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1.
Effects of surfactant concentration, antioxidants with different polarities, and chelator type on the oxidative stability of water‐in‐stripped walnut oil (W/O) emulsions stabilized by polyglycerol polyricinoleate (PGPR) were evaluated. The formation of primary oxidation products (lipid hydroperoxides) and secondary oxidation products (hexanal) decreased with increasing PGPR concentrations (0.3–1.0 wt% of emulsions). Excess surfactant might solubilize lipid hydroperoxides out of the oil–water interface, resulting in the decreased lipid oxidation rates in W/O emulsions. At concentrations of 10–1000 μM, the polar Trolox demonstrated concentration‐dependent antioxidant activity according to both hydroperoxide and hexanal formation. The antioxidant efficiency of the non‐polar α‐tocopherol was slightly reduced at the higher range of 500–1000 μM based on hydroperoxide formation. Both ethylenediaminetetraacetic acid (EDTA) and deferoxamine (DFO) at concentrations of 5–100 μM reduced the rates of lipid oxidation at varying degrees, indicating that endogenous transition metals may promote lipid oxidation in W/O emulsions. EDTA was a stronger inhibitor of lipid oxidation than DFO. These results suggest that the oxidative stability of W/O emulsions could be improved by the appropriate choice of surfactant concentration, antioxidants, and chelators.  相似文献   

2.
Association colloids formed by surface active minor components play an important role in the oxidative stability of bulk oils. To imitate the formation of nanostructures in refined oils, multiple surface active minor components including phospholipids, free fatty acids, diacylglycerols and sterols were added to stripped corn oil. The critical micelle concentration (CMC) of the mixed components was determined. The impact of mixed minor components at below and above their CMC on oxidative stability of bulk oil and on antioxidant activity of α-tocopherol and Trolox was investigated. The CMC of the mixed surface active components in bulk oil was 20 µmol/kg oil in the presence of 383 ± 2 ppm of water. 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) played an important role on the formation of association colloids since it was the most important component in forming the association colloids as confirmed by CMC and fluorescence probe studies. The association colloids formed by the mixed components showed prooxidative activity in bulk oil as determined by monitoring the formation of lipid hydroperoxide and hexanal. The activity of α-tocopherol or Trolox was not changed by mixed components association colloids. These results suggest that association colloids both physically and chemically impacted the oxidative stability and activity of antioxidants in bulk oil.  相似文献   

3.
Association colloids such as phospholipid reverse micelles could increase the rate of lipid oxidation in bulk oils. In addition to phospholipids, other surface active minor components in commercial oils such as free fatty acids may impact lipid oxidation rates and the physical properties of reverse micelles. In this study, the effects of free fatty acids on changes in the critical micelle concentration (CMC) of 1,2-Dioleoyl-sn-glycero-3-phosphocholine (DOPC) in stripped corn oil (SCO) were determined by using the 7,7,8,8-tetracyanoquinodimethane solubilization technique. Different free fatty acids including myristoleic, oleic, elaidic, linoleic and eicosenoic were added at 0.5 % by wt along with the DOPC into the bulk oils. There was no significant effect of free fatty acids with different chain length, configuration and number of double bonds on the CMC value for DOPC in bulk oil. However, increasing concentrations of oleic acid (0.5 to 5 % by wt) caused the CMC value for DOPC in bulk oils to increase from 400 to 1,000 μmol/kg oil. Physical properties of DOPC reverse micelles in the presence of free fatty acids in bulk oils were also investigated by the small angle X-ray scattering technique. Results showed that free fatty acids could impact on the reverse micelle structure of DOPC in bulk oils. Moreover, free fatty acid decreased pH inside reverse micelle as confirmed by the NMR studies. The oxidation studies done by monitoring the lipid hydroperoxide and hexanal formation revealed that free fatty acids exhibited pro-oxidative activity in the presence and absence of DOPC. Different types of free fatty acids had similar pro-oxidative activity in bulk oil.  相似文献   

