134454-31-2Relevant articles and documents
Studies on the aroma of five fresh tomato cultivars and the precursors of cis- and trans-4,5-epoxy-(E)-2-decenals and methional
Mayer, Florian,Takeoka, Gary R.,Buttery, Ron G.,Whitehand, Linda C.,Naim, Michael,Rabinowitch, Haim D.
, p. 3749 - 3757 (2008)
Three tasty (BR-139, FA-624, and FA-612) and two less tasty (R-144 and R-175) fresh greenhouse tomato cultivars, which significantly differ in their flavor profiles, were screened for potent odorants using aroma extract dilution analysis (AEDA). On the basis of AEDA results, 19 volatiles were selected for quantification in those 5 cultivars using gas chromatography-mass spectrometry (GC-MS). Compounds such as 1-penten-3-one, (E,E)- and (E,Z)-2,4-decadienal, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol) had higher odor units in the more preferred cultivars, whereas methional, phenylacetaldehyde, 2-phenylethanol, or 2-isobutylthiazole had higher odor units in the less preferred cultivars. Simulation of the odor of the selected tomato cultivars by preparation of aroma models and comparison with the corresponding real samples confirmed that all important fresh tomato odorants were identified, that their concentrations were determined correctly in all five cultivars, and that differences in concentration, especially of the compounds mentioned above, make it possible to distinguish between them and are responsible for the differential preference. To help elucidate formation pathways of key odorants, labeled precursors were added to tomatoes. Biogenesis of cis-and trans-4,5-epoxy-(E)-2- decenals from linoleic acid and methional from methionine was confirmed.
Characterization of the key aroma compounds in apricots (Prunus armeniaca) by application of the molecular sensory science concept
Greger, Veronika,Schieberle, Peter
, p. 5221 - 5228 (2007)
An aroma extract dilution analysis applied on an aroma distillate prepared from fresh apricots revealed (R)-γ-decalactone, (E)-β-damascenone, δ-decalactone, and (R/S)-linalool with the highest flavor dilution (FD) factors among the 26 odor-active compounds identified. On the basis of quantitative measurements performed by application of stable isotope dilution assays, followed by a calculation of odor activity values (OAVs), β-ionone, (Z)-1,5-octadien-3-one, γ-decalactone, (E,Z)-2,6-nonadienal, linalool, and acetaldehyde appeared with OAVs >100, whereas in particular certain lactones, often associated with an apricot aroma note, such as γ-undecalactone, γ-nonalactone, and δ-decalactone, showed very low OAVs (5). An aroma recombinate prepared by mixing the 18 most important odorants in concentrations as they occurred in the fresh fruits showed an overall aroma very similar to that of apricots. Omission experiments indicated that previously unknown constituents of apricots, such as (E,Z)-2,6-nonadienal or (Z)-1,5-octadien-3-one, are key contributors to the apricot aroma.
Characterization of the aroma-active compounds in pink guava (Psidium guajava, L.) by application of the aroma extract dilution analysis
Steinhaus, Martin,Sinuco, Diana,Polster, Johannes,Osorio, Coralia,Schieberle, Peter
, p. 4120 - 4127 (2008)
The volatiles present in fresh, pink-fleshed Colombian guavas (Psidium guajava, L.), variety regional rojo, were carefully isolated by solvent extraction followed by solvent-assisted flavor evaporation, and the aroma-active areas in the gas chromatogram were screened by application of the aroma extract dilution analysis. The results of the identification experiments in combination with the FD factors revealed 4-methoxy-2,5-dimethyl-3(2H)-furanone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-sulfanylhexyl acetate, and 3-sulfanyl-1-hexanol followed by 3-hydroxy-4,5-dimethyl-2(5H)-furanone, (Z)-3-hexenal, trans-4,5-epoxy-(E)-2-decenal, cinnamyl alcohol, ethyl butanoate, hexanal, methional, and cinnamyl acetate as important aroma contributors. Enantioselective gas chromatography revealed an enantiomeric distribution close to the racemate in 3-sulfanylhexyl acetate as well as in 3-sulfanyl-1-hexanol. In addition, two fruity smelling diastereomeric methyl 2-hydroxy-3- methylpentanoates were identified as the (R,S)- and the (S,S)-isomers, whereas the (S,R)- and (R,R)-isomers were absent. Seven odorants were identified for the first time in guavas, among them 3-sulfanylhexyl acetate, 3-sulfanyl-1-hexanol, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, frans-4,5-epoxy-(E)-2-decenal, and methional were the most odor-active.
