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Showing metabocard for 4-Methylcatechol (HMDB0000873)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:16 UTC
HMDB IDHMDB0000873
Secondary Accession Numbers
  • HMDB00873
Metabolite Identification
Common Name4-Methylcatechol
Description4-Methylcatechol, also known as homocatechol or toluene-3,4-diol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Outside of the human body, 4-Methylcatechol is found, on average, in the highest concentration within a few different foods such as coffee and cocoa powders and in a lower concentration in beers. 4-Methylcatechol has also been detected, but not quantified in eggplants. This could make 4-methylcatechol a potential biomarker for the consumption of these foods. Recent studies have suggested that a lack of brain-derived neurotrophic factor (BDNF) in the limbic system may cause neuropathic pain (PMID:22198556 ). It is both a substrate and a suicide inhibitor of catechol 2,3-dioxygenase (PMID:15006807 ). 4-Methylcatechol is a metabolite of homoprotocatechuic acid (PMID:4974346 ). 4-Methylcatechol is known to induce the production of BDNF.
Structure
Data?1676999716
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000873 (4-Methylcatechol)


  Mrv1652304272019022D          

  9  9  0  0  0  0            999 V2000
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for HMDB0000873 (4-Methylcatechol)

HMDB0000873
     RDKit          3D
4-Methylcatechol
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.5524   -0.0888   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456   -0.1512    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.3767    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.3862    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652   -0.2169    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612   -0.2395    0.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0361    0.9980   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944    2.1753   -0.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.0199   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    0.4194   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -1.0895    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    0.5875    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -2.2641    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -2.3327    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -1.1052    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    3.0619   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    1.9890   -0.2634 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  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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3D SDF for HMDB0000873 (4-Methylcatechol)


  Mrv1652304272019022D          

  9  9  0  0  0  0            999 V2000
    0.8250    1.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  2  3  2  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000873

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3

> <INCHI_KEY>
ZBCATMYQYDCTIZ-UHFFFAOYSA-N

> <FORMULA>
C7H8O2

> <MOLECULAR_WEIGHT>
124.1372

> <EXACT_MASS>
124.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
12.819775304884702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methylbenzene-1,2-diol

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.8795365619999997

> <ALOGPS_LOGS>
-0.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.01183434905554

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.552176595160123

> <JCHEM_PKA_STRONGEST_BASIC>
-6.244242730605078

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
35.06099999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methyl-1,2-benzenediol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000873 (4-Methylcatechol)

HMDB0000873
     RDKit          3D
4-Methylcatechol
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.5524   -0.0888   -0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0456   -0.1512    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358   -1.3767    0.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9441   -1.3862    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652   -0.2169    0.0448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0612   -0.2395    0.0573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0361    0.9980   -0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7944    2.1753   -0.2701 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    1.0199   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    0.4194   -0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9873   -1.0895    0.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    0.5875    0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -2.2641    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4656   -2.3327    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5547   -1.1052    0.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3229    3.0619   -0.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8172    1.9890   -0.2634 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  1  0
  7  9  2  0
  9  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  6 15  1  0
  8 16  1  0
  9 17  1  0
M  END
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PDB for HMDB0000873 (4-Methylcatechol)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.540  -2.667   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.080   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    5    7                                                       
CONECT    5    1    2    4                                                  
CONECT    6    3    7    8                                                  
CONECT    7    4    6    9                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0000873 (4-Methylcatechol)

COMPND    HMDB0000873
HETATM    1  C1  UNL     1       2.552  -0.089  -0.001  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.046  -0.151   0.018  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.436  -1.377   0.183  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.944  -1.386   0.194  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.665  -0.217   0.045  1.00  0.00           C  
HETATM    6  O1  UNL     1      -3.061  -0.240   0.057  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.036   0.998  -0.120  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.794   2.175  -0.270  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.340   1.020  -0.132  1.00  0.00           C  
HETATM   10  H1  UNL     1       2.796   0.419  -0.975  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.987  -1.090   0.046  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.833   0.587   0.814  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.037  -2.264   0.296  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.466  -2.333   0.323  1.00  0.00           H  
HETATM   15  H6  UNL     1      -3.555  -1.105   0.175  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.323   3.062  -0.390  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.817   1.989  -0.263  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3    3    9
CONECT    3    4   13
CONECT    4    5    5   14
CONECT    5    6    7
CONECT    6   15
CONECT    7    8    9    9
CONECT    8   16
CONECT    9   17
END
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SMILES for HMDB0000873 (4-Methylcatechol)

CC1=CC(O)=C(O)C=C1
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INCHI for HMDB0000873 (4-Methylcatechol)

InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,2-Dihydroxy-4-methylbenzeneChEBI
2-Hydroxy-4-methylphenolChEBI
3,4-DihydroxytolueneChEBI
4-Methyl-1,2-benzenediolChEBI
4-Methyl-1,2-dihydroxybenzeneChEBI
4-MethylpyrocatecholChEBI
HomocatecholChEBI
HomopyrocatecholChEBI
p-MethylcatecholChEBI
p-MethylpyrocatecholChEBI
Toluene-3,4-diolChEBI
1-Methyl-3,4-dihydroxybenzeneHMDB
4-Methyl-pyrocatecholHMDB
4-MethylcateholHMDB
4-MetylcatecholHMDB
5-MethylcatecholHMDB
Chemical FormulaC7H8O2
Average Molecular Weight124.1372
Monoisotopic Molecular Weight124.0524295
IUPAC Name4-methylbenzene-1,2-diol
Traditional Name4-methyl-1,2-benzenediol
CAS Registry Number452-86-8
SMILES
CC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
InChI KeyZBCATMYQYDCTIZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • P-cresol
  • M-cresol
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling Point247.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility24900 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.37HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available121.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00002102
Predicted Molecular Properties
PropertyValueSource
Water Solubility37.9 g/LALOGPS
logP1.02ALOGPS
logP1.88ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m³·mol⁻¹ChemAxon
Polarizability12.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+125.96931661259
DarkChem[M-H]-122.57531661259
AllCCS[M+H]+124.25732859911
AllCCS[M-H]-121.58732859911
DeepCCS[M+H]+124.32830932474
DeepCCS[M-H]-120.49630932474
DeepCCS[M-2H]-157.7930932474
DeepCCS[M+Na]+133.3330932474
AllCCS[M+H]+124.332859911
AllCCS[M+H-H2O]+119.432859911
AllCCS[M+NH4]+128.832859911
AllCCS[M+Na]+130.132859911
AllCCS[M-H]-121.632859911
AllCCS[M+Na-2H]-123.632859911
AllCCS[M+HCOO]-125.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.21 minutes32390414
Predicted by Siyang on May 30, 202210.7149 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.11 minutes32390414

