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1.
The reaction of 4-hydroxy-2-nonenal, an oxidative stress product, with phenylalanine in acetonitrile-water (2:1, 1:1, and 1:2) at 37, 60, and 80 degrees C was investigated to determine whether 4-hydroxy-2-alkenals degrade amino acids, analogously to 4,5-epoxy-2-alkenals, and to compare the reactivities of both hydroxyalkenals and epoxyalkenals for production of Strecker aldehydes. In addition to the formation of N-substituted 2-pentylpyrrole and 2-pentylfuran, the studied hydroxyalkenal also degraded phenylalanine to phenylacetaldehyde with a reaction yield of 17%. The reaction mechanism is suggested to be produced through the corresponding imine, which is then decarboxylated and hydrolyzed. This reaction also produced a conjugated amine, which both may be one of the origins of the produced 2-pentyl-1H-pyrrole and may contribute to the development of browning in these reactions. 4-Hydroxy-2-nonenal and 4,5-epoxy-2-decenal degraded phenylalanine in an analogous extent, which is likely a consequence of the similarity of the degradation mechanisms involved. These results suggest that different lipid oxidation products are able to degrade amino acids; therefore, the Strecker type degradation of amino acids produced by oxidized lipids may be quantitatively significant in foods.  相似文献   

2.
The reaction of methyl 9,10-epoxy-13-oxo-11(E)-octadecenoate, methyl 12,13-epoxy-9-oxo-11(E)-octadecenoate, 4,5(E)-epoxy-2(E)-heptenal, and 4,5(E)-epoxy-2(E)-decenal with phenylalanine in acetonitrile-water (2:1, 1:1, and 1:2) at 80 degrees C and at different pHs and carbonyl compound/amino acid ratios was investigated both to determine if epoxyoxoene fatty esters were able to produce the Strecker-type degradation of the amino acid and to study the relative ability of oxidized long-chain fatty esters and short chain aldehydes with identical functional systems to degrade amino acids. The studied epoxyoxoene fatty esters degraded phenylalanine to phenylacetaldehyde. The mechanism of the reaction was analogous to that described for epoxyalkenals and is suggested to be produced through the corresponding imine, which is then decarboxylated and hydrolyzed. This reaction also produced a conjugated hydroxylamine, which was the origin of the long-chain pyridine-containing fatty ester isolated in the reaction and characterized as methyl 8-(6-pentylpyridin-2-yl)octanoate. Epoxyoxoene fatty esters and epoxyalkenals exhibited a similar reactivity for producing phenylacetaldehyde, therefore suggesting that nonvolatile lipid oxidation products, which are produced to a greater extent than volatile products, should be considered for determining the overall contribution of lipids to Strecker degradation of amino acids produced during nonenzymatic browning. In addition, the obtained data confirm that, analogously to carbohydrates, lipid oxidation products are also able to produce the Strecker degradation of amino acids.  相似文献   

3.
Strecker degradation is one of the most important reactions leading to final aroma compounds in the Maillard reaction. In an attempt to clarify whether lipid oxidation products may be contributing to the Strecker degradation of amino acids, this study analyzes the reaction of 4,5-epoxy-2-alkenals with phenylalanine. In addition to N-substituted 2-(1-hydroxyalkyl)pyrroles and N-substituted pyrroles, which are major products of the reaction, the formation of both the Strecker aldehyde phenylacetaldehyde and 2-alkylpyridines was also observed. The aldehyde, which was produced at 37 degrees C-as could be determined by forming its corresponding thiazolidine with cysteamine-and pH 6-7, was not produced when the amino acid was esterified. This aldehyde is suggested to be produced through imine formation, which is then decarboxylated and hydrolyzed. This reaction also produces a hydroxyl amino derivative, which is the origin of the 2-alkylpyridines identified. All these data indicate that Strecker-type degradation of amino acids is produced at 37 degrees C by some lipid oxidation products. This is a new proof of the interrelations between lipid oxidation and Maillard reaction, which are able to produce common products by analogue mechanisms.  相似文献   

