You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2006-05-22 14:17:36 UTC
Update Date2016-02-11 01:05:17 UTC
HMDB IDHMDB02107
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
O-Phthalic acidKegg
1,2-Benzenedicarboxylic acidKegg
O-PhthalateGenerator
PhthalateGenerator
1,2-BenzenedicarboxylateGenerator
AlizarinateHMDB
Alizarinic acidHMDB
M 2HMDB
NaphthalinateHMDB
Naphthalinic acidHMDB
O-BenzenedicarboxylateHMDB
O-Benzenedicarboxylic acidHMDB
O-CarboxybenzoateHMDB
O-Carboxybenzoic acidHMDB
O-DicarboxybenzeneHMDB
PhthalinateHMDB
Phthalinic acidHMDB
Sunftal 20HMDB
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 KeyInChIKey=XNGIFLGASWRNHJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Toxin/Pollutant
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point205 - 230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.01 mg/mL at 25 °CNot Available
LogP0.73HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.12 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.57 m3·mol-1ChemAxon
Polarizability14.95 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0910000000-13ae6bbb9f0d5dcc636cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-0f913d45c1daa3650138View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9400000000-ba393489337831b167f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-998fd73fa45b918fbbd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-473374d725e62e2c60efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00fr-4900000000-863cf771373d1802f7d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9200000000-acf56d82f3969fd63b3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9100000000-c03297cff4e455fc9a56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-00di-9000000000-88a6558d781ff1f9c6c5View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue Location
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
SalivaDetected and Quantified0.0638 uMAdult (>18 years old)BothNormal 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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified31.4 +/- 23.7 uMAdult (>18 years old)BothHemodialysis details
UrineDetected and Quantified2.116 +/- 0.589 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
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. [4002227 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB010566
KNApSAcK IDNot Available
Chemspider ID992
KEGG Compound IDC01606
BioCyc IDPHTHALATE
BiGG IDNot Available
Wikipedia LinkPhthalic acid
NuGOwiki LinkHMDB02107
Metagene LinkHMDB02107
METLIN ID6489
PubChem Compound1017
PDB IDPHT
ChEBI ID29069
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. [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. [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. [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. [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. [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. [15016950 ]