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Mandelonitrile beta-glucuronide, the compound patented as Laetrile, has been synthesized from rabbit liver uridine diphosphate-glucuronosyl transferase immobilized on beaded sepharose, has been analyzed by thin-layer chromatography, nuclear magnetic resonance, and gas chromatography-mass spectrometry, and has been tested for cytotoxicity and mutagenic activity with Salmonella typhimurium strains TA 98 and TA 100. Several commercial laetrile preparations contained no glucuronide; they contained amygdalin and neoamygdalin instead. Mandelonitrile, mandelonitrile glucuronide, and a mixture of amygdalin and neoamygdalin were each found to be mutagenic.

When acid chlorides were added to acetylene in the presence of aluminum chloride, irons-jS-chlorovinyl ketones were formed as shown by n.m.r. spectra. When these ketones were treated with trimethylamine in an inert solvent, a series of /3-acylvinyltrimethylammonium chlorides were formed which gave complete retention of the trans configuration. The ultraviolet and infrared spectra of these systems were examined and indicated the C-C-C=0 system to be most likely in the transoid conformation.