alphacyano4hydroxycinnamic

Alpha-cyano-4-hydroxycinnamic acid is a synthetic derivative of 4-hydroxycinnamic acid in which a cyano group is introduced at the alpha position of the propenoic side chain. In structural terms, the molecule combines a para-hydroxy substituent on the phenyl ring with a nitrile-bearing, conjugated side chain characteristic of cinnamic acids. It is categorized as a nitrile-containing aryl-alkene carboxylic acid.

The compound is not widely reported as a natural product and is mainly described in the context of synthetic organic chemistry as a potential building block for further transformations. Public literature on detailed preparation methods is limited, and reported routes, when present, generally involve methods to introduce a cyano substituent at the alpha carbon of cinnamic-type scaffolds or to convert suitable precursors through cyanation steps under specialized conditions. Its reactivity is influenced by the electron-withdrawing cyano group and the conjugated system, which can participate in diverse transformations such as additions, condensations, or hydrolysis of the nitrile under appropriate catalysis.

In terms of properties and applications, alpha-cyano-4-hydroxycinnamic acid is expected to be a polar, relatively reactive intermediate with potential uses as a synthetic building block in pharmaceutical, agrochemical, or dye chemistry. Safety considerations for nitrile-containing aromatics apply, including precautions for handling and disposal in accord with established chemical hygiene practices.

See also: 4-hydroxycinnamic acid (p-coumaric acid), cinnamic acid, nitrile-containing aryl-alkenes.