Formation of 3-Hydroxy-4,5-dimethyl-2(5H)-furanone (Sotolone) from 4-Hydroxy-l-isoleucine and 3-Amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone

The proposed formation of 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) from 4-hydroxy-l-isoleucine (1) and the corresponding lactone 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone (2) by thermally induced oxidative deamination was corroborated. The formation of sotolone was studied in model sys...

Full description

Saved in:
Bibliographic Details
Published in:Journal of agricultural and food chemistry 1996-07, Vol.44 (7), p.1851-1856
Main Authors: Blank, Imre, Lin, Jianming, Fumeaux, René, Welti, Dieter H, Fay, Laurent B
Format: Article
Language:English
Subjects:
ANALISIS CUANTITATIVO
ANALYSE QUANTITATIVE
Aroma and flavouring agent industries
Biological and medical sciences
CETONAS
CETONE
COMPOSE DE LA FLAVEUR
COMPUESTOS DEL SABOR
DESAMINACION
DESAMINATION
ESPECTROMETRIA
Food industries
Fundamental and applied biological sciences. Psychology
FURANE
FURANOS
ISOLEUCINA
ISOLEUCINE
ISOTOPE
ISOTOPOS
MODELE
MODELOS
OXIDACION
OXYDATION
REACCIONES QUIMICAS
REACTION CHIMIQUE
SPECTROMETRIE
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The proposed formation of 3-hydroxy-4,5-dimethyl-2(5H)-furanone (sotolone) from 4-hydroxy-l-isoleucine (1) and the corresponding lactone 3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone (2) by thermally induced oxidative deamination was corroborated. The formation of sotolone was studied in model systems by reacting 1 or 2 with different carbonyl compounds in a phosphate buffer at pH 5 at 100 °C for 1 h. The amount of sotolone was quantified by stable isotope dilution assays using 13C2-labeled sotolone as internal standard and GC-MS operating in the selected ion monitoring mode. In general, α-ketoaldehydes were found to be more reactive than α-diketones. Methylglyoxal gave rise to about 64 μg sotolone per mg 1 (7.4 mol %) compared to less than 1 μg (
ISSN:0021-8561
1520-5118
DOI:10.1021/jf9506702