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
Intermediate role of α-keto acids in the formation of Strecker aldehydes
Hidalgo, Francisco J.,Delgado, Rosa M.,Zamora, Rosario
, p. 1140 - 1146 (2013/10/08)
The ability of α-keto acids to covert amino acids into Strecker aldehydes was investigated in an attempt to both identify new pathways for Strecker degradation, and analyse the role of α-keto acids as intermediate compounds in the formation of Strecker aldehydes by oxidised lipids. The results obtained indicated that phenylalanine was converted into phenylacetaldehyde to a significant extent by all α-keto acids assayed; glyoxylic acid being the most reactive α-keto acid for this reaction. It has been proposed that the reaction occurs by formation of an imine between the keto group of the α-keto acid, and the amino group of the amino acid. This then undergoes an electronic rearrangement with the loss of carbon dioxide to produce a new imine. This final imine is the origin of both the Strecker aldehyde and the amino acid from which the α-keto acid is derived. When glycine was incubated in the presence of 4,5-epoxy-2-decenal, the amino acid was converted into glyoxylic acid, and this α-keto acid was then able to convert phenylalanine into phenylacetaldehyde. All these results suggest that Strecker aldehydes can be produced by amino acid degradation initiated by different reactive carbonyl compounds, included those coming from amino acids and proteins. In addition, α-keto acids may act as intermediates for the Strecker degradation of amino acids by oxidised lipids.
Contribution of lipid oxidation products to acrylamide formation in model systems
Zamora, Rosario,Hidalgo, Francisco J.
experimental part, p. 6075 - 6080 (2010/04/02)
The reactions of asparagine with methyl linoleate (1), methyl 13-hydroperoxyoctadeca-9,11-dienoate (2), methyl 13-hydroxyoctadeca-9,11- dienoate (3), methyl 13-oxooctadeca-9,11-dienoate (4), methyl 9,10-epoxy-13-hydroxy-11-octadecenoate (5), methyl 9,10-epoxy-13-oxo-11- octadecenoate (6), 2,4-decadienal (7), 2-octenal (8), 4,5-epoxy-2-decenal (9), and benzaldehyde (10) were studied to determine the potential contribution of lipid derivatives to acrylamide formation in heated foodstuffs. Reaction mixtures were heated in sealed tubes for 10 min at 180°C under nitrogen. The reactivity of the assayed compounds was 7 ? 9 > 4 > 2 ? 8 ～ 6 ? 10 ～ 5. The presence of compounds 1 and 3 did not result in the formation of acrylamide. These results suggested that α,β,γ, δ-diunsaturated carbonyl compounds were the most reactive compounds for this reaction followed by lipid hydroperoxides, more likely as a consequence of the thermal decomposition of these last compounds to produce α,β,γ,δ-diunsaturated carbonyl compounds. However, in the presence of glucose this reactivity changed, and compound 1/glucose mixtures showed a positive synergism (synergism factor = 1.6), which was observed neither in methyl stearate/glucose mixtures nor in the presence of antioxidants. This synergism is proposed to be a consequence of the formation of free radicals during the asparagine/glucose Maillard reaction, which oxidized the lipid and facilitated its reaction with the amino acid. These results suggest that both unoxidized and oxidized lipids are able to contribute to the conversion of asparagine into acrylamide, but unoxidized lipids need to be oxidized as a preliminary step.
Characterization of epoxydecenal isomers as potent odorants in black tea (Dimbula) infusion
Kumazawa, Kenji,Wada, Yoshiyuki,Masuda, Hideki
, p. 4795 - 4801 (2007/10/03)
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.
A highly efficient practical method for the synthesis of chiral polyhydroxy-(E,E)-1-chlorodienols and (E)-5-hydroxy enynes
Yadav,Barma,Dutta, Dinah
, p. 4479 - 4482 (2007/10/03)
An efficient protocol for the synthesis of chiral polyhydroxy-(E, E)-1-chlorodienols and (E)-5-hydroxy enynes from chiral 4,5-epoxy trans allyl chlorides and 4,5-O-isopropylidene allyl chlorides is described by using stoichiometric amount of LiNH2 or LDA in HMPA : THF (1 : 5) useful in the synthesis of biologically active natural products.
Regio- and Enantioselective Catalytic Epoxidation of Conjugated Polyenes. Formal Synthesis of LTA4 Methyl Ester
Chang, Sukbok,Lee, Nam Ho,Jacobsen, Eric N.
, p. 6939 - 6941 (2007/10/02)
The (salen)Mn(III)-catalyzed asymmetric epoxidation reaction exhibits regioselectivity for attack at cis double bonds of conjugated dienes to afford enantiomerically enriched trans-vinyl epoxides as the major products.
THE STEREOSPECIFIC SYNTHESIS OF 14S,15S-OXIDO 5Z,8Z,10E,12E-EICOSATETRAENOIC ACID
Zamboni, Robert,Milette, Suzanne,Rokach, Joshua
, p. 4899 - 4902 (2007/10/02)
The first total and stereospecific synthesis of 14S,15S-oxido 5Z,8Z,10E,12E-eicosatetraenoic acid from 2-deoxy-D-ribose has been achieved.
