Trapping of Carbonyl Compounds by Epicatechin: Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk

Research output: Contribution to journal › Journal article › Research › peer-review

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Trapping of Carbonyl Compounds by Epicatechin : Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk. / Zhu, Hongkai; Poojary, Mahesha M.; Andersen, Mogens L.; Lund, Marianne N.

In: Journal of Agricultural and Food Chemistry, Vol. 68, No. 29, 2020, p. 7718-7726.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Zhu, H, Poojary, MM, Andersen, ML & Lund, MN 2020, 'Trapping of Carbonyl Compounds by Epicatechin: Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk', Journal of Agricultural and Food Chemistry, vol. 68, no. 29, pp. 7718-7726. https://doi.org/10.1021/acs.jafc.0c01761

APA

Zhu, H., Poojary, M. M., Andersen, M. L., & Lund, M. N. (2020). Trapping of Carbonyl Compounds by Epicatechin: Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk. Journal of Agricultural and Food Chemistry, 68(29), 7718-7726. https://doi.org/10.1021/acs.jafc.0c01761

Vancouver

Zhu H, Poojary MM, Andersen ML, Lund MN. Trapping of Carbonyl Compounds by Epicatechin: Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk. Journal of Agricultural and Food Chemistry. 2020;68(29):7718-7726. https://doi.org/10.1021/acs.jafc.0c01761

Author

Zhu, Hongkai ; Poojary, Mahesha M. ; Andersen, Mogens L. ; Lund, Marianne N. / Trapping of Carbonyl Compounds by Epicatechin : Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk. In: Journal of Agricultural and Food Chemistry. 2020 ; Vol. 68, No. 29. pp. 7718-7726.

Bibtex

@article{0f3622b5d2404142b1d26e54bdd5cc81,
title = "Trapping of Carbonyl Compounds by Epicatechin: Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk",
abstract = "The kinetics of the reaction between epicatechin and various carbonyl compounds typically formed in cooked and stored foods were evaluated in model systems at pH 7.4 and 37 degrees C, and the corresponding reaction products in stored ultrahigh temperature (UHT) milk-added epicatechin were identified by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). The rate constants for the reactions of carbonyl compounds with epicatechin decreased in the following the order: methylglyoxal; 1.6 +/- 0.2 M-1 s(-1) > glyoxal; (5.9 +/- 0.3) X 10(-2) M-1 s(-1) > 5-(hydroxymethyl)furfural; (4.0 +/- 0.2) X 10(-2) M-1 s(-1) > acetaldehyde; (2.6 +/- 0.3) x 10(-2) M-1 s(-1) >= phenylacetaldehyde; (2.1 +/- 0.2) x 10(-2) M-1 s(-1) >= furfural; (4.3 +/- 0.1) x 10(-3) M-1 s(-1) > 2-methylbutanal and 3-methylbutanal; similar to 0 M-1 s(-1). Reaction products generated by epicatechin and methylglyoxal, glyoxal, S-(hydroxymethyl)furfural, and acetaldehyde were detected in UHT milk samples by incubating milk samples with epicatechin at 37 degrees C for 24 h. The lack of reaction between epicatechin and phenylacetaldehyde, furfural, 2-methylbutanal, and 3-methylbutanal in stored UHT milk may be due to their slow reaction rates or low concentration in stored UHT milk. It is demonstrated that epicatechin traps 5-(hydroxymethyl)furfural, acetaldehyde, glyoxal, and methylglyoxal and may thereby reduce off-flavor formation in UHT milk during storage both by trapping of precursors (methylglyoxal and glyoxal) for off-flavor formation and by direct trapping of off-flavors.",
keywords = "UHT milk, Strecker aldehydes, furfural, reaction kinetics, epicatechin, alpha-dicarbonyls, Maillard reaction, STRECKER ALDEHYDES, MAILLARD REACTION, (+)-CATECHIN, TEMPERATURE, STORAGE, MODEL, ACETALDEHYDE, FLAVONOIDS, FOODS, (-)-EPICATECHIN",
author = "Hongkai Zhu and Poojary, {Mahesha M.} and Andersen, {Mogens L.} and Lund, {Marianne N.}",
year = "2020",
doi = "10.1021/acs.jafc.0c01761",
language = "English",
volume = "68",
pages = "7718--7726",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "29",

}

RIS

TY - JOUR

T1 - Trapping of Carbonyl Compounds by Epicatechin

T2 - Reaction Kinetics and Identification of Epicatechin Adducts in Stored UHT Milk

AU - Zhu, Hongkai

AU - Poojary, Mahesha M.

