Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:00 UTC |
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Update date | 2019-11-26 02:56:32 UTC |
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Primary ID | FDB001512 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | 1,2-Benzenediol |
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Description | Pyrocatechol, also known as 1,2-benzenediol or 2-hydroxyphenol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Pyrocatechol is an extremely weak basic (essentially neutral) compound (based on its pKa). Pyrocatechol exists in all living organisms, ranging from bacteria to humans. Pyrocatechol is found, on average, in the highest concentration within a few different foods, such as arabica coffee, coffee, and cocoa powders and in a lower concentration in beers. Pyrocatechol has also been detected, but not quantified in, several different foods, such as bamboo shoots, mandarin orange (clementine, tangerine), scarlet beans, naranjilla, and asparagus. This could make pyrocatechol a potential biomarker for the consumption of these foods. Pyrocatechol is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. |
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CAS Number | 120-80-9 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C6H6O2 |
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IUPAC name | benzene-1,2-diol |
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InChI Identifier | InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H |
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InChI Key | YCIMNLLNPGFGHC-UHFFFAOYSA-N |
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Isomeric SMILES | OC1=CC=CC=C1O |
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Average Molecular Weight | 110.1106 |
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Monoisotopic Molecular Weight | 110.036779436 |
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Classification |
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Description | Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenols |
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Sub Class | Benzenediols |
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Direct Parent | Catechols |
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Alternative Parents | |
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Substituents | - Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Organic oxygen compound
- 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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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Environmental role: Industrial application: |
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Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
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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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EI-MS | Mass Spectrum (Electron Ionization) | splash10-03di-9600000000-b8e03f4f3ea89044828e | 2014-09-20 | View Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-0udr-1950000000-16187bb35dcb40c26e78 | Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-03di-8900000000-4e15f35dca47661de590 | Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-03di-9600000000-032a40483dec93738075 | Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-03di-7900000000-83f892852c355a3863e9 | Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-03di-9400000000-90885264baa17f65d954 | Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-0udr-1950000000-16187bb35dcb40c26e78 | Spectrum | GC-MS | 1,2-Benzenediol, non-derivatized, GC-MS Spectrum | splash10-0udr-1930000000-24d2e0a8e36245d9e187 | Spectrum | Predicted GC-MS | 1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03di-7900000000-8b112b8af75eb2d08676 | Spectrum | Predicted GC-MS | 1,2-Benzenediol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fl9-9730000000-a35befff1c602124f29e | Spectrum | Predicted GC-MS | 1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 1,2-Benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 1,2-Benzenediol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 1,2-Benzenediol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | 1,2-Benzenediol, TBDMS_2_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, Positive (Annotated) | splash10-01ox-9400000000-d59dce8c5e56b026f8b2 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-014i-9000000000-632cabc9b371835019c1 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-02t9-9200000000-ac902cb99981017de3b5 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive | splash10-03di-8900000000-95af3d2738de98d27f26 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (Unknown) , Positive | splash10-03di-9600000000-032a40483dec93738075 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive | splash10-03di-7900000000-f5cb1c53768e05ca1530 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0a4i-0900000000-c94dab4d218dbb3bb108 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative | splash10-0a4i-1900000000-edd8ba1e77bbb2f76304 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0900000000-c94dab4d218dbb3bb108 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-1900000000-edd8ba1e77bbb2f76304 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - , negative | splash10-0a4i-0900000000-12053747e62e910151ad | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-72e952ea8e487994be54 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-19b1bae28f3dfde3323a | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-0006-9000000000-33b2a7e7a951547dfafa | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-6e731d4eaba18fcad18f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1900000000-a7c1a830ea96e82252bf | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-3772b2cca96bf4a1b05f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-9531f3e0c85e67d6c6ed | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-1900000000-5886b926a1814092c4b1 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-66523f3122b954e6400f | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-1900000000-5fd776e479836f7464af | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-9000000000-2c46a1375dbb634ef735 | 2015-05-26 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0900000000-986c93875cb12d90fa90 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0900000000-a301685abb4194689ca3 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9500000000-2017b42835ace86f16ee | 2015-05-27 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 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 | 13837760 |
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ChEMBL ID | CHEMBL280998 |
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KEGG Compound ID | C15571 |
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Pubchem Compound ID | 289 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18135 |
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Phenol-Explorer ID | 654 |
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DrugBank ID | DB02232 |
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HMDB ID | HMDB00957 |
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CRC / DFC (Dictionary of Food Compounds) ID | HJX14-Z:HJX14-Z |
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EAFUS ID | Not Available |
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Dr. Duke ID | PYROCATECHOL|(+)-CATECHOL|CATECHOL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002644 |
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HET ID | CAQ |
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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 | Pyrocatechol |
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Phenol-Explorer Metabolite ID | 654 |
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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 | |
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Enzymes | |
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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. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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