4.
The antioxidative effects of γ‐ and mainly δ‐tocopherol in a multiphase system were hardly considered up to now. The aim of this study was i) to assess the effects and ii) to follow the degradation of α‐, γ‐ and δ‐tocopherol in concentrations of 0.01%, 0.05%, 0.1% and 0.25% during the oxidation of a 10% purified rapeseed oil triacylglycerol‐in‐water emulsion at 40 °C in the dark for 15 wk in a system containing a low oxygen concentration. Oxidation experiments were performed weekly by assessing the formation of hydroperoxides and hexanal, and the stability of the tocopherols was determined using high‐performance liquid chromatography. Storage tests were conducted with and without the addition of 0.01% α, α′‐azoisobutyronitrile (AIBN), which is a known radical initiator. α‐Tocopherol increased the formation of hydroperoxides in both tests as well as the generation of hexanal when the radical initiator was added; furthermore it was the least stable. γ‐Tocopherol delayed the formation of hexanal and prolonged the stability of the emulsion in a dose‐dependant manner. δ‐Tocopherol was the most stable and also the most effective in delaying lipid oxidation in the emulsions. Each concentration that was tested reduced the rate of hydroperoxide and especially hexanal formation. Hexanal was only formed to a slight extent after 15 wk of oxidation in the test with AIBN and the lowest dose of 0.01% δ‐tocopherol. For all tocopherols, strong correlations were found between tocopherol stability and the extent of oxidation. Results suggest that i) mainly δ‐tocopherol, but also γ‐tocopherol even less pronounced, are very good antioxidants in order to stabilize and prolong the shelf life of oil‐in‐water emulsions, ii) the antioxidative effects were intensified with increasing amounts.  相似文献   

5.
The effects of α‐ and δ‐tocopherol on inhibition of hydroperoxides, keto and hydroxy compounds under Rancimat conditions, i.e. 100 °C and air bubbling, were studied in samples of fatty acid methyl esters (FAME) obtained from high linoleic (HL) and high oleic (HO) sunflower oils. Primary hydroperoxides from methyl linoleate and methyl oleate and secondary keto and hydroxy compounds derived from methyl linoleate hydroperoxides were analyzed by HPLC–UV‐ELS. Different tocopherol concentrations, namely, 10, 50, 100, 500 and 1000 mg/kg, were tested. Irrespective of the lipid substrate and the initial concentration of tocopherol, results showed that the content of hydroperoxides accumulated during the induction period was remarkably higher in the samples containing δ‐tocopherol. The relative concentrations of oleate hydroperoxides in the HO samples were also higher in the presence of δ‐tocopherol. α‐Tocopherol was more effective in inhibiting hydroperoxides at low levels, with 100 mg/kg as optimal concentration, while δ‐tocopherol displayed optimal protection at 1000 mg/kg. Under the oxidation conditions applied, neither α‐ nor δ‐tocopherol showed a protective effect on hydroperoxide decomposition at any level assayed. Formation of keto‐ and hydroxy‐dienes was more related to the concentration of their hydroperoxide precursors. Furthermore, both tocopherols gave rise to increased concentrations of ketodienes at 500 and 1000 mg/kg compared to the controls. Such an effect was more pronounced for α‐tocopherol and in the HL samples.  相似文献   

6.
A kinetic analysis was performed to evaluate the antioxidant behavior of α‐ and γ‐to‐copherols (5—2000 ppm) in purified triacylglycerols obtained from sunflower oil (TGSO) and soybean oil (TGSBO) at 100 °C. Different kinetic parameters were determined, viz. the stabilization factor as a measure of effectiveness, the oxidation rate ratio as a measure of strength, and the antioxidant activity which combines the other two parameters. In the low concentration range (up to 400 ppm in TGSBO and up to 700 ppm in TGSO) α‐tocopherol was a more active antioxidant than γ‐tocopherol whereas the latter was more active at higher concentrations. It has been found that the different activity of the tocopherols is not due to their participation in chain initiation reactions, but that the loss of antioxidant activity at high tocopherol concentrations is due to their consumption in side reactions. The rates of these reactions are higher in TGSBO than in TGSO. Both α‐tocopherol itself and its radicals participated more readily in side reactions than γ‐tocopherol and its radicals. Both α‐ and γ‐tocopherol reduce lipid hydroperoxides, thus generating alkoxyl radicals which are able to amplify the rate of lipid oxidation by participating in chain propagation reactions.  相似文献   

