Quinic Acid


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Related to Quinic Acid: Caffeic acid, Chlorogenic acid, Shikimic acid

quinic acid

[′kwin·ik ′as·əd]
(organic chemistry)
C6H7(OH)4COOH·H2O Ether-insoluble, white crystals with acid taste; melts at 162°C; soluble in alcohol, water, and glacial acetic acid; used in medicine. Also known as chinic acid; kinic acid.

Quinic Acid

 

C6H7(OH)4COOH, a monobasic hydroxy poly-carboxylic acid; an important intermediate product in the biosynthesis of aromatic compounds (flavonoids and phenol carboxylic acid) in higher plants and some microorganisms. Quinic acid is obtained in the form of colorless crystals, which dissolve readily in water. It has a melting point of 162°C. It is found primarily in peaches, pears, and coffee berries, as well as in the bark of the cinchona tree and the summer needles of pines. In both plants and microorganisms, it is formed from acyclic carbohydrates, namely, heptuloses. In higher plants, quinic acid is readily converted to shikimic acid, phenylalanine, and tyrosine. In bacteria, it usually does not participate in the biosynthesis of aromatic acids. Esters of quinic acid are often encountered in plants, for example, chlorogenic acid.

REFERENCES

Zaprometov, M. N. Osnovy biokhimii fenol’nykh soedinenii. Moscow, 1974.
Kretovich, V. L. Osnovy biokhimii rastenii, 5th ed. Moscow, 1971.
References in periodicals archive ?
Quinic acid derivatives from Pimpinella brachycarpa exert anti-neuroinflammatory activity in lipopolysaccharide-induced microglia.
In turn, other compounds initially not present or present only in low quantities in green coffee are generated in the roasting process, such as quinic acid, one of the important products generated during the degrading process of chlorogenic acid, lactic acid, acetic acid as well as formic acid.
Peer-reviewed studies have been published that document the presence of CAEs such as quinic acid esters in water extracts of Uncaria tomentosa bark (see reviews by Pero ref.
Apigenin and luteolin derivatives, and quinic acid esters of caffeic and p-coumaric acids showed also similarity in accumulation pattern among clones.
Pero and colleagues (4) while working at Lund University in Southern Sweden were the first to identify quinic acid analogs as the primary bioactive component of hot water extracts of Cat's Claw called C-Med-100.
Green leaves consisted of 55% ellagitannins, 29% gallic acid derivatives and 11% flavonoids, with the remaining gallic acid, arbutin, bergenin and caffeoyl quinic acid.
quinic acid derivatives (chlorogenic acid, 4,5-dicaffeoylquinic acid, 3-0-caffeoyl-5-0-sinapoylquinic acid, etc.
The attachment positions of the caffeoyl moieties to the quinic acid could not, however, be determined.
3,5-dicaffeoyl quinic acid (2), 3,4-dicaffeoyl quinic acid (3), 4,5-dicaffeoyl quinic acid (4), apigenin (5),apigenin-7-O-[beta]-D-glucoside (6), apigenin-4-O-[beta]-D-glucoside (7), luteolin (8).
A study of human chlorogenic acid metabolism showed that the unabsorbed chlorogenic acid which reaches the colon is hydrolysed to caffeic acid and quinic acid by the microflora present there (Olthof et al.
Bioassay-directed fractionation of EHS following by inhibition of 12-0-tetradecanoyl-13-acetate (TPA)-mediated NF-[kappa]B activation led to the isolation of the cyclitols quinic acid (1) (85.
Four quinic acid gallates were isolated from the dried pods of Tara [Caesalpinia spinosa (Molina) Kuntze].