Furanone Extreme

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In 1991, Thomas reported88a that the reaction between vinylketene complexes (221) and several phosphonoacetate anions generated vinylallene complexes (246), in some cases with extremely high stereoselectivity.88,89 This Wadsworth-Emmons type reaction occurs via attack by the phosphonoacetate carbanion at the ketene carbonyl carbon, and product ratios clearly depend on the steric bulk of the R and R substituents. The relative stereochemistry of the major isomers of 246 were determined by X-ray analysis. Upon oxidation of the vinylallene complexes with iron(III) chloride, a range of substituted furanones were isolated.8813,89... 

A number of solvents have been used to extract volatiles for aroma analysis but the optimum choice depends on a compromise. Table Gl.1.2 lists the most common solvents used to extract odorants from foods. Although pentane and ethyl acetate are flammable, they have a very low toxicity, represent extremes in polarity, and a sequential extraction using these two solvents will remove most of the volatile odorants from aqueous samples (see Basic Protocol 2) however, if the desire is to do a simpler one-step extraction, then a solvent should be chosen with a polarity that will extract the volatiles of interest. For example, maltol is not extracted well with pentane, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone, the smell of strawberry, is almost insoluble therefore, the choice of the optimum solvent depends on the analyte and may require some testing to find. 

As for coriander, in the unripe fruits and the vegetative parts of the plant, aliphatic aldehydes predominate in the steam-volatile oil and are responsible for the peculiar aroma. On ripening, the fruits acquire a more pleasant and sweet odour and the major constituent of the volatile oil is the monoterpene alcohol, linalool. Sotolon (also known as sotolone, caramel furanone, sugar lactone and fenugreek lactone) is a lactone and an extremely powerful aroma compound and is the major aroma and flavour component of fenugreek seeds (Mazza et al., 2002). 

We note some references giving useful long range couplings.338,363,364-369-405a.406 LIS techniques used with furan compounds,407 of course, but are of no immediate consequence because the furan oxygen atom is an extremely poor site for complexation 408 An interesting comparison between the proton spectra of 3-furanones and those of parallel dihydropyrones has been made.125... 

Several chlorinated 5-hydroxy-4-methyl-2(5i/)-furanones 73 (HMFs) and mucochloric acid 3,4-dichloro-5-hydroxy-2(5i/)-furanone 74 (MCA) have been identified as byproducts of the chlorine disinfection of drinking water and of chlorine bleaching of pulp [93EST(27)1811]. These compounds have been shown to generate mutagenicity in the Salmonella typhinurium assay 3-chloro-4-(dichloromethyl)-5-hydroxy-2(5i/)-furanone 75 (MX) proved to be an extremely potent bacterial mutagen [90MR(240)109]. 

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