DETERMINATION OF THE CHEMICAL-STRUCTURE OF THE INTENSE ROASTY, POPCORN-LIKE ODORANT 5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE

被引:27
作者
HOFMANN, T
HASSNER, R
SCHIEBERLE, P
机构
[1] TECH UNIV MUNICH,DEUTSCH FORSCH ANSTALT LEBENSMITTELCHEM,INST ORGAN CHEM,D-85748 GARCHING,GERMANY
[2] TECH UNIV MUNICH,INST LEBENSMITTELCHEM,D-85748 GARCHING,GERMANY
关键词
5-ACETYL-2,3-DIHYDRO-1,4-THIAZINE; 5-PROPIONYL-2,3-DIHYDRO-1,4-THIAZINE; 5-BUTANOYL-2,3-DIHYDRO-1,4-THIAZINE; ODOR THRESHOLD; SYNTHESIS; CYSTEAMINE; 2,3-BUTANEDIONE;
D O I
10.1021/jf00056a043
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
The chemical structure of a novel intense popcorn-like odorant isolated from the reaction of cysteine and ribose was studied by one- and two-dimensional NMR spectroscopy and high-resolution mass spectrometry, and the structure elucidation was confirmed by synthetic experiments. Thus, the odorant was identified as 5-acetyl-2,3-dihydro-1,4-thiazine (ADT). A sensory study including 5-propionyl- (PDT) and 5-butanoyl-2,3-dihydro-1,4-thiazine (BDT) revealed that also PDT and BDT elicited roasty, popcorn-like odors. However, the odor threshold of the BDT was by a factor of 50 000 higher than those of ADT and PDT (0.06 and 0.1 ng/L of air, respectively).
引用
收藏
页码:2195 / 2198
页数:4
相关论文
共 11 条
[1]   H-1 AND C-13 ASSIGNMENTS FROM SENSITIVITY-ENHANCED DETECTION OF HETERONUCLEAR MULTIPLE-BOND CONNECTIVITY BY 2D MULTIPLE QUANTUM NMR [J].
BAX, A ;
SUMMERS, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2093-2094
[2]  
BUCHI G, 1971, J ORG CHEM, V36, P609
[3]  
BUTTERY RG, 1982, CHEM IND-LONDON, P958
[4]   EVALUATION OF POTENT ODORANTS IN ROASTED BEEF BY AROMA EXTRACT DILUTION ANALYSIS [J].
CERNY, C ;
GROSCH, W .
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1992, 194 (04) :322-325
[5]   PRIMARY ODORANTS OF CHICKEN BROTH - A COMPARATIVE-STUDY WITH MEAT BROTHS FROM COW AND OX [J].
GASSER, U ;
GROSCH, W .
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1990, 190 (01) :3-8
[6]   EVALUATION OF THE KEY ODORANTS IN A THERMALLY TREATED SOLUTION OF RIBOSE AND CYSTEINE BY AROMA EXTRACT DILUTION TECHNIQUES [J].
HOFMANN, T ;
SCHIEBERLE, P .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1995, 43 (08) :2187-2194
[7]  
ROBERTS DD, 1994, ACS SYM SER, V543, P71
[8]   EVALUATION OF THE FLAVOR OF WHEAT AND RYE BREAD CRUSTS BY AROMA EXTRACT DILUTION ANALYSIS [J].
SCHIEBERLE, P ;
GROSCH, W .
ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1987, 185 (02) :111-113
[9]   PRIMARY ODORANTS IN POPCORN [J].
SCHIEBERLE, P .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1991, 39 (06) :1141-1144
[10]  
SCHIEBERLE P, 1990, MAILLARD REACTION FO, P187