Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:30 UTC |
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Update date | 2019-11-26 02:54:36 UTC |
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Primary ID | FDB000264 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 5-8'-Dehydrodiferulic acid |
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Description | 5-8'-dehydrodiferulic acid is a member of the class of compounds known as stilbenes. Stilbenes are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 5-8'-dehydrodiferulic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). 5-8'-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, rye, and semolina, which makes 5-8'-dehydrodiferulic acid a potential biomarker for the consumption of these food products. 8,5'-Diferulic acid is a non cyclic type of diferulic acid. It is the predominant diferulic acid in sugar beet pulp. It is also found in barley, in maize bran and rye. 8-5'-Diferulic acid has also been identified to be covalently linked to carbohydrate moieties of the arabinogalactan-protein fraction of gum arabic . |
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CAS Number | Not Available |
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Structure | |
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Synonyms | Synonym | Source |
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Not Available | Not Available |
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Predicted Properties | |
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Chemical Formula | C20H18O8 |
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IUPAC name | (2E)-2-{5-[(1Z)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid |
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InChI Identifier | InChI=1S/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4-,14-8+ |
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InChI Key | DEPVSDIYICBTJE-FGDQGFBNSA-N |
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Isomeric SMILES | COC1=CC(\C=C/C(O)=O)=CC(\C(=C/C2=CC(OC)=C(O)C=C2)C(O)=O)=C1O |
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Average Molecular Weight | 386.3521 |
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Monoisotopic Molecular Weight | 386.100167552 |
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Classification |
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Description | Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Stilbenes |
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Sub Class | Not Available |
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Direct Parent | Stilbenes |
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Alternative Parents | |
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Substituents | - Stilbene
- Cinnamic acid
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Anisole
- Phenoxy compound
- Methoxybenzene
- Phenol ether
- Styrene
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Benzenoid
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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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 | Not Available |
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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 | splash10-00kr-0009000000-9309da9b6c48dc402a11 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00mo-0129000000-6faee2ae1becb43365b0 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05nb-1292000000-10852496bd047600f76f | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000l-0009000000-89d16ccdb6f1d713570d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002o-0619000000-31307225a037c52bd661 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-2905000000-9281f1b9256c00054757 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gb9-0009000000-d1934f91ded5382516cf | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0fri-0009000000-6c3fe92c9bacefc95d4d | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-066r-0179000000-38012ef8810a1bc20927 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0019000000-b65d7265ce7ff9a86269 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-0049000000-ff8af18dc70fb3fcf006 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-0079000000-71051967f95174d5b919 | 2021-10-21 | 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 | Not Available |
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Pubchem Compound ID | Not Available |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 508 |
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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 | NNB85-F:NNB85-F |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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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 | Not Available |
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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 | 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 | 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 | — 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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