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| | Ellagic acid Basic information |
| Product Name: | Ellagic acid | | Synonyms: | eleagicacid;gallogen(astringent);TIMTEC-BB SBB006501;2,3,7,8-tetrahydroxy(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,10-dione;ELLAGIC ACID;BENZOARIC ACID;AKOS NCG1-0028;4,4',5,5',6,6'-HEXAHYDROXYDIPHENIC ACID 2,6,2',6'-DILACTONE | | CAS: | 476-66-4 | | MF: | C14H6O8 | | MW: | 302.19 | | EINECS: | 207-508-3 | | Product Categories: | Anthraquinones, Hydroquinones and Quinones;Natural Plant Extract;Antioxidant;Biochemistry;Inhibitors;Building block;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Food additive;Plant extracts;plant extract;VX:15169101773;476-66-4 | | Mol File: | 476-66-4.mol |  |
| | Ellagic acid Chemical Properties |
| Melting point | ≥350 °C | | Boiling point | 363.24°C (rough estimate) | | density | 1.667 | | refractive index | 1.5800 (estimate) | | storage temp. | 2-8°C | | solubility | 1 M NaOH: 10 mg/mL, dark green | | form | powder | | pka | 5.02±0.20(Predicted) | | color | tan to gray | | biological source | tree bark | | Water Solubility | <0.1 g/100 mL at 21 ºC | | Sensitive | Air & Light Sensitive | | Merck | 14,3547 | | BRN | 47549 | | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. | | Major Application | food and beverages | | Cosmetics Ingredients Functions | SKIN CONDITIONING | | 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 | | InChIKey | AFSDNFLWKVMVRB-UHFFFAOYSA-N | | SMILES | Oc1cc2C(=O)Oc3c(O)c(O)cc4C(=O)Oc(c1O)c2-c34 | | LogP | 0.239 (est) | | CAS DataBase Reference | 476-66-4(CAS DataBase Reference) | | EPA Substance Registry System | Ellagic acid (476-66-4) |
| | Ellagic acid Usage And Synthesis |
| Chemical Properties | cream to light yellow crystalline solid, soluble in methanol, ethanol, DMSO and other organic solvents, derived from Mangiferaindica, Eucalyptuscitriodora, Lythrumsalicaria, Geranium sibiricum, Agrimoniapilosavar.japonica. | | Uses | Ellagic Acid is a phenol antioxidant found naturally in various fruits and vegetables. Ellagic Acid was shown to exhibit high levels of hemostatic, antineoplastic, antimutagenic, antiproliferative and antioxidant properties in studies, which suggests its potential health benefits following ellagic acid consumption. | | Application | Ellagic acid is used in medicine and cosmetics, as an antioxidant, and has anti-cancer and anti-viral effects.
Ellagic acid, a common plant polyphenol, is an inhibitor of glutathione S-transferase with Exhibits antitumor activity. It can be used for the determination of factor XIIa in plasma. Contact activation can occur in blood coagulation. It is also used as selective, ATP-competitive inhibitor of casein kinase 2 and a Topo I and II, FGR, GSK, and PKA inhibitor. | | Definition | ChEBI: Ellagic acid is an organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor and a geroprotector. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It is functionally related to a gallic acid. | | Preparation | Ellagic acid is mainly extracted from plants, and it is present in several fruits such as cranberries, strawberries, raspberries, and pomegranates. Usually, the raw materials are degreasing and then extracted with an alkaline aqueous solution or extracted with ethanol. Then, after removing water-soluble proteins and gliadins, the sugar ligands can be decomposed by enzymes to obtain purer ellagic acid. | | General Description | Cream-colored needles (from pyridine) or yellow powder. Odorless. | | Air & Water Reactions | Insoluble in water. | | Reactivity Profile | Ellagic acid reacts as a weak acid. Incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated. Heat is also generated by the acid-base reaction between phenols and bases. May be sulfonated exothermically very readily (for example, by concentrated sulfuric acid at room temperature). May be nitrated very rapidly, even by dilute nitric acid. | | Fire