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Showing NP-Card for 4-Hydroxy-3-methylbenzoic acid (NP0000473)

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Record Information
Version1.0
Created at2006-08-24 12:35:05 UTC
Updated at2024-05-09 16:25:40 UTC
NP-MRD IDNP0000473
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Hydroxy-3-methylbenzoic acid
Description4-Hydroxy-3-methylbenzoic acid, also known as 4,3-cresotic acid or 4-hydroxy-m-toluic acid, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and hydroxyl groups.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

Untitled Document-1
  Mrv1652305261923592D          

 11 11  0  0  0  0            999 V2000
   -1.4437   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563   -0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  2  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

HMDB0004815
     RDKit          3D
4-Hydroxy-3-methylbenzoic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.2047   -1.4174   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0776   -0.4391   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -0.8255    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.0440    0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592   -0.4405    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8712   -1.6527    0.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    0.4165    0.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    1.3924   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674    1.8014   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    0.8978   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958    1.3431   -0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -1.5444   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242   -2.4083    0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.0837    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4440   -1.8686    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    0.1908    0.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    2.0655   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    2.8560   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491    0.6726   -0.4971 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  1  0
  5  6  2  0
  5  7  1  0
  4  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

Untitled Document-1
  Mrv1652305261923592D          

 11 11  0  0  0  0            999 V2000
   -1.4437   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6187   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2062   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563   -1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8563    0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0313    1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8563   -0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  7  1  0  0  0  0
  2  7  2  0  0  0  0
  1  8  2  0  0  0  0
  1  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=CC=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
LTFHNKUKQYVHDX-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.012770305365652

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-3-methylbenzoic acid

> <ALOGPS_LOGP>
1.86

> <JCHEM_LOGP>
1.8406847916666664

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.030048480614669

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.383307033592636

> <JCHEM_PKA_STRONGEST_BASIC>
-6.048238962650697

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
40.3363

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.52e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-methylbenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

HMDB0004815
     RDKit          3D
4-Hydroxy-3-methylbenzoic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
   -2.2047   -1.4174   -0.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0776   -0.4391   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292   -0.8255    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3111    0.0440    0.1241 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592   -0.4405    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8712   -1.6527    0.5332 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7342    0.4165    0.3525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0329    1.3924   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2674    1.8014   -0.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    0.8978   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5958    1.3431   -0.5011 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -1.5444   -1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8242   -2.4083    0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.0837    0.6082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4440   -1.8686    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5828    0.1908    0.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    2.0655   -0.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4313    2.8560   -0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3491    0.6726   -0.4971 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  1  0
  5  6  2  0
  5  7  1  0
  4  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10  2  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-1                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.695  -0.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.155  -0.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.385   0.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.155   0.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.925  -0.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.155  -2.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.385  -2.001   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.465  -2.001   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.465   0.667   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.925   2.001   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.465  -0.667   0.000  0.00  0.00           O+0
CONECT    1    2    8    9                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10    4                                                            
CONECT   11    5                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

COMPND    HMDB0004815
HETATM    1  C1  UNL     1      -2.205  -1.417  -0.083  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.078  -0.439  -0.085  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.229  -0.825   0.117  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.311   0.044   0.124  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.659  -0.441   0.345  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.871  -1.653   0.533  1.00  0.00           O  
HETATM    7  O2  UNL     1       3.734   0.417   0.353  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.033   1.392  -0.090  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.267   1.801  -0.295  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.312   0.898  -0.293  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.596   1.343  -0.501  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.662  -1.544  -1.074  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.824  -2.408   0.264  1.00  0.00           H  
HETATM   14  H3  UNL     1      -3.013  -1.084   0.608  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.444  -1.869   0.283  1.00  0.00           H  
HETATM   16  H5  UNL     1       4.583   0.191   0.834  1.00  0.00           H  
HETATM   17  H6  UNL     1       1.872   2.065  -0.085  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.431   2.856  -0.457  1.00  0.00           H  
HETATM   19  H8  UNL     1      -3.349   0.673  -0.497  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    3   10
CONECT    3    4   15
CONECT    4    5    8    8
CONECT    5    6    6    7
CONECT    7   16
CONECT    8    9   17
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   19
END
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SMILES for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

CC1=CC(=CC=C1O)C(O)=O
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INCHI for NP0000473 (4-Hydroxy-3-methylbenzoic acid)

InChI=1S/C8H8O3/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4,9H,1H3,(H,10,11)
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View in JSmol
Synonyms
ValueSource
4,3-Cresotic acidChEBI
4-Hydroxy-m-toluic acidChEBI
4,3-CresotateGenerator
4-Hydroxy-m-toluateGenerator
4-Hydroxy-3-methylbenzoateGenerator
3-Methyl-4-hydroxybenzoateHMDB
3-Methyl-4-hydroxybenzoic acidHMDB
4-Hydroxy-3-methyl-benzoateHMDB
4-Hydroxy-3-methyl-benzoic acidHMDB
4-Hydroxy-3-methoxybenzoic acidHMDB
Vanillic acidHMDB
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name4-hydroxy-3-methylbenzoic acid
Traditional Name4-hydroxy-3-methylbenzoic acid
CAS Registry Number499-76-3
SMILES
CC1=CC(=CC=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-5-4-6(8(10)11)2-3-7(5)9/h2-4,9H,1H3,(H,10,11)
InChI KeyLTFHNKUKQYVHDX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D_DEPT NMR13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
1D NMR[13C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-19View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-19View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-19View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-19View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-19View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201.216488466 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)BgnzkMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-10View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-08-10View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Euphorbia fischerianaLOTUS Database
Gallus gallusFooDB
Incarvillea delavayiLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • O-cresol
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mL at 100 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.52 g/LALOGPS
logP1.86ALOGPS
logP1.84ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.34 m³·mol⁻¹ChemAxon
Polarizability15.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004815
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023425
KNApSAcK IDNot Available
Chemspider ID61446
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68138
PDB IDNot Available
ChEBI ID85239
Good Scents IDNot Available
References
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Chen YF, Chao H, Zhou NY: The catabolism of 2,4-xylenol and p-cresol share the enzymes for the oxidation of para-methyl group in Pseudomonas putida NCIMB 9866. Appl Microbiol Biotechnol. 2014 Feb;98(3):1349-56. doi: 10.1007/s00253-013-5001-z. Epub 2013 Jun 5. [PubMed:23736872 ]
  3. Jobelius C, Frimmel FH, Zwiener C: Mass spectrometric screening and identification of acidic metabolites in fulvic acid fractions of contaminated groundwater. Anal Bioanal Chem. 2014 May;406(14):3415-29. doi: 10.1007/s00216-014-7783-y. Epub 2014 Apr 9. [PubMed:24714970 ]
  4. Hedbavna P, Rolfe SA, Huang WE, Thornton SF: Biodegradation of phenolic compounds and their metabolites in contaminated groundwater using microbial fuel cells. Bioresour Technol. 2016 Jan;200:426-34. doi: 10.1016/j.biortech.2015.09.092. Epub 2015 Nov 11. [PubMed:26512868 ]
  5. Viggor S, Heinaru E, Loponen J, Merimaa M, Tenno T, Heinaru A: Biodegradation of dimethylphenols by bacteria with different ring-cleavage pathways of phenolic compounds. Environ Sci Pollut Res Int. 2002;Spec No 1:19-26. doi: 10.1007/BF02987421. [PubMed:12638744 ]
  6. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
  7. Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:28876831 ]
  8. Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
  9. Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]
  10. Authors unspecified: Testicular Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389404 ]
  11. Authors unspecified: Rectal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389402 ]