Amygdalin Chemistry

Amygdalin is a cyanogenic glycoside acquired from the ambrosial amino acid phenylalanine. Amygdalin and prunasin are actual accepted a part of plants of the Rosaceae family, decidedly the brand Prunus, Poaceae (grasses), Fabaceae (legumes), and in added aliment plants, including linseed and manioc. Within these plants, amygdalin and the enzymes all-important to hydrolyze them are stored in extracted locations so that they will mix in acknowledgment to tissue damage. This provides a accustomed aegis system.

Amygdalin is independent in rock bake-apple kernels, such as apricot (8%), acceptable (6%), absinthian almond (5%), and asset (2.5%); amygdalin is aswell begin in the seeds of the apple. The stones are taken out of the bake-apple and absurd to access the kernels, which are broiled in the sun or in ovens. The kernels are above in ethanol; on dehydration of the band-aid and the accession of diethyl ether, amygdalin is precipitated as white minute crystals. Accustomed amygdalin has the (R)-configuration at the chiral phenyl center. Under balmy basal conditions, this stereogenic centermost isomerizes; the (S)-epimer is alleged neoamygdalin. Although the actinic adaptation of amygdalin is the (R)-epimer, the stereogenic centermost absorbed to the nitrile and phenyl groups calmly epimerizes if the architect does not abundance the admixture correctly.

Amygdalin is anatomize by abdominal β-glucosidase (emulsin) and amygdalase to accord gentiobiose and L-mandelonitrile. Gentiobiose is added anatomize to accord glucose, admitting the cyanohydrin of mandelonitrile decomposes to accord benzaldehyde and hydrogen cyanide. Hydrogen cyanide in acceptable quantities (allowable circadian intake: ~0.6 mg) causes cyanide contagion (fatal articulate dose: 0.6–1.5 mg/kg). Apricot pits accommodate 89–2,170 mg/kg hydrogen cyanide (wet weight).