85213-22-5Relevant articles and documents
Methylglyoxal binds to amines in honey matrix and 2′-methoxyacetophenone is released in gaseous form into the headspace on the heating of manuka honey
Kato, Mai,Kato, Yoji,Kawai, Masaki,Kishi, Yui,Miyoshi, Noriyuki,Nagata, Akika,Okano, Yayako,Shimizu, Michiyo,Suga, Naoko,Yakemoto, Chisato
, (2021)
Reports on the thermal stability of manuka honey in terms of food processing have been few. This study investigated changes in nine characteristic chemicals of manuka honey during heating. Among these, methylglyoxal (MGO) and 2′-methoxyacetophenone (MAP) were significantly decreased by heating at 90 °C. To elucidate the mechanism for this decrease, artificial honey was prepared from sugars and water with MAP or MGO and then heated. The decrease of MGO was enhanced with L-proline, lysine, or arginine derivatives, accompanied by formation of 2-acetyl-1-pyrroline, MGO-derived lysine dimer, or argpyrimidine, respectively, suggesting that an amino–carbonyl reaction is one pathway for the loss of MGO. The decrease of MAP in the artificial honey depended on the volume of headspace in a vessel. MAP from heated manuka honey was also detected in the gas phase, indicating that MAP was vaporized. Heating could thus reduce the beneficial and/or signature molecules in honey.
Efficient Analysis of 2-Acetyl-1-pyrroline in Foods Using a Novel Derivatization Strategy and LC-MS/MS
Jost, Tobias,Heymann, Thomas,Glomb, Marcus A.
, p. 3046 - 3054 (2019/03/11)
2-Acetyl-1-pyrroline (2-AP) is a key odorant in many foods, such as aromatic rice and wheat bread, with a very low odor threshold of 0.05 μg/L in water. The small molecule with a popcornlike, roasty odor is generated biologically or by Strecker degradation within the Maillard-reaction cascades during thermal food processing with methylglyoxal and 1-pyrroline as the main direct precursors. Numerous gas-chromatographic methods for the analysis of 2-AP have been published, but the reactivity of the compound leads to discrimination or degradation during sample workup. We developed a novel derivatization method for 2-AP with o-phenylenediamine followed by HPLC-MS/MS analysis of the resulting stable quinoxaline. The precision (7%), repeatability (14%), recovery (92%), linearity (0.79-500 μg/kg), limit of detection (LOD, 0.26 μg/kg), and limit of quantitation (LOQ, 0.79 μg/kg) were validated for rice matrix and were excellent as compared with those of methods published before. With the novel method, 2-AP levels in typical foods like aromatic rice (131 μg/kg), wheat bread (18 μg/kg), brown bread (18 μg/kg), rye bread (18 μg/kg), and popcorn (38 μg/kg) were determined.
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
Deblander, Jurgen,Van Aeken, Sam,Adams, An,De Kimpe, Norbert,Abbaspour Tehrani, Kourosch
, p. 327 - 331 (2015/01/30)
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.
