ellagic acid ellagic acid ellagic acid names preferred iupac name 2,3,7,8-tetrahydroxybenzopyranobenzopyran-5,10-dione other names 4,4′,5,5′,6,6′-hexahydroxydiphenic acid 2,6,2′,6′-dilactone identifiers cas number 476-66-4 y 3d model (jsmol) interactive image chebi chebi:4775 y chembl chembl6246 y chemspider 4445149 y drugbank db08468 y echa infocard 100.006.827 kegg c10788 y pubchem cid 5281855 unii 19yrn3zs9p y comptox dashboard (epa) dtxsid2020557 inchi 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 ykey: afsdnflwkvmvrb-uhfffaoysa-n yinchi=1/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/h1-2,15-18hkey: afsdnflwkvmvrb-uhfffaoyaq smiles o=c1oc3c2c4c1cc(o)c(o)c4oc(=o)c2cc(o)c3o properties chemical formula c14h6o8 molar mass 302.197 g/mol density 1.67 g/cm3 except where otherwise noted, data are given for materials in their standard state (at 25 °c , 100 kpa). y verify (what is yn ?) infobox references uv visible spectrum of ellagic acid ellagic acid is a polyphenol found in numerous fruits and vegetables. it is the dilactone of hexahydroxydiphenic acid. name the name comes from the french term acide ellagique, from the word galle spelled backwards because it can be obtained from noix de galle (galls), and to distinguish it from acide gallique (gallic acid). the molecule structure resembles to that of two gallic acid molecules being assembled "head to tail" and bound together by a c–c bond (as in biphenyl, or in diphenic acid) and two lactone links (cyclic carboxylic esters). metabolism biosynthesis plants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin. biodegradation urolithins are gut flora human metabolites of dietary ellagic acid derivatives. ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolintins. history ellagic acid was first discovered by chemist henri braconnot in 1831. maximilian nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905. he also suggested its formation from galloyl-glycine by penicillium in 1915. julius löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide. natural occurrences ellagic acid is found in oak species such as the north american white oak (quercus alba) and european red oak (quercus robur). the macrophyte myriophyllum spicatum produces ellagic acid. ellagic acid can be found in the medicinal mushroom phellinus linteus. in food the highest levels of ellagic acid are found in raw chestnuts, walnuts, pecans, cranberries, raspberries, strawberries, and grapes, as well as distilled beverages. it is also found in peaches and pomegranates. dietary source ellagic acid fruits (mg/100g fresh weight) blackberries 150 black raspberries 90 boysenberries 70 cloudberries 315.1 pomegranate 269.9 raspberries 270 rose hip 109.6 strawberries 77.6 strawberry jam 24.5 yellow raspberries 1900 nuts (mg/100g fresh weight) pecans 33 walnuts 59 beverages (mg/l) pomegranate juice 811.1 cognac 31–55 oak-aged red wine 33 whiskey 1.2 seeds (mg/g) black raspberries 6.7 red raspberries 8.7 boysenberries 30 mango 1.2 research and health claims ellagic acid has been marketed as a dietary supplement with various claimed benefits against cancer, heart disease, and other diseases. in the 21st century, numerous u.s.-based supplement companies received fda warning letters for promoting ellagic acid with false anti-disease claims that violate the federal food, drug, and cosmetic act. ellagic acid has been identified by the fda as a "fake cancer 'cure'". there is no scientific evidence to support the claims that ellagic acid can treat or prevent cancer.