| Record Information |
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| Version | 1.0 |
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| Created at | 2006-05-22 14:17:36 UTC |
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| Updated at | 2024-04-19 09:51:38 UTC |
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| NP-MRD ID | NP0000166 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Phthalic acid |
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| 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 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 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 | HMDB | | Phthalic acid, disodium salt | HMDB | | Phthalic acid, monobarium salt | HMDB | | Phthalic acid, monopotassium salt | HMDB | | Phthalic acid, sodium salt | HMDB | | Potassium hydrogen phthalate | HMDB | | Phthalic acid, copper salt | HMDB | | Phthalic acid, monocalcium salt | HMDB | | Phthalic acid, monoruthenium salt | HMDB | | Phthalic acid, potassium salt | HMDB | | Phthalic acid, potassium, sodium salt | HMDB | | Phthalic acid, monoiron (2+) salt | HMDB | | Phthalic acid, monolead (2+) salt | HMDB | | Phthalic acid, monosodium salt | HMDB | | Phthalic acid | Generator | | Disodium phthalate | MeSH |
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| Chemical Formula | C8H6O4 |
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| Average Mass | 166.1308 Da |
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| Monoisotopic Mass | 166.02661 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 88-99-3 |
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| SMILES | Not Available |
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| 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) |
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| InChI Key | XNGIFLGASWRNHJ-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-09-05 | View Spectrum | | 1D NMR | [1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-09-05 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Benzoic acids and derivatives |
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| Direct Parent | Benzoic acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| 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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | Not Available |
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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 ]
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