17427-08-6Relevant articles and documents
Characterization of Carbonyl-Phenol Adducts Produced by Food Phenolic Trapping of 4-Hydroxy-2-hexenal and 4-Hydroxy-2-nonenal
Hidalgo, Francisco J.,Zamora, Rosario
, p. 2043 - 2051 (2019/02/26)
4-Hydroxy-2-alkenals disappear in the presence of food phenolics (i.e., cathechin or quercetin), and the corresponding carbonyl-phenol adducts are produced. In an attempt to identify structure(s) of formed adducts, the reactions between model phenolics (resorcinol, 2-methylresorcinol, orcinol, and 2,5-dimethylresorcinol) and hydroxyalkenals (4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal) were studied and the produced adducts were isolated by column chromatography and unambiguously characterized by one- A nd two-dimensional nuclear magnetic resonance and mass spectrometry as dihydrobenzofuranols (1), chromane-2,7-diols (2), and 2H-chromen-7-ols (3). These compounds were mainly produced at slightly basic pH values and moderate temperatures. Their activation energies (Ea) of formation were a25 kJ mol-1 for adducts 1, a32 kJ mol-1 for adducts 2, and a38 kJ mol-1 for adducts 3. A reaction pathway that explains their formation is proposed. All of these results confirm that, analogously to other lipid-derived carbonyl compounds, phenolics can trap 4-hydroxy-2-alkenals in an efficient way. Obtained results provide the basis for the potential detection of carbonyl-phenol adducts derived from hydroxyalkenals in food products.
(2E)-4-hydroxyalk-2-enals and 2-substituted furans as products of reactions of (2E)-4,4-dimethoxybut-2-enal with Grignard compounds
Garibyan,Ovanesyan,Makaryan,Petrosyan,Chobanyan
experimental part, p. 406 - 409 (2010/09/12)
Methods have been developed for the synthesis of (2E)-1,1-dimethoxyalk-2- en-4-ols and (2E)-4-hydroxyalk-2-enals by reaction of (2E)-4,4-dimethoxybut-2- enals and Grignard compounds. Thermal isomerization of (2E)-4-hydroxyalk-2-enals gave the corresponding 2-alkylfurans.
Natural (5′-oxoheptene-1′E,3′E-dienyl)-5,6-dihydro-2H- pyran-2-one: Total synthesis and revision of its absolute configuration
Bouzbouz, Samir,De Lemos, Elsa,Cossy, Janine,Saez, Jairo,Franck, Xavier,Figadère, Bruno
, p. 2615 - 2617 (2007/10/03)
The synthesis of (5′-oxoheptene-1′E,3′E-dienyl)-5,6- dihydro-2H-pyran-2-one has been performed in seven steps using four key steps: a ring-closing metathesis reaction to build up the unsaturated lactone, a Wittig reaction to control the C6-C7 (E) double bond, a cross-metathesis reaction to control the (E) double bond at C8-C9, and an enantioselective allyltitanation to control the absolute configuration at C5. Spectroscopic data (IR, MS, 1H, and 13C NMR) were identical to those of the natural compound except for the optical rotation, which led us to re-assign the absolute configuration of the natural product.
