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 Å²
H-bond donors: 5
H-bond acceptors: 11
Formal charge: 0

via PubChem

Wikidata facts

Mass: 359.034473124

Show 4 more facts

chemical formula: C₁₀H₁₇NO₉S₂
isomeric 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
canonical SMILES: O=S(=O)(O)ON=C(SC1OC(CO)C(O)C(O)C1O)CC=C
Commons category: Sinigrin

Sources (2)

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Article

8 sections

Contents

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= }}