Structure via PubChem · Public domain (PubChem)
glucobrassicin
Sign in to saveAlso known as 3-IMG, 3-Indolylmethylglucosinolate, 3-Indolylmethyl glucosinolate, indol-3-ylmethylglucosinolate, Indolylmethyl glucosinolate
Glucobrassicin is a type of glucosinolate that can be found in almost all cruciferous plants, such as cabbages, broccoli, mustards, and woad. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are indole-3-carbinol and thiocyanate ion (plus glucose, sulfate, and hydrogen ion), which are envisioned to result from
Chemical data
- Formula
- C16H20N2O9S2
- Molecular weight
- 448.5 g/mol
- IUPAC name
- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] 2-(1H-indol-3-yl)-N-sulfooxyethanimidothioate
- SMILES
- C1=CC=C2C(=C1)C(=CN2)CC(=NOS(=O)(=O)O)S[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
- InChIKey
- DNDNWOWHUWNBCK-JZYAIQKZSA-N
- XLogP
- -0.1
- Polar surface area
- 216 Ų
- H-bond donors
- 6
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 448.061
Show 4 more facts
- found in taxon
- Brassica cretica
- chemical formula
- C₁₆H₂₀N₂O₉S₂
- canonical SMILES
- C1=CC=C2C(=C1)C(=CN2)CC(=NOS(=O)(=O)O)SC3C(C(C(C(O3)CO)O)O)O
- isomeric SMILES
- C1=CC=C2C(=C1)C(=CN2)CC(=NOS(=O)(=O)O)S[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Biosynthesis from tryptophan
- See also
- References
- Further reading
Glucobrassicin is a type of glucosinolate that can be found in almost all cruciferous plants, such as cabbages, broccoli, mustards, and woad. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocyanate, indol-3-ylmethylisothiocyanate. However, this specific isothiocyanate is expected to be highly unstable, and has indeed never been detected. The observed hydrolysis products when isolated glucobrassicin is degraded by myrosinase are indole-3-carbinol and thiocyanate ion (plus glucose, sulfate, and hydrogen ion), which are envisioned to result from a rapid reaction of the unstable isothiocyanate with water. However, a large number of other reaction products are known, and indole-3-carbinol is not the dominant degradation product when glucosinolate degradation takes place in crushed plant tissue or in intact plants.
Glucobrassicin is also known to be a highly active egg-laying stimulant of cabbage white butterflies such as the small white (Pieris rapae) and the large white (Pieris brassicae).
Excerpted from Wikipedia’s “glucobrassicin” article, available under the CC BY-SA 4.0 licence.