Discovery and structure determination of a novel Maillard-derived sweetness enhancer by application of the comparative taste dilution analysis (cTDA)

Journal of Agricultural and Food Chemistry

Volumn 51, Issue 4, 2003, Pages 1035-1041

  Ottinger, Harald ^a   Soldo, Tomislav ^a   Hofmann, Thomas ^b  

^a DEUTSCHE FORSCHUNGSANSTALT FÜR LEBENSMITTELCHEMIE   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Alapyridaine; Comparative taste dilution analysis; Maillard reaction; N (1 carboxyethyl) 6 (hydroxymethyl)pyridinium 3 ol inner salt; Sweetness enhancer; Taste compound

Indexed keywords

ALANINE; ALAPYRIDAINE; AMINO ACID; ASPARTAME; DRUG DERIVATIVE; GLUCOSE; N (1 CARBOXYETHYL) 6 (HYDROXYMETHYL)PYRIDINIUM 3 OL; PYRIDINE DERIVATIVE; SUGAR; SWEETENING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DILUTION; DRUG STABILITY; GLYCATION; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; STEREOCHEMISTRY; SWEETNESS; SYNTHESIS; TASTE; THERMOSTABILITY;

ALANINE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; GLUCOSE; HEAT; HUMANS; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MAILLARD REACTION; MASS SPECTROMETRY; MOLECULAR STRUCTURE; PYRIDINES; SWEETENING AGENTS; TASTE;

EID: 0037433173     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf020977i     Document Type: Article

References (15)

1. Cerny, M.; Grosch, W. Evaluation of potent odorants in roasted beef by aroma extract dilution analysis. Z. Lebensm. Unters. Forsch, 1992, 194, 322-325.
2. Fickert, B.; Schieberle, P. Identification of the key odorants in barley malt (caramalt) using GC/MS techniques and odour dilution analyses. Food 1998, 42, 371-375.
3. Hofmann, T.; Schieberle, P. Evaluation of the key odorants in a thermally treated solution of ribose and cysteine by aroma extract dilution techniques. J. Agric. Food Chem. 1995, 43, 2187-2194.
4. Hofmann, T.; Schieberle, P. Flavor contribution and formation of the intense roast-smelling odorants 2-propionyl-1-pyrroline and 2-propionyl-tetrahydropyridine in Maillard-type reactions. J. Agric. Food Chem. 1998, 46, 2721-2726.
5. Papst, H. M. E.; Ledl, F.; Belitz, H.-D. Bitter tasting compounds in heated proline/sucrose mixtures (in German). Z. Lebensm. Unters. Forsch. 1984, 178, 356-360.
6. Papst, H. M. E.; Ledl, F.; Belitz, H.-D. Bitter tasting compounds in heated mixtures of sucrose, maltose and L-proline (in German). Z. Lebensm. Unters. Forsch. 1985, 181, 386-390.
7. Tressl, R.; Helak, B.; Spengler, K.; Schröder, A.; Rewicki, D. Cyclo[b]azepine derivatives-novel proline-specific Maillard reaction products (in German). Liebigs Ann. Chem. 1985, 2017-2027.
8. Hofmann, T. Influence of k-cysteine on the formation of bitter-tasting aminohexose reductones from glucose and L-proline: Identification of a novel furo[2,3-b]thiazine. J. Agric. Food Chem. 1999, 47, 4763-4768.
9. Frank, O.; Ottinger, H.; Hofmann, T. Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods. J. Agric. Food Chem. 2001, 49, 231-238.
10. 13C-labeling experiments. J. Agric. Food Chem. 2002, 50, 6027-6036.
11. Ottinger, H.; Bareth, A.; Hofmann, T. Characterization of natural "cooling" compounds formed from glucose and L-proline in dark malt by application of taste dilution analysis. J. Agric. Food Chem. 2001, 49, 1336-1344.
12. Namiki, T.; Nakamura, T. Enhancement of sugar sweetness by furanones and/or cyclotene. Jpn. Patent JP 04008264, 1992.
13. Wieser, H.; Belitz, H.-D. Studies on the structure/activity relationship of bitter tasting amino acids and peptides (in German). Z. Lebensm. Unters. Forsch. 1975, 159, 65-72.
14. Aue, W. P.; Bartholdi, E.; Ernst R. R. Two-dimensional spectroscopy. Application to nuclear magnetic resonance. J. Chem. Phys. 1976, 64, 2229-2246.
15. Wokaun, A.; Ernst, R. R. Selective detection of multiple quantum transitions in NMR by two-dimensional spectroscopy. Chem. Phys. Lett. 1977, 52, 407-412.