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Showing metabocard for p-Cresol (HMDB0001858)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-22 10:50:16 UTC
Update Date2023-02-21 17:15:50 UTC
HMDB IDHMDB0001858
Secondary Accession Numbers
  • HMDB0013762
  • HMDB01858
  • HMDB13762
Metabolite Identification
Common Namep-Cresol
Descriptionpara-Cresol, also 4-methylphenol, is an organic compound with the formula CH3C6H4(OH). P-cresol is a cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals. It has a role as a uremic toxin, a human metabolite and an Escherichia coli metabolite. It is a colourless solid that is widely used intermediate in the production of other chemicals. It is a derivative of phenol and is an isomer of o-cresol and m-cresol. It is a partially lipophilic moiety which strongly binds to plasma protein (close to 100%) under normal conditions. p-Cresol is metabolized through conjugation, mainly sulphation and glucuronization, but removal of the unconjugated p-cresol is, at least in part, via the urine. Therefore it is not surprising that this compound, together with several other phenoles, is retained when the kidneys fail. P-Cresol is an end-product of protein breakdown, and an increase of the nutritional protein load in healthy individuals results in enhanced generation and urinary excretion. The serum p-cresol concentration in uremic patients can be decreased by changing to a low-protein diet. 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). In uremia, modifications in the intestinal flora result in the specific overgrowth of bacteria that are specific p-cresol producers. The administration of antibiotics reduces urinary excretion of p-cresol, as a result of the liquidation of the producing bacteria. Environmental factors might also contribute. The liver cytochrome P450 metabolizes toluene to benzyl alcohol, but also to o-cresol and p-cresol. Toluene is not only used industrially, but it is also the most widely abusively inhaled solvent. Furthermore, p-cresol is a metabolite of menthofuran, one of the metabolites of R-(+)-pulegone, which is found in extracts from the plants Mentha pulegium and Hedeoma pulegioides, commonly known as pennyroyal oil and pennyroyal tea. These extracts are popular as unconventional herbal therapeutic agents and are applied as abortiva, diaphoretics, emmenagogues, and psychedelic drugs. Pennyroyal oil is extensively used for its pleasant mint-like smell in the flavoring industry. The toxicity of pennyroyal oil and menthofuran is well known. Another compound used in traditional medicine, especially in Japan, which is a precursor of p-cresol is wood tar creosote. p-Cresol has been reported to affect several 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 ). p-Cresol is a uremic toxin that is at least partially removed by peritoneal dialysis in haemodialysis patients, and has been involved in the progression of renal failure (PMID:11169029 ). At concentrations encountered during uremia, p-cresol inhibits phagocyte function and decreases leukocyte adhesion to cytokine-stimulated endothelial cells. (PMID:14681860 ). p-Cresol can be found in Bacteroides, Bifidobacterium, Clostridium, Enterobacter and Lactobacillus (PMID:2394806 ; PMID:30208103 ). As a volatile organic compound, it has been identified as a fecal biomarker of Clostridium difficile infection (PMID:30986230 ).
Structure
Data?1676999750
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001858 (p-Cresol)


  Mrv1652309272007362D          

  8  8  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    0.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0001858 (p-Cresol)

HMDB0001858
     RDKit          3D
p-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.4917    0.0122   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.0026   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -1.1791   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004   -1.1644   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    0.0083   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.0251    0.0037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.1759    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1789    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257   -0.8254   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842    1.0063   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -0.1906    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -2.1089   -0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -2.0960   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6584   -0.0457    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    2.0913    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    2.1146    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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3D SDF for HMDB0001858 (p-Cresol)


  Mrv1652309272007362D          

  8  8  0  0  0  0            999 V2000
    0.5801    1.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5801    0.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    0.6918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2946    1.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0092    1.9294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482    0.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  1  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001858

> <DATABASE_NAME>
hmdb

> <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_KEY>
IWDCLRJOBJJRNH-UHFFFAOYSA-N

> <FORMULA>
C7H8O

> <MOLECULAR_WEIGHT>
108.1378

> <EXACT_MASS>
108.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
11.926991180769898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylphenol

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.1831018836666667

> <ALOGPS_LOGS>
-0.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.357335371423924

> <JCHEM_PKA_STRONGEST_BASIC>
-5.436049745016864

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
33.0801

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-cresol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0001858 (p-Cresol)

HMDB0001858
     RDKit          3D
p-Cresol
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.4917    0.0122   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.0026   -0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -1.1791   -0.1632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004   -1.1644   -0.1355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8225    0.0083   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2196    0.0251    0.0037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0871    1.1759    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2912    1.1789    0.0319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8257   -0.8254   -0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7842    1.0063   -0.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8746   -0.1906    0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -2.1089   -0.2507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6608   -2.0960   -0.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6584   -0.0457    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6601    2.0913    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8383    2.1146    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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PDB for HMDB0001858 (p-Cresol)

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       1.083   3.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.250   2.832   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.250   1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.083   0.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.417   1.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.417   2.832   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.750   3.602   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.583   0.522   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0001858 (p-Cresol)

