Chapter 2: Chemistry of Anthocyanins

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

In this chapter, the current state of knowledge regarding anthocyanin chemistry and the corresponding reversible multistate system of the chemical species is presented. Mathematical equations to account for the kinetics and thermodynamics of the multistate system of anthocyanins are presented in a simple form to allow their use by non-specialists. The calculation of all rate and equilibrium constants of malvidin-3-glucoside in diluted solutions has been carried out to illustrate the use of these expressions. The irreversible reactivity of anthocyanins in foodstuffs, particularly in wine, leading to pyranoanthocyanins of the first and second generation is discussed. The use of the relative energy level diagrams of the multistate species together with their pH-dependent mole fraction distribution is reported and their usefulness emphasized. Using the morning glory flower as an example, the expression of its blue colour is rationalized by considering the thermodynamics and kinetics of the multistate system.

Original languageEnglish
Title of host publicationSteviol Glycosides: Cultivation, Processing, Analysis and Applications in Food
EditorsMarianne Su-Ling Brooks, Giovana B. Celli
PublisherRoyal Society of Chemistry
Pages34-76
Number of pages43
Edition12
DOIs
Publication statusPublished - 1 Jan 2019

Publication series

NameFood Chemistry, Function and Analysis
PublisherRoyal Society of Chemistry
Number12
Volume2019-January
ISSN (Print)2398-0656
ISSN (Electronic)2398-0664

Fingerprint

Anthocyanins
anthocyanins
chemistry
Thermodynamics
thermodynamics
Clerodendrum bungei
kinetics
malvidin
chemical speciation
Kinetics
Wine
Equilibrium constants
Electron energy levels
glucosides
wines
Rate constants
Color
color
energy

Cite this

Pina, F., Parola, A. J., Melo, M. J., Lima, J. C., & Freitas, V. D. (2019). Chapter 2: Chemistry of Anthocyanins. In M. S-L. Brooks, & G. B. Celli (Eds.), Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food (12 ed., pp. 34-76). (Food Chemistry, Function and Analysis; Vol. 2019-January, No. 12). Royal Society of Chemistry. https://doi.org/10.1039/9781788012614-00034
Pina, F. ; Parola, A. J. ; Melo, M. J. ; Lima, J. C. ; Freitas, V. de. / Chapter 2: Chemistry of Anthocyanins. Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food. editor / Marianne Su-Ling Brooks ; Giovana B. Celli. 12. ed. Royal Society of Chemistry, 2019. pp. 34-76 (Food Chemistry, Function and Analysis; 12).
@inbook{b4c9f9d2e66a40748b50aae39c822494,
title = "Chapter 2: Chemistry of Anthocyanins",
abstract = "In this chapter, the current state of knowledge regarding anthocyanin chemistry and the corresponding reversible multistate system of the chemical species is presented. Mathematical equations to account for the kinetics and thermodynamics of the multistate system of anthocyanins are presented in a simple form to allow their use by non-specialists. The calculation of all rate and equilibrium constants of malvidin-3-glucoside in diluted solutions has been carried out to illustrate the use of these expressions. The irreversible reactivity of anthocyanins in foodstuffs, particularly in wine, leading to pyranoanthocyanins of the first and second generation is discussed. The use of the relative energy level diagrams of the multistate species together with their pH-dependent mole fraction distribution is reported and their usefulness emphasized. Using the morning glory flower as an example, the expression of its blue colour is rationalized by considering the thermodynamics and kinetics of the multistate system.",
author = "F. Pina and Parola, {A. J.} and Melo, {M. J.} and Lima, {J. C.} and Freitas, {V. de}",
note = "info:eu-repo/grantAgreement/FCT/5876/147218/PT# This work was supported by the Associated Laboratory for Sustainable Chemistry Clean Processes and Technologies LAQV. The latter is financed by national funds from FCT/MEC (UID/QUI/50006/2013) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265). FCT/MEC is also acknowledged through the Projects PTDC/QEQ-QFI/ 1971/2014.",
year = "2019",
month = "1",
day = "1",
doi = "10.1039/9781788012614-00034",
language = "English",
series = "Food Chemistry, Function and Analysis",
publisher = "Royal Society of Chemistry",
number = "12",
pages = "34--76",
editor = "Brooks, {Marianne Su-Ling} and Celli, {Giovana B.}",
booktitle = "Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food",
address = "United Kingdom",
edition = "12",

