Sinigrin


Sinigrin is a glucosinolate that belongs to the family of glucosides found in some plants of the family Brassicaceae such as Brussels sprouts, broccoli, and the seeds of black mustard. Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil, which is responsible for the pungent taste of mustard and horseradish. Seeds of white mustard, Sinapis alba, will give a much less pungent mustard because this species contains a different glucosinolate, sinalbin.
The chemical name of sinigrin is allylglucosinolate or 2-propenylglucosinolate.
Sinigrin stereochemical configuration on the C=N double bond was for a time uncertain, and has been resolved by X-ray crystallography in 1963 to be the Z isomer.
Singrin is also known to be allelopathic.