Model Reactions on the Stability of Disulfides in Heated Foods

Helmut Guth; Thomas Hofmann; Peter Schieberle; Werner Grosch

doi:10.1021/jf00056a044

Model Reactions on the Stability of Disulfides in Heated Foods

Helmut Guth, Thomas Hofmann, Peter Schieberle, Werner Grosch^*

^*Corresponding author for this work

Technical University of Munich

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

18 Scopus citations

Abstract

Bis(2-methyl-3-furyl) disulfide (MFT-MFT) and bis(2-furfuryl) disulfide (FFT-FFT) dissolved either in benzene or in water were heated at 100 °C for 2 h. In benzene, 2-methyl-3-furanthiol and 2-furfurylthiol were formed when the hydrogen donor 1,4-cyclohexadiene or 1,4-hexadiene or the antioxidant BHT was present. In water, MFT-MFT, FFT-FFT, and also cystine were hydrolyzed with formation of the corresponding thiols, which were trapped by the reaction with 4-vinylpyridine. Labeling experiments and the measurement of EPR spectra gave an insight into the mechanism of the disulfide cleavage.

Original language	English
Pages (from-to)	2199-2203
Number of pages	5
Journal	Journal of Agricultural and Food Chemistry
Volume	43
Issue number	8
DOIs	https://doi.org/10.1021/jf00056a044
State	Published - 1 Aug 1995
Externally published	Yes

Keywords

bis(2-furfuryl) disulfide
Bis(2-methyl-3-furyl) disulfide
disulfide cleavage
disulfides
formation from thiols

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10.1021/jf00056a044

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@article{9705ece2599a4be4a3eab3379f68d1ce,

title = "Model Reactions on the Stability of Disulfides in Heated Foods",

abstract = "Bis(2-methyl-3-furyl) disulfide (MFT-MFT) and bis(2-furfuryl) disulfide (FFT-FFT) dissolved either in benzene or in water were heated at 100 °C for 2 h. In benzene, 2-methyl-3-furanthiol and 2-furfurylthiol were formed when the hydrogen donor 1,4-cyclohexadiene or 1,4-hexadiene or the antioxidant BHT was present. In water, MFT-MFT, FFT-FFT, and also cystine were hydrolyzed with formation of the corresponding thiols, which were trapped by the reaction with 4-vinylpyridine. Labeling experiments and the measurement of EPR spectra gave an insight into the mechanism of the disulfide cleavage.",

keywords = "bis(2-furfuryl) disulfide, Bis(2-methyl-3-furyl) disulfide, disulfide cleavage, disulfides, formation from thiols",

author = "Helmut Guth and Thomas Hofmann and Peter Schieberle and Werner Grosch",

year = "1995",

month = aug,

day = "1",

doi = "10.1021/jf00056a044",

language = "English",

volume = "43",

pages = "2199--2203",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

publisher = "American Chemical Society",

number = "8",

}

TY - JOUR

T1 - Model Reactions on the Stability of Disulfides in Heated Foods

AU - Guth, Helmut

AU - Hofmann, Thomas

AU - Schieberle, Peter

AU - Grosch, Werner

PY - 1995/8/1

Y1 - 1995/8/1

N2 - Bis(2-methyl-3-furyl) disulfide (MFT-MFT) and bis(2-furfuryl) disulfide (FFT-FFT) dissolved either in benzene or in water were heated at 100 °C for 2 h. In benzene, 2-methyl-3-furanthiol and 2-furfurylthiol were formed when the hydrogen donor 1,4-cyclohexadiene or 1,4-hexadiene or the antioxidant BHT was present. In water, MFT-MFT, FFT-FFT, and also cystine were hydrolyzed with formation of the corresponding thiols, which were trapped by the reaction with 4-vinylpyridine. Labeling experiments and the measurement of EPR spectra gave an insight into the mechanism of the disulfide cleavage.

AB - Bis(2-methyl-3-furyl) disulfide (MFT-MFT) and bis(2-furfuryl) disulfide (FFT-FFT) dissolved either in benzene or in water were heated at 100 °C for 2 h. In benzene, 2-methyl-3-furanthiol and 2-furfurylthiol were formed when the hydrogen donor 1,4-cyclohexadiene or 1,4-hexadiene or the antioxidant BHT was present. In water, MFT-MFT, FFT-FFT, and also cystine were hydrolyzed with formation of the corresponding thiols, which were trapped by the reaction with 4-vinylpyridine. Labeling experiments and the measurement of EPR spectra gave an insight into the mechanism of the disulfide cleavage.

KW - bis(2-furfuryl) disulfide

KW - Bis(2-methyl-3-furyl) disulfide

KW - disulfide cleavage

KW - disulfides

KW - formation from thiols

UR - https://www.scopus.com/pages/publications/0001394097

U2 - 10.1021/jf00056a044

DO - 10.1021/jf00056a044

M3 - Article

AN - SCOPUS:0001394097

SN - 0021-8561

VL - 43

SP - 2199

EP - 2203

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 8

ER -

Model Reactions on the Stability of Disulfides in Heated Foods

Abstract

Keywords

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