Details
| Original language | English |
|---|---|
| Pages (from-to) | 262-269 |
| Number of pages | 8 |
| Journal | Current Research in Food Science |
| Volume | 4 |
| Publication status | Published - 19 Apr 2021 |
Abstract
Three phenolic acids, p-coumaric, ferulic and caffeic acid as well as cinnamic acid were added to raw potatoes and sweet potatoes before frying. A distinct mitigation of acrylamide was not detected. Fried samples were analysed for postulated adducts of a direct reaction between acrylamide and these phenolic acids using LC-MS. In a model system with pure compounds (phenylacrylic acid and acrylamide) heated on 10% hydrated silica gel one specific adduct (respective m/z for M + H+) was formed in each reaction. MS/MS-data suggested an oxa-Michael formation of 3-amino-3-oxopropyl-phenylacrylates, which was confirmed by de novo syntheses along an SN2 substitution of 3-chloropropanamide. Exemplarily, the structure of the ester was confirmed for p-coumaric acid by NMR-data. Standard addition revealed that 3-amino-(3-oxopropyl-phenyl)-acrylates occurred neither in fried potato nor in sweet potato, while a formation was shown in phenylacrylic acid plus acrylamide supplemented potatoes and sweet potatoes.
Keywords
- 3-Amino-3-oxopropyl-phenylacrylates, Acrylamide mitigation, Oxa-michael-addition, Phenylacrylic acids, Potato, Sweet potato
ASJC Scopus subject areas
- Agricultural and Biological Sciences(all)
- Food Science
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Immunology and Microbiology(all)
- Applied Microbiology and Biotechnology
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In: Current Research in Food Science, Vol. 4, 19.04.2021, p. 262-269.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Phenylacrylic acids addition to potato and sweet potato showed no impact on acrylamide concentration via oxa-Michael-addition during frying
AU - Rottmann, Eric
AU - Fohrer, Jörg
AU - Krings, Ulrich
AU - Berger, Ralf G.
AU - Volkmann, Kristina
N1 - Funding Information: The authors acknowledge the skilful assistance of C. Theobald and the interest of Wernsing Feinkost GmbH (Addrup-Essen, Germany). Graphical abstract was created with BioRender.com
PY - 2021/4/19
Y1 - 2021/4/19
N2 - Three phenolic acids, p-coumaric, ferulic and caffeic acid as well as cinnamic acid were added to raw potatoes and sweet potatoes before frying. A distinct mitigation of acrylamide was not detected. Fried samples were analysed for postulated adducts of a direct reaction between acrylamide and these phenolic acids using LC-MS. In a model system with pure compounds (phenylacrylic acid and acrylamide) heated on 10% hydrated silica gel one specific adduct (respective m/z for M + H+) was formed in each reaction. MS/MS-data suggested an oxa-Michael formation of 3-amino-3-oxopropyl-phenylacrylates, which was confirmed by de novo syntheses along an SN2 substitution of 3-chloropropanamide. Exemplarily, the structure of the ester was confirmed for p-coumaric acid by NMR-data. Standard addition revealed that 3-amino-(3-oxopropyl-phenyl)-acrylates occurred neither in fried potato nor in sweet potato, while a formation was shown in phenylacrylic acid plus acrylamide supplemented potatoes and sweet potatoes.
AB - Three phenolic acids, p-coumaric, ferulic and caffeic acid as well as cinnamic acid were added to raw potatoes and sweet potatoes before frying. A distinct mitigation of acrylamide was not detected. Fried samples were analysed for postulated adducts of a direct reaction between acrylamide and these phenolic acids using LC-MS. In a model system with pure compounds (phenylacrylic acid and acrylamide) heated on 10% hydrated silica gel one specific adduct (respective m/z for M + H+) was formed in each reaction. MS/MS-data suggested an oxa-Michael formation of 3-amino-3-oxopropyl-phenylacrylates, which was confirmed by de novo syntheses along an SN2 substitution of 3-chloropropanamide. Exemplarily, the structure of the ester was confirmed for p-coumaric acid by NMR-data. Standard addition revealed that 3-amino-(3-oxopropyl-phenyl)-acrylates occurred neither in fried potato nor in sweet potato, while a formation was shown in phenylacrylic acid plus acrylamide supplemented potatoes and sweet potatoes.
KW - 3-Amino-3-oxopropyl-phenylacrylates
KW - Acrylamide mitigation
KW - Oxa-michael-addition
KW - Phenylacrylic acids
KW - Potato
KW - Sweet potato
UR - http://www.scopus.com/inward/record.url?scp=85104468609&partnerID=8YFLogxK
U2 - 10.1016/j.crfs.2021.04.005
DO - 10.1016/j.crfs.2021.04.005
M3 - Article
AN - SCOPUS:85104468609
VL - 4
SP - 262
EP - 269
JO - Current Research in Food Science
JF - Current Research in Food Science
ER -