Rosmarinic acid

Chembox new
Name = Rosmarinic acid
ImageFile = Rosmarinic acid.png ImageName = Rosmarinic acid
IUPACName =(2"R")-2-(2"E")-3-(3,4-Dihydroxyphenyl)-
1-oxo-2-propenyloxy] -3-(3,4-
dihydroxyphenyl)propanoic acid
Section1 = Chembox Identifiers
SMILES = OC1=CC=C(/C=C/C(O [C@@H] ( [C@@]
(O)=O)CC2=CC=C(O)C(O)=C2)=O)C=C1O
Section2 = Chembox Properties
Formula = C₁₈H₁₆O₈
MolarMass = 360.31 g/mol
Density =
MeltingPt = 171-175 °C

Rosmarinic acid, C₁₈H₁₆O₈, is a natural polyphenol antioxidant carboxylic acid found in many "Lamiaceae" herbs used commonly as culinary herbs such as rosemary, oregano, sage, thyme and peppermint. [Clifford, M.N. Chlorogenic acids and other cinnamates. Nature, occurrence and dietary burden. J. Sci. Food. Agric. (79) 362-372, 1999] Chemically, rosmarinic acid is a dimer of caffeic acid. It is a red-orange powder that is slightly soluble in water, but well soluble is most organic solvents. [ [http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/44699 MSDS for rosmarinic acid] ]

Biological importance

Because of the antioxidant activity of "Lamiacaea" herbs in laboratory test models they have been suggested to have beneficial effects in humans. [ 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]

Metabolism

Rosmarinic acid is known to undergo metabolism in humans and rats to methylated rosmarinic acid, coumaric acid, ferulic acid and caffeic acid.Fact|date=February 2007

References

ee also

*Caffeic acid
*Coumaric acid
*Ferulic acid