10300. Rosmarinic Acid

Nomenclature

CAS number: 20283-92-5
(αR)-α-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxybenzenepropanoic acid; 3,4-dihydroxycinnamic acid 2-ester with 3-(3,4-dihydroxyphenyl)lactic acid; α-O-caffeoyl-(3,4-dihydroxyphenyl)lactic acid.
C18H16O8; mol wt 360.31.
C 60.00%, H 4.48%, O 35.52%.

Description and references

Naturally occurring antioxidant principally found in rosemary, sage, and other aromatic herbs of the mint family; occurs in lesser amounts in wide variety of plants. Isoln from Rosmarinus officinalis L., Lamiaceae: M. L. Scarpati, G. Oriente, Ricerca Sci. 28, 2329 (1958); from lemon balm, peppermint, and sage: K. Herrmann, Arch. Pharm. 293, 1043 (1960) DOI PubMed. Synthesis: T. Eicher et al., Synthesis 1996, 755 DOI. Large scale production in plant cell suspensions: A. I. Pavlov et al., Biotechnol. Prog. 21, 394 (2005) DOI PubMed. HPLC determn in plant material: H. Wang et al., Food Chem. 87, 307 (2004) DOI. Biosynthesis in Mentha species: B. E. Ellis, G. H. N. Towers, Biochem. J. 118, 291 (1970) PubMed. Antioxidant activity in bulk corn oil: E. N. Frankel et al., J. Agric. Food Chem. 44, 131 (1996) DOI. Clinical evaluation as anti-allergic: N. Osakabe et al., BioFactors 21, 127 (2004) PubMed. Review: M. Petersen, M. S. J. Simmonds, Phytochemistry 62, 121-125 (2003) DOI PubMed.

Chemical structure

Properties

White crystalline powder, mp 172-174°. [α]D25 +39.2° (c = 1.0 in methanol). Soly (mg/ml): 25 in ethanol, DMSO, DMF; 15 in phosphate buffered saline (pH 7.2).

Use

Antioxidant in cosmetics, edible oils; dietary supplement.