An Unambiguous Nomenclature for the Acyl-quinic Acids Commonly Known as Chlorogenic Acids

被引:58
作者
Abranko, Laszlo [1 ]
Clifford, Michael N. [2 ]
机构
[1] Szent Istvan Univ, Fac Food Sci, Dept Appl Chem, H-1118 Budapest, Hungary
[2] Univ Surrey, Sch Biosci & Med, Fac Hlth & Med Sci, Guildford GU2 7XH, Surrey, England
关键词
chlorogenic acids; nomenclature; quinic acids; DIASTEREOMERS; TANNINS;
D O I
10.1021/acs.jafc.7b00729
中图分类号
S [农业科学];
学科分类号
082806 [农业信息与电气工程];
摘要
The history of the acyl-quinic acids is briefly reviewed, the merits and limitations of the various nomenclature systems applicable are critically compared, and their limitations are highlighted, in particular their inability to provide an unambiguous description of all quinic acid enantiomers and diastereoisomers and associated acyl-quinic acids. Recommendations are made for a nomenclature system that in combination with IUPAC numbering achieves this objective. A comprehensive set of structures for the quinic acid enantiomers and diastereoisomers is presented. The Supporting Information provides an explanation of trivial names and a decision tree to determine which quinic acid isomer a structure represents.
引用
收藏
页码:3602 / 3608
页数:7
相关论文
共 26 条
[1]
[Anonymous], 1976, BIOCHEM J
[2]
[Anonymous], 1964, J CHEM EDUC, DOI DOI 10.1021/ED041P116
[3]
ISOCHLOROGENIC ACID - ISOLATION FROM COFFEE AND STRUCTURE STUDIES [J].
BARNES, HM ;
FELDMAN, JR ;
WHITE, WV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (09) :4178-4182
[4]
SPECIFICATION OF MOLECULAR CHIRALITY [J].
CAHN, RS ;
INGOLD, C ;
PRELOG, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (04) :385-&
[5]
Clifford M.N., 2017, RESEARCHGATE, DOI 10.13140/RG.2.2.21311.71848
[6]
COOKMAN GERALD, 1965, PHYTOCHEMISTRY, V4, P773, DOI 10.1016/S0031-9422(00)86249-4
[7]
DIASTEREOMERS OF QUINIC ACID - CHEMICAL AND NUCLEAR MAGNETIC RESONANCE STUDIES [J].
CORSE, J ;
LUNDIN, RE .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1904-+
[8]
CORSE JOSEPH, 1965, PHYTOCHEMISTRY, V4, P527, DOI 10.1016/S0031-9422(00)86209-3
[9]
Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid [J].
Deshpande, Sagar ;
Matei, Marius Febi ;
Jaiswal, Rakesh ;
Bassil, Bassem S. ;
Kortz, Ulrich ;
Kuhnert, Nikolai .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2016, 64 (38) :7298-7306
[10]
(-)-quinic acid: configurational (stereochemical) descriptors [J].
Eliel, EL ;
Ramirez, MB .
TETRAHEDRON-ASYMMETRY, 1997, 8 (21) :3551-3554