# Goitrin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Goitrin
> Markdown URL: https://mediated.wiki/source/Goitrin.md
> Source: https://en.wikipedia.org/wiki/Goitrin
> Source revision: 1279731796
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 420915478
|ImageFile=Goitrin.png
|ImageSize=125
| ImageFile1 = Goitrin 3D Balls.png
| ImageSize1 = 250px
| PIN = 5-Ethenyl-1,3-oxazolidine-2-thione
| IUPACName = 5-Vinyl-1,3-oxazolidine-2-thione
| OtherNames = Goitrin
|Section1={{Chembox Identifiers
|  CASNo_Ref = {{cascite|correct|??}}
| CASNo=13190-34-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O8KVD7J2P5
|  PubChem = 3034683
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2299106
| ChEBI = 183226
|  SMILES = S=C1OC(\C=C)CN1
|  InChI = 1/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)
|  InChIKey = UZQVYLOFLQICCT-UHFFFAOYAN
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UZQVYLOFLQICCT-UHFFFAOYSA-N
  }}
|Section2={{Chembox Properties
|  Formula=C<sub>5</sub>H<sub>7</sub>NOS
|  MolarMass=129.18 g/mol
  }}
}}

'''Goitrin''' is an [organosulfur compound](/source/organosulfur_compound) classified as a derivative of [oxazolidine](/source/oxazolidine) and as a cyclic [thiocarbamate](/source/thiocarbamate).  It reduces the production of [thyroid hormone](/source/thyroid_hormone)s such as [thyroxine](/source/thyroxine).<ref>{{cite journal |vauthors=McMillan M, Spinks EA, Fenwick GR |title=Preliminary Observations on the Effect of Dietary Brussels Sprouts on Thyroid Function |journal=Hum Toxicol |volume=5 |issue=1 |pages=15–19 |date=January 1986 |pmid=2419242 |doi=10.1177/096032718600500104}}</ref> It is found in cruciferous vegetables such as [cabbage](/source/cabbage), [brussels sprout](/source/brussels_sprout)s and [rapeseed oil](/source/rapeseed_oil),<ref>{{cite journal |vauthors=Lüthy J, Carden B, Friederich U, Bachmann M |title=Goitrin — a nitrosatable constituent of plant foodstuffs |journal=Experientia |volume=40 |issue=5 |pages=452–453 |date=May 1984 |pmid=6723906 |doi=10.1007/BF01952381}}</ref> and is formed by the hydrolysis of a [glucosinolate](/source/glucosinolate): [progoitrin](/source/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](/source/glucobrassicin) and [sinalbin](/source/sinalbin) which liberate [thiocyanate ion](/source/thiocyanate_ion)) have [goitrogen](/source/goitrogen)ic 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.<ref name=Verhoeven>{{cite journal |vauthors=Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G |title=A review of mechanisms underlying anticarcinogenicity by brassica vegetables |journal=Chem. Biol. Interact. |volume=103 |issue=2 |pages=79–129 |date=February 1997 |pmid=9055870 |doi= 10.1016/S0009-2797(96)03745-3}}</ref>

== See also ==
*[Goitrogen](/source/Goitrogen)

== References ==
{{reflist}}

{{Cruciferous Biochemistry}}
Category:Oxazolidines
Category:Thiocarbamates
Category:Vinyl compounds

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Adapted from the Wikipedia article [Goitrin](https://en.wikipedia.org/wiki/Goitrin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Goitrin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.