sinigrin
Also known as 2-Propenyl glucosinolate, sinigrin (sulfonic acid)
Sinigrin or allyl glucosinolate 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. Seeds of white mustard, Sinapis alba, give a less pungent mustard because this species contains a different glucosinolate, sinalbin.
Chemical data
- Formula
- C10H17NO9S2
- Molecular weight
- 359.4 g/mol
- IUPAC name
- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1Z)-N-sulfooxybut-3-enimidothioate
- SMILES
- 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
- InChIKey
- PHZOWSSBXJXFOR-GLVDENFASA-N
- XLogP
- -1.1
- Polar surface area
- 200 Ų
- H-bond donors
- 5
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Article
8 sectionsContents
- Occurrence
- Structure
- Synthesis
- Biosynthesis
- Laboratory synthesis
- Function
- See also
- References
{{chembox | ImageFile = Sinigrin structure.svg | IUPACName = (Z)-N-[1-(β-D-glucopyranosylsulfanyl)but-3-en-1-ylidene]hydroxylamine-O-sulfonic acid | SystematicName = (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-sulfonic acid | OtherNames = Allyl glucosinolate; 2-Propenyl glucosinolate; (1Z)-N-(Sulfooxy)but-3-enimidoyl 1-thio-β-D-glucopyranoside |Section1= |Section2= |Section3= }}
Sinigrin or allyl glucosinolate 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. Seeds of white mustard, Sinapis alba, give a less pungent mustard because this species contains a different glucosinolate, sinalbin.