Chicoric acid (dicaffeyltartic acid): Its isolation from chicory (Chicorium intybus) and synthesis

Synthesis of tartaric acid analogues of FR258900 and their evaluation as glycogen phosphorylase inhibitors

“…A similar derivative to our target compounds is chicoric acid 20 (2) with immunostimulator and HIV-1 integrase inhibitor activities. Crucial points for both the syntheses of chicoric acid [20][21][22][23] and 100 the preparation of our target compounds are the protections of phenolic OH and COOH groups.…”

“…Acylation of unprotected tartaric acids with carbonylcaffeoyl chloride is feasible, but this carbonate type protection can be used only for caffeic acid. 20 Benzylic protection of both functionalities seemed very attractive, however, for the removal an equimolar amount of Pd(OAc) 2 for each protective group was necessary rendering this method extremely expensive. 23 Orthogonal ester type protection (acetyl for OH and tert-butyl for COOH 22 or methoxycarbonyl for OH and diphenylmethyl for COOH 21 ) were also applied in the syntheses of 2 and their ana-110 logues.…”

“…Crucial points for both the syntheses of chicoric acid [20][21][22][23] and 100 the preparation of our target compounds are the protections of phenolic OH and COOH groups. Acylation of unprotected tartaric acids with carbonylcaffeoyl chloride is feasible, but this carbonate type protection can be used only for caffeic acid.…”

Caffeoyl Derivatives: Major Antioxidant Compounds of Some Wild Herbs of the <i>Asteraceae</i> Family

“…Chicoric acid (dicaffeoyltartaric acid) and 1,5-, 3,5-and 4,5-di-O-caffeoylquinic acids were isolated as described elsewhere [7,15,18]. All other reagents were of pharmacopoeia purity and organic solvents were HPLC grade (Merck, Darmstadt, Germany).…”

“…The most common flavonoids are the 7-glycosides of apigenin and luteolin [4,5]. Among the dihydroxycinnamic derivatives, the oldest known are cynarin (dicaffeoylquinic acid) from artichoke and chicoric acid (dicaffeoyltartaric acid) from chicory [6,7]. Among the 18 medicinal or food species of Asteraceae studied, recent work has helped clarify the caffeoylquinic acid composition or show the presence of these constituents in some of these plants.…”