Peracetic acid residues in orange juice can lead to a 5-vinylguaiacol-induced clove-like off-flavor via Baeyer-Villiger oxidation of hesperidin.

A balanced flavor is a major quality attribute of orange juice. Formation of 4-vinylguaiacol during storage can lead to an undesirable clove-like off-flavor. However, clove-like off-flavors were occasionally reported despite low 4-vinylguaiacol concentrations, suggesting an alternative molecular background. Application of gas chromatography-olfactometry and aroma extract dilution analysis to an orange juice with a pronounced clove-like off-flavor resulted in the identification of 5-vinylguaiacol. The compound showed the same odor as 4-vinylguaiacol, but was previously unknown in orange juice. In five of six commercial orange juices with clove-like off-flavors, 5-vinylguaiacol was even more odor-active than 4-vinylguaiacol. Spiking and model studies suggested that 5-vinylguaiacol is formed during pasteurization from the natural orange juice component hesperidin and residual peracetic acid used as cleaning agent by a Baeyer-Villiger oxidation. An activity-guided screening approach confirmed the role of hesperidin as 5-vinylguaiacol precursor. In conclusion, peracetic acid should no longer be used in orange juice processing plants.