7.
The competitive oxidation between α‐tocopherol and unsaturated fatty acyls at thermoxidation conditions (180 and 240 °C) was evaluated using purified triacylglycerols from nine fats and oils (refined coconut, palm, tallow, olive, high oleic sunflower, sunflower, corn, soybean, and flaxseed oil). α‐Tocopherol degraded faster in less unsaturated lipids and a linear correlation between the iodine value (x) and the residual tocopherol content (y) was obtained after 2 h of heating at 240 °C (y = 3.72x + 137.5, R2 = 0.9463). The formation of polar oxidation products was established and the results were explained by a non‐selective oxidation of unsaturated fatty acyls and α‐tocopherol by highly reactive alkoxyl and hydroxyl radicals generated by decomposition of hydroperoxides.  相似文献   

8.
The antioxidant activity of myricetin, a natural flavonol found in fruits and vegetables, was determined in soybean oil methyl esters (SME) and compared with α‐tocopherol and tert‐butylhydroquinone (TBHQ) over a 90‐day period employing EN 14112, acid value, and kinematic viscosity methods. Myricetin had greater antioxidant activity than α‐tocopherol, but was inferior to TBHQ. Synergism was observed between myricetin and TBHQ, but antagonism between α‐tocopherol and either myricetin or TBHQ was discovered. A binary mixture of myricetin and TBHQ at 1000 ppm (1:1) was the most effective treatment investigated at inhibiting oxidation of SME. Myricetin was not completely soluble in SME at 1000 ppm, suggesting that 500 ppm is a more appropriate treatment level. Pro‐oxidant activity of α‐tocopherol was observed when added to SME obtained from crude soybean oil, but antioxidant behavior was observed in distilled SME. Addition of α‐tocopherol to methyl esters initially free of antioxidants revealed that 600–700 ppm was the optimum concentration for antioxidant activity. Acid value and kinematic viscosity remained within prescribed specifications after 90 days, despite failure of a number of samples with regard to EN 14112, suggesting that these parameters are insufficient as sole indicators of oxidation stability.  相似文献   

9.
Phospholipids are important minor components in edible oil that play a role in lipid oxidation. Surface active phospholipids have an intermediate hydrophilic–lipophilic balance value, which allows them to form association colloids such as reverse micelles in bulk oil. These association colloids can influence lipid oxidation since they create lipid–water interfaces where prooxidants and antioxidants can interact with triacylglycerols. In this study, we examined the formation of reverse micelles in a stripped oil system by dioleoyl phosphoethanolamine (DOPE) and the effect of these physical structures on lipid oxidation kinetics. The critical micelle concentration (CMC) of DOPE was approximately 200 µmol/kg oil at 45 °C. Oxidation kinetics studies showed that DOPE was prooxidative when it was above its CMC (400 and 1,000 µM), reducing the lag phase from 14 days (control) to 8 days. The addition of combinations of DOPE and dioleoyl phosphocholine (DOPC) resulted in formation of mixed micelles with a CMC of 80 µmol/kg oil at 45 °C. These mixed micelles were also prooxidative when concentrations (100 and 500 µM) were above the CMC, decreasing the lag phase from 14 to 8 days. These findings provide a better understanding of the role of phospholipids in lipid oxidation of edible oil and could contribute to better antioxidant solutions.  相似文献   

10.
The effects of α‐, γ‐ and δ‐tocopherols on the stability and decomposition reactions of lipid hydroperoxides were studied. Isomerization and decomposition of cis,trans methyl linoleate hydroperoxides (cis,trans ML‐OOH) in hexadecane at 40 °C were followed by high‐performance liquid chromatography. Due to its higher hydrogen donating ability, α‐tocopherol was more efficient than γ‐ and δ‐tocopherols in inhibiting the isomerization of cis,trans ML‐OOH to trans,trans ML‐OOH. α‐Tocopherol stabilized hydroperoxides into the cis,trans configuration, whereas γ‐ and δ‐tocopherols allowed hydroperoxides to convert into trans,trans isomers. Thus, the biological importance of α‐tocopherol as compared to other tocopherols may be partly due to its better efficacy in protecting the cis,trans configuration of hydroperoxides formed, for example, in the enzymatic oxidation of polyunsaturated fatty acids. The isomeric configuration of hydroperoxides has an impact on biological activities of further oxidation products of polyunsaturated fatty acids. Paradoxically, the order of activity of tocopherols with regard to hydroperoxide decomposition was different from that obtained for hydroperoxide isomerization. γ‐ and δ‐tocopherols were more efficient inhibitors of ML‐OOH decomposition when compared to α‐tocopherol. A loss of antioxidant efficiency, observed as the tocopherol concentration increased from 2 to 20 mM, was highest for α‐tocopherol but was also evident for γ‐ and δ‐tocopherols. Thus, the differences in the relative effects of tocopherols at differing concentrations seem to result from a compromise between their radical scavenging efficiency and participation in side reactions of peroxidizing nature.  相似文献   

