Goitrin

Goitrin
Names
Preferred IUPAC name
5-Vinyl-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 100.032.845 Edit this at Wikidata
PubChem CID
  • 3034683
UNII
  • O8KVD7J2P5 checkY
CompTox Dashboard (EPA)
  • DTXSID10274235 Edit this at Wikidata
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
  • 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).
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Infobox references
Chemical compound

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.[1] It is found in cruciferous vegetables such as cabbage, brussels sprouts and rapeseed oil,[2] 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.[3]

See also

References

  1. ^ McMillan M, Spinks EA, Fenwick GR (January 1986). "Preliminary Observations on the Effect of Dietary Brussels Sprouts on Thyroid Function". Hum Toxicol. 5 (1): 15–19. doi:10.1177/096032718600500104. PMID 2419242.
  2. ^ Lüthy J, Carden B, Friederich U, Bachmann M (May 1984). "Goitrin — a nitrosatable constituent of plant foodstuffs". Experientia. 40 (5): 452–453. doi:10.1007/BF01952381. PMID 6723906.
  3. ^ Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G (February 1997). "A review of mechanisms underlying anticarcinogenicity by brassica vegetables". Chem. Biol. Interact. 103 (2): 79–129. doi:10.1016/S0009-2797(96)03745-3. PMID 9055870.