113973-12-9Relevant articles and documents
Polymer supported perruthenate (PSP): Clean oxidation of primary alcohols to carbonyl compounds using oxygen as cooxidant
Hinzen, Berthold,Lenz, Roman,Ley, Steven V.
, p. 977 - 979 (1998)
Molecular oxygen has been used as stoichiometric oxidant in polymer supported perruthenate (PSP) catalysed conversion of primary alcohols to carbonyl compounds affording pure products without the need for conventional workup procedures.
Asymmetric synthesis of (2R,3S)-2,3-epoxyoctanal, a key intermediate of 14,15-leukotriene A4
Tsuboi,Furutani,Takeda
, p. 833 - 835 (1987)
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Carbon-carbon bond forming reactions with oxiranyl radicals
Ziegler, Frederick E.,Wang, Yizhe
, p. 6299 - 6302 (1996)
Substituted oxiranyl radicals have been generated from glycidic acids. The cyclization of these species, the stereochemistry of the resultant products, and an intermolecular application of these reactive species is considered.
Characterization of epoxydecenal isomers as potent odorants in black tea (Dimbula) infusion
Kumazawa, Kenji,Wada, Yoshiyuki,Masuda, Hideki
, p. 4795 - 4801 (2006)
In a black tea (Dimbula) infusion, the potent "sweet and/or juicy" odorants were identified as the cis-and trans-4,5-epoxy-(E)-2- decenals by comparison of their gas chromatography retention indices, mass spectra, and odor quality to those of the actual synthetic compounds. Of the two odorants, cis-4,5-epoxy-(E)-2-decenal has been identified for the first time in the black tea. On the basis of the aroma extract dilution analysis on the flavor distillate obtained using the solvent-assisted flavor evaporation technique from the black tea infusion, these isomers showed higher flavor dilution (FD) factors. The FD factors and concentrations of these odorants in the black tea infusion were observed to be much higher than those from Japanese green tea. In addition, the model studies showed that these odorants were generated from linoleic acid and its hydroperoxides by heating, but the generated amounts of these odorants from linoleic acid were much less than those of its hydroperoxides. It can be assumed from these results that the withering and fermentation, which are characteristic processes during the manufacturing of the black tea, which includes the enzymatic reaction such as lipoxygenase, is one of the most important factors for the formation of the epoxydecenal isomers.
Mammalian blood odorant and chirality: synthesis and sensory evaluation by humans and mice of the racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal
Mori, Kenji,Osada, Kazumi,Amaike, Masayasu
, p. 861 - 867 (2015/08/18)
Abstract The racemate and enantiomers of trans-4,5-epoxy-(E)-2-decenal 1, an odorant with a metallic blood smell, were synthesized. The detection threshold for humans was 0.019 ppb for (2E,4S,5S)-(-)-1 and 0.62 ppb for (2E,4R,5R)-(+)-1, respectively. The
Synthesis of the four stereoisomers of 2,3-epoxy-4-hydroxynonanal and their reactivity with deoxyguanosine
Petrova, Katya V.,Stec, Donald F.,Voehler, Markus,Rizzo, Carmelo J.
supporting information; experimental part, p. 1960 - 1971 (2011/04/22)
2,3-Epoxy-4-hydroxynonanal (EHN) is a potential product of lipid peroxidation that gives rise to genotoxic etheno adducts. We have synthesized all four stereoisomers of EHN and individually reacted them with 2′-deoxyguanosine. In addition to 1,N2-etheno-2′- deoxyguanosine, 12 stereoisomeric products were isolated and characterized by 1H NMR and circular dichroism spectroscopy. The stereochemical assignments were consistent with selective NOE spectra, vicinal coupling constants, and molecular mechanics calculations. Reversed-phase HPLC conditions were developed that could separate most of the adduct mixture.
