Sinigrin

Sinigrin

Names
IUPAC name potassium [(E)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylbut-3-enylideneamino] sulfate
Identifiers
CAS Number	3952-98-5
ChEBI	CHEBI:79317
Jmol 3D model	Interactive image
MeSH	Sinigrin
PubChem	23682211
SMILES C=CCC(=NOS(=O)(=O)[O-])SC1C(C(C(C(O1)CO)O)O)O.[K+]
Properties
Chemical formula	C10H16KNO9S2
Molar mass	397.46 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sinigrin is a glucosinolate that belongs to the family of glucosides found in some plants of the Brassicaceae family such as Brussels sprouts, broccoli, and the seeds of black mustard (Brassica nigra) to name but a few. Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil (allyl isothiocyanate), which is responsible for the pungent taste of mustard and horseradish.^[1] 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.

Singrin is also known to be allelopathic (Lankau 2008).

See also

• Allyl isothiocyanate
• Gluconasturtiin
• List of phytochemicals in food

References

1. Richard, H. "Arômes alimentaires" (PDF) (in French).

Lankau R. 2008. A chemical trait creates a genetic trade-off between intra- and interspecific competitive ability. Eco. 89(5): 1181-1187.

External links

• "Institute of Food Research". Why your best friend could be a Brassica. Retrieved 2006-01-21.
• Norwich Research Park website