title: New short and general synthesis of three key Maillard flavour compounds: 2-Acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine.
abstract: A new general synthetic route towards three key Maillard flavour compounds, namely 2-acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine and 5-acetyl-2,3-dihydro-4H-1,4-thiazine, was developed. The key step in the process is the methylenation reaction of azaheterocyclic carboxylic esters by means of dimethyltitanocene, giving rise to intermediate vinyl ethers which can be considered as excellent and stable precursors for the title compounds, as a simple acidic treatment of these precursors suffices to release the characteristic Maillard flavours.
authors.affiliation: Laboratory of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.
authors.forename: Jurgen
authors.initials: J
authors.lastname: Deblander
authors.affiliation: Laboratory of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium.
authors.forename: Sam
authors.initials: S
authors.lastname: Van Aeken
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: An
authors.initials: A
authors.lastname: Adams
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
authors.affiliation: Laboratory of Organic Chemistry, Vrije Universiteit Brussel, Pleinlaan 2, B-1050 Brussels, Belgium; Organic Synthesis, Faculty of Sciences, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium. Electronic address: Kourosch.abbaspourtehrani@uantwerpen.be.
authors.forename: Kourosch
authors.initials: K
authors.lastname: Abbaspour Tehrani
mesh_terms: D005421:Flavoring Agents / Q000138:chemical synthesis*; D015416:Maillard Reaction; D011725:Pyridines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013649:Taste; D013843:Thiazines / Q000138:chemical synthesis*
chemical_list: C521129:5-acetyl-2,3-dihydro-4H-thiazine; C492489:6-acetyl-1,2,3,4-tetrahydropyridine; D005421:Flavoring Agents; D011725:Pyridines; D011758:Pyrroles; D013843:Thiazines; C426303:2-acetyl-1-pyrroline
keywords: Food flavour; Maillard reaction; Nitrogen heterocycles; Olefination; Oxidation