| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 08:17:36 -0600 |
| Update Date |
2013-02-08 17:11:23 -0700 |
| HMDB ID |
HMDB02107 |
| Secondary Accession Numbers |
None |
| 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Alizarinate
- Alizarinic acid
- M 2
- Naphthalinate
- Naphthalinic acid
- O-Benzenedicarboxylate
- O-Benzenedicarboxylic acid
- O-Carboxybenzoate
- O-Carboxybenzoic acid
- O-Dicarboxybenzene
- Phthalate
- Phthalic acid
- Phthalinate
- Phthalinic acid
- Sunftal 20
|
| Chemical Formula |
C8H6O4 |
| Average Molecular Weight |
166.1308 |
| Monoisotopic Molecular Weight |
166.02660868 |
| IUPAC Name |
benzene-1,2-dicarboxylic acid |
| Traditional IUPAC 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 |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Aromatic Homomonocyclic Compounds |
| Class |
Benzoic Acid and Derivatives |
| Sub Class |
Phthalic Acid and Derivatives |
| Other Descriptors |
- Organic Compounds
- benzenedicarboxylic acid(ChEBI)
|
| Substituents |
- Benzoyl
- Carboxylic Acid
- Dicarboxylic Acid Derivative
|
| Direct Parent |
o-Phthalic Acid and Derivatives |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
Not Available |
| Application |
Not Available |
| Cellular locations |
Not Available |
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
205 - 230 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
7.01 mg/mL at 25 °C |
Not Available |
| LogP |
0.73 |
HANSCH,C ET AL. (1995) |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
Not Available
|
| Biofluid Locations |
|
| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Saliva |
Detected and Quantified |
|
0.0638 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
75.3 (27.5-109.5) umol/mmol creatinine |
Newborn (0-30 days old) |
Both |
Normal |
Not Available |
| Urine |
Detected and Quantified |
|
30.5 (22.8-98.3) umol/mmol creatinine |
Infant (0-1 year old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
31.4 +/- 23.7 uM |
Adult (>18 years old) |
Both |
Hemodialysis |
Not Available |
|
| 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
|
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| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB010566 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
992 |
| KEGG Compound ID |
C01606 |
| BioCyc ID |
PHTHALATE |
| BiGG ID |
Not Available |
| Wikipedia Link |
Phthalic acid |
| NuGOwiki Link |
HMDB02107 |
| Metagene Link |
HMDB02107 |
| METLIN ID |
6489 |
| PubChem Compound |
1017 |
| PDB ID |
PHT |
| ChEBI ID |
29069 |
| References |
|---|
| Synthesis Reference |
Schep, Raymond Albert. Production of carboxylic acid. Brit. UK Pat. Appl. (1979), 7 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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
- 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
- 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
|
