“…The potential prevention mechanism involves the capture of the electrophilic carbon of the carbonyl group by the aromatic rings of phenols or phenolic acid through an ortho-or para-directed electrophilic aromatic substitution (r20). 77 Although products of this mechanism, such as dihydroxycinnamic-acid-2-glyoxal and benzenetriol-2-butanedione, were not detected in biocrudes due to their non-volatile nature, several meta-hydroxyl-containing phenols (e.g., 3,5-dihydroxycinnamic acid, 1,3,5-benzenetriol, 5-tert-butylpyrogallol, and 3,5-dihydroxybenzoic acid) were detected with an increased extent in the HTL-AP of lignin-rich feedstock (see Table S8, ESI †). Since a meta conguration of the electron donor (-OH group) at carbons number 3 or 5 in the phenol ring has a higher reactivity toward carbonyl-capturing at the ortho or para position, their increased detection suggests that the capturing reaction (r20) is likely to occurr.…”