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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:36 UTC

Update Date

2023-02-21 17:16:10 UTC

HMDB ID

HMDB0002107

Secondary Accession Numbers

HMDB02107

Metabolite Identification

Common Name

Phthalic acid

Description

Phthalic 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Benzenedicarboxylic acid	ChEBI
O-Benzenedicarboxylic acid	ChEBI
Ortho-phthalic acid	ChEBI
O-Phthalic acid	Kegg
1,2-Benzenedicarboxylate	Generator
O-Benzenedicarboxylate	Generator
Ortho-phthalate	Generator
O-Phthalate	Generator
Phthalate	Generator
Alizarinate	HMDB
Alizarinic acid	HMDB
M 2	HMDB
Naphthalinate	HMDB
Naphthalinic acid	HMDB
O-Carboxybenzoate	HMDB
O-Carboxybenzoic acid	HMDB
O-Dicarboxybenzene	HMDB
Phthalinate	HMDB
Phthalinic acid	HMDB
Sunftal 20	HMDB
Phthalic acid, dipotassium salt	MeSH, HMDB
Phthalic acid, disodium salt	MeSH, HMDB
Phthalic acid, monobarium salt	MeSH, HMDB
Phthalic acid, monopotassium salt	MeSH, HMDB
Phthalic acid, sodium salt	MeSH, HMDB
Potassium hydrogen phthalate	MeSH, HMDB
Phthalic acid, copper salt	MeSH, HMDB
Phthalic acid, monocalcium salt	MeSH, HMDB
Phthalic acid, monoruthenium salt	MeSH, HMDB
Phthalic acid, potassium salt	MeSH, HMDB
Phthalic acid, potassium, sodium salt	MeSH, HMDB
Phthalic acid, monoiron (2+) salt	MeSH, HMDB
Phthalic acid, monolead (2+) salt	MeSH, HMDB
Phthalic acid, monosodium salt	MeSH, HMDB
Phthalic acid	Generator
Disodium phthalate	MeSH

Chemical Formula

C₈H₆O₄

Average Molecular Weight

166.1308

Monoisotopic Molecular Weight

166.02660868

IUPAC Name

benzene-1,2-dicarboxylic acid

Traditional Name

phthalic acid

CAS Registry Number

88-99-3

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 Key

XNGIFLGASWRNHJ-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

benzenedicarboxylic acid (CHEBI:29069 )

Ontology

Physiological effect

Health effect

Hemodialysis (HMDB: HMDB0002107)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0002107)
Saliva (HMDB: HMDB0002107)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002107)
Feces (PMID: 25037050)

Organ

Liver (HMDB: HMDB0002107)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002107)

Source

Exogenous

Food

Food (HMDB: HMDB0002107)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Fruit

Berry

Red raspberry (FooDB: FOOD00162)

Endogenous

Plant

Plant (HMDB: HMDB0002107)

Process

Not Available

Role

Environmental role

Environmental contaminant (HMDB: HMDB0002107)

