Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins

Sławomir Wybraniec; Yosef Mizrahi

doi:10.1016/j.chroma.2003.12.055

Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins

Sławomir Wybraniec, Yosef Mizrahi

Department of Life Sciences

Research output: Contribution to journal › Article › peer-review

26 Scopus citations

Abstract

The ability of trifluoroacetic acid, pentafluoropropionic acid and heptafluorobutyric acid to act as ion-pairing agents for betacyanins and 17-decarboxy-betacyanins during HPLC analysis on a Luna C₁₈(2) reversed-phase column is reported. While the perfluorinated carboxylic acids affect the retention of both groups of compounds by changing the pH of the mobile phase, the possibility of ion-pair chromatography for 17-decarboxy-betacyanins was noticed. In order to explain the accessibility of the positive charge for the counter-anion in decarboxy-betacyanins, the mesomeric structures of the polymethine system at low pH (around a value of 1.5), when the carboxylic group in the 2 position is protonated, should be taken into consideration.

Original language	English
Pages (from-to)	97-101
Number of pages	5
Journal	Journal of Chromatography A
Volume	1029
Issue number	1-2
DOIs	https://doi.org/10.1016/j.chroma.2003.12.055
State	Published - 12 Mar 2004

Keywords

Betacyanins
Betalains
Betanin
Carboxylic acids
Decarboxy-betacyanins
Fluorinated carboxylic acids
Hylocerenin
Hylocereus polyrhizus
Phyllocactin

ASJC Scopus subject areas

Analytical Chemistry
Biochemistry
Organic Chemistry

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10.1016/j.chroma.2003.12.055

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@article{385e78f47f8f40f6ba412c99b018b418,

title = "Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins",

abstract = "The ability of trifluoroacetic acid, pentafluoropropionic acid and heptafluorobutyric acid to act as ion-pairing agents for betacyanins and 17-decarboxy-betacyanins during HPLC analysis on a Luna C18(2) reversed-phase column is reported. While the perfluorinated carboxylic acids affect the retention of both groups of compounds by changing the pH of the mobile phase, the possibility of ion-pair chromatography for 17-decarboxy-betacyanins was noticed. In order to explain the accessibility of the positive charge for the counter-anion in decarboxy-betacyanins, the mesomeric structures of the polymethine system at low pH (around a value of 1.5), when the carboxylic group in the 2 position is protonated, should be taken into consideration.",

keywords = "Betacyanins, Betalains, Betanin, Carboxylic acids, Decarboxy-betacyanins, Fluorinated carboxylic acids, Hylocerenin, Hylocereus polyrhizus, Phyllocactin",

author = "S{\l}awomir Wybraniec and Yosef Mizrahi",

note = "Funding Information: This study was financed in part by Foundation for Supporting of Polish Pharmacy and Medicine Development at Polpharma S.A. Pharmaceutical Plant in the frame of research project No. 015/2002.",

year = "2004",

month = mar,

day = "12",

doi = "10.1016/j.chroma.2003.12.055",

language = "English",

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pages = "97--101",

journal = "Journal of Chromatography A",

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T1 - Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins

AU - Wybraniec, Sławomir

AU - Mizrahi, Yosef

N1 - Funding Information: This study was financed in part by Foundation for Supporting of Polish Pharmacy and Medicine Development at Polpharma S.A. Pharmaceutical Plant in the frame of research project No. 015/2002.

PY - 2004/3/12

Y1 - 2004/3/12

N2 - The ability of trifluoroacetic acid, pentafluoropropionic acid and heptafluorobutyric acid to act as ion-pairing agents for betacyanins and 17-decarboxy-betacyanins during HPLC analysis on a Luna C18(2) reversed-phase column is reported. While the perfluorinated carboxylic acids affect the retention of both groups of compounds by changing the pH of the mobile phase, the possibility of ion-pair chromatography for 17-decarboxy-betacyanins was noticed. In order to explain the accessibility of the positive charge for the counter-anion in decarboxy-betacyanins, the mesomeric structures of the polymethine system at low pH (around a value of 1.5), when the carboxylic group in the 2 position is protonated, should be taken into consideration.

AB - The ability of trifluoroacetic acid, pentafluoropropionic acid and heptafluorobutyric acid to act as ion-pairing agents for betacyanins and 17-decarboxy-betacyanins during HPLC analysis on a Luna C18(2) reversed-phase column is reported. While the perfluorinated carboxylic acids affect the retention of both groups of compounds by changing the pH of the mobile phase, the possibility of ion-pair chromatography for 17-decarboxy-betacyanins was noticed. In order to explain the accessibility of the positive charge for the counter-anion in decarboxy-betacyanins, the mesomeric structures of the polymethine system at low pH (around a value of 1.5), when the carboxylic group in the 2 position is protonated, should be taken into consideration.

KW - Betacyanins

KW - Betalains

KW - Betanin

KW - Carboxylic acids

KW - Decarboxy-betacyanins

KW - Fluorinated carboxylic acids

KW - Hylocerenin

KW - Hylocereus polyrhizus

KW - Phyllocactin

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U2 - 10.1016/j.chroma.2003.12.055

DO - 10.1016/j.chroma.2003.12.055

M3 - Article

AN - SCOPUS:1042299050

SN - 0021-9673

VL - 1029

SP - 97

EP - 101

JO - Journal of Chromatography A

JF - Journal of Chromatography A

IS - 1-2

ER -

Influence of perfluorinated carboxylic acids on ion-pair reversed-phase high-performance liquid chromatographic separation of betacyanins and 17-decarboxy-betacyanins

Abstract

Keywords

ASJC Scopus subject areas

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