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 (Brassica nigra).[lower-alpha 1] 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.

Sinigrin
Names
IUPAC name
S-β-D-glucopyranosyl (Z)-O-(potassium sulfonato)but-3-enehydroximothioate[1]
Preferred IUPAC name
Potassium (Z)-N-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)hydroxylamine-O-sulfonate
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]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)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).
N verify (what is YN ?)
Infobox references

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. Named after the black mustard, under the synonym Sinapis nigra.
  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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