Goitrin

Goitrin
Names
	IUPAC name 5-ethenyl-1,3-oxazolidine-2-thione
	Other names Goitrin
Identifiers
CAS Number	13190-34-6;
3D model (JSmol)	Interactive image;
ChemSpider	2299106;
ECHA InfoCard	100.032.845
PubChem CID	3034683;
CompTox Dashboard (EPA)	DTXSID10274235 ;
	InChI InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8) Key: UZQVYLOFLQICCT-UHFFFAOYSA-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). verify (what is ?) Infobox references

Goitrin is a sulfur-containing oxazolidine, a cyclic thiocarbamate, that reduces the production of thyroid hormones such as thyroxine.^[1] It is found in cruciferous vegetables such as cabbage, brussels sprouts and oil-seed rape,^[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]

References

^ McMillan M, Spinks EA, Fenwick GR (1986). "Preliminary observations on the effect of dietary brussels sprouts on thyroid function". Hum Toxicol. 5 (1): 15–9. doi:10.1177/096032718600500104. PMID 2419242. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Lüthy J, Carden B, Friederich U, Bachmann M (1984). "Goitrin--a nitrosatable constituent of plant foodstuffs". Experientia. 40 (5): 452–3. doi:10.1007/BF01952381. PMID 6723906. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[1] McMillan M, Spinks EA, Fenwick GR (1986). "Preliminary observations on the effect of dietary brussels sprouts on thyroid function". Hum Toxicol. 5 (1): 15–9. doi:10.1177/096032718600500104. PMID 2419242. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[2] Lüthy J, Carden B, Friederich U, Bachmann M (1984). "Goitrin--a nitrosatable constituent of plant foodstuffs". Experientia. 40 (5): 452–3. doi:10.1007/BF01952381. PMID 6723906. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[Verhoeven-3] Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[1]

[2]

[3]

See also

References