Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:02 UTC |
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Update date | 2019-11-26 03:06:23 UTC |
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Primary ID | FDB012200 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 2,3-Dihydroxybenzoic acid |
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Description | Occurs in Gentiana lutea (yellow gentian)
2-Pyrocatechuic acid is a normal human benzoic acid metabolite found in plasma (PMID 16351159), and is normally found with increased levels after consumption of many nutrients and drugs, i.e.: cranberry juice (PMID 14733499), aspirin ingestion. (PMID 3342084) It has been found associated with idiopathic oro-facial pain due to stress (oxidative stress might enhance the production of free radicals); it has been suggested that OH radicals are responsible for the production of many systemic and local tissue injury diseases which may initially manifest as pain syndrome, and 2-Pyrocatechuic acid is a biological marker for the detection and quantification of OH radicals, and patients had significantly increased circulating levels of 2-Pyrocatechuic acid after aspirin ingestion than control subjects. (PMID 7748148) |
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CAS Number | 303-38-8 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C7H6O4 |
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IUPAC name | 2,3-dihydroxybenzoic acid |
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InChI Identifier | InChI=1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) |
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InChI Key | GLDQAMYCGOIJDV-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)C1=C(O)C(O)=CC=C1 |
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Average Molecular Weight | 154.121 |
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Monoisotopic Molecular Weight | 154.026608673 |
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Classification |
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Description | Belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. |
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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 | Salicylic acids |
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Alternative Parents | |
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Substituents | - Salicylic acid
- Benzoic acid
- Benzoyl
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Vinylogous acid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-0924000000-1ed6156dbe82344d29af | Spectrum | GC-MS | 2,3-Dihydroxybenzoic acid, 3 TMS, GC-MS Spectrum | splash10-0a4u-3922000000-0b326da278c57df03c1a | Spectrum | GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrum | splash10-0a4i-0924000000-1ed6156dbe82344d29af | Spectrum | GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrum | splash10-0a4u-3922000000-0b326da278c57df03c1a | Spectrum | GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, GC-MS Spectrum | splash10-0a4l-0922000000-beddd6836f31d4813a14 | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0zg0-4900000000-44419ba3a3e768caaeee | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-008a-5192000000-86efa4079dcb0a7d6174 | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 2,3-Dihydroxybenzoic acid, TBDMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-0zfr-0900000000-9d9306f70123d5d263ef | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-4900000000-702a14e999a2e830a9d5 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0a4i-7900000000-a88a9646fb3070aef98d | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a4i-0900000000-9bbc26971da28557772e | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0pb9-0900000000-7f5ec409ec11ea326d42 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0a4i-0900000000-ba9640b66d655cdb3295 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0201-0900000000-40f4ec4c2b33e147f78b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-6900000000-c5444a948b6dfffe4059 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0a4i-0900000000-6000163ae935d019ab25 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0pb9-0900000000-b9e3e795548fcdc52ee4 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-2900000000-9aef155a0507c9c6d986 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0pb9-0900000000-5d283030559c5931b824 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0900000000-68a4f0df325353ecd082 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-0900000000-1b11ae0f71a80e056a93 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9200000000-f64ac01c6efb684a4f55 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0zfr-0900000000-cb45151fcc0e74008de3 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-df3ca8c192f0fcf2b620 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9700000000-e3faafae5f2aad580cdd | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-f9afef76ab6c6ac97e51 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-5900000000-0ca2af142a25251b2a85 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ue9-9100000000-18f4a8eefdb99c1dd8ff | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-31cc76875b7e828b57e3 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-2900000000-2b91af5de3160a31b13d | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-066u-9100000000-1810b7542f18d07d2e10 | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 18 |
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ChEMBL ID | CHEMBL1432 |
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KEGG Compound ID | C00196 |
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Pubchem Compound ID | 19 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18026 |
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Phenol-Explorer ID | 430 |
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DrugBank ID | DB01672 |
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HMDB ID | HMDB00397 |
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CRC / DFC (Dictionary of Food Compounds) ID | HFB57-G:HFB57-G |
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EAFUS ID | Not Available |
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Dr. Duke ID | PYROCATECHUIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002669 |
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HET ID | DBH |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | 2,3-Dihydroxybenzoic_acid |
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Phenol-Explorer Metabolite ID | 430 |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
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