Difference between revisions of "Maillard reaction"
| Line 1: | Line 1: | ||
The Maillard reaction is responsible for many colors and flavors in foods, in combination with other processes. The heat-induced reaction of amino groups of amino acids, peptides, and proteins with carbonyl groups of reducing sugars such as glucose results in the concurrent formation of so-called Maillard browning products, such as [http://www.waiwiki.org/index.php/Heterocyclic_Amines_(HCA) heterocyclic amines (HCAs)], [http://www.waiwiki.org/index.php/Acrylamide acrylamides], Pent-4-en-1-amine, Styrene, Acetamide, Chloropropanols and Furan, which are all present in cooked foods. | The Maillard reaction is responsible for many colors and flavors in foods, in combination with other processes. The heat-induced reaction of amino groups of amino acids, peptides, and proteins with carbonyl groups of reducing sugars such as glucose results in the concurrent formation of so-called Maillard browning products, such as [http://www.waiwiki.org/index.php/Heterocyclic_Amines_(HCA) heterocyclic amines (HCAs)], [http://www.waiwiki.org/index.php/Acrylamide acrylamides], Pent-4-en-1-amine, Styrene, Acetamide, Chloropropanols and Furan, which are all present in cooked foods. | ||
| + | |||
| + | ==Pent-4-en-1-amine== | ||
| + | Is considered the lysine-glucose counterpart of [http://www.waiwiki.org/index.php/Acrylamide acrylamide] (instead of asparagine-glucose). In the presence of sugars, lysine, similarly to asparagine and phenylalanine, can undergo carbonyl-assisted decarboxylative deamination reaction to generate pent-4-en-1-amine. Alternatively, decarboxylation of lysine generates cadaverine (1,5-diaminopentane) followed by deamination to form pent-4-en-1-amine.[http://www.ncbi.nlm.nih.gov/pubmed/20205470] | ||
| + | |||
| + | ==Styrene== | ||
| + | Styrene oxide is neurotoxic (synergistically with acrylamide).[http://www.ncbi.nlm.nih.gov/pubmed/8442002] Styrene is considered the phenylalanine-glucose counterpart of [http://www.waiwiki.org/index.php/Acrylamide acrylamide] (instead of asparagine-glucose). In the presence of sugars, phenylalanine, similarly to asparagine and lysine, can undergo carbonyl-assisted decarboxylative deamination reaction to generate styrene. But phenylalanine heated together with 1-hydroxyacetone or methylglyoxal yielded only 0.03 mol% styrene.[http://www.ncbi.nlm.nih.gov/pubmed/19680933] | ||
| + | |||
| + | ==Acetamide== | ||
| + | Amides are derivates of ammonia or (carboxylated) amines. Acetamide is a carcinogenic derived from acetic acid, by dehydrating ammonium acetate[http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0003], or by hydrolysis of acetonitrile[http://onlinelibrary.wiley.com/doi/10.1002/14356007.a01_045.pub2/abstract]. Thermal degradation (>200°C) of chitin also yields acetamide.[http://www.ncbi.nlm.nih.gov/pubmed/494808] Chitin is a good inducer for defense mechanisms in plants[http://www.yeacrops.com/Crop%20Protection%20Article.pdf], and present in fungi, the exoskeletons of crustaceans such as crabs, lobsters and shrimps, in mollusks, and in the internal shells of squid and octopus. Acetamide is also a byproduct of thermochemical treatment of lignocellulosic biomass.[http://www.ncbi.nlm.nih.gov/pubmed/21444255] | ||
| + | |||
| + | ==Chloropropanols== | ||
| + | 3-monochloropropane-1,2-diol (3-MCPD) is a chloropropanol. | ||
| + | |||
| + | ==Furan== | ||
| + | (Fur)furan (5-oxacyclopenta-1,3-diene or 1,4-epoxy-1,3-butadiene) is a toxic heterocyclic organic compound, readily converted to other compounds. Furan is present in coffee, canned and jarred food, and baby food. | ||
| + | * 5-hydroxymethylfurfural | ||
| + | * furosine | ||
Revision as of 14:56, 12 December 2012
The Maillard reaction is responsible for many colors and flavors in foods, in combination with other processes. The heat-induced reaction of amino groups of amino acids, peptides, and proteins with carbonyl groups of reducing sugars such as glucose results in the concurrent formation of so-called Maillard browning products, such as heterocyclic amines (HCAs), acrylamides, Pent-4-en-1-amine, Styrene, Acetamide, Chloropropanols and Furan, which are all present in cooked foods.
Pent-4-en-1-amine
Is considered the lysine-glucose counterpart of acrylamide (instead of asparagine-glucose). In the presence of sugars, lysine, similarly to asparagine and phenylalanine, can undergo carbonyl-assisted decarboxylative deamination reaction to generate pent-4-en-1-amine. Alternatively, decarboxylation of lysine generates cadaverine (1,5-diaminopentane) followed by deamination to form pent-4-en-1-amine.[1]
Styrene
Styrene oxide is neurotoxic (synergistically with acrylamide).[2] Styrene is considered the phenylalanine-glucose counterpart of acrylamide (instead of asparagine-glucose). In the presence of sugars, phenylalanine, similarly to asparagine and lysine, can undergo carbonyl-assisted decarboxylative deamination reaction to generate styrene. But phenylalanine heated together with 1-hydroxyacetone or methylglyoxal yielded only 0.03 mol% styrene.[3]
Acetamide
Amides are derivates of ammonia or (carboxylated) amines. Acetamide is a carcinogenic derived from acetic acid, by dehydrating ammonium acetate[4], or by hydrolysis of acetonitrile[5]. Thermal degradation (>200°C) of chitin also yields acetamide.[6] Chitin is a good inducer for defense mechanisms in plants[7], and present in fungi, the exoskeletons of crustaceans such as crabs, lobsters and shrimps, in mollusks, and in the internal shells of squid and octopus. Acetamide is also a byproduct of thermochemical treatment of lignocellulosic biomass.[8]
Chloropropanols
3-monochloropropane-1,2-diol (3-MCPD) is a chloropropanol.
Furan
(Fur)furan (5-oxacyclopenta-1,3-diene or 1,4-epoxy-1,3-butadiene) is a toxic heterocyclic organic compound, readily converted to other compounds. Furan is present in coffee, canned and jarred food, and baby food.
- 5-hydroxymethylfurfural
- furosine
