1019. Synthesis of 3-O-p-coumaroylquinic acid

Abstract

A substance previously isolated from cider apples is shown by synthesis Its biogenetic relationship to chlorogenic to be 3-0-p-coumaroylquinic acid. acid is briefly discussed. CHLOROGENIC ACID was first isolated from coffee beans by Gorter who showed it to be a derivative of quinic acid (Ia). Freundenberg showed that the enzyme tannase hydrolysed chlorogenic acid to equimolar amounts of quinic and caffeic acid, and its structure as the 3-caffeic ester (Ib) of quinic acid was later deduced by Fischer and Dangschat from its methylation and subsequent hydrolysis to 3,4-di-O-methylcaffeic acid and 1,4,5tri-0-methylquinic acid (isolated as the 1,3-lactone). A synthesis of chlorogenic acid by Panizzi, Scarpati, and Oriente Since its initial isolation from coffee beans, chlorogenic acid has been found in other plant species and the advent of modern methods of plant analysis, notably paper chromatography, has shown its widespread distribution in the fruit, leaves, and other tissues of a variety of dicotyledenous plants.6 Paper-chromatographic analysis of the chemical constituents of plant tissues has also enabled additional related phenolic compounds to be identified and later isolated. Thus in 1958 Williams isolated from cider apples a compound which

Chlorogenic Acids

“…28 This protection can be removed by treatment with hydrazine hydrate in methanol, preferably before removing the protection on the unesterified hydroxy group(s) in the quinic acid residue to minimise acyl migration and saponification of the ultimate CGA. 2 7 Haslam et al 29 preferred benzoylation with removal by palladium-charcoal hydrogenation for the oxidation-sensitive GQA. The protected aroma tic acids can be converted to acyl chlorides by treatment with sulphonyl chloride.…”

“…Alberti et al 32 reported that 1,3,4-triCQA could be selectively saponified using barium hydroxide to yield 1,4-diCQA. Another approach would be controlled isomerisation of 1,5-diCQA (see Section 3.4 29 used diphenylmethylquinate in the preparation of 1,3,4,5-tetraGQA.…”

“…26 For example, Panizzi and Scarpati 14 used 15 h at room temperature for 1,4-diCQA; Haslam el al. 29 used 10 days at 60°C for 5-GQA but 60 ac for 25 days for 1,3,4,5-tetraGQA.…”

Discovery of Quinic Acid Derivatives as Oral Anti-inflammatory Agents

“…11,12 Derivatives of QA, such as chlorogenic acid (CGA) ( Figure 1-1), p-coumaryl quinate, etc., are also common in plants. [13][14][15] …”

“…The solvent was removed under high vacuum to get yellow foam. ]undecan-9-one (14). A mixture of quinic qcid (1) (20g, 104.1 mMol), p-totuenesulfonic acid monohydrate (0.2g), 2,2-dimethoxypropane ( 38g, 364 mMol), and acetone ( 100 mL) was heated to reflux for 2 hr.…”