11.
Lipid oxidation is one of the major causes of oil deterioration causing off-flavors and consumer rejection. Fast, easy, and dependable assays for predicting lipid oxidation rates in foods are important for shelf-life prediction. In this study, an electron paramagnetic resonance (EPR) spin-trapping technique with N-tert-butyl-α-phenylnitrone (PBN) was tested to determine the lag phase of lipid oxidation in stripped soybean oil (SSO), SSO with added α-tocopherol, and commercial soybean, canola and corn oils. EPR intensity of spin-trapped products from SSO correlated well with lipid hydroperoxides formation for samples stored at 37 and 55 °C respectively. When the antioxidant α-tocopherol was added, the EPR signal intensity of oil samples increased—indicating sample deterioration—after 50–65% of α-tocopherol was consumed. When using the EPR method with commercial soybean, canola or corn oil stored at 55 °C, there was a poor relationship between EPR intensity and lipid hydroperoxides lag phases. However, a linear correlation was found between EPR signal intensity and hexanal formation. For example, EPR signal intensity lag phases were 5, 13 and 27 days for soybean, canola and corn oils, respectively which was similar to the hexanal lag phases of 5, 13 and 25 days for the same oils. The EPR spin-trapping assay method has several advantages over headspace hexanal measurements, especially with regard to easier sample handling and shorter analysis times.  相似文献   

12.
The objective of this research was to investigate the antioxidative properties of extract from blackcurrant seeds (BCSs) and commercially available rosemary extracts (Stabiloton OS, oil‐soluble and WS, water soluble) in soybean oil (SO). The antioxidant activity of plant extracts was compared with those of α‐tocopherol and butylated hydroxytoluene (BHT). The results of present research reveal differentiation of action of investigated extracts toward primary (peroxide value (PV), conjugated dienes (CDs)) and secondary (measured as anisidine value (AV), hexanal) oxidation products in SO. WS and OS rosemary extracts show high efficiency in delaying primary and secondary oxidative changes. BCSs extract markedly retards oxidation, nevertheless its activity falls down with formation and succeeding deterioration of primary products. Although the use of BCSs, residues of fruit processing, as a source of antioxidants would be reasonable because of economic and environmental reasons, it may be limited by low activity toward secondary oxidation products in certain lipid substrates. Taking primary oxidative changes into consideration, all extracts studied perform better than used standard antioxidants – BHT and α‐tocopherol.  相似文献   

13.
The aim of this work was to study the evolution of oxidation and the efficiency of phenolic antioxidants in sunflower oil‐in‐water emulsions containing sodium caseinate and lactose (Cas‐Lac) or stabilized by Tween‐20 (T‐20). Two groups of phenolic antioxidants which are structurally similar were tested, i.e. (1) α‐tocopherol and its water‐soluble analogue, Trolox; and (2) gallic acid and its ester derivatives propyl gallate and dodecyl gallate. Emulsion samples were oxidized at 40 °C and the progress of oxidation was followed through quantitation of oxidized triacylglycerol monomers, dimers and oligomers. Results showed that Cas‐Lac emulsions were more stable to oxidation than T‐20 emulsions. In both types of emulsions, the most protective antioxidants were the compounds of lower polarity, namely, α‐tocopherol and dodecyl gallate. It was also found that substantial amounts of α‐tocopherol coexisted with significant polymerization, which was indicative of the heterogeneity of oxidation, i.e. differences of oxidation rate in oil droplets.  相似文献   

