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 | 2020-02-24 19:10:23 UTC |
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Primary ID | FDB001514 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 1,5-Dicaffeoylquinic acid |
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Description | 1,5-Dicaffeoylquinic acid, also known as cynarin, belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 1,5-Dicaffeoylquinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,5-Dicaffeoylquinic acid has been detected, but not quantified in, a few different foods, such as cardoons, fennels, and globe artichokes. This could make 1,5-dicaffeoylquinic acid a potential biomarker for the consumption of these foods. |
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CAS Number | 30964-13-7 |
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Structure | |
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Synonyms | Synonym | Source |
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Cynarin | ChEBI | 1,5-Dicaffeoylquinate | Generator | 1,5-Di-O-caffeoylquinic acid | HMDB | Cinarine | HMDB | Cynarine | HMDB | 1,3-Dicaffeoylquinate | Generator | Cinarin | MeSH | Cynarix | MeSH | Listrocol | MeSH | Phemocil | MeSH | 1,5-Dicaffeoylquinic acid | MeSH | Nivellipid | MeSH | Cinarina | MeSH | Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer | MeSH | 1-Carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate) | MeSH | Cynarex | MeSH | Listricol | MeSH |
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Predicted Properties | |
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Chemical Formula | C25H24O12 |
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IUPAC name | (1R,3R,4S,5R)-1,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid |
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InChI Identifier | InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1 |
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InChI Key | YDDUMTOHNYZQPO-RVXRWRFUSA-N |
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Isomeric SMILES | O[C@@H]1C[C@](C[C@@H](OC(=O)\C=C\C2=CC=C(O)C(O)=C2)[C@H]1O)(OC(=O)\C=C\C1=CC=C(O)C(O)=C1)C(O)=O |
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Average Molecular Weight | 516.4509 |
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Monoisotopic Molecular Weight | 516.126776232 |
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Classification |
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Description | belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent | Quinic acids and derivatives |
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Alternative Parents | |
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Substituents | - Quinic acid
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Cinnamic acid ester
- Hydroxycinnamic acid or derivatives
- Tricarboxylic acid or derivatives
- Catechol
- Styrene
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Cyclohexanol
- Phenol
- Fatty acid ester
- Monocyclic benzene moiety
- Fatty acyl
- Benzenoid
- Alpha,beta-unsaturated carboxylic ester
- Enoate ester
- 1,2-diol
- Carboxylic acid ester
- Secondary alcohol
- Carboxylic acid
- Carboxylic acid derivative
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- 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 | 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 | 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 | Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03dl-8592200000-bf336f61df2036277f1e | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-000i-1945103000-92e839d6fb722a93bc0b | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-02tj-0709640000-93a124ca1ee347170ee5 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0907300000-c1b3f5ea82ad93560c14 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-024u-0902200000-aeb4454f422056c292f4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0gb9-0419580000-83812afaf2e5ea383af6 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0r99-0729300000-eba47ae47a52917059ab | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06vi-0915000000-c68bce1e5294ad4dca56 | JSpectraViewer |
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External Links |
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ChemSpider ID | 4445082 |
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ChEMBL ID | CHEMBL487258 |
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KEGG Compound ID | C10445 |
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Pubchem Compound ID | 5281769 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 528 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB30093 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | CYNARIN |
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BIGG ID | Not Available |
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KNApSAcK ID | C00002733 |
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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 | Cynarine |
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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 | — 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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