}

Pina, F, Parola, AJ, Melo, MJ, Lima, JC & Freitas, VD 2019, Chapter 2: Chemistry of Anthocyanins. in MS-L Brooks & GB Celli (eds), Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food. 12 edn, Food Chemistry, Function and Analysis, no. 12, vol. 2019-January, Royal Society of Chemistry, pp. 34-76. https://doi.org/10.1039/9781788012614-00034

Chapter 2: Chemistry of Anthocyanins. / Pina, F.; Parola, A. J.; Melo, M. J.; Lima, J. C.; Freitas, V. de.

Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food. ed. / Marianne Su-Ling Brooks; Giovana B. Celli. 12. ed. Royal Society of Chemistry, 2019. p. 34-76 (Food Chemistry, Function and Analysis; Vol. 2019-January, No. 12).

Research output: Chapter in Book/Report/Conference proceedingChapter

TY - CHAP

T1 - Chapter 2: Chemistry of Anthocyanins

AU - Pina, F.

AU - Parola, A. J.

AU - Melo, M. J.

AU - Lima, J. C.

AU - Freitas, V. de

N1 - info:eu-repo/grantAgreement/FCT/5876/147218/PT# This work was supported by the Associated Laboratory for Sustainable Chemistry Clean Processes and Technologies LAQV. The latter is financed by national funds from FCT/MEC (UID/QUI/50006/2013) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265). FCT/MEC is also acknowledged through the Projects PTDC/QEQ-QFI/ 1971/2014.

PY - 2019/1/1

Y1 - 2019/1/1

N2 - In this chapter, the current state of knowledge regarding anthocyanin chemistry and the corresponding reversible multistate system of the chemical species is presented. Mathematical equations to account for the kinetics and thermodynamics of the multistate system of anthocyanins are presented in a simple form to allow their use by non-specialists. The calculation of all rate and equilibrium constants of malvidin-3-glucoside in diluted solutions has been carried out to illustrate the use of these expressions. The irreversible reactivity of anthocyanins in foodstuffs, particularly in wine, leading to pyranoanthocyanins of the first and second generation is discussed. The use of the relative energy level diagrams of the multistate species together with their pH-dependent mole fraction distribution is reported and their usefulness emphasized. Using the morning glory flower as an example, the expression of its blue colour is rationalized by considering the thermodynamics and kinetics of the multistate system.

AB - In this chapter, the current state of knowledge regarding anthocyanin chemistry and the corresponding reversible multistate system of the chemical species is presented. Mathematical equations to account for the kinetics and thermodynamics of the multistate system of anthocyanins are presented in a simple form to allow their use by non-specialists. The calculation of all rate and equilibrium constants of malvidin-3-glucoside in diluted solutions has been carried out to illustrate the use of these expressions. The irreversible reactivity of anthocyanins in foodstuffs, particularly in wine, leading to pyranoanthocyanins of the first and second generation is discussed. The use of the relative energy level diagrams of the multistate species together with their pH-dependent mole fraction distribution is reported and their usefulness emphasized. Using the morning glory flower as an example, the expression of its blue colour is rationalized by considering the thermodynamics and kinetics of the multistate system.

UR - http://www.scopus.com/inward/record.url?scp=85062384627&partnerID=8YFLogxK

U2 - 10.1039/9781788012614-00034

DO - 10.1039/9781788012614-00034

M3 - Chapter

T3 - Food Chemistry, Function and Analysis

SP - 34

EP - 76

BT - Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food

A2 - Brooks, Marianne Su-Ling

A2 - Celli, Giovana B.

PB - Royal Society of Chemistry

ER -

Pina F, Parola AJ, Melo MJ, Lima JC, Freitas VD. Chapter 2: Chemistry of Anthocyanins. In Brooks MS-L, Celli GB, editors, Steviol Glycosides: Cultivation, Processing, Analysis and Applications in Food. 12 ed. Royal Society of Chemistry. 2019. p. 34-76. (Food Chemistry, Function and Analysis; 12). https://doi.org/10.1039/9781788012614-00034