Document Detail


New bitter-masking compounds: hydroxylated benzoic acid amides of aromatic amines as structural analogues of homoeriodictyol.
MedLine Citation:
PMID:  17061836     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Starting from the known bitter-masking flavanones eriodictyol and homoeriodictyol from herba santa some structurally related hydroxybenzoic acid amides of benzylamines were synthesized and evaluated as masking agents toward bitterness of caffeine by sensory methods. The closest structural relatives of homoeriodictyol, the hydroxybenzoic acid vanillylamides 5-9, were the most active and were able to reduce the bitterness of a 500 mg L(-1) caffeine solution by about 30% at a concentration of 100 mg L(-1). 2,4-Dihydroxybenzoic acid vanillylamide 7 showed a clear dose-dependent activity as inhibitor of the bitter taste of caffein between 5 and 500 mg L(-1). Additionally, it was possible to reduce the bitterness of quinine and salicine but not of the bitter peptide N-l-leucyl-l-tryptophan. Combinations of homoeriodictyol and amide 7 showed no synergistic or antagonistic changes in activity. The results for model compound 7 suggested that the hitherto unknown masking mechanism is probably the same for flavanones and the new amides. In the future, the new amides may be alternatives for the expensive flavanones to create flavor solutions to mask bitterness of pharmaceuticals or foodstuffs.
Authors:
Jakob P Ley; Maria Blings; Susanne Paetz; Gerhard E Krammer; Heinz-Jürgen Bertram
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  54     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2006 Nov 
Date Detail:
Created Date:  2006-10-25     Completed Date:  2007-01-04     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8574-9     Citation Subset:  IM    
Affiliation:
Symrise GmbH & Co. KG, Flavor & Nutrititon Research & Innovation, 37601 Holzminden, Germany. jakob.ley@symrise.com
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MeSH Terms
Descriptor/Qualifier:
Amides / chemistry*
Amines / chemistry*
Benzoic Acid / chemistry*
Flavones / chemical synthesis,  chemistry*
Humans
Hydroxylation
Molecular Structure
Taste*
Chemical
Reg. No./Substance:
0/Amides; 0/Amines; 0/Flavones; 0/homoeriodictyol; 65-85-0/Benzoic Acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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