14.
The peroxidation of linoleic acid (LA) in the absence and presence of either Cu(II) ions alone or Cu(II)‐ascorbate combination was investigated in aerated and incubated emulsions at 37°C and pH 7. LA peroxidation induced by either copper(II) or copper(II)‐ascorbic acid system followed pseudo‐first order kinetics with respect to primary (hydroperoxides) and secondary (aldehydes‐ and ketones‐like) oxidation products, detected by ferric‐thiocyanate and TBARS tests, respectively. α‐Tocopherol showed both antioxidant and prooxidant effects depending on concentration and also on the simultaneous presence of Cu(II) and ascorbate. Copper(II)‐ascorbate combinations generally led to distinct antioxidant behavior at low concentrations of α‐tocopherol and slight prooxidant behavior at high concentrations of α‐tocopherol, probably associated with the recycling of tocopherol by ascorbate through reaction with tocopheroxyl radical, while the scavenging effect of α‐tocopherol on lipid peroxidation was maintained as long as ascorbate was present. On the other hand, in Cu(II) solutions without ascorbate, the antioxidant behavior of tocopherol required higher concentrations of this compound because there was no ascorbate to regenerate it. Practical applications: Linoleic acid (LA) peroxidation induced by either copper(II) or copper(II)‐ascorbic acid system followed pseudo‐first order kinetics with respect to primary (hydroperoxides) and secondary (e.g., aldehydes and ketones) oxidation products. α‐Tocopherol showed both antioxidant and prooxidant effects depending on concentration and also on the simultaneous presence of Cu(II) and ascorbate. The findings of this study are believed to be useful to better understand the actual role of α‐tocopherol in the preservation of heterogenous food samples such as lipid emulsions. Since α‐tocopherol (vitamin E) is considered to be physiologically the most important lipid‐soluble chain‐breaking antioxidant of human cell membranes, the results can be extended to in vivo protection of lipid oxidation.  相似文献   

15.
The antioxidant activities of the essential oil and crude methanolic extract (CEx) of cumin seed (Cuminum cyminum) were evaluated. Total phenolics and tocopherols contents, reducing power, DPPH radical‐scavenging capacity (EC50), and the oxidative/oil stability index were assessed. The contents of total phenolics and total tocopherols in the essential oil (18.47 and 0.11 mg/g, respectively) were significantly lower than those of the CEx (29.12 and 0.42 mg/g, respectively). The CEx had an EC50 value (0.74 mg/mL) significantly lower than those of the essential oil and α‐tocopherol (1.20 and 32.50 mg/mL, respectively). The reducing power of the CEx (459.46 mmol Fe2+ per mass) was significantly higher than those of the essential oil (18.47 mmol/L) and α‐tocopherol (99.96 mmol/L). The addition of CEx to the purified sunflower oil significantly improved its oxidative stability at the levels of 800 ppm and higher whereas the essential oil indicated no antioxidant activity at the levels experimented (200–2000 ppm). The CEx was considered to be a useful antioxidative compound in bulk oil and emulsion systems but the essential oil showed no antioxidant activities. The CEx in the bulk oil system had higher antioxidant activities than in the emulsion system. The CEx concentration of 2000 ppm showed the highest antioxidant activity and reduced the formation of hydroperoxides and secondary products more than the other antioxidative compounds applied in this study.  相似文献   

16.
This study investigates the oxidative stability of sunflower oil body suspensions (10 wt‐% lipid). Two washed suspensions of oil bodies were evaluated over 8 days at three temperatures (5, 25 and 45 °C) against three comparable sunflower oil emulsions stabilized with dodecyltrimethylammonium bromide (DTAB), polyoxyethylene‐sorbitan monolaurate (Tween 20) and sodium dodecyl sulfate (SDS) (17 mM). The development of oxidation was monitored by measuring the presence of lipid hydroperoxides and the formation of hexanal. Lipid hydroperoxide concentrations in the DTAB, SDS and Tween 20 emulsions were consistently higher than in the oil body suspensions; furthermore, hexanal formation was not detected in the oil body emulsions, whereas hexanal was present in the headspace of the formulated emulsions. The reasons for the extended resistance to oxidation of the oil body suspensions are hypothesized to be due to the presence of residual seed proteins in the continuous phase and the presence of a strongly stabilized lipid‐water interface.  相似文献   

