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Showing metabocard for Phthalic acid (HMDB0002107)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2023-02-21 17:16:10 UTC
HMDB IDHMDB0002107
Secondary Accession Numbers
  • HMDB02107
Metabolite Identification
Common NamePhthalic acid
DescriptionPhthalic acid is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. Phthalic acid is used mainly in the form of the anhydride to produce other chemicals such as dyes, perfumes, saccharin, phthalates and many other useful products. Phthalic acid, when found in tissues or biofluids arises from exposure to these phthalate products. Phthalate is an environmental chemical of heightened public concern because reports of its potential risk to male reproductive health (PMID 16804814 ), being significantly associated with reduced sperm concentration to pesticide concentration in men's urine (PMID 16804812 ). Within the reproductive tract, the male is exquisitely vulnerable to the effects of anti-androgens during development due the reliance on the synthesis and action of androgens for the masculinization of the male reproductive tract. The ability of phthalates to suppress androgen synthesis during development and to induce testicular dysgenesis together with cryptorchidism and hypospadias has raised considerable concern. (PMID 15016950 ).
Structure
Data?1676999770
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002107 (Phthalic acid)


  Mrv1652305271900262D          

 12 12  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
Download

3D MOL for HMDB0002107 (Phthalic acid)

HMDB0002107
     RDKit          3D
Phthalic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.4300   -0.7566    1.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -1.0456    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -2.3837    0.7835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795    0.0700    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664    1.3689    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113    2.4680    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    2.2685   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    1.0270   -0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5786   -0.1354   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -1.3968   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2797   -1.3956   -1.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -2.6355   -0.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -3.0155    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771    1.4573    1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    3.4949    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2812    3.1469   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713    0.8802   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223   -3.4173   -0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 12 18  1  0
M  END
Download

3D SDF for HMDB0002107 (Phthalic acid)


  Mrv1652305271900262D          

 12 12  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002107

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=CC=CC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)

> <INCHI_KEY>
XNGIFLGASWRNHJ-UHFFFAOYSA-N

> <FORMULA>
C8H6O4

> <MOLECULAR_WEIGHT>
166.1308

> <EXACT_MASS>
166.02660868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.944453060347534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzene-1,2-dicarboxylic acid

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.2884116319999999

> <ALOGPS_LOGS>
-1.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.488012703021749

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9412111090751636

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
40.5704

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phthalic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0002107 (Phthalic acid)

HMDB0002107
     RDKit          3D
Phthalic acid
 18 18  0  0  0  0  0  0  0  0999 V2000
    2.4300   -0.7566    1.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3465   -1.0456    0.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961   -2.3837    0.7835 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795    0.0700    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664    1.3689    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4113    2.4680    0.1484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7504    2.2685   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    1.0270   -0.8003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5786   -0.1354   -0.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1865   -1.3968   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2797   -1.3956   -1.3223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7471   -2.6355   -0.3308 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8703   -3.0155    0.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9771    1.4573    1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7875    3.4949    0.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2812    3.1469   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1713    0.8802   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3223   -3.4173   -0.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9  4  1  0
  3 13  1  0
  5 14  1  0
  6 15  1  0
  7 16  1  0
  8 17  1  0
 12 18  1  0
M  END
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PDB for HMDB0002107 (Phthalic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0002107 (Phthalic acid)

COMPND    HMDB0002107
HETATM    1  O1  UNL     1       2.430  -0.757   1.525  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.347  -1.046   0.877  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.096  -2.384   0.783  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.580   0.070   0.358  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.066   1.369   0.598  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.411   2.468   0.148  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.750   2.268  -0.552  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.248   1.027  -0.800  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.579  -0.135  -0.340  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.187  -1.397  -0.655  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.280  -1.396  -1.322  1.00  0.00           O  
HETATM   12  O4  UNL     1      -0.747  -2.636  -0.331  1.00  0.00           O  
HETATM   13  H1  UNL     1       1.870  -3.015   0.527  1.00  0.00           H  
HETATM   14  H2  UNL     1       1.977   1.457   1.150  1.00  0.00           H  
HETATM   15  H3  UNL     1       0.788   3.495   0.332  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.281   3.147  -0.915  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.171   0.880  -1.358  1.00  0.00           H  
HETATM   18  H6  UNL     1      -1.322  -3.417  -0.026  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   13
CONECT    4    5    5    9
CONECT    5    6   14
CONECT    6    7    7   15
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   18
END
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SMILES for HMDB0002107 (Phthalic acid)

OC(=O)C1=CC=CC=C1C(O)=O
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INCHI for HMDB0002107 (Phthalic acid)

InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1,2-Benzenedicarboxylic acidChEBI
O-Benzenedicarboxylic acidChEBI
Ortho-phthalic acidChEBI
O-Phthalic acidKegg
1,2-BenzenedicarboxylateGenerator
O-BenzenedicarboxylateGenerator
Ortho-phthalateGenerator
O-PhthalateGenerator
PhthalateGenerator
AlizarinateHMDB
Alizarinic acidHMDB
M 2HMDB
NaphthalinateHMDB
Naphthalinic acidHMDB
O-CarboxybenzoateHMDB
O-Carboxybenzoic acidHMDB
O-DicarboxybenzeneHMDB
PhthalinateHMDB
Phthalinic acidHMDB
Sunftal 20HMDB
Phthalic acid, dipotassium saltMeSH, HMDB
Phthalic acid, disodium saltMeSH, HMDB
Phthalic acid, monobarium saltMeSH, HMDB
Phthalic acid, monopotassium saltMeSH, HMDB
Phthalic acid, sodium saltMeSH, HMDB
Potassium hydrogen phthalateMeSH, HMDB
Phthalic acid, copper saltMeSH, HMDB
Phthalic acid, monocalcium saltMeSH, HMDB
Phthalic acid, monoruthenium saltMeSH, HMDB
Phthalic acid, potassium saltMeSH, HMDB
Phthalic acid, potassium, sodium saltMeSH, HMDB
Phthalic acid, monoiron (2+) saltMeSH, HMDB
Phthalic acid, monolead (2+) saltMeSH, HMDB
Phthalic acid, monosodium saltMeSH, HMDB
Phthalic acidGenerator
Disodium phthalateMeSH
Chemical FormulaC8H6O4
Average Molecular Weight166.1308
Monoisotopic Molecular Weight166.02660868
IUPAC Namebenzene-1,2-dicarboxylic acid
Traditional Namephthalic acid
CAS Registry Number88-99-3
SMILES
OC(=O)C1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C8H6O4/c9-7(10)5-3-1-2-4-6(5)8(11)12/h1-4H,(H,9,10)(H,11,12)
InChI KeyXNGIFLGASWRNHJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Dicarboxylic 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
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationEnvironmental role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point205 - 230 °CNot Available
Boiling Point132.00 to 133.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility7.01 mg/mL at 25 °CNot Available
LogP0.73HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.12 g/LALOGPS
logP1.22ALOGPS
logP1.29ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)2.94ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.57 m³·mol⁻¹ChemAxon
Polarizability14.94 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]+136.21931661259
DarkChem[M-H]-129.40331661259
DeepCCS[M+H]+133.88230932474
DeepCCS[M-H]-130.05430932474
DeepCCS[M-2H]-167.27630932474
DeepCCS[M+Na]+142.81530932474
AllCCS[M+H]+134.932859911
AllCCS[M+H-H2O]+130.532859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.232859911
AllCCS[M-H]-128.532859911
AllCCS[M+Na-2H]-129.532859911
AllCCS[M+HCOO]-130.632859911

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, 2022.3.54 minutes32390414
Predicted by Siyang on May 30, 202210.0954 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.51 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid97.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1236.6 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid332.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid96.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid204.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid82.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid321.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid415.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)125.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid726.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid299.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1013.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid227.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid308.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate516.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA202.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water212.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phthalic acidOC(=O)C1=CC=CC=C1C(O)=O2700.6Standard polar33892256
Phthalic acidOC(=O)C1=CC=CC=C1C(O)=O1443.9Standard non polar33892256
Phthalic acidOC(=O)C1=CC=CC=C1C(O)=O1640.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phthalic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O1674.4Semi standard non polar33892256
Phthalic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C1699.0Semi standard non polar33892256
Phthalic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O1909.2Semi standard non polar33892256
Phthalic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C2133.4Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected and Quantified2.179 (0.211-21.573) nmol/g wet fecesAdult (>18 years old)Both
Normal		 details
SalivaDetected and Quantified0.0638 uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.0397 +/- 0.0623 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.0841 +/- 0.0878 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.146 +/- 0.00566 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
SalivaDetected and Quantified0.174 +/- 0.499 uMAdult (>18 years old)Both
Normal
    • Sugimoto et al. (...
 details
UrineDetected and Quantified75.3 (27.5-109.5) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified30.5 (22.8-98.3) umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified31.4 +/- 23.7 uMAdult (>18 years old)BothHemodialysis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified2.116 +/- 0.589 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Hemodialysis
  1. Pollack GM, Buchanan JF, Slaughter RL, Kohli RK, Shen DD: Circulating concentrations of di(2-ethylhexyl) phthalate and its de-esterified phthalic acid products following plasticizer exposure in patients receiving hemodialysis. Toxicol Appl Pharmacol. 1985 Jun 30;79(2):257-67. [PubMed:4002227 ]
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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDDB02746
Phenol Explorer Compound IDNot Available
FooDB IDFDB010566
KNApSAcK IDC00055600
Chemspider ID992
KEGG Compound IDC01606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhthalic_acid
METLIN ID6489
PubChem Compound1017
PDB IDNot Available
ChEBI ID29069
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1451041
References
Synthesis ReferenceSchep, Raymond Albert. Production of carboxylic acid. Brit. UK Pat. Appl. (1979), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silva MJ, Reidy JA, Samandar E, Herbert AR, Needham LL, Calafat AM: Detection of phthalate metabolites in human saliva. Arch Toxicol. 2005 Nov;79(11):647-52. Epub 2005 Jul 2. [PubMed:15995852 ]
  2. Lapinskas PJ, Brown S, Leesnitzer LM, Blanchard S, Swanson C, Cattley RC, Corton JC: Role of PPARalpha in mediating the effects of phthalates and metabolites in the liver. Toxicology. 2005 Feb 1;207(1):149-63. [PubMed:15590130 ]
  3. Hurst CH, Waxman DJ: Activation of PPARalpha and PPARgamma by environmental phthalate monoesters. Toxicol Sci. 2003 Aug;74(2):297-308. Epub 2003 Jun 12. [PubMed:12805656 ]
  4. Hauser R: The environment and male fertility: recent research on emerging chemicals and semen quality. Semin Reprod Med. 2006 Jul;24(3):156-67. [PubMed:16804814 ]
  5. Swan SH: Does our environment affect our fertility? Some examples to help reframe the question. Semin Reprod Med. 2006 Jul;24(3):142-6. [PubMed:16804812 ]
  6. Fisher JS: Environmental anti-androgens and male reproductive health: focus on phthalates and testicular dysgenesis syndrome. Reproduction. 2004 Mar;127(3):305-15. [PubMed:15016950 ]