| Record Information |
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| Version | 4.0 |
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| Status | Detected and Quantified |
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| Creation Date | 2006-05-22 15:12:18 UTC |
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| Update Date | 2020-02-26 21:24:18 UTC |
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| HMDB ID | HMDB0002899 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Ellagic acid |
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| Description | Ellagic acid, also known as ellagate or acide ellagique, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption. Ellagic acid's therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects. Ellagic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Ellagic acid is found, on average, in the highest concentration within a few different foods, such as chestnuts, common walnuts, and japanese walnuts and in a lower concentration in whiskies, arctic blackberries, and cloudberries. Ellagic acid has also been detected, but not quantified in, several different foods, such as lowbush blueberries, bilberries, guava, strawberry guava, and bog bilberries. This could make ellagic acid a potential biomarker for the consumption of these foods. ; cranberries; pecans; pomegranates; strawberries; walnuts. ; and other plant foods. Widely distributed in higher plants especies dicotyledons. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione | ChEBI | | 4,4',5,5',6,6'-Hexahydroxydiphenic acid 2,6,2',6'-dilactone | ChEBI | | Acide ellagique | ChEBI | | Acido elagico | ChEBI | | Acidum ellagicum | ChEBI | | Benzoaric acid | ChEBI | | Ellagsaeure | ChEBI | | Lagistase | ChEBI | | 4,4',5,5',6,6'-Hexahydroxydiphenate 2,6,2',6'-dilactone | Generator | | Benzoarate | Generator | | Ellagate | Generator | | Alizarine yellow | HMDB | | Elagostasine | HMDB | | Eleagate | HMDB | | Eleagic acid | HMDB | | Ellagic acid dihydrate | HMDB | | Ellagic acid hydrate | HMDB | | Gallogen | HMDB | | Llagate | HMDB | | Llagic acid | HMDB | | Acid, benzoaric | HMDB | | Acid, ellagic | HMDB |
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| Chemical Formula | C14H6O8 |
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| Average Molecular Weight | 302.194 |
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| Monoisotopic Molecular Weight | 302.006267153 |
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| IUPAC Name | 6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione |
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| Traditional Name | 6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione |
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| CAS Registry Number | 476-66-4 |
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| SMILES | OC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2 |
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| InChI Identifier | InChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H |
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| InChI Key | AFSDNFLWKVMVRB-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Tannins |
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| Sub Class | Hydrolyzable tannins |
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| Direct Parent | Hydrolyzable tannins |
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| Alternative Parents | |
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| Substituents | - Hydrolyzable tannin
- Ellagic_acid
- 7,8-dihydroxycoumarin
- Coumarin
- Isocoumarin
- Benzopyran
- 2-benzopyran
- 1-benzopyran
- 1-hydroxy-2-unsubstituted benzenoid
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Lactone
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | > 360 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0uk9-0095000000-fbb3052375510a43a32e | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0100-3000090000-98c2eaf6f099a674f556 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0009000000-40fcade2aa63aa93a2ae | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0zi0-0192000000-778eac8f3ed58bcaac74 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-0zi0-0093000000-8a6cc05fc65249815e82 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0zfr-1589000000-a4f6e3a25012f7426f7d | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , negative | splash10-0a6r-0192000000-39923f8b1dd96716ea79 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-001i-0090000000-a1f823c8fd710f0476d9 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - Linear Ion Trap , positive | splash10-0udi-0039000000-911cfbddb0cc618af274 | Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-0zfr-1589000000-a4f6e3a25012f7426f7d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0009000000-67c5a949d6d186ed40d5 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0039000000-d2f61e8b5cdaa0f142ba | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0090000000-961daa97dff240069d92 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0029000000-246b5797e3aacdc8f2f2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0059000000-cc29f1c85d471f50bb6b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-114i-0190000000-6c3c3d5d2c468609b612 | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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| General References | - Glover D, Warner ED: The CLUE test. A multiparameter coagulation and fibrinolysis screening test using the platelet aggregometer. Am J Clin Pathol. 1975 Jan;63(1):74-80. [PubMed:1111277 ]
- Banzouzi JT, Prado R, Menan H, Valentin A, Roumestan C, Mallie M, Pelissier Y, Blache Y: In vitro antiplasmodial activity of extracts of Alchornea cordifolia and identification of an active constituent: ellagic acid. J Ethnopharmacol. 2002 Aug;81(3):399-401. [PubMed:12127243 ]
- Cerda B, Espin JC, Parra S, Martinez P, Tomas-Barberan FA: The potent in vitro antioxidant ellagitannins from pomegranate juice are metabolised into bioavailable but poor antioxidant hydroxy-6H-dibenzopyran-6-one derivatives by the colonic microflora of healthy humans. Eur J Nutr. 2004 Aug;43(4):205-20. Epub 2004 Jan 6. [PubMed:15309440 ]
- Kaiser B, Fareed J, Hoppensteadt D, Birdsong B, Walenga JM, Markwardt F: Influence of recombinant hirudin and unfractionated heparin on thrombin and factor Xa generation in extrinsic and intrinsic activated systems. Thromb Res. 1992 Jan 15;65(2):157-64. [PubMed:1579892 ]
- Jimenez F, Mitts TF, Liu K, Wang Y, Hinek A: Ellagic and tannic acids protect newly synthesized elastic fibers from premature enzymatic degradation in dermal fibroblast cultures. J Invest Dermatol. 2006 Jun;126(6):1272-80. [PubMed:16601672 ]
- Stoner GD, Sardo C, Apseloff G, Mullet D, Wargo W, Pound V, Singh A, Sanders J, Aziz R, Casto B, Sun X: Pharmacokinetics of anthocyanins and ellagic acid in healthy volunteers fed freeze-dried black raspberries daily for 7 days. J Clin Pharmacol. 2005 Oct;45(10):1153-64. [PubMed:16172180 ]
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