Identification of 2‐Pentyl Furan in Fats and Oils and Its Relationship to the Reversion Flavor of Soybean Oil

Abstract

SUMMARY— 2‐Pentyl furan is identified as a component of the volatile decomposition products of slightly autoxidized soybean and cottonseed oils and those of thermal oxidation of corn oil and hydrogenated cottonseed oil. The flavor threshold of this compound in oil at room temperature is 1 ppm. At concentrations of 1‐10 ppm, it imparts to the oil a characteristic beany odor and flavor reminiscent of those of a reverted soybean oil. Expert organoleptic panels consistently identified a deodorized cottonseed oil containing 5 ppm of 2.pentyl furan as a reverted soybean oil. It is proposed that this compound is formed by autoxidation of linoleic acid.

Formation of the beef flavour precursors and their correlation with chemical parameters during the controlled thermal oxidation of tallow

“…However, there were not apparent changes in the concentrations of volatile compounds with increasing time; this phenomenon might be due to the fact that single-or dicarbonyl-intermediates are extremely sensitive to further oxidation and decomposition. For instance, 2,4-decadienel was easily decomposed to 2-octenel, hexanal and acetaldehyde, through further oxidation (Krishnamurthy, Smouse, Mookherjee, Reddy, & Chang, 1967). The formation of some volatiles will be positive to the development of beef flavour, whilst for others it can be negative (Mottram, 1998).…”

Headspace Solid-phase Microextraction Analysis of the Volatile Flavour Compounds of Roasted Chickpea (Cicer arietinum L)

“…In general, all the main classes of compounds commonly listed as thermally generated flavours in pulses were identified in the roasted chickpea, with the most important from a flavour standpoint being 2-ethylfuran, 2-butylfuran, 2-pentylfuran, 3-hydroxybutan-2-one, Y-butyrolactone, 1-penten-2-ol, 1-octen-3-ol, 1, 2, 4-trimethylbenzene, and decane. 2-Pentylfuran was recently reported in tropical almond nuts [27] and previously identified as a compound of the volatile decomposition products of slightly autooxidised soybean [28]. Furans are products of carbohydrate thermal degradation and rearrangement [29].…”

Dynamics of Aroma-Active Volatiles in Miso Prepared from Lizardfish Meat and Soy during Fermentation: A Comparative Analysis

“…The Maillard reaction between reducing sugar and free amino acids might play an important role in the development of several aroma-active compounds, including aldehydes, ketones, phenolic compounds, pyrazines, and furan derivatives, in miso during the advanced stages of maturation as shown in Fig.5. Furans and their derivatives can be a result of dehydrated or fermented condensates of carbohydrates either from koji or the nucleotide derivative ribose by Amadori rearrangement pathways [30,31]; however, they can also be produced as a result of oxidation of fatty acids such as 2-pentylfuran [32,33]. The presence of several furans and their derivatives such as furfural, which could be a result of glucose pyrolysis and the Maillard reaction, was confirmed in the fermented soybean paste [34].…”