160708-91-8Relevant academic research and scientific papers
Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents
Nagatomo, Hidetaka,Matsushita, Yoh-Ichi,Sugamoto, Kazuhiro,Matsui, Takanao
, p. 2339 - 2350 (2003)
The reduction of racemic γ-hydroperoxy-α,β-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantioselectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively.
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.
Tandem IBX-Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ-Diolcarbonate Aldehydes to (E)-γ-Hydroxy-α,β-enals
Kumari, Anupama,Gholap, Sachin P.,Fernandes, Rodney A.
, p. 2278 - 2290 (2019/06/17)
A tandem IBX-promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ-diolcarbonate aldehyde to (E)-γ-hydroxy-α,β-enal has been developed. Remarkably, the carbonate opening delivered exclusively (E)-olefin and no over-oxidation of γ-hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both (S)- and (R)-coriolides and d-xylo- and d-arabino-C-20 guggultetrols.
(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.
An expeditious synthesis of 4-hydroxy-2(E)-nonenal (4-HNE), its dimethyl acetal and of related compounds
Soulere, Laurent,Queneau, Yves,Doutheau, Alain
, p. 239 - 243 (2008/03/14)
The facile one step synthesis of 4-hydroxy-2(E)-nonenal and its dimethyl acetal via a cross-metathesis reaction between commercially available octen-3-ol and acrolein or its dimethyl acetal is reported. The method was extended to the synthesis of C6 and C12 4-hydroxy-2(E)-enals, their dimethyl acetal and of the 4-hydroxy-2(E)-nonenoic acid (4-HNA).
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.
Blue fluorescence generated during lipid oxidation of rat liver microsomes cannot be derived from malonaldehyde but can be from other aldehyde species
Inoue, Tadamichi,Kikugawa, Kiyomi
, p. 319 - 325 (2007/10/03)
Generation of blue fluorescence together with phospholipid hydroperoxides and aldehyde species in rat liver microsomes during oxidation with FeCl2-ADP-ascorbic acid was monitored, and the kind of lipid oxidation products participating in the formation of blue fluorescence was investigated. Contents of phospholipid hydroperoxides were increased in an early stage of oxidation, and were decreased in an advanced stage of oxidation. Contents of components that liberated malonaldehyde, 4- hydroxyalkenals and other unsaturated aldehydes under the acidic assay conditions were increased in the advanced stage of oxidation. Water-soluble blue fluorescence with a maximum at 440-450 nm determined after separation through gel filtration accumulated in the advanced stage of oxidation, and was characterized as resistant to borohydride treatment and to be little dependent on pH values of the solvent. Wavelength of the maximum fluorescence and characteristics of the fluorescence were similar to those of fluorescence with maxima at 440-450 nm formed by reaction of unoxidized microsomes, bovine serum albumin or methylamine with alkenals, and different from those of fluorescence with maxima at above 460 nm obtained by the reaction with a mixture containing malonaldehyde. Hence, blue fluorescence accumulated in oxidized microsomes cannot be derived from free malonaldehyde but can be from other aldehyde species including alkenals.
A practical synthesis of (R)- and (S)-(E)-4-hydroxyalk-2-enals, cytotoxic products of the microsomal lipid peroxidation
Allevi,Anastasia,Ciuffreda,Sanvito
, p. 927 - 934 (2007/10/02)
The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out via enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediates obtained from two diastereomeric diepoxide