17.
The formation of conjugated diene hydroperoxides and hexanal was compared to the development of aroma profiles during initial lipid oxidation of a vegetable oil and its 40% oil-in-water emulsion at 60°C. The aroma profiles of the oil and the emulsion with and without addition of ascorbic acid or ascorbyl palmitate were compared. The aroma compounds were isolated under a model mouth system and analyzed by gas chromatography/sniffing port analysis. Detectable odors were found and corresponded to 11 and 14 volatile compounds in the oil and the emulsion, respectively. The emulsion had higher lipid oxidation rates than the oil. Addition of ascorbic acid and ascorbyl palmitate had little influence on the aroma composition of the oil. In the emulsion, addition of these compounds resulted in diminished generation of odor active compounds. Results of measurements of conjugated diene hydroperoxides and headspace hexanal corresponded to that of the lipid oxidation rate in general, but predicted insufficiently the alterations in the aroma compositions by antioxidants.  相似文献   

18.
Phospholipids have been reported to inhibit lipid oxidation in bulk oils, but very little is known about their influence on oxidation in oil-in-water emulsions. In the present study, the impact of 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) on lipid oxidation was studied in 1% stripped soybean oil-in-water (O/W) emulsions as a function of DOPC concentration and pH (3 and 7). At pH 7.0, DOPC inhibited lipid oxidation in O/W emulsions, while DOPC was prooxidative at pH 3.0. DOPC did not affect emulsion droplet charge or size at either pH 3.0 or 7.0. The antioxidant activity at pH 7.0 was observed in a series of phospholipids (PL) that varied in fatty acid unsaturation level and chain length as well as type of phosphate head group. Overall, phosphatidylcholine with either oleic or palmitic acid were the most effective at inhibiting lipid hydroperoxide and hexanal formation of all of the PL tested. Antioxidant mechanism of PL could not be ascribed to their ability to decompose lipid hydroperoxides. It might be possible that, at pH 7.0, the PL antioxidant activity is related to their ability to form structures within the lipid phase of the emulsions droplets or to chelate metals.  相似文献   

19.
Effects of moisture and amphiphilic compounds, including oleic acid, lecithin, and monoacylglycerols (MAGs), on the oxidative stability are evaluated in microwave-treated corn oil. Moreover, the physical properties including critical micelle concentration (CMC) and moisture content are determined in oils treated by microwave irradiation. The CMC of lecithin and moisture content of oils decreases remarkably, whereas the temperature of the oil increases rapidly with microwave irradiation. The addition of lecithin results in increased moisture content significantly in the edible oils, whereas oleic acid and MAGs do not exhibit these effects. Primary oxidation products in all the oil samples increase, despite the type of amphiphilic compounds used. Corn oil containing oleic acid and samples with lecithin exhibits lower and higher p-anisidine values (p-AV), respectively. Remarkably high moisture content in corn oils containing lecithin may contribute to the formation of volatile compounds and high p-AV. Collectively, moisture and amphiphilic compounds affect the degree of lipid oxidation in microwave-irradiated bulk oils. Practical application: A microwave oven is an irreplaceable home appliance and is widely used in households nowadays. Effects of amphiphilic compounds and moisture on the oxidative stability are evaluated and it is found that the amphiphilic compounds in lipids affect heat transfer and oxidative stability of oils. The results of this study can provide fundamental insights into lipid oxidation in edible oils, and can provide a direction to the food industry with respect to the development of more efficient and safe methods for the preparation of microwavable foods.  相似文献   

20.
The relative ability of α‐, γ‐ and δ‐tocopherol (TOH) to influence the distribution of volatile secondary oxidation products in fish oil was studied, with particular emphasis on oxidation products expected to be important for adverse flavour formation. Purified fish oil samples with 100 ppm or 1000 ppm of the different tocopherols were analysed by dynamic headspace analysis of the volatiles formed after 2, 5 and 8 d of storage at 30 �C. The tocopherol type and concentration affected not only the overall formation of volatile secondary oxidation products, but also the composition of this group of oxidation products. Principal component analysis of the data obtained suggested that high tocopherol hydrogen‐donating power, i.e. a high tocopherol concentration or the use of αTOH as opposed to γTOH or δTOH, directs the formation of hydrocarbons, unsaturated carbonyl compounds of relatively high molecular weight, as well as the formation of cis, trans isomers of unsaturated aldehydes. Although an active inhibitor of overall volatile formation, αTOH at a high concentration thus appears to direct the formation of the more flavour‐potent aldehydes, such as those linking the carbonyl group with ethylenic conjugated unsaturation.  相似文献   

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