| 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] Rosmarinic acid has a number of interesting biological activities, e.g. antiviral, antibacterial, antiinflammatory and antioxidant. The presence of rosmarinic acid in medicinal plants, herbs and spices has beneficial and health promoting effects. In plants, rosmarinic acid is supposed to act as a preformed constitutively accumulated defense compound. [4]
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
- ^ Petersen M, Simmonds MS.Institut für Pharmazeutische Biologie, Philipps-Universität Marburg, Deutschhausstr. 17A, D-35037 Marburg, Germany. petersen@mailer.uni-marburg.de
See also
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