4.
The reactions of 4,5-epoxy-2-decenal with octylamine, benzylamine, and 2-phenylglycine methyl ester were studied to investigate if amines may suffer a Strecker type degradation by epoxyalkenals analogously to amino acids. In addition to other reactions, the studied amines were converted into their corresponding Strecker aldehydes (octanal, benzaldehyde, and methyl 2-oxo-2-phenylacetate, respectively) to an extent that depended on the pH, the temperature, the amount of epoxyalkenal, and the amine involved. Each amine exhibited an optimum pH for the reaction, but the corresponding Strecker aldehydes were produced to a significant extent within a broad pH range. In addition, the temperature mostly influenced the reaction rate, which was increased between 6.5 and 9.5 times when the reaction was carried out at 60 degrees C than when it took place at 37 degrees C. Furthermore, Strecker aldehyde formation was linearly correlated with the amount of the epoxyalkenal present in the reaction mixture. Nevertheless, the reaction yield mostly depended on the amine involved. Thus, octylamine only produced trace amounts of octanal, benzylamine was converted into benzaldehyde with a yield of 4.3%, and 2-phenylglycine methyl ester was converted into methyl 2-oxo-2-phenylacetate with a reaction yield of 49%. All of these results suggest that suitable amines can be degraded by epoxyalkenals to their corresponding Strecker aldehydes to a significant extent.  相似文献   

5.
The effect of lipids on the formation of the Strecker aldehyde phenylacetaldehyde during wort boiling was studied to determine the role that small changes in the lipid content of the wort have in the production of significant flavor compounds in beer. Wort was treated with 0-2.77 mmol per liter of glucose, linoleic acid, or 2,4-decadienal and heated at 60-98 degrees C for 1 h. After this time, the amount of the Strecker aldehyde phenylacetaldehyde increased in the samples treated with linoleic acid or decadienal but not in the samples treated with glucose. Thus, the amount of phenylacetaldehyde produced in the presence of linoleic acid was 1.1-2.5 times the amount of the Strecker aldehyde produced in the control wort, and this amount increased to 3.6-4.6 times when decadienal was employed. The higher reactivity of decadienal than linoleic acid for this reaction decreased with temperature and was related to the oxidation of linoleic acid that occurred to a higher extent at higher temperatures. The above results suggest that lipids can contribute to the formation of Strecker aldehydes during wort boiling and that changes in the lipid content of the wort will produce significant changes in the formation of Strecker aldehydes in addition to other well-known consequences in beer quality and yeast metabolism. On the other hand, because of the high glucose content in wort, small changes in its content are not expected to affect the amount of Strecker aldehydes produced.  相似文献   

6.
2,4-Decadienal was heated under an inert atmosphere and in the presence of phenylalanine to investigate whether this secondary lipid oxidation product is a final product of lipid oxidation or it reacts with the amino acid. The results obtained showed that, in the presence of the alkadienal, the amino acid was degraded to styrene. This reaction was favored in dry systems at pH approximately 6 and in the absence of oxygen. If oxygen was present, the alkadienal was oxidized and the Strecker degradation of the amino acid was produced. The activation energy for the formation of styrene from phenylalanine was 150.4 kJ/mol. The reaction mechanism is suggested to be produced either by an electronic rearrangement of the imine produced between the aldehyde and the amino acid with the formation of styrene, 2-pentylpyridine, carbon dioxide, and hydrogen, or by Michael addition of the amino compound to the alkadienal followed by beta-elimination to produce the same compounds. Both reaction schemes were supported on the results obtained by studying both the degradation of phenylethylamine and phenylalanine methyl ester produced by 2,4-decadienal, and the formation of ethylbenzene in decadienal/phenylalanine reaction mixtures heated in the presence of platinum oxide. All these results suggest that, analogously to carbohydrates, certain lipid oxidation products may degrade appropriate amino acids to their corresponding vinylogous derivatives.  相似文献   

