 | |
| Names | |
|---|---|
| Preferred IUPAC name (3R,4R)-3,4-Bis[(4-hydroxyphenyl)methyl]oxolan-2-one | |
| Other names (−)-Enterolactone | |
| Identifiers | |
3D model (JSmol) | |
| Abbreviations | ENL |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.162.708 |
| EC Number |
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| KEGG |
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| UNII | |
| |
| |
| Properties | |
| C18H18O4 | |
| Molar mass | 298.338 g·mol−1 |
| Hazards | |
| GHS labelling:[1] | |
 | |
| Warning | |
| H315,H319,H335 | |
| P261,P264,P264+P265,P271,P280,P302+P352,P304+P340,P305+P351+P338,P319,P321,P332+P317,P337+P317,P362+P364,P403+P233,P405,P501 | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Enterolactone is anorganic compound classified as anenterolignan. It is formed by the action of intestinal bacteria on plantlignan precursors present in the diet.
Many dietary plant lignan precursors, such assecoisolariciresinol,matairesinol,lariciresinol,pinoresinol, andsesamin, can be metabolized bygut microbes to enterolactone.[1][2][3] In edible plants lignans are bound to the fiber fraction and therefore fiber-rich food products, such as cereals, vegetables, fruits and berries, are generally good sources of lignans and enterolactone. The richest known dietary sources of enterolactone precursors areflaxseed andsesame seed.[4][5][6] Since enterolactone is produced by specific species of gut microbiota, the capacity to produce it varies between people.[7] Antibiotic treatments can abolish the capacity to produce enterolactone. It may take up to a year before enterolactone production is restored.[8][9]
Enterolactone is suggested to possess beneficial health effects in humans. In epidemiological studies lower concentrations of enterolactone have been observed inbreast cancer patients compared to healthy controls, which may suggest that enterolactone isanti-carcinogenic. Enterolactone and lignans may also be protective againstcardiovascular disease.[10][11]
