Sinigrin

Sinigrin
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
PubChem	23682211
MeSH	Sinigrin
SMILES	C=CCC(=NOS(=O)(=O)[O-])SC1C(C(C(C(O1)CO)O)O)O.[K+]
Properties
Molecular formula	C10H16KNO9S2
Molar mass	397.46 g/mol
Exact mass	396.990354
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sinigrin is a glucosinolate which belongs to the family of glucosides found in some plants of the Brassica 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-propenylglucosinlate.

Research carried out at Norwich Research Park (NRP), in the east of England, has suggested that sinigrin may destroy pre-cancerous cells (apoptosis).^[1] It has been suggested, therefore, that sinigrin may prevent cancer of the colon if foods containing it are eaten regularly.

See also

• Allyl isothiocyanate
• Gluconasturtiin
• List of phytochemicals in food

References

External links

1. ^ "Institute of Food Research". Why your best friend could be a Brassica. http://www.ifr.ac.uk/public/foodinfosheets/brassicas.html. Retrieved 2006-01-21. 

• Norwich Research Park website

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