Details
| Original language | English |
|---|---|
| Pages (from-to) | 3103-3107 |
| Number of pages | 5 |
| Journal | Journal of Agricultural and Food Chemistry |
| Volume | 51 |
| Issue number | 10 |
| Publication status | Published - 15 Apr 2003 |
Abstract
Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines. Their odor qualities were evaluated, and their odor thresholds were estimated. Among these pyrazine derivatives, 2-ethyl-3,5-dimethyl-5,6-dihydropyrazine (roasted, nutty, 0.002 ng/L air), 2,3-diethyl-5-methyl-5,6-dihydropyrazine (roasted, 0.004 ng/L air), and 2-ethyl-3,5-dimethyltetrahy-dropyrazine (bread crustlike, 1.9 ng/L air) were the most intensive-smelling aroma active compounds.
Keywords
- Acyloins, Baker's yeast, Carboligation, Flavor, Pyrazine derivatives
ASJC Scopus subject areas
- Chemistry(all)
- General Chemistry
- Agricultural and Biological Sciences(all)
- General Agricultural and Biological Sciences
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In: Journal of Agricultural and Food Chemistry, Vol. 51, No. 10, 15.04.2003, p. 3103-3107.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Chemoenzymatic synthesis of aroma active 5,6-dihydro- and tetrahydropyrazines from aliphatic acyloins produced by baker's yeast
AU - Kurniadi, Toshinari
AU - Bel Rhlid, Rachid
AU - Fay, Laurent Bernard
AU - Juillerat, Marcel Alexandre
AU - Berger, Ralf Günter
PY - 2003/4/15
Y1 - 2003/4/15
N2 - Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines. Their odor qualities were evaluated, and their odor thresholds were estimated. Among these pyrazine derivatives, 2-ethyl-3,5-dimethyl-5,6-dihydropyrazine (roasted, nutty, 0.002 ng/L air), 2,3-diethyl-5-methyl-5,6-dihydropyrazine (roasted, 0.004 ng/L air), and 2-ethyl-3,5-dimethyltetrahy-dropyrazine (bread crustlike, 1.9 ng/L air) were the most intensive-smelling aroma active compounds.
AB - Twenty-five acyloins were generated by biotransformation of aliphatic aldehydes and 2-ketocarboxylic acids using whole cells of baker's yeast as catalyst. Six of these acyloins were synthesized and tentatively characterized for the first time. Subsequent chemical reaction with 1,2-propanediamine under mild conditions resulted in the formation of thirteen 5,6-dihydropyrazines and six tetrahydropyrazines. Their odor qualities were evaluated, and their odor thresholds were estimated. Among these pyrazine derivatives, 2-ethyl-3,5-dimethyl-5,6-dihydropyrazine (roasted, nutty, 0.002 ng/L air), 2,3-diethyl-5-methyl-5,6-dihydropyrazine (roasted, 0.004 ng/L air), and 2-ethyl-3,5-dimethyltetrahy-dropyrazine (bread crustlike, 1.9 ng/L air) were the most intensive-smelling aroma active compounds.
KW - Acyloins
KW - Baker's yeast
KW - Carboligation
KW - Flavor
KW - Pyrazine derivatives
UR - http://www.scopus.com/inward/record.url?scp=0037624905&partnerID=8YFLogxK
U2 - 10.1021/jf0261809
DO - 10.1021/jf0261809
M3 - Article
C2 - 12720399
AN - SCOPUS:0037624905
VL - 51
SP - 3103
EP - 3107
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 10
ER -