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
Jmol-3D images	Image 1
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
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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-propenylglucosinlate.

Research carried out at Norwich Research Park, in the east of England, has suggested sinigrin may destroy precancerous cells (apoptosis).^[1] Sinigrin has been suggested as a colon cancer prevention if foods containing it are eaten regularly.

See also

• Allyl isothiocyanate
• Gluconasturtiin
• List of phytochemicals in food

References

1. ^ (French) RICHARD H. Arômes alimentaires PDF Document

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