Vanillyl

Vanillyl is a chemical substituent derived from vanillin, used as a descriptive name for a specific arylmethyl motif. The vanillyl group corresponds to the 4-hydroxy-3-methoxybenzyl moiety, attached to the rest of a molecule through a benzylic carbon (CH2–). This means the benzene ring bears a hydroxyl group at the para position and a methoxy group at the meta position relative to the benzylic linkage.

In practical terms, the vanillyl group appears in a range of natural products and flavor/aroma compounds. It is most commonly encountered in vanillyl alcohol (the benzylic alcohol derived from vanillin) and in various vanillyl esters and amides. The group is also a characteristic component of capsaicin and related capsaicinoids, where the vanillyl moiety is linked via an amide to a long hydrophobic tail.

Synthesis and occurrence: The vanillyl motif is typically introduced or derived from vanillin in laboratory settings, for example by reducing the aldehyde of vanillin to give vanillyl alcohol or by forming esters and amides from the vanillyl alcohol or vanillin. In nature, compounds bearing the vanillyl group arise in plant secondary metabolism and in flavor chemistry, contributing phenolic character and distinctive aroma.

See also: vanillin; vanillyl alcohol; capsaicin; vanilla flavor compounds.