AU - Andersen, Mogens L.

AU - Lund, Marianne N.

PY - 2020

Y1 - 2020

N2 - The kinetics of the reaction between epicatechin and various carbonyl compounds typically formed in cooked and stored foods were evaluated in model systems at pH 7.4 and 37 degrees C, and the corresponding reaction products in stored ultrahigh temperature (UHT) milk-added epicatechin were identified by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). The rate constants for the reactions of carbonyl compounds with epicatechin decreased in the following the order: methylglyoxal; 1.6 +/- 0.2 M-1 s(-1) > glyoxal; (5.9 +/- 0.3) X 10(-2) M-1 s(-1) > 5-(hydroxymethyl)furfural; (4.0 +/- 0.2) X 10(-2) M-1 s(-1) > acetaldehyde; (2.6 +/- 0.3) x 10(-2) M-1 s(-1) >= phenylacetaldehyde; (2.1 +/- 0.2) x 10(-2) M-1 s(-1) >= furfural; (4.3 +/- 0.1) x 10(-3) M-1 s(-1) > 2-methylbutanal and 3-methylbutanal; similar to 0 M-1 s(-1). Reaction products generated by epicatechin and methylglyoxal, glyoxal, S-(hydroxymethyl)furfural, and acetaldehyde were detected in UHT milk samples by incubating milk samples with epicatechin at 37 degrees C for 24 h. The lack of reaction between epicatechin and phenylacetaldehyde, furfural, 2-methylbutanal, and 3-methylbutanal in stored UHT milk may be due to their slow reaction rates or low concentration in stored UHT milk. It is demonstrated that epicatechin traps 5-(hydroxymethyl)furfural, acetaldehyde, glyoxal, and methylglyoxal and may thereby reduce off-flavor formation in UHT milk during storage both by trapping of precursors (methylglyoxal and glyoxal) for off-flavor formation and by direct trapping of off-flavors.

AB - The kinetics of the reaction between epicatechin and various carbonyl compounds typically formed in cooked and stored foods were evaluated in model systems at pH 7.4 and 37 degrees C, and the corresponding reaction products in stored ultrahigh temperature (UHT) milk-added epicatechin were identified by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). The rate constants for the reactions of carbonyl compounds with epicatechin decreased in the following the order: methylglyoxal; 1.6 +/- 0.2 M-1 s(-1) > glyoxal; (5.9 +/- 0.3) X 10(-2) M-1 s(-1) > 5-(hydroxymethyl)furfural; (4.0 +/- 0.2) X 10(-2) M-1 s(-1) > acetaldehyde; (2.6 +/- 0.3) x 10(-2) M-1 s(-1) >= phenylacetaldehyde; (2.1 +/- 0.2) x 10(-2) M-1 s(-1) >= furfural; (4.3 +/- 0.1) x 10(-3) M-1 s(-1) > 2-methylbutanal and 3-methylbutanal; similar to 0 M-1 s(-1). Reaction products generated by epicatechin and methylglyoxal, glyoxal, S-(hydroxymethyl)furfural, and acetaldehyde were detected in UHT milk samples by incubating milk samples with epicatechin at 37 degrees C for 24 h. The lack of reaction between epicatechin and phenylacetaldehyde, furfural, 2-methylbutanal, and 3-methylbutanal in stored UHT milk may be due to their slow reaction rates or low concentration in stored UHT milk. It is demonstrated that epicatechin traps 5-(hydroxymethyl)furfural, acetaldehyde, glyoxal, and methylglyoxal and may thereby reduce off-flavor formation in UHT milk during storage both by trapping of precursors (methylglyoxal and glyoxal) for off-flavor formation and by direct trapping of off-flavors.

KW - UHT milk

KW - Strecker aldehydes

KW - furfural

KW - reaction kinetics

KW - epicatechin

KW - alpha-dicarbonyls

KW - Maillard reaction

KW - STRECKER ALDEHYDES

KW - MAILLARD REACTION

KW - (+)-CATECHIN

KW - TEMPERATURE

KW - STORAGE

KW - MODEL

KW - ACETALDEHYDE

KW - FLAVONOIDS

KW - FOODS

KW - (-)-EPICATECHIN

U2 - 10.1021/acs.jafc.0c01761

DO - 10.1021/acs.jafc.0c01761

M3 - Journal article

C2 - 32597649

VL - 68

SP - 7718

EP - 7726

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 29

ER -

ID: 247154593