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Record Information
Version1.0
Created at2006-05-22 14:17:36 UTC
Updated at2024-04-19 09:51:38 UTC
NP-MRD IDNP0000166
Secondary Accession NumbersNone
Natural Product 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
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 saltHMDB
Phthalic acid, disodium saltHMDB
Phthalic acid, monobarium saltHMDB
Phthalic acid, monopotassium saltHMDB
Phthalic acid, sodium saltHMDB
Potassium hydrogen phthalateHMDB
Phthalic acid, copper saltHMDB
Phthalic acid, monocalcium saltHMDB
Phthalic acid, monoruthenium saltHMDB
Phthalic acid, potassium saltHMDB
Phthalic acid, potassium, sodium saltHMDB
Phthalic acid, monoiron (2+) saltHMDB
Phthalic acid, monolead (2+) saltHMDB
Phthalic acid, monosodium saltHMDB
Phthalic acidGenerator
Disodium phthalateMeSH
Chemical FormulaC8H6O4
Average Mass166.1308 Da
Monoisotopic Mass166.02661 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number88-99-3
SMILESNot Available
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-05View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-05View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium ampeloprasum
Angelica gigas
Angelica sinensis
Arabidopsis thaliana
Homo sapiens
Papaver somniferum
Polygonum minusPlant
Rubus idaeusFooDB
Terminalia chebula
Trypanosoma brucei
Vaccinium macrocarpon
Vitis vinifera
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
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted PropertiesNot Available
HMDB IDHMDB0002107
DrugBank IDDB02746
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010566
KNApSAcK IDNot Available
Chemspider ID992
KEGG Compound IDC01606
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhthalic_acid
METLIN ID6489
PubChem Compound1017
PDB IDNot Available
ChEBI ID29069
Good Scents IDNot Available
References
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 ]