COMPND    HMDB0001858
HETATM    1  C1  UNL     1       2.492   0.012  -0.107  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.996  -0.003  -0.080  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.280  -1.179  -0.163  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.100  -1.164  -0.135  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.823   0.008  -0.024  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.220   0.025   0.004  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.087   1.176   0.058  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.291   1.179   0.032  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.826  -0.825  -0.754  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.784   1.006  -0.484  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.875  -0.191   0.927  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.828  -2.109  -0.251  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.661  -2.096  -0.202  1.00  0.00           H  
HETATM   14  H6  UNL     1      -3.658  -0.046   0.935  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.660   2.091   0.145  1.00  0.00           H  
HETATM   16  H8  UNL     1       0.838   2.115   0.099  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    8
CONECT    3    4   12
CONECT    4    5    5   13
CONECT    5    6    7
CONECT    6   14
CONECT    7    8    8   15
CONECT    8   16
END
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SMILES for HMDB0001858 (p-Cresol)

CC1=CC=C(O)C=C1
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INCHI for HMDB0001858 (p-Cresol)

InChI=1S/C7H8O/c1-6-2-4-7(8)5-3-6/h2-5,8H,1H3
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View in JSmolView Stereo Labels
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 Weight108.1378
Monoisotopic Molecular Weight108.057514878
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 effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Indirect biological roleEnvironmental roleBiological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point35.5 °CNot Available
Boiling Point201.80 to 202.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility21.5 mg/mL at 25 °CNot Available
LogP1.94HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+121.79631661259
DarkChem[M-H]-118.99531661259
AllCCS[M+H]+119.13532859911
AllCCS[M-H]-118.72332859911
DeepCCS[M+H]+123.03430932474
DeepCCS[M-H]-119.75330932474
DeepCCS[M-2H]-156.56630932474
DeepCCS[M+Na]+131.65730932474
AllCCS[M+H]+119.132859911
AllCCS[M+H-H2O]+114.132859911
AllCCS[M+NH4]+123.932859911
AllCCS[M+Na]+125.232859911
AllCCS[M-H]-118.732859911
AllCCS[M+Na-2H]-121.232859911
AllCCS[M+HCOO]-124.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
p-CresolCC1=CC=C(O)C=C12029.4Standard polar33892256
p-CresolCC1=CC=C(O)C=C11044.3Standard non polar33892256
p-CresolCC1=CC=C(O)C=C11057.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
p-Cresol,1TMS,isomer #1CC1=CC=C(O[Si](C)(C)C)C=C11147.5Semi standard non polar33892256
p-Cresol,1TBDMS,isomer #1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11374.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-5900000000-1d2bdfde621a5af9be732017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-5900000000-b76093f53701327ab25f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-4900000000-7d25deb1e39c6ef4866f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-7900000000-15d473146e11e4b049b22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol GC-EI-TOF (Non-derivatized)splash10-014l-4900000000-14fef90a661a094579762017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-5900000000-1d2bdfde621a5af9be732018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-5900000000-b76093f53701327ab25f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-4900000000-7d25deb1e39c6ef4866f2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol EI-B (Non-derivatized)splash10-0a4i-7900000000-15d473146e11e4b049b22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - p-Cresol GC-EI-TOF (Non-derivatized)splash10-014l-4900000000-14fef90a661a094579762018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cresol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6900000000-27534de20ade11dd54542016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cresol GC-MS (1 TMS) - 70eV, Positivesplash10-06fr-9700000000-f41dd95ca553de6bafff2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cresol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - p-Cresol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4i-6900000000-729e6f5bdb0da3ed9ded2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a4i-5900000000-ab55ada5cae0538f383e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0006-9000000000-385a7a99e0409c7f060d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-02tl-9000000000-205f4e5245868e9debcc2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol EI-B (VARIAN MAT-44) , Positive-QTOFsplash10-0a4i-5900000000-fd438231ac0ed75fdf092012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0a4i-5900000000-b76093f53701327ab25f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol EI-B (JEOL JMS-D-3000) , Positive-QTOFsplash10-0a4i-4900000000-7d25deb1e39c6ef4866f2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0a4i-7900000000-0cdab17a1a95f3e65f452012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - p-Cresol NA 35V, negative-QTOFsplash10-0a6u-9600000000-276b44cbbdb079cac7182020-07-21HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 10V, Positive-QTOFsplash10-0a4i-0900000000-cf0bed2b3a203309d9aa2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 20V, Positive-QTOFsplash10-0a4i-1900000000-4f20c8bd2dde845b499c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 40V, Positive-QTOFsplash10-0fb9-9100000000-393b5f734646352622f92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 10V, Negative-QTOFsplash10-0a4i-0900000000-0c45920f40546c2d89442016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 20V, Negative-QTOFsplash10-0a4i-0900000000-417774c01b748db1609d2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 40V, Negative-QTOFsplash10-0a4i-9600000000-5583b6dc3ae583b8dab02016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 10V, Negative-QTOFsplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 20V, Negative-QTOFsplash10-0a4i-0900000000-3f09649991cc4cfcf1ec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 40V, Negative-QTOFsplash10-0006-9000000000-6eb0884733967edc9e6b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 10V, Positive-QTOFsplash10-0a4i-3900000000-621936189d60e194cefd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 20V, Positive-QTOFsplash10-056u-9100000000-2740c99af64b11309dfb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - p-Cresol 40V, Positive-QTOFsplash10-00kf-9000000000-1c2034d922354f5d66822021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodDetected and Quantified5.556 +/- 9.259 uMAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified720500.448-3063806.859 nmol/g wet fecesChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified72595.645 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal		 details
FecesDetected and Quantified41363.889 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified52827.658 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified136.585 +/- 69.263 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified95.249 +/- 98.948 nmol/g wet fecesNot SpecifiedNot Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified17.6 umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified24.7 (1.2-110.7) umol/mmol creatinineChildren (1-13 years old)Both
Normal		 details
UrineDetected and Quantified46.0 (1.2-118.9) umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified23.0 (11.4-114.0) umol/mmol creatinineAdolescent (13-18 years old)Both
Normal		 details
UrineDetected and Quantified0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected and Quantified52.6 (38.8-71.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
 details
UrineDetected and Quantified2.933 +/- 2.099 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified9.9 +/- 5.1 uMAdult (>18 years old)BothHemodialysis details
BloodDetected and Quantified186.111 +/- 95.370 uMAdult (>18 years old)Both
Uremia		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection		 details
FecesDetected and Quantified0-3012051.907 nmol/g wet fecesChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) non progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothImmunoglobulin A nephropathy (IgAN) progressor details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Intestinal infections		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Irritable bowel syndrome		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Clostridium difficile infection 		details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)Not Specified
Treated celiac disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Crohn's disease		 details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Ulcerative colitis		 details
FecesDetected and Quantified0.00197 (0.000166-0.00543) nmol/g wet fecesNot SpecifiedNot Specified
Irritable bowel syndrome		 details
FecesDetected and Quantified0.00204 (0.00108-0.00888) nmol/g wet fecesNot SpecifiedNot Specified
Ulcerative colitis		 details
FecesDetected and Quantified0.00461 (0.00106-0.0113) nmol/g wet fecesNot SpecifiedNot Specified
Crohns disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS		 details
UrineDetected and Quantified5.14 +/- 2.998 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. De Smet R, Van Kaer J, Liebich H, Lesaffer G, Verstraete A, Dhondt A, Duym P, Lameire N, Vanholder R: Heparin-induced release of protein-bound solutes during hemodialysis is an in vitro artifact. Clin Chem. 2001 May;47(5):901-9. [PubMed:11325895 ]
Uremia
  1. Vanholder R, De Smet R, Glorieux G, Argiles A, Baurmeister U, Brunet P, Clark W, Cohen G, De Deyn PP, Deppisch R, Descamps-Latscha B, Henle T, Jorres A, Lemke HD, Massy ZA, Passlick-Deetjen J, Rodriguez M, Stegmayr B, Stenvinkel P, Tetta C, Wanner C, Zidek W: Review on uremic toxins: classification, concentration, and interindividual variability. Kidney Int. 2003 May;63(5):1934-43. doi: 10.1046/j.1523-1755.2003.00924.x. [PubMed:12675874 ]
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  3. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  4. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
  2. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
Celiac disease
  1. Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Crohn's disease
  1. Walton C, Fowler DP, Turner C, Jia W, Whitehead RN, Griffiths L, Dawson C, Waring RH, Ramsden DB, Cole JA, Cauchi M, Bessant C, Hunter JO: Analysis of volatile organic compounds of bacterial origin in chronic gastrointestinal diseases. Inflamm Bowel Dis. 2013 Sep;19(10):2069-78. doi: 10.1097/MIB.0b013e31829a91f6. [PubMed:23867873 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Enteritis
  1. Probert CS, Jones PR, Ratcliffe NM: A novel method for rapidly diagnosing the causes of diarrhoea. Gut. 2004 Jan;53(1):58-61. [PubMed:14684577 ]
Clostridium difficile infection
  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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Colorectal cancer
  1. Cheng Y, Xie G, Chen T, Qiu Y, Zou X, Zheng M, Tan B, Feng B, Dong T, He P, Zhao L, Zhao A, Xu LX, Zhang Y, Jia W: Distinct urinary metabolic profile of human colorectal cancer. J Proteome Res. 2012 Feb 3;11(2):1354-63. doi: 10.1021/pr201001a. Epub 2011 Dec 28. [PubMed:22148915 ]
  2. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  3. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDDB01688
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDPCRESOL
MarkerDB IDMDB00000347
Good Scents IDrw1003851
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. Lameire N, Vanholder R, De Smet R: Uremic toxins and peritoneal dialysis. Kidney Int Suppl. 2001 Feb;78:S292-7. [PubMed:11169029 ]
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