Crotonic acid

Crotonic acid, or trans-2-butenoic acid, is a short-chain unsaturated carboxylic acid, described by the formula CH3CH=CHCO2H. Crotonic acid is so named because it was erroneously thought to be a saponification product of croton oil. It crystallizes as needles from hot water.

Isocrotonic acid (or quartenylic acid) is the cis analogue of crotonic acid. It is an oil, possessing a smell similar to that of brown sugar. It boils at 171.9°C, concomitant with conversion into crotonic acid. Isomerizaton is complete when the cis acid is heated to 170-180°C in a sealed tube.

Racemic threonine can be prepared from crotonic acid by alpha-functionalization using mercury(II) acetate.