Sinigrin

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Sinigrin
Names
IUPAC name
S-β-D-glucopyranosyl (Z)-O-(potassium sulfonato)but-3-enehydroximothioate[1]
Systematic IUPAC name
Potassium [(Z)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylbut-3-enylideneamino] sulfate
Other names
Allylglucosinolate; 2-Propenylglucosinolate
Identifiers
3D model (JSmol)
ChEBI
MeSH Sinigrin
UNII
  • C=CCC(=NOS(=O)(=O)[O-])SC1C(C(C(C(O1)CO)O)O)O.[K+]
  • C=CC/C(=N/OS(=O)(=O)[O-])/S[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O.[K+]
Properties
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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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 (Brassica nigra). 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.[2] 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 (or syn) isomer.[3]

Singrin is also known to be allelopathic.[4]

See also

References

  1. ^ Moss, G. P. (1996). "2-Carb-33. Glycosides and glycosyl compounds: Thioglycosides". Nomenclature of Carbohydrates. School of Biological and Chemical Sciences, Queen Mary University of London. Retrieved March 30, 2020 – via sbcs.qmul.ac.uk.
  2. ^ Richard, H. "Arômes alimentaires" (PDF) (in French). Archived from the original (PDF) on 2007-02-14.
  3. ^ Waser, Jürg; Watson, William H. (1963). "Crystal Structure of Sinigrin". Nature. 198 (4887): 1297–1298. doi:10.1038/1981297b0. ISSN 0028-0836.
  4. ^ Lankau R (2008). "A chemical trait creates a genetic trade-off between intra- and interspecific competitive ability". Eco. 89 (5): 1181–1187.
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