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Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2020-11-24 22:12:09 UTC |
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NP-MRD ID | NP0000017 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Gentisic acid |
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Description | Gentisic acid, also known as gentisate or 2,5-dioxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. A dihydroxybenzoic acid having the two hydroxy groups at the 2- and 5-positions. Gentisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Gentisic acid exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Gentisic acid is found, on average, in the highest concentration within a few different foods, such as tarragons, common thymes, and common sages and in a lower concentration in lemon balms, parsley, and soy beans. Gentisic acid has also been detected, but not quantified in, several different foods, such as garden tomato (var.), Cocoa beans, spearmints, common pea, and carrots. This could make gentisic acid a potential biomarker for the consumption of these foods. |
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Structure | |
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Synonyms | Value | Source |
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2,5-Dihydroxybenzoate | ChEBI | 5-Hydroxysalicylic acid | ChEBI | Gentisate | ChEBI | Hydroquinonecarboxylic acid | ChEBI | 2,5-Dihydroxybenzoic acid | Kegg | 5-Hydroxysalicylate | Generator | Hydroquinonecarboxylate | Generator | 2,5-Dioxybenzoate | HMDB | 2,5-Dioxybenzoic acid | HMDB | 3,6-Dihydroxybenzoate | HMDB | 3,6-Dihydroxybenzoic acid | HMDB | 5-Hydroxy-salicylate | HMDB | 5-Hydroxy-salicylic acid | HMDB | Carboxyhydroquinone | HMDB | Dihydroxybenzoicacid | HMDB | Gensigen | HMDB | Gensigon | HMDB | Gentisinate | HMDB | Gentisinic acid | HMDB | 2,5-Dihydroxybenzoic acid, monosodium salt | HMDB | Lithium 2,5-dihydroxybenzoate | HMDB | Gentisic acid | ChEBI | Hydroquinone carboxylic acid | |
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Chemical Formula | C7H6O4 |
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Average Molecular Weight | 154.121 |
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Monoisotopic Molecular Weight | 154.026608673 |
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IUPAC Name | 2,5-dihydroxybenzoic acid |
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Traditional Name | 2,5-dihydroxybenzoic acid |
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CAS Registry Number | 490-79-9 |
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SMILES | OC(=O)C1=C(O)C=CC(O)=C1 |
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InChI Identifier | InChI=1S/C7H6O4/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,8-9H,(H,10,11) |
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InChI Key | WXTMDXOMEHJXQO-UHFFFAOYSA-N |
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Spectra |
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| | Species of Origin |
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Species | Animalia; Plantae |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. |
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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 | Hydroxybenzoic acid derivatives |
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Alternative Parents | |
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Substituents | - Dihydroxybenzoic acid
- Salicylic acid
- Salicylic acid or derivatives
- Hydroxybenzoic acid
- Benzoic acid
- Benzoyl
- Hydroquinone
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Vinylogous acid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- 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 | 199.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 5 mg/mL at 5 °C | Not Available | LogP | 1.74 | SANGSTER (1994) |
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Predicted Properties | |
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User Submitted Data |
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| Not Available |
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External Links |
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HMDB ID | HMDB0000152 |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | 416 |
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FoodDB ID | FDB000844 |
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KNApSAcK ID | C00002648 |
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Chemspider ID | 3350 |
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KEGG Compound ID | C00628 |
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BioCyc ID | CPD-633 |
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BiGG ID | Not Available |
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Wikipedia Link | Gentisic_acid |
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METLIN ID | 618 |
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PubChem Compound | 3469 |
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PDB ID | Not Available |
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ChEBI ID | 17189 |
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References |
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General References | - Ohsako M, Matsumoto Y, Goto S: Transport of aspirin and its metabolites through human erythrocyte membrane. Biol Pharm Bull. 1993 Feb;16(2):154-7. [PubMed:8364451 ]
- Almaas R, Rootwelt T, Oyasaeter S, Saugstad OD: Ascorbic acid enhances hydroxyl radical formation in iron-fortified infant cereals and infant formulas. Eur J Pediatr. 1997 Jun;156(6):488-92. [PubMed:9208249 ]
- Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [PubMed:3378323 ]
- Palumbo G, Carlucci G, Mazzeo P, Frieri G, Pimpo MT, Fanini D: Simultaneous determination of 5-aminosalicylic acid, acetyl-5-aminosalicylic acid and 2,5-dihydroxybenzoic acid in endoscopic intestinal biopsy samples in humans by high-performance liquid chromatography with electrochemical detection. J Pharm Biomed Anal. 1995 Dec;14(1-2):175-80. [PubMed:8833980 ]
- Grootveld M, Halliwell B: Aromatic hydroxylation as a potential measure of hydroxyl-radical formation in vivo. Identification of hydroxylated derivatives of salicylate in human body fluids. Biochem J. 1986 Jul 15;237(2):499-504. [PubMed:3026319 ]
- Peleg H, Noble AC: Perceptual properties of benzoic acid derivatives. Chem Senses. 1995 Aug;20(4):393-400. [PubMed:8590024 ]
- Buskin JN, Upton RA, Williams RL: Improved liquid-chromatography of aspirin, salicylate, and salicyluric acid in plasma, with a modification for determining aspirin metabolites in urine. Clin Chem. 1982 May;28(5):1200-3. [PubMed:7074905 ]
- Liu JH, Smith PC: Direct analysis of salicylic acid, salicyl acyl glucuronide, salicyluric acid and gentisic acid in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):61-70. [PubMed:8634769 ]
- Coudray C, Talla M, Martin S, Fatome M, Favier A: High-performance liquid chromatography-electrochemical determination of salicylate hydroxylation products as an in vivo marker of oxidative stress. Anal Biochem. 1995 May 1;227(1):101-11. [PubMed:7668368 ]
- Bochner F, Graham GG, Cham BE, Imhoff DM, Haavisto TM: Salicylate metabolite kinetics after several salicylates. Clin Pharmacol Ther. 1981 Aug;30(2):266-75. [PubMed:7249509 ]
- Cham BE, Bochner F, Imhoff DM, Johns D, Rowland M: Simultaneous liquid-chromatographic quantitation of salicylic acid, salicyluric acid, and gentisic acid in urine. Clin Chem. 1980 Jan;26(1):111-4. [PubMed:7356541 ]
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