Names | |
---|---|
Preferred IUPAC name
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione | |
Other names
4,4′,5,5′,6,6′-
Hexahydroxydiphenic acid 2,6,2′,6′-dilactone
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.006.827 |
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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 [77 °F], 100 kPa).
|
Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.
The name comes from the French term acide ellagique, from the word galle spelled backward [1] 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).
Plants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin. [2]
Urolithins are gut flora human metabolites of dietary ellagic acid derivatives. [3] [4] Ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolintins. [4]
Ellagic acid was first discovered by chemist Henri Braconnot in 1831. [5] Maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905. [5] He also suggested its formation from galloyl-glycine by Penicillium in 1915. [6] Julius Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide. [5] [7]
Ellagic acid is found in oak species such as the North American white oak ( Quercus alba) and European red oak ( Quercus robur). [8]
The macrophyte Myriophyllum spicatum produces ellagic acid. [9]
Ellagic acid can be found in the medicinal mushroom Phellinus linteus. [10]
The highest levels of ellagic acid are found in raw chestnuts, walnuts, pecans, cranberries, raspberries, strawberries, and grapes, as well as distilled beverages. [11] It is also found in peaches [12] and pomegranates. [13]
Dietary source | Ellagic acid [14] |
---|---|
Fruits (mg/100g fresh weight) | |
Blackberries | 150 |
Black raspberries | 90 |
Boysenberries | 70 |
Cloudberries | 315.1 |
Pomegranate | 269.9 [15] |
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 [15] |
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 |
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. [16] [17] [18] Ellagic acid has been identified by the FDA as a "fake cancer 'cure'". [17] There is no scientific evidence to support the claims that ellagic acid can treat or prevent cancer. [17]
Names | |
---|---|
Preferred IUPAC name
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione | |
Other names
4,4′,5,5′,6,6′-
Hexahydroxydiphenic acid 2,6,2′,6′-dilactone
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.006.827 |
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
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 [77 °F], 100 kPa).
|
Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.
The name comes from the French term acide ellagique, from the word galle spelled backward [1] 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).
Plants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin. [2]
Urolithins are gut flora human metabolites of dietary ellagic acid derivatives. [3] [4] Ellagic acid has low bioavailability, with 90% remaining unabsorbed from the intestines until metabolized by microflora to the more bioavailable urolintins. [4]
Ellagic acid was first discovered by chemist Henri Braconnot in 1831. [5] Maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905. [5] He also suggested its formation from galloyl-glycine by Penicillium in 1915. [6] Julius Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide. [5] [7]
Ellagic acid is found in oak species such as the North American white oak ( Quercus alba) and European red oak ( Quercus robur). [8]
The macrophyte Myriophyllum spicatum produces ellagic acid. [9]
Ellagic acid can be found in the medicinal mushroom Phellinus linteus. [10]
The highest levels of ellagic acid are found in raw chestnuts, walnuts, pecans, cranberries, raspberries, strawberries, and grapes, as well as distilled beverages. [11] It is also found in peaches [12] and pomegranates. [13]
Dietary source | Ellagic acid [14] |
---|---|
Fruits (mg/100g fresh weight) | |
Blackberries | 150 |
Black raspberries | 90 |
Boysenberries | 70 |
Cloudberries | 315.1 |
Pomegranate | 269.9 [15] |
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 [15] |
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 |
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. [16] [17] [18] Ellagic acid has been identified by the FDA as a "fake cancer 'cure'". [17] There is no scientific evidence to support the claims that ellagic acid can treat or prevent cancer. [17]