Showing Compound Card for p-Cresol (CDB005788)

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Record Information
Version1.0
Created at2020-04-27 16:56:38 UTC
Updated at2021-01-05 16:44:23 UTC
CannabisDB IDCDB005788
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namep-Cresol
Descriptionp-Cresol, also known as 4-methylphenol or para-Cresol, 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. Three isomers of cresol are known, including o-Cresol, m-Cresol and p-Cresol which differ in the position of the methyl group relative to the hydroxyl groups, on the phenol ring. p-Cresol exists as a colorless to white crystals. It is moderately soluble in water and has a strong phenolic, floral, narcissus or mimosa-like odor and a phenolic, tarry or barnyard taste. Industrially p-Cresol can be extracted from coal tar (the volatilized materials obtained in the roasting of coal to produce coke) and petroleum residues. p-Cresol is used in the production of antioxidants such as butylated hydroxytoluene (BHT). In the cosmetic industry p-Cresol is used as an antimicrobial agent and a perfuming agent. Cresols, such as p-Cresol are strong germicides, and in low concentrations they are effective disinfectants and antiseptics. Cresol solutions are used as household cleaners and disinfectants, perhaps most famously under the trade name Lysol. They are also used in low concentrations in sheep-dips (disinfectants often containing insecticides and pesticides). p-Cresol is an important component of creosote, a wood preservative produced as a by-product of coal tar distillation. Cresols give creosote its antibacterial and insecticidal properties, as well as its toxicity and its ability to irritate bare skin. Most exposures to cresols are at very low levels that are not harmful. When cresols are inhaled, 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. p-Cresol is also naturally produced at low levels and can be found in almost all organisms from bacteria to plants to humans. In mammals, p-Cresol is a well-known end-product of protein breakdown, i.e. the bacterial fermentation of protein in the large intestine. An increase of the nutritional protein load in healthy individuals results in enhanced generation and urinary excretion of p-Cresol and its conjugates. More specifically, p-Cresol is derived from the breakdown of the amino acid tyrosine, and to a more limited extent phenylalanine, which are both converted to 4-hydroxyphenylacetic acid by intestinal bacteria, before being decarboxylated to p-cresol (putrefaction). The main contributing bacteria to this gut fermentation process are aerobes (mainly enterobacteria), but to a certain extent also anaerobes play a role (mainly Clostridium perfringens). Because p-Cresol is not very water soluble, it is further metabolized through conjugation, mainly sulfation and glucuronidation, and secreted in the urine as p-Cresol-sulfate or p-Cresol-glucuronide. p-Cresol is also secreted (unconjugated) in feces. Indeed, p-Cresol has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230 ). Because of its lipophilicity, p-Cresol strongly binds to plasma proteins such as serum albumin (close to 100%) under normal conditions. p-Cresol is a uremic toxin. Uremic toxins are small molecule toxins that are endogenously produced by the body and which accumulate in the body contribute to the symptoms of uremia. As a toxin, p-Cresol inhibits phagocyte function, decreases leukocyte adhesion to cytokine-stimulated endothelial cells and is known to be involved in the progression of renal failure (PMID: 14681860 ). p-Cresol has been reported to affect several other biochemical, biological and physiological functions: (i) it diminishes the oxygen uptake of rat cerebral cortex slices; (ii) it increases the free active drug concentration of warfarin and diazepam; (iii) it has been related to growth retardation in the weanling pig; (iv) it alters cell membrane permeability, at least in bacteria; (v) it induces LDH leakage from rat liver slices; (vi) it induces susceptibility to auditive epileptic crises; and (vii) it blocks cell K+ channels. (PMID: 10570076 ). Patients suffering from uremia or kidney failure have high serum p-Cresol concentrations. The serum p-cresol concentration in uremic patients can be decreased by changing to a low-protein diet. p-Cresol can also be partially removed by peritoneal dialysis in haemodialysis patients (PMID: 11169029 ). Likewise, the administration of antibiotics can reduce the production and urinary excretion of p-Cresol, as a result of the elimination of p-Cresol producing bacteria (Bacteroides, Bifidobacterium, Clostridium, Enterobacter and Lactobacillus (PMID: 2394806 ; PMID: 30208103 )). p-Cresol can also appear in the body due to exposure to toluene (inhalation or skin exposure). Liver cytochrome P450 enzymes metabolize toluene to benzyl alcohol, but also to o-Cresol and p-Cresol. Furthermore, p-Cresol is a known metabolite of menthofuran and wood tar creosote, both of which are used in certain traditional medicines. p-Cresol is also naturally present in a number of plants and plant foods. Among plants, p-Cresol has been detected in almonds, anise, asparagus, blueberries, bilberries, sour cherries, coffee, jasmin, mustard, olive oil, bell peppers, peppermint, raspberries, tamarind and tea. p-Cresol is a known constituent of automobile exhaust, fires and tobacco smoke (PMID 21556207 ) and is a major component of pig odor. It is also an insect pheromone and a known attractant for the orchid bee (doi:10.2307/1541248). p-Cresol is also a key component of human sweat that attracts female mosquitoes (PMID 14724626 ). p-Cresol is one of several phenolic compounds found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-4-methylbenzeneChEBI
4-CresolChEBI
4-HydroxytolueneChEBI
4-MethylphenolChEBI
p-KresolChEBI
p-MethylphenolChEBI
p-Tolyl alcoholChEBI
ParacresolChEBI
