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'''Goitrin''' is a sulfur-containing ], Goitrin.pnga cyclic ], that reduces the production of ]s such as ].<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 ], ]s and ],<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 ]: ] 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 ] and ] which liberate ]) have ]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> '''Goitrin''' is an ] classified as a derivative of ] and as a cyclic ]. It reduces the production of ]s such as ].<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 ], ]s and ],<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 ]: ] 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 ] and ] which liberate ]) have ]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 == == See also ==

Latest revision as of 19:43, 2 January 2024

Goitrin
Names
Preferred IUPAC name 5-Vinyl-1,3-oxazolidine-2-thione
Other names Goitrin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.032.845 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
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 , 100 kPa). ☒verify (what is  ?) 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. 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

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.
Cruciferous biochemistry
Types of compounds
Glucosinolates
Isothiocyanates (ITC, mustard oils)
Bioactive metabolites
Categories: