| Rosmarinic acid | |
|---|---|
 |
|
| IUPAC name |
(2R)-2-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]]oxy]-3-(3,4-dihydroxyphenyl)propanoic acid
|
| Identifiers | |
| CAS number | 537-15-5 |
| PubChem | 5281792 |
| SMILES |
OC1=CC=C(/C=C/C(O[C@@H]([C@@]
(O)=O)CC2=CC=C(O)C(O)=C2)=O)C=C1O |
| Properties | |
| Molecular formula | C18H16O8 |
| Molar mass | 360.31 g/mol |
| Melting point |
171-175 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Rosmarinic acid, C18H16O8, is a natural polyphenol antioxidant carboxylic acid found in many Lamiaceae herbs used commonly as culinary herbs such as lemon balm, rosemary, oregano, sage, thyme and peppermint.[1] Chemically, rosmarinic acid is an ester of caffeic acid with 3,4-dihydroxyphenyl lactic acid. It is a red-orange powder that is slightly soluble in water, but well soluble in most organic solvents.[2]
Contents |
Biological importance
Because of the antioxidant activity of Lamiaceaeous herbs in laboratory test models they have been suggested to have beneficial effects in humans.[3]
Metabolism
Rosmarinic acid is known to undergo metabolism in humans and rats to methylated rosmarinic acid, coumaric acid, ferulic acid and caffeic acid.[citation needed]
References
- ^ Clifford, M.N. Chlorogenic acids and other cinnamates. Nature, occurrence and dietary burden. J. Sci. Food. Agric. (79) 362-372, 1999
- ^ MSDS for rosmarinic acid
- ^ Triantaphyllou, K.;Blekas, G.; Boskou, D. Antioxidative properties of water extracts obtained from herbs of the species Lamiacaea. Int. J. Food. Sci. Nutr. (52) 313-317, 2001
See also
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