Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:33 UTC |
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Update date | 2020-02-24 19:10:06 UTC |
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Primary ID | FDB000379 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Malic acid caffeate |
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Description | Caffeoylmalic acid, also known as caffeoylmalate, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Caffeoylmalic acid has been detected, but not quantified in, several different foods, such as radishes (Raphanus sativus), pears (Pyrus communis), herbs and spices, herbal tea, and black tea. This could make caffeoylmalic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Caffeoylmalic acid. |
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CAS Number | 53755-04-7 |
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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 | C13H12O8 |
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IUPAC name | 2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid |
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InChI Identifier | InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+ |
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InChI Key | PMKQSEYPLQIEAY-DUXPYHPUSA-N |
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Isomeric SMILES | OC(=O)CC(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O |
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Average Molecular Weight | 296.2296 |
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Monoisotopic Molecular Weight | 296.05321736 |
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Classification |
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Description | Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Cinnamic acids and derivatives |
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Sub Class | Hydroxycinnamic acids and derivatives |
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Direct Parent | Coumaric acids and derivatives |
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Alternative Parents | |
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Substituents | - Coumaric acid or derivatives
- Cinnamic acid ester
- Tricarboxylic acid or derivatives
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Fatty acid ester
- Phenol
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- Carboxylic acid ester
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen 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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Disposition | Route of exposure: Source: Biological location: |
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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 | C 52.71%; H 4.08%; O 43.21% | DFC |
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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 | [a]25D +28.3 (H2O) | DFC |
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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 | L-Malic acid caffeate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-03di-1910000000-74e3c09316c8d9fb3ea5 | Spectrum | Predicted GC-MS | L-Malic acid caffeate, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0avi-4146190000-5a765f56e5efd99345a3 | Spectrum | Predicted GC-MS | L-Malic acid caffeate, 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 | splash10-0401-1790000000-ef531f4b3f8db4d508cb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03xr-3940000000-ff40fcbd1f957b9e680e | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dr-7900000000-187b75c221f4f3c49fff | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0ftb-1970000000-6b43ca38ba19571e6a67 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00bi-3920000000-98c6d2f5b48eb1a9ccc3 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03g0-3900000000-60d5ea04840a20f30f6b | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0290000000-a44daa816456bebdbd8a | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9540000000-6be49add441a49df34b9 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-3910000000-46381cd1c0d16863ebb5 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0920000000-a4c71d6efa8a850a8ec6 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0900000000-ecf10995634e427e58a9 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01p9-1900000000-ca91bf87f1f063f2269a | 2021-09-24 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4816367 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 6124299 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB29318 |
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CRC / DFC (Dictionary of Food Compounds) ID | DCG74-V:BBN70-X |
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EAFUS ID | Not Available |
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Dr. Duke ID | PHASEOLIC-ACID |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002765 |
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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 | — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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