Document Detail


Thermal Generation of 3-Amino-4,5-dimethylfuran-2(5H)-one the Postulated Precursor of Sotolone, from Amino Acid Model Systems Containing Glyoxylic and Pyruvic Acids.
MedLine Citation:
PMID:  21417407     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The 4,5-dimethyl-3-hydroxy-2(5H)-furanone (sotolone) a naturally occurring flavor impact compound can be isolated from various sources especially fenugreek seeds. It can also be thermally produced from intermediates generated from the Maillard reaction such as pyruvic and ketoglutaric acids, glyoxal and 2,3-butanedione. A naturally occurring precursor of sotolone the 3-amino-4,5-dimethyl-2(5H)-furanone was thermally generated for the first time from pyruvic acid and glycine or from glyoxylic acid and alanine model systems. Isotope labeling studies have implicated 4,5-dimethylfuran-2,3-dione as an intermediate that can be converted into 3-amino-4,5-dimethyl-2(5H)-furanone through Strecker-like interaction with any amino acid. Furthermore, these studies have also indicated the presence of two pathways for the formation of 4,5-dimethylfuran-2,3-dione; one requiring pyruvic acid and a formaldehyde source and the other requiring glyoxylic acid and acetaldehyde. Self-aldol condensation of pyruvic acid followed by lactonization and further aldol reaction with formaldehyde can generate the same intermediate as the self-aldol addition product of acetaldehyde with glyoxylic acid followed by lactonization. The pyruvic acid pathway was found to be more efficient route than glyoxylic acid pathway. Furthermore, the pyruvic acid/glycine model system was able to generate sotolone in the presence of moisture and in the presence of ammonia commercial sotolone was converted back into 3-amino-4,5-dimethyl-2(5H)-furanone.
Authors:
Varoujan Antranik Yaylayan; Paula Vanessa Guerra
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-3-19
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  -     ISSN:  1520-5118     ISO Abbreviation:  -     Publication Date:  2011 Mar 
Date Detail:
Created Date:  2011-3-22     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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