Hazard | Flash point data for Ellagic acid are not available; however, Ellagic acid is probably combustible. | | Biological Activity | Selective, ATP-competitive inhibitor of casein kinase 2 (CK2) (IC 50 values are 40, 2900, 3500, 4300 and 9400 nM for CK2, Lyn, PKA, Syk and FGR respectively). Exhibits antioxidant, antitumor and anticarcinogenic activity and also inhibits glutathione S-transferase. | | Biochem/physiol Actions | Commonly occurring plant polyphenol, inhibitor of glutathione S-transferase. Used for the assay of factor XIIa in plasma. Contact activation in blood coagulation. | | Mechanism of action | The molecular mechanism of Ellagic acid is mainly reflected in inhibiting the proliferation of tumor cells through VEGFR-2 signaling pathway, Notch signaling pathway, PKC signaling pathway and COX-2 signaling pathway. PI3K/Akt signaling pathway, JNK (cJun) signaling pathway, mitochondrial pathway, Bcl-2 / Bax signaling pathway, TGF-β/Smad3 signaling pathway induced apoptosis of tumor cells and blocked EMT process and MMP SDF1α/CXCR4 signaling pathway inhibits the metastasis and invasion of tumor cells, induces autophagy and affects tumor metabolic reprogramming to produce anti-tumor effects[1]. | | Anticancer Research | Ellagic acid is a naturally occurring phenolic constituent present in natural productsand nuts, most elevated amounts of which are found in raspberries (Daniel et al.1990). EA is considered as a potent anticarcinogenic and antimutagenic compound.EA shows anti-angiogenic property by repressing PDGF-R movement and phosphorylationof its substrate. It can intrude with endothelial cell-associated VEGR-2phosphorylation bringing about the restraint of the downstream signaling activatedby this receptor and in the hindrance of two key events fundamental in angiogenesis,i.e., EC movement and morphogenic separation into capillary-like structure. In parallel,EA indicated robust inhibitory activity against perivascular cells through itsrestraint of PDGF-R action and signaling prompting hindrance of VSMC relocation(Labrecque et al. 2005).
It is a phenolic compound extracted from pomegranate. It is an antiproliferative andantioxidant compound (Murakami et al. 1996). It induces apoptosis in cancer cellsof the prostate and breast and prevents the process of metastasis in different cancers(Singh et al. 2016b). | | Source | Fruits including strawberries, berries, pomegranate, and nuts and seeds are rich in edible Ellagitannins (ETs), within which raspberries and cloudberries are the most abundant sources. In general, fruits of the genus Rubus are the most studied for their content in ETs and ellagic acid (EA). Among them, raspberries of different species, such as R. idaeus, R. occidentalis, and R. ursinusxidaeus, have been investigated showing an ETs/EA content ranging from 16 to 17.92 mg/g. In addition, other kinds of fruits native to tropical countries have been found to contain significant amounts of ETs and EA.[2] | | storage | Room temperature | | Purification Methods | This antioxidant crystallises from pyridine. It forms a dark green solution in aqueous N NaOH. The tetraactetate dilactone crystallises from Ac2O, with m 340o. [Beilstein 19 H 261, 19 III/IV 3164, 19/7 V 108.] | | References |
[1] Lu, G., Wang, X., Cheng, M., Wang, S., Ma, K. (2023). The multifaceted mechanisms of ellagic acid in the treatment of tumors: State-of-the-art. Biomedicine & Pharmacotherapy, 165, Article 115132. https://doi.org/10.1016/j.biopha.2023.115132
[2] Mantzourani, C., Kakouri, E., Palikaras, K., Tarantilis, P., Kokotou, M. G. (2024). Urolithins and Their Precursors Ellagic Acid and Ellagitannins: Natural Sources, Extraction and Methods for Their Determination. Separations, 41 6. https://doi.org/10.3390/separations11060174
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| | Ellagic acid Preparation Products And Raw materials |
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