7.
The comparative formation of phenylalanine and phenylpyruvic acid in the reaction of 4,5-epoxy-2-decenal with phenylalanine was studied to determine whether epoyalkenals may also degrade amino acids without producing their decarboxylation. Both compounds were produced in the reaction to an extent that depended on the reaction pH, the amount of lipid oxidation product, and the reaction time and temperature. The optimum pH was 3 for producing both carbonyl derivatives, and the amount of both compounds increased linearly with the amount of epoxyalkenal present in the reaction mixture. In addition, phenylpyruvic acid was produced to a higher extent than phenylacetaldehyde at 37 degrees C. However, at 60 degrees C the degradation of phenylpyruvic acid was observed and phenylacetaldehyde was usually found to a higher extent than the alpha-keto acid in the overnight-incubated reaction mixtures. The degradation of phenylpyruvic acid produced benzaldehyde and phenylacetaldehyde. All these results suggest that epoxyalkenals can not only degrade amino acids by a Strecker-type mechanism but convert them into their corresponding alpha-keto acids. This new reaction may be an alternative chemical route for the formation in foods of alpha-keto acids, which can later participate in the generation of important amino acid-derived flavor compounds.  相似文献   

8.
The reaction of methyl 13-hydroperoxyoctadeca-9,11-dienoate (MeLOOH), methyl 13-hydroperoxyoctadeca-9,11,15-trienoate (MeLnOOH), methyl 13-hydroxyoctadeca-9,11-dienoate (MeLOH), methyl 13-oxooctadeca-9,11-dienoate (MeLCO), methyl 9,10-epoxy-13-hydroxy-11-octadecenoate (MeLEPOH), and methyl 9,10-epoxy-13-oxo-11-octadecenoate (MeLEPCO) with phenylalanine was studied to determine the comparative reactivity of primary, secondary, and tertiary lipid oxidation products in the Strecker degradation of amino acids. All assayed lipids were able to degrade the amino acid to a high extent, although the lipid reactivity decreased slightly in the following order: MeLEPCO > or = MeLCO > MeLEPOH > or = MeLOH > MeLOOH approximately = MeLnOOH. These data confirmed the ability of many lipid oxidation products to degrade amino acids by a Strecker-type mechanism and suggested that, once the lipid oxidation is produced, a significant Strecker degradation of surrounding amino acids should be expected. The contribution of different competitive mechanisms to this degradation is proposed, among which the conversion of the different lipid oxidation products assayed into the most reactive MeLEPCO and the fractionation of long-chain primary and secondary lipid oxidation products into short-chain aldehydes are likely to play a major role.  相似文献   

9.
The reaction of 2,4-decadienal and methyl 13-oxooctadeca-9,11-dienoate with phenylalanine was studied to determine if alkadienals and ketodienes are able to produce the Strecker-type degradation of amino acids to the corresponding Strecker aldehydes. When reactions were carried out at 180 degrees C, both carbonyl compounds degraded phenylalanine to phenylacetaldehyde, among other compounds. The yield of the phenylacetaldehyde produced depended on the reaction pH and increased linearly with both the amount of the lipid and the reaction time. The yield of this conversion was approximately 8% when starting from decadienal and approximately 6% when starting from methyl 13-oxooctadeca-9,11-dienoate, and the reaction rate was lower for the ketone than for the aldehyde. Simultaneous to these reactions, the lipid was converted into pyrrole, pyridine, or aldehyde derivatives as a result of several competitive reactions. In particular, 9-14% of the decadienal was converted into hexanal under the assayed conditions. All these reactions are suggested to be produced as a consequence of the oxidation of the alkadienal or the ketodiene to the corresponding epoxyalkenal or unsaturated epoxyketone, which were identified in the reaction mixtures by GC-MS. All these results suggest that alkadienals and ketodienes, which are quantitatively important secondary lipid oxidation products, can degrade amino acids to their corresponding Strecker aldehydes. Therefore, under appropriate conditions, these products are not final products of the lipid oxidation and can participate in carbonyl-amine reactions analogously to other lipid oxidation products with two oxygenated functions.  相似文献   

10.
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 degrees C under nitrogen. The reactivity of the assayed compounds was 7 > 9 > 4 > 2 > 8 approximately 6 > 10 approximately 5. The presence of compounds 1 and 3 did not result in the formation of acrylamide. These results suggested that alpha,beta,gamma,delta-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 alpha,beta,gamma,delta-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.  相似文献   

