Mandelonitrile benzoate

Mandelonitrile benzoate is a defensive secretion of millipedes that releases other chemicals during the cyanidation process in addition to hydrocyanic acid (HCN) and benzaldehyde. Several families of millipedes, including Polydesmidae, Paradoxosomatidae, and Euryuridae, have been shown to secrete phenols and guaiaeol, with one Paradoxosomatid also producing ethylbenzoic acid and benzoic acid. In addition, members of the Xystodesmidae family commonly produce three compounds: benzoic acid, mandelonitrile benzoate, and benzoyl cyanide. Benzoyl cyanide has not been previously discovered as a natural product. These additional natural products are discussed as defensive antipredator and antibiotic agents. Benzoyl cyanide appears to have anesthetic properties for some predators. The study provides a preliminary chemotaxonomic basis for distinguishing various taxonomic groups of millipedes.