut M, Schaffer V, Kozianowski G, Theis S, Klingeberg M, Dombrowski Y, Martin D, Ehrhardt S, Taras D, Schwiertz A, Kleessen B, Luhrs H, Schauber J, Dorbath D, Menzel T, Scheppach W: Effect of isomalt consumption on faecal microflora and colonic metabolism in healthy volunteers. Br J Nutr. 2006 Jan;95(1):40-50. Pubmed: 16441915
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Letelier ME, Rodriguez E, Wallace A, Lorca M, Repetto Y, Morello A, Aldunate J: Trypanosoma cruzi: a possible control of transfusion-induced Chagas' disease by phenolic antioxidants. Exp Parasitol. 1990 Nov;71(4):357-63. Pubmed: 2121515
  • Nishiyama T, Ohnishi J, Hashiguchi Y: Fused heterocyclic antioxidants: antioxidative activities of hydrocoumarins in a homogeneous solution. Biosci Biotechnol Biochem. 2001 May;65(5):1127-33. Pubmed: 11440127
  • Ogata N, Shibata T: Binding of alkyl- and alkoxy-substituted simple phenolic compounds to human serum proteins. Res Commun Mol Pathol Pharmacol. 2000;107(1-2):167-73. Pubmed: 11334365
  • Vanholder, R., De Smet, R., Lesaffer, G. (1999). "p-cresol: a toxin revealing many neglected but relevant aspects of uraemic toxicity." Nephrol Dial Transplant 14:2813-2815. Pubmed: 10570076
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17847
HMDB IDHMDB01858
Pubchem Compound ID2879
Kegg IDC01468
ChemSpider ID13839082
WikipediaP-Cresol
BioCyc IDCPD-108
EcoCyc IDCPD-108
Ligand ExpoPCR

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the rearrangement of 1-deoxy-D-xylulose 5- phosphate (DXP) to produce the thiazole phosphate moiety of thiamine. Sulfur is provided by the thiocarboxylate moiety of the carrier protein ThiS. In vitro, sulfur can be provided by H(2)S
Gene Name:
thiG
Uniprot ID:
P30139
Molecular weight:
26896
Reactions
1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS] = 2-((2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + [sulfur-carrier protein ThiS] + 2 H(2)O.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the radical-mediated cleavage of tyrosine to dehydroglycine and p-cresol
Gene Name:
thiH
Uniprot ID:
P30140
Molecular weight:
43320
Reactions
L-tyrosine + S-adenosyl-L-methionine + reduced acceptor = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H(+).