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002107)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	205 - 230 °C	Not Available
Boiling Point	132.00 to 133.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	7.01 mg/mL at 25 °C	Not Available
LogP	0.73	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.12 g/L	ALOGPS
logP	1.22	ALOGPS
logP	1.29	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.94	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.57 m³·mol⁻¹	ChemAxon
Polarizability	14.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.219	31661259
DarkChem	[M-H]-	129.403	31661259
DeepCCS	[M+H]+	133.882	30932474
DeepCCS	[M-H]-	130.054	30932474
DeepCCS	[M-2H]-	167.276	30932474
DeepCCS	[M+Na]+	142.815	30932474
AllCCS	[M+H]+	134.9	32859911
AllCCS	[M+H-H2O]+	130.5	32859911
AllCCS	[M+NH4]+	139.0	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	128.5	32859911
AllCCS	[M+Na-2H]-	129.5	32859911
AllCCS	[M+HCOO]-	130.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phthalic acid	OC(=O)C1=CC=CC=C1C(O)=O	2700.6	Standard polar	33892256
Phthalic acid	OC(=O)C1=CC=CC=C1C(O)=O	1443.9	Standard non polar	33892256
Phthalic acid	OC(=O)C1=CC=CC=C1C(O)=O	1640.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phthalic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O	1674.4	Semi standard non polar	33892256
Phthalic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C	1699.0	Semi standard non polar	33892256
Phthalic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O	1909.2	Semi standard non polar	33892256
Phthalic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	2133.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phthalic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0002-0910000000-13ae6bbb9f0d5dcc636c	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phthalic acid EI-B (Non-derivatized)	splash10-0zor-9500000000-e5ec33e3312a4a87ea39	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phthalic acid EI-B (Non-derivatized)	splash10-0002-0910000000-b0d922c04c2f5dd6e4c7	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phthalic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-13ae6bbb9f0d5dcc636c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phthalic acid GC-EI-TOF (Non-derivatized)	splash10-0002-0900000000-9308910720abd784ba33	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-5900000000-68084b3e65fcd1cea856	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8390000000-d238ce57194d1385d919	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phthalic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0002-0900000000-0f913d45c1daa3650138	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-00kf-9400000000-ba393489337831b167f0	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-014i-9000000000-998fd73fa45b918fbbd4	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0900000000-473374d725e62e2c60ef	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-00fr-4900000000-863cf771373d1802f7d0	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-004i-9200000000-acf56d82f3969fd63b3b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-004i-9100000000-c03297cff4e455fc9a56	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-00di-9000000000-88a6558d781ff1f9c6c5	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-473374d725e62e2c60ef	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOF	splash10-00fr-4900000000-863cf771373d1802f7d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOF	splash10-004i-9200000000-9b673ed6e8d6d73b74b4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOF	splash10-004i-9100000000-c03297cff4e455fc9a56	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid LC-ESI-QQ , negative-QTOF	splash10-00di-9000000000-88a6558d781ff1f9c6c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid 20V, Negative-QTOF	splash10-004i-9000000000-79444e6f1e1cad82c9af	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid 10V, Negative-QTOF	splash10-00fr-7900000000-69919220fe286719b154	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid 40V, Negative-QTOF	splash10-004i-9000000000-f8cd37ad5a7de3510c1c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid 35V, Positive-QTOF	splash10-0002-0900000000-0bf84650c197f00d2d4b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid 35V, Negative-QTOF	splash10-00di-0900000000-9e9de7b1b9755cbc0c83	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phthalic acid 30V, Negative-QTOF	splash10-00di-0900000000-17c7a2e06ddf58f100a3	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phthalic acid 10V, Positive-QTOF	splash10-014i-0900000000-544e377d1efe0d8040f2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phthalic acid 20V, Positive-QTOF	splash10-014j-0900000000-88ea8f2e083f769b4ecc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phthalic acid 40V, Positive-QTOF	splash10-0pb9-6900000000-f4a09894e4cd81ff485e	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phthalic acid 10V, Negative-QTOF	splash10-014i-0900000000-e9d3605c3e0f232735dc	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phthalic acid 20V, Negative-QTOF	splash10-00xr-2900000000-f0bd93b089cec9e1caf2	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phthalic acid 40V, Negative-QTOF	splash10-00b9-9700000000-699743d9f7786056612c	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected and Quantified	2.179 (0.211-21.573) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	0.0397 +/- 0.0623 uM	Adult (>18 years old)	Male	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0841 +/- 0.0878 uM	Adult (>18 years old)	Female	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.146 +/- 0.00566 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.174 +/- 0.499 uM	Adult (>18 years old)	Both	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.0638 uM	Adult (>18 years old)	Both	Normal	15995852	details
Urine	Detected and Quantified	75.3 (27.5-109.5) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	30.5 (22.8-98.3) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	31.4 +/- 23.7 uM	Adult (>18 years old)	Both	Hemodialysis	4002227	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	2.116 +/- 0.589 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Hemodialysis
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
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
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB02746

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phthalic_acid

METLIN ID

6489

PubChem Compound

1017

PDB ID

Not Available

ChEBI ID

29069

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1451041

References

Synthesis Reference

Schep, Raymond Albert. Production of carboxylic acid. Brit. UK Pat. Appl. (1979), 7 pp.

Material Safety Data Sheet (MSDS)

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General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Phthalic acid (HMDB0002107)

MOL for HMDB0002107 (Phthalic acid)

3D MOL for HMDB0002107 (Phthalic acid)

3D SDF for HMDB0002107 (Phthalic acid)

3D-SDF for HMDB0002107 (Phthalic acid)

PDB for HMDB0002107 (Phthalic acid)

3D PDB for HMDB0002107 (Phthalic acid)

SMILES for HMDB0002107 (Phthalic acid)

INCHI for HMDB0002107 (Phthalic acid)

Structure for HMDB0002107 (Phthalic acid)

3D Structure for HMDB0002107 (Phthalic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra