Goitrin

Goitrin

File:Goitrin.png
File:Goitrin 3D Balls.png
Names
IUPAC name 5-Vinyl-1,3-oxazolidine-2-thione
Preferred IUPAC name 5-Ethenyl-1,3-oxazolidine-2-thione
Other names Goitrin
Identifiers
CAS Number	13190-34-6 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:183226
ChemSpider	2299106 ☒N
ECHA InfoCard
E number
PubChem CID	3034683
UNII	O8KVD7J2P5 checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8) ☒N Key: UZQVYLOFLQICCT-UHFFFAOYSA-N ☒N InChI=1/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8) Key: UZQVYLOFLQICCT-UHFFFAOYAN
SMILES S=C1OC(\C=C)CN1
Properties
Chemical formula	C5H7NOS
Molar mass	129.18 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 checkY☒N ?) Infobox 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