11.
alpha-Dicarbonyls, generated by sugar degradation, catalyze the formation of the so-called Strecker aldehydes from alpha-amino acids. To check the effectiveness of Amadori compounds (suggested as important intermediates in alpha-dicarbonyl formation from carbohydrates) in Strecker aldehyde formation, the amounts of phenylacetaldehyde (PA) formed from either an aqueous solution of L-phenylalanine/glucose or the corresponding Amadori compound N-(1-deoxy-D-fructosyl-1-yl)-L-phenylalanine (ARP-Phe) were compared. The results revealed the ARP-Phe as a much more effective precursor in PA generation. On the contrary, a binary mixture of glucose/phenylalanine yielded preferentially phenylacetic acid, in particular, when reacted in the presence of oxygen and copper ions. Further model experiments gave evidence that a transition-metal-catalyzed oxidation of the ARP-Phe by air oxygen into the 2-hexosulose-(phenylalanine) imine is the key step responsible for the favored formation of phenylacetaldehyde from the Amadori compound. This mechanism might explain differences in the ratios of Strecker aldehydes and the corresponding acids depending on the structures of carbohydrate degradation products involved.  相似文献   

12.
With the aim of determining the formation of alpha-dicarbonyl intermediates during beer aging on the shelf, alpha-dicarbonyls were identified and quantified after derivatization with 1,2-diaminobenze to generate quinoxalines. The sensory effects of alpha-dicarbonyls were evaluated by the quantification of key Strecker aldehydes and by GC-olfactometry (GCO)analysis of beer headspace using solid phase microextraction. Four alpha-dicarbonyls, reported here for the first time, were detected in fresh and aged beers, three were derived from the 2,3-enolization pathway of mono- and disaccharides, and the fourth was derived from the epimerization of 3-deoxy-2-hexosulose. Ten alpha-dicarbonyls were quantified during beer processing and during different periods of beer aging at 28 degrees C. The aging periods were from 15 to 105 days. During beer aging, 1-deoxydiuloses were produced and degraded, while 1,4-dideoxydiuloses were produced at the highest rates. The GCO analysis indicated that forced beer aging increased the amounts of furaneol, trans-2-nonenal, and phenylacetaldehyde. The blockage of alpha-dicarbonyls inhibited the accumulation of sensory-active aldehydes in the beer headspace.  相似文献   

13.
Application of aroma extract dilution analysis on the volatiles formed by reacting glucose and L-phenylalanine (30 min, 100 degrees C) revealed the Strecker aldehyde, phenylacetaldehyde (PA), and, in addition, phenylacetic acid (PAA) as the two key odorants among the volatiles formed. Quantitative measurements on alpha-dicarbonyl formation revealed that the 3-deoxyosone and glyoxal were formed as the first prominent sugar degradation products, whereas 2-oxopropanal became predominant after approximately 4 h at 100 degrees C. Among the four alpha-dicarbonyls analyzed, 2-oxopropanal proved to be the most effective in generating PA as well as PAA from phenylalanine, but the reaction parameters significantly influenced the ratio of both odorants; for example, at pH 3.0 the ratio of PA to PAA was 3:1, whereas at pH 9.0 the ratio was 1:5. Furthermore, in the presence of oxygen and copper ions the formation of the acid was further increased. 3-Deoxyosone and glucosone were found to be effective precursors of phenylacetaldehyde, but neither was very effective in acid generation. On the basis of the results, a new oxygen-dependent formation pathway of the Strecker reaction is proposed.  相似文献   

14.
On the basis of a derivatization with dansyl chloride prior to LC‐MS/MS measurement, a new quantitation method by means of stable isotope dilution analysis was developed for different amines, such as 2‐ and 3‐methylbutylamine, methylpropylamine, and 2‐phenylethylamine. The method was applied both to different cereal products and to a model system, revealing that the amines stemming from the parent amino acids l ‐isoleucine, l ‐leucine, l ‐valine, and l ‐phenylalanine can also be generated by a “thermogenic” pathway besides the well‐established enzymatic formation. A model system simulating the Strecker reaction by heating single amino acids with an α‐dicarbonyl compound (2‐oxopropanal) showed besides the formation of the well‐known desired aroma‐active Strecker aldehydes also the generation of the corresponding Strecker amines, which are undesired in food due to their negative physiological impacts on human health. Thus, a thermal formation of “biogenic” amines was shown, both in cereal‐based foods and in a model system. A contribution of these amines to the overall food aroma is also possible. With this knowledge at hand, mitigation strategies for the formation of amines undesired for health reasons in parallel with a favored generation of the corresponding aroma‐active aldehydes, depending on the processing parameters, can be suggested to food manufacturers.  相似文献   

