Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:17 UTC |
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Update date | 2019-11-26 03:07:20 UTC |
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Primary ID | FDB012662 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Glucocaffeic acid |
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Description | Glucocaffeic acid, also known as glucocaffeate, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Glucocaffeic acid is found, on average, in the highest concentration within a few different foods, such as highbush blueberries (Vaccinium corymbosum), jostaberries (Ribes × nidigrolaria), and gooseberries (Ribes uva-crispa) and in a lower concentration in blackcurrants (Ribes nigrum) and redcurrants (Ribes rubrum). Glucocaffeic acid has also been detected, but not quantified in, several different foods, such as black tea, robusta coffees (Coffea canephora), rubus (blackberry, raspberry), strawberries (Fragaria X ananassa), and red tea. This could make glucocaffeic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Glucocaffeic acid. |
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CAS Number | 17093-82-2 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C15H18O9 |
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IUPAC name | (2E)-3-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid |
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InChI Identifier | InChI=1S/C15H18O9/c16-6-10-12(20)13(21)14(22)15(24-10)23-9-3-1-7(5-8(9)17)2-4-11(18)19/h1-5,10,12-17,20-22H,6H2,(H,18,19)/b4-2+ |
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InChI Key | OHEYCHKLBCPRLZ-DUXPYHPUSA-N |
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Isomeric SMILES | OCC1OC(OC2=C(O)C=C(\C=C\C(O)=O)C=C2)C(O)C(O)C1O |
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Average Molecular Weight | 342.298 |
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Monoisotopic Molecular Weight | 342.095082174 |
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Classification |
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Description | Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. |
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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 | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Phenolic glycosides |
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Alternative Parents | |
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Substituents | - Phenolic glycoside
- Cinnamic acid
- Cinnamic acid or derivatives
- Coumaric acid or derivatives
- Hexose monosaccharide
- Hydroxycinnamic acid
- Hydroxycinnamic acid or derivatives
- O-glycosyl compound
- Phenoxy compound
- Styrene
- Phenol ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Monosaccharide
- Oxane
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid
- Carboxylic acid derivative
- Acetal
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Primary alcohol
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic 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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Role | Biological role: |
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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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Predicted GC-MS | Glucocaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01x0-6935000000-23334bdef41332ea934d | Spectrum | Predicted GC-MS | Glucocaffeic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-014i-3503129000-0d88edd96503e6843575 | Spectrum | Predicted GC-MS | Glucocaffeic acid, TBDMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucocaffeic acid, TBDMS_4_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucocaffeic acid, TBDMS_4_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucocaffeic acid, TBDMS_4_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucocaffeic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Glucocaffeic acid, "Glucocaffeic acid,3TBDMS,#5" TMS, 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 | splash10-01sl-0916000000-fece99020b1ba2f431ce | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01q9-0900000000-3426b030fe1c2f380216 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0089-1900000000-453bcfd801322563f49d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002f-2928000000-88b5911db1f82a296ebe | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-1911000000-d59fdc4b46b9803828a6 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-01u3-2900000000-66020d3549687cbf760d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0005-0293000000-79d8746a5db9047e63dc | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-1490000000-92a6455fd6f33e2cf92b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001r-0900000000-6470eb3015c4debbcea9 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0400-0906000000-c18c09fc539faa69158e | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-08ir-0934000000-a9a600a879e01c89c9ac | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01bi-2910000000-79bdaeeb30dfde578e48 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 4823601 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 6148082 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 488 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB34313 |
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CRC / DFC (Dictionary of Food Compounds) ID | CMK09-G:HJP66-C |
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EAFUS ID | Not Available |
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Dr. Duke ID | LINOCAFFEIN |
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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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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. — 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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