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethylcatecholCC1=CC=C(O)C(O)=C12692.8Standard polar33892256
4-MethylcatecholCC1=CC=C(O)C(O)=C11137.4Standard non polar33892256
4-MethylcatecholCC1=CC=C(O)C(O)=C11279.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methylcatechol,1TMS,isomer #1CC1=CC=C(O[Si](C)(C)C)C(O)=C11294.6Semi standard non polar33892256
4-Methylcatechol,1TMS,isomer #2CC1=CC=C(O)C(O[Si](C)(C)C)=C11288.2Semi standard non polar33892256
4-Methylcatechol,2TMS,isomer #1CC1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11366.3Semi standard non polar33892256
4-Methylcatechol,1TBDMS,isomer #1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C11539.6Semi standard non polar33892256
4-Methylcatechol,1TBDMS,isomer #2CC1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C11529.2Semi standard non polar33892256
4-Methylcatechol,2TBDMS,isomer #1CC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C11851.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Methylcatechol GC-EI-TOF (Non-derivatized)splash10-014i-1930000000-6225053efa0739efca3d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylcatechol GC-EI-TOF (Non-derivatized)splash10-014i-1930000000-6225053efa0739efca3d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-2d8d69f64905f6f9396e2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (2 TMS) - 70eV, Positivesplash10-0udj-3940000000-d5331c4c752130a850842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylcatechol GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0a6r-1900000000-9045a710867168d6cc512012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39ab2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39ab2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol , negative-QTOFsplash10-00di-0900000000-7db9fcc9e56ad8a390802017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 40V, Negative-QTOFsplash10-014j-9200000000-f6f538341319fcc5433b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOFsplash10-00di-0900000000-97cd131a887e2f8701862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 10V, Positive-QTOFsplash10-014i-9000000000-6981a2924f054e884c5c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 35V, Negative-QTOFsplash10-00di-0900000000-0aaf237b7039ed11a1d72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 40V, Positive-QTOFsplash10-0553-9000000000-fe5754c269058c591feb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 20V, Positive-QTOFsplash10-0006-9000000000-c1c0f17738a12823f96d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOFsplash10-00di-2900000000-e5f3b6d9329514c202a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOFsplash10-00di-1900000000-d5abc716689493ede24f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOFsplash10-00di-0900000000-6bd82a87c9fe3a5ac3f72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylcatechol 40V, Negative-QTOFsplash10-03dj-9000000000-5833215eaa6163ad44f42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Positive-QTOFsplash10-004i-0900000000-efa52ff0e22aa918c8322017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Positive-QTOFsplash10-004i-2900000000-1813508ce877db8f3b512017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 40V, Positive-QTOFsplash10-0v00-9200000000-42f7207a63d63607822f2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOFsplash10-00di-0900000000-965e88496dc55d1d3a082017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOFsplash10-00di-1900000000-528bea85898c5bbee9742017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 40V, Negative-QTOFsplash10-05fu-9400000000-25d222489152bbee48942017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Positive-QTOFsplash10-056r-2900000000-f83a6dc29f504d8a27ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Positive-QTOFsplash10-004i-9400000000-f09039303c5f740d5e992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 40V, Positive-QTOFsplash10-0gdi-9000000000-5a1ebbe40df7d21e329f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 10V, Negative-QTOFsplash10-00di-0900000000-ee9e9b8403f62cfc7fdf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylcatechol 20V, Negative-QTOFsplash10-00di-2900000000-5af433d114ee67df4fda2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)2022-02-11FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX 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+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 LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected and Quantified7.814 +/- 1.128 nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified14.339 nmol/g wet fecesAdult (>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
UrineDetected and Quantified1.8 +/- 1.2 umol/mmol creatinineAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified3.6 +/- 1.5 umol/mmol creatinineAdult (>18 years old)Male
Smoking		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Smoking
  1. Carmella SG, La Voie EJ, Hecht SS: Quantitative analysis of catechol and 4-methylcatechol in human urine. Food Chem Toxicol. 1982 Oct;20(5):587-90. [PubMed:6890513 ]
Associated OMIM IDs
DrugBank IDDB04120
Phenol Explorer Compound ID704
FooDB IDFDB008861
KNApSAcK IDC00002660
Chemspider ID9564
KEGG Compound IDC06730
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylcatechol
METLIN ID5834
PubChem Compound9958
PDB IDNot Available
ChEBI ID17254
Food Biomarker OntologyNot Available
VMH ID4MCAT
MarkerDB IDNot Available
Good Scents IDrw1205021
References
Synthesis ReferenceLiang, Zesheng; Zhang, Ying; Wu, Baojun; Zhang, Mingsen; Wang, Xiu'en. Preparation of 4-methylcatechol with good yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Baba S, Furuta T, Horie M, Nakagawa H: Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans. J Pharm Sci. 1981 Jul;70(7):780-2. [PubMed:7264927 ]
  2. Alanko J, Riutta A, Holm P, Mucha I, Vapaatalo H, Metsa-Ketela T: Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties. Free Radic Biol Med. 1999 Jan;26(1-2):193-201. [PubMed:9890654 ]
  3. Carmella SG, La Voie EJ, Hecht SS: Quantitative analysis of catechol and 4-methylcatechol in human urine. Food Chem Toxicol. 1982 Oct;20(5):587-90. [PubMed:6890513 ]
  4. Glasser G, Graefe EU, Struck F, Veit M, Gebhardt R: Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine. 2002 Jan;9(1):33-40. [PubMed:11924762 ]
  5. Ridder L, Briganti F, Boersma MG, Boeren S, Vis EH, Scozzafava A, Veeger C, Rietjens IM: Quantitative structure/activity relationship for the rate of conversion of C4-substituted catechols by catechol-1,2-dioxygenase from Pseudomonas putida (arvilla) C1. Eur J Biochem. 1998 Oct 1;257(1):92-100. [PubMed:9799107 ]
  6. Capasso R, Evidente A, Schivo L, Orru G, Marcialis MA, Cristinzio G: Antibacterial polyphenols from olive oil mill waste waters. J Appl Bacteriol. 1995 Oct;79(4):393-8. [PubMed:7592132 ]
  7. Okuta A, Ohnishi K, Harayama S: Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol. Appl Environ Microbiol. 2004 Mar;70(3):1804-10. [PubMed:15006807 ]
  8. Shen Y: In vitro cytotoxicity of BTEX metabolites in HeLa cells. Arch Environ Contam Toxicol. 1998 Apr;34(3):229-34. [PubMed:9504968 ]
  9. Graefe EU, Veit M: Urinary metabolites of flavonoids and hydroxycinnamic acids in humans after application of a crude extract from Equisetum arvense. Phytomedicine. 1999 Oct;6(4):239-46. [PubMed:10589442 ]
  10. Fukuhara K, Ishikawa K, Yasuda S, Kishishita Y, Kim HK, Kakeda T, Yamamoto M, Norii T, Ishikawa T: Intracerebroventricular 4-methylcatechol (4-MC) ameliorates chronic pain associated with depression-like behavior via induction of brain-derived neurotrophic factor (BDNF). Cell Mol Neurobiol. 2012 Aug;32(6):971-7. doi: 10.1007/s10571-011-9782-2. Epub 2011 Dec 25. [PubMed:22198556 ]
  11. Scheline RR: Drug metabolism by intestinal microorganisms. J Pharm Sci. 1968 Dec;57(12):2021-37. doi: 10.1002/jps.2600571202. [PubMed:4974346 ]