title: Thermal transformation of trans-5-O-caffeoylquinic acid (trans-5-CQA) in alcoholic solutions.
abstract: Chlorogenic acid (CQA), the ester of caffeic acid with quinic acid supplied to human organisms mainly with coffee, tea, fruit and vegetables, has been one of the most studied polyphenols. It is potentially useful in pharmaceuticals, food additives, and cosmetics due to its recently discovered biomedical activity, which revived interest in its properties, isomers and natural occurrence. We found that the heating of the alcoholic solution of trans-5-O-caffeoylquinic acid produced at least twenty compounds (chlorogenic acid derivatives and its reaction products with water and alcohol). The formation of three of them (methoxy, ethoxy and propoxy adducts) has not been reported yet. No reports exist either on methoxy adducts of 3- and 4-O-caffeoylquinic acid appearing in buffered methanol/water mixtures at pH exceeding 7. We observed that the amount of each formed component depended on the heating time, type of alcohol, its concentration in alcoholic/water mixture, and pH.
authors.affiliation: Faculty of Chemistry, Maria Curie Sklodowska University, 20-031 Lublin, Pl. Maria Curie Sklodowska 3, Poland. Electronic address: dawid@poczta.umcs.lublin.pl.
authors.forename: Andrzej L
authors.initials: AL
authors.lastname: Dawidowicz
authors.affiliation: Faculty of Chemistry, Maria Curie Sklodowska University, 20-031 Lublin, Pl. Maria Curie Sklodowska 3, Poland.
authors.forename: Rafal
authors.initials: R
authors.lastname: Typek
mesh_terms: D002726:Chlorogenic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D062385:Hydroxybenzoates / Q000378:metabolism*; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D002726:Chlorogenic Acid; D062385:Hydroxybenzoates; D011801:Quinic Acid; C017616:phenolic acid; C473200:5-caffeoylquinic acid
keywords: Chlorogenic acid; Extraction; Phenolic acid; Transesterification; trans-5-CQA isomerisation; trans-5-CQA transformation