Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:29 UTC |
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Update date | 2020-02-24 19:11:07 UTC |
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Primary ID | FDB000229 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Gallic acid 3-O-gallate |
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Description | 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid, also known as gallic acid 3-monogallate or digallic acid, belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid is found, on average, in the highest concentration within beers. 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid has also been detected, but not quantified in, evening primroses and tea. This could make 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid a potential biomarker for the consumption of these foods. |
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CAS Number | 536-08-3 |
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Structure | |
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Synonyms | Synonym | Source |
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Gallic acid 3-monogallate | ChEBI | Digallic acid | Kegg | Gallate 3-monogallate | Generator | Gallic acid 3-monogallic acid | Generator | Digallate | Generator | 3,4-Dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoate | Generator | Gallate 3-O-gallate | HMDB | Gallic acid 3-O-gallic acid | HMDB | Gallic acid 5,6-dihydroxy-3-carboxyphenyl ester | HMDB | m-Digallic acid | manual |
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Predicted Properties | |
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Chemical Formula | C14H10O9 |
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IUPAC name | 3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyloxy)benzoic acid |
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InChI Identifier | InChI=1S/C14H10O9/c15-7-2-6(3-8(16)11(7)18)14(22)23-10-4-5(13(20)21)1-9(17)12(10)19/h1-4,15-19H,(H,20,21) |
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InChI Key | COVFEVWNJUOYRL-UHFFFAOYSA-N |
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Isomeric SMILES | OC(=O)C1=CC(O)=C(O)C(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C1 |
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Average Molecular Weight | 322.225 |
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Monoisotopic Molecular Weight | 322.032481902 |
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Classification |
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Description | Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Depsides and depsidones |
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Sub Class | Not Available |
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Direct Parent | Depsides and depsidones |
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Alternative Parents | |
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Substituents | - Depside backbone
- Galloyl ester
- Gallic acid or derivatives
- M-hydroxybenzoic acid ester
- P-hydroxybenzoic acid ester
- Dihydroxybenzoic acid
- Hydroxybenzoic acid
- Phenol ester
- Benzoate ester
- Benzenetriol
- Benzoic acid or derivatives
- Pyrogallol derivative
- Benzoic acid
- Catechol
- Benzoyl
- Phenoxy compound
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Carboxylic acid derivative
- Polyol
- Carboxylic acid
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Organic oxygen 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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Disposition | Source: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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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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Predicted GC-MS | Gallic acid 3-O-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-0900000000-99dc70c2502325372598 | Spectrum | Predicted GC-MS | Gallic acid 3-O-gallate, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01b9-1009003000-cd8acb11ec0152f73253 | Spectrum | Predicted GC-MS | Gallic acid 3-O-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Gallic acid 3-O-gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0fk9-0739000000-04e8b3e46aa76053cc6d | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ufr-0932000000-54a763c58dbe078119b8 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-3910000000-f9a95cbd1ede0185b416 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0449000000-24813c6833d97ef0ef4f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00b9-0953000000-5e2c3c2d517061d39a78 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fvi-1900000000-5bc32bc1d2843a063327 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0039000000-dd7885813975516d0009 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0zor-0941000000-34740d009e8361464c9c | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fry-7970000000-6ad4837f49fb741a5787 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0409000000-662f28e040bd0781b2e4 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fk9-0935000000-16a824368c7d75f77183 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxs-6940000000-c25e9d2eb97002d82ac7 | 2021-09-25 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C01572 |
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Pubchem Compound ID | 341 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 30814 |
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Phenol-Explorer ID | 438 |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | CMT08-Y:CMT08-Y |
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EAFUS ID | Not Available |
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Dr. Duke ID | DIGALLIC-ACID|M-DIGALLIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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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 | Digallic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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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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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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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 | Not Available |
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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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