Structure via PubChem · Public domain (PubChem)
(±)-goitrin
Sign in to saveAlso known as goitrin, 5-vinyl-1,3-oxazolidine-2-thione, 5-ethenyl-1,3-oxazolidine-2-thione
Goitrin is an organosulfur compound classified as a derivative of oxazolidine and as a cyclic thiocarbamate. It reduces the production of thyroid hormones such as thyroxine. It is found in cruciferous vegetables such as cabbage, brussels sprouts and rapeseed oil, and is formed by the hydrolysis of a glucosinolate: progoitrin or 2-hydroxy-3-butenyl glucosinolate. The unstable isothiocyanate (2-hydroxy-3-butenyl isothiocyanate) derived from the latter glucosinolate spontaneously cyclizes to goitrin, because the hydroxy group is situated in proximity to the isothiocyanate group (allowing a five-m
Chemical data
- Formula
- C5H7NOS
- Molecular weight
- 129.18 g/mol
- IUPAC name
- 5-ethenyl-1,3-oxazolidine-2-thione
- SMILES
- C=CC1CNC(=S)O1
- InChIKey
- UZQVYLOFLQICCT-UHFFFAOYSA-N
- XLogP
- 1
- Polar surface area
- 53.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 129.025
Show 4 more facts
- chemical formula
- C₅H₇NOS
- canonical SMILES
- C=CC1CNC(=S)O1
- has characteristic
- bitterness
- found in taxon
- Isatis tinctoria
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Goitrin is an organosulfur compound classified as a derivative of oxazolidine and as a cyclic thiocarbamate. It reduces the production of thyroid hormones such as thyroxine. It is found in cruciferous vegetables such as cabbage, brussels sprouts and rapeseed oil, and is formed by the hydrolysis of a glucosinolate: progoitrin or 2-hydroxy-3-butenyl glucosinolate. The unstable isothiocyanate (2-hydroxy-3-butenyl isothiocyanate) derived from the latter glucosinolate spontaneously cyclizes to goitrin, because the hydroxy group is situated in proximity to the isothiocyanate group (allowing a five-membered ring to be formed). Hence, the oxygen in the molecule stems from the hydroxy group of the original unstable isothiocyanate. Plants containing this specific glucosinolate (or glucosinolates such as glucobrassicin and sinalbin which liberate thiocyanate ion) have goitrogenic potential due to the goitrin and thiocyanate they contain. However, they do not seem to alter thyroid function in humans at realistic amounts in the diet.
== See also == Goitrogen
Excerpted from Wikipedia’s “(±)-goitrin” article, available under the CC BY-SA 4.0 licence.