1-Methyl-4-hydroxybenzeneHMDB
4-(Pentafluorosulfanyl)phenolHMDB
4-Methyl phenolHMDB
4-Methyl-phenolHMDB
P-CresylateHMDB
P-Cresylic acidHMDB
P-HydroxytolueneHMDB
P-Methyl phenolHMDB
P-MethylhydroxybenzeneHMDB
P-OxytolueneHMDB
P-ToluolHMDB
Paramethyl phenolHMDB
4-Cresol, potassium saltMeSH, HMDB
m-CresolMeSH, HMDB
4-Cresol, aluminum saltMeSH, HMDB
4-Cresol, sodium saltMeSH, HMDB
Para-cresolMeSH, HMDB
Chemical FormulaC7H8O
Average Molecular Weight108.14
Monoisotopic Molecular Weight108.0575
IUPAC Name4-methylphenol
Traditional NameP-cresol
CAS Registry Number106-44-5
SMILES
CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
InChI KeyIWDCLRJOBJJRNH-UHFFFAOYSA-N
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point35.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.5 mg/mL at 25 °CNot Available
logP1.94HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4i-6900000000-729e6f5bdb0da3ed9ded2014-09-20View Spectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-1d2bdfde621a5af9be73Spectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-b76093f53701327ab25fSpectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-7d25deb1e39c6ef4866fSpectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-15d473146e11e4b049b2Spectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-014l-4900000000-14fef90a661a09457976Spectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-1d2bdfde621a5af9be73Spectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-5900000000-b76093f53701327ab25fSpectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-4900000000-7d25deb1e39c6ef4866fSpectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-0a4i-7900000000-15d473146e11e4b049b2Spectrum
GC-MSp-Cresol, non-derivatized, GC-MS Spectrumsplash10-014l-4900000000-14fef90a661a09457976Spectrum
Predicted GC-MSp-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-6900000000-27534de20ade11dd5454Spectrum
Predicted GC-MSp-Cresol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06fr-9700000000-f41dd95ca553de6bafffSpectrum
Predicted GC-MSp-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSp-Cresol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-5900000000-ab55ada5cae0538f383e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-385a7a99e0409c7f060d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-02tl-9000000000-205f4e5245868e9debcc2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positivesplash10-0a4i-5900000000-fd438231ac0ed75fdf092012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0a4i-5900000000-b76093f53701327ab25f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-D-3000) , Positivesplash10-0a4i-4900000000-7d25deb1e39c6ef4866f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0a4i-7900000000-0cdab17a1a95f3e65f452012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - NA 35V, negativesplash10-0a6u-9600000000-276b44cbbdb079cac7182020-07-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-cf0bed2b3a203309d9aa2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-4f20c8bd2dde845b499c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9100000000-393b5f734646352622f92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-0c45920f40546c2d89442016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-417774c01b748db1609d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-5583b6dc3ae583b8dab02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-6eb0884733967edc9e6b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-621936189d60e194cefd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056u-9100000000-2740c99af64b11309dfb2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-1c2034d922354f5d66822021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001858
DrugBank IDDB01688
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008789
KNApSAcK IDC00002645
Chemspider ID13839082
KEGG Compound IDC01468
BioCyc IDCPD-108
BiGG IDNot Available
Wikipedia LinkP-cresol
METLIN ID4236
PubChem Compound2879
PDB IDNot Available
ChEBI ID17847
References
General References
  1. Patel M, Fowler D, Sizer J, Walton C: Faecal volatile biomarkers of Clostridium difficile infection. PLoS One. 2019 Apr 15;14(4):e0215256. doi: 10.1371/journal.pone.0215256. eCollection 2019. [PubMed:30986230 ]
  2. Brunet P, Dou L, Cerini C, Berland Y: Protein-bound uremic retention solutes. Adv Ren Replace Ther. 2003 Oct;10(4):310-20. doi: 10.1053/j.arrt.2003.08.002. [PubMed:14681860 ]
  3. Vanholder R, De Smet R, Lesaffer G: p-cresol: a toxin revealing many neglected but relevant aspects of uraemic toxicity. Nephrol Dial Transplant. 1999 Dec;14(12):2813-5. doi: 10.1093/ndt/14.12.2813. [PubMed:10570076 ]
  4. Lameire N, Vanholder R, De Smet R: Uremic toxins and peritoneal dialysis. Kidney Int Suppl. 2001 Feb;78:S292-7. doi: 10.1046/j.1523-1755.2001.59780292.x. [PubMed:11169029 ]
  5. Sivsammye G, Sims HV: Presumptive identification of Clostridium difficile by detection of p-cresol in prepared peptone yeast glucose broth supplemented with p-hydroxyphenylacetic acid. J Clin Microbiol. 1990 Aug;28(8):1851-3. doi: 10.1128/JCM.28.8.1851-1853.1990. [PubMed:2394806 ]
  6. Passmore IJ, Letertre MPM, Preston MD, Bianconi I, Harrison MA, Nasher F, Kaur H, Hong HA, Baines SD, Cutting SM, Swann JR, Wren BW, Dawson LF: Para-cresol production by Clostridium difficile affects microbial diversity and membrane integrity of Gram-negative bacteria. PLoS Pathog. 2018 Sep 12;14(9):e1007191. doi: 10.1371/journal.ppat.1007191. eCollection 2018 Sep. [PubMed:30208103 ]
  7. Talhout R, Schulz T, Florek E, van Benthem J, Wester P, Opperhuizen A: Hazardous compounds in tobacco smoke. Int J Environ Res Public Health. 2011 Feb;8(2):613-28. doi: 10.3390/ijerph8020613. Epub 2011 Feb 23. [PubMed:21556207 ]
  8. Hallem EA, Nicole Fox A, Zwiebel LJ, Carlson JR: Olfaction: mosquito receptor for human-sweat odorant. Nature. 2004 Jan 15;427(6971):212-3. doi: 10.1038/427212a. [PubMed:14724626 ]