Acrylamide formation mechanism in heated foods.
Recent findings of a potential human carcinogen, acrylamide, in foods have focused research on the possible mechanisms of formation. We present a mechanism for the formation of acrylamide from the reaction of the amino acid asparagine and a carbonyl-containing compound at typical cooking temperatures. The mechanism involves formation of a Schiff base followed by decarboxylation and elimination of either ammonia or a substituted imine under heat to yield acrylamide. Isotope substitution studies and mass spectrometric analysis of heated model systems confirm the presence of key reaction intermediates. Further confirmation of this mechanism is accomplished through selective removal of asparagine with asparaginase that results in a reduced level of acrylamide in a selected heated food.
Zyzak
David V
DV
The Procter & Gamble Company, Winton Hill Business Center, 6210 Center Hill Avenue, Cincinnati, Ohio 45224, USA. Zyzak.dv@pg.com
Sanders
Robert A
RA
Stojanovic
Marko
M
Tallmadge
Daniel H
DH
Eberhart
B Loye
BL
Ewald
Deborah K
DK
Gruber
David C
DC
Morsch
Thomas R
TR
Strothers
Melissa A
MA
Rizzi
George P
GP
Villagran
Maria D
MD
D020106:Acrylamide / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D001216:Asparagine / Q000737:chemistry; D002273:Carcinogens / Q000032:analysis / Q000138:chemical synthesis*; D005504:Food Analysis; D006358:Hot Temperature; D012545:Schiff Bases / Q000737:chemistry; D011198:Solanum tuberosum / Q000737:chemistry
D002273:Carcinogens; D012545:Schiff Bases; D020106:Acrylamide; D001216:Asparagine