| Revision as of 02:32, 27 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 19:43, 2 January 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,523 edits rephrase |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 375959759 |
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| Watchedfields = changed |
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| verifiedrevid = 420915478 |
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|ImageFile=Goitrin.png |
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|ImageFile=Goitrin.png |
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|ImageSize=150 |
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|ImageSize=125 |
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| ImageFile1 = Goitrin 3D Balls.png |
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|IUPACName=5-ethenyl-1,3-oxazolidine-2-thione |
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| ImageSize1 = 250px |
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|OtherNames=Goitrin |
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| PIN = 5-Vinyl-1,3-oxazolidine-2-thione |
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| OtherNames = Goitrin |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=13190-34-6 |
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| CASNo=13190-34-6 |
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| PubChem=3034683 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C=CC1CNC(=S)O1 |
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| UNII = O8KVD7J2P5 |
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| PubChem = 3034683 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 2299106 |
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| ChEBI = 183226 |
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| SMILES = S=C1OC(\C=C)CN1 |
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| InChI = 1/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8) |
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| InChIKey = UZQVYLOFLQICCT-UHFFFAOYAN |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UZQVYLOFLQICCT-UHFFFAOYSA-N |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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'''Goitrin''' is a sulfur-containing ], a cyclic ], that reduces the production of ]s such as ].<ref>{{cite journal |author=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=15–9 |year=1986 |month=January |pmid=2419242 |doi=10.1177/096032718600500104}}</ref> It is found in cruciferous vegetables such as ], ]s and ],<ref>{{cite journal |author=Lüthy J, Carden B, Friederich U, Bachmann M |title=Goitrin--a nitrosatable constituent of plant foodstuffs |journal=Experientia |volume=40 |issue=5 |pages=452–3 |year=1984 |month=May |pmid=6723906 |doi=10.1007/BF01952381}}</ref> and is formed by the hydrolysis of a ]; 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 ] 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 |author=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 |year=1997 |month=February |pmid=9055870 |doi= 10.1016/S0009-2797(96)03745-3|url=http://linkinghub.elsevier.com/retrieve/pii/S0009-2797(96)03745-3}}</ref> |
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'''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> |
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==See also== |
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== See also == |
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==References== |
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== References == |
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{{reflist}} |
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{{reflist}} |
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{{Cruciferous Biochemistry}} |
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