15.
Benzaldehyde, a potent aroma chemical of bitter almond, can also be formed thermally from phenylalanine and may contribute to the formation of off-aroma. To identify the precursors involved in its generation during Maillard reaction, various model systems containing phenylalanine, phenylpyruvic acid, phenethylamine, or phenylacetaldehyde were studied in the presence and absence of moisture using oxidative and nonoxidative Py-GC-MS. Analysis of the data indicated that phenylacetaldehyde, the Strecker aldehyde of phenylalanine, is the most effective precursor and that both air and water significantly enhanced the rate of benzaldehyde formation from phenylacetaldehyde. Phenylpyruvic acid was the most efficient precursor under nonoxidative conditions. Phenethylamine, on the other hand, needed the presence of a carbonyl compound to generate benzaldehyde only under oxidative conditions. On the basis of the results obtained, a free radical initiated oxidative cleavage of the carbon-carbon double bond of the enolized phenylacetaldehyde was proposed as a possible major mechanism for benzaldehyde formation, and supporting evidence was provided through monitoring of the evolution of the benzaldehyde band from heated phenylacetaldehyde in the presence and absence of 1,1'-azobis(cyclohexanecarbonitrile) on the ATR crystal of an FTIR spectrophotometer. In the presence of the free radical initiator, the enol band of the phenylacetaldehyde centered at 1684 cm(-1) formed and increased over time, and after 18 min of heating time the benzaldehyde band centered at 1697 cm(-1) formed and increased at the expense of the enol band of phenylacetaldehyde, indicating a precursor product relationship.  相似文献   

16.
Fruits and vegetables contain naturally occurring polyphenolic compounds that can undergo enzyme-catalyzed oxidation during food preparation. Many of these compounds contain catechol (1,2-dihydroxybenzene) moieties that may be transformed into o-quinone derivatives by polyphenoloxidases and molecular oxygen. Secondary reactions of the o-quinones include the Strecker degradation of ambient amino acids to form flavor-important volatile aldehydes. The purpose of this work was to investigate the mechanism of the polyphenol/o-quinone/Strecker degradation sequence in a nonenzymic model system. By using ferricyanide ion as the oxidant in pH 7.17 phosphate buffer at 22 degrees C, caffeic acid, chlorogenic acid, (+) catechin, and (-) epicatechin were caused to react with methionine and phenylalanine to produce Strecker aldehydes methional and phenylacetaldehyde in 0.032-0.42% molar yields (0.7-10 ppm in reaction mixtures). Also, by employing l-proline methyl ester in a reaction with 4-methylcatechol, a key reaction intermediate, 4-(2'-carbomethoxy-1'-pyrrolidinyl)-5-methyl-1,2-benzoquinone (7), was isolated and tentatively identified.  相似文献   

17.
Mixtures of either sunflower oil or thermodegraded sunflower oil and a standard meal were submitted to an in vitro digestion model. The same experiment was carried out with fluid deep-frying fat and thermodegraded fluid deep-frying fat. The thermodegradation of the oil and fat was provoked by submitting them to 190 degrees C with aeration in a convection oven, and the presence in the headspace of the thermodegraded oil and fat of oxygenated alpha,beta-unsaturated aldehydes (OalphabetaUAs), such as 4-hydroxy-2-nonenal (HNE), 4-oxo-2-nonenal (ONE), and 4,5-epoxy-2-decenal (EDE), was monitored by solid phase microextraction (SPME) followed by gas chromatography-mass spectrometry (GC-MS). The digestion products were separated by centrifugation in a lipidic phase, an aqueous phase, and a pellet phase. The headspace of these three phases was also studied by SPME/GC-MS to check if the toxic and very reactive OalphabetaUAs above-mentioned remained unaltered after the in vitro digestion process or if they had reacted with the various compounds present in the digestion products, so disappearing from the samples. With the same aim the extract in ethyl acetate of the aqueous and pellet phases, and of the lipidic phase after dilution, were studied by GC-MS. All results obtained showed that a certain proportion of the toxic OalphabetaUAs remains unaltered after digestion, dispersed in the three phases above-mentioned, and thus are bioaccessible in the gastrointestinal tract and so could reach the systemic circulation. Compounds that may originate in Maillard type reactions (2-pentylpyridine) are found among digestion products, proving that these reactions are possible in this process if adequate substrates are present. In addition, it has been shown that toxic metabolites from the synthetic antioxidant BHT, present in fat before digestion, remain unaltered after this process and could reach the systemic circulation.  相似文献   

18.
An investigation by aroma extract dilution analysis (AEDA) of the aroma concentrate of soy milk made from a major Japanese soybean cultivar, Fukuyutaka (FK), revealed 20 key aroma compounds having flavor dilution (FD) factors of not less than 64. Among them, 2-isopropyl-3-methoxypyrazine, cis-4,5-epoxy-(E)-2-decenal, trans-4,5-epoxy-(E)-2-decenal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, and 2'-aminoacetophenone were identified as the key aroma compounds in soy milk for the first time. (E,E)-2,4-Decadienal exhibiting a fatty note and trans-4,5-epoxy-(E)-2-decenal exhibiting a metallic/sweet note were detected as having the highest FD factors of 4096, followed by hexanal (green), (E)-2-nonenal (fatty), and (E,E)-2,4-nonadienal (fatty) having FD factors of 1024. Although all of these compounds might be generated from lipids, various aroma components, which were thought to be generated from amino acids, sugars, and ferulic acid, were detected having FD factors of 64-256. Investigation by comparative AEDA experiments of the soy milk aroma concentrates of two cultivars for soybean curd and soy milk, FK and Vinton81 (VT), and one cultivar for boiled beans, Miyagishirome (MY), revealed that most of the key aroma compounds were common to all of them, but 2-isopropyl-3-methoxypyrazine, exhibiting a pea-like/earthy note, was detected only in FK and VT. In addition, a sensory experiment revealed that the pea-like/earthy notes in FK and VT were significantly stronger than that in MY. These results demonstrated that a pea-like/earthy note contributed by 2-isopropyl-3-methoxypyrazine might be one of the essential characteristics to describe soy milk aromas.  相似文献   

19.
20.
Hydrolyzed vegetable protein (HVP) was prepared from rice bran protein concentrate (RBPc) by partial hydrolysis with aqueous 0.5 N HCl at 95 degrees C for 12 or 36 h (H-RBPc-12 and H-RBPc-36, respectively). Aroma components of the RBPc and the HVPs were characterized by gas chromatography-olfactometry, gas chromatography-mass spectrometry, aroma extract dilution analysis, and calculation of odor activity values (OAVs). The predominant odorants in RBPc were 3-methylbutanal, hexanal, 2-aminoacetophenone, (E)-2-nonenal, phenylacetaldehyde, and beta-damascenone. Among these, the odor of 2-aminoacetophenone, present at 59 ng/g in RBPc, was reminiscent of the typical odor of RBPc. Most of the predominant odorants had higher log3FD factors in the H-RBPc-36 as compared to H-RBPc-12. Aroma impact compounds of H-RBPc-12 and H-RBPc-36 were 2-methoxyphenol (guaiacol), 4-hydroxy-2,5-dimethyl-3(2H)furanone, 3-hydroxy-4,5-dimethyl-2(5H)furanone (sotolon), vanillin, 3-methylbutanal, (E)-2-nonenal, 4-vinyl-2-methoxyphenol (p-vinylguaiacol), and beta-damascenone. Guaiacol had the highest OAV values of 2770 and 17650 in H-RBPc-12 and H-RBPc-36, respectively.  相似文献   

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