243:
168:
33:
355:
24:
430:
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).
431:
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
368:
599:
546:
Verhoeven DT, Verhagen H, Goldbohm RA, van den Brandt PA, van Poppel G (February 1997). "A review of mechanisms underlying anticarcinogenicity by brassica vegetables".
292:
447:
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.
476:
McMillan M, Spinks EA, Fenwick GR (January 1986). "Preliminary
Observations on the Effect of Dietary Brussels Sprouts on Thyroid Function".
820:
585:
257:
592:
375:
200:
221:
511:
Lüthy J, Carden B, Friederich U, Bachmann M (May 1984). "Goitrin — a nitrosatable constituent of plant foodstuffs".
746:
857:
758:
852:
105:
163:
809:
847:
752:
740:
734:
391:
728:
45:
238:
664:
620:
71:
815:
790:
563:
528:
493:
145:
555:
520:
485:
315:
209:
81:
704:
679:
674:
440:
415:
403:
242:
167:
125:
659:
651:
432:
346:
559:
841:
669:
423:
399:
156:
189:
825:
805:
717:
626:
419:
708:
641:
395:
489:
32:
684:
427:
334:
136:
456:
444:
407:
577:
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532:
497:
723:
694:
689:
631:
436:
636:
524:
411:
176:
769:
764:
345:
Except where otherwise noted, data are given for materials in their
23:
116:
104:
94:
581:
226:
363:
266:
InChI=1S/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)
276:
InChI=1/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)
778:
703:
650:
613:
410:. It is found in cruciferous vegetables such as
188:
80:
593:
8:
600:
586:
578:
241:
166:
144:
15:
208:
468:
422:, and is formed by the hydrolysis of a
297:
262:
237:
157:
269:Key: UZQVYLOFLQICCT-UHFFFAOYSA-N
124:
7:
279:Key: UZQVYLOFLQICCT-UHFFFAOYAN
179:
14:
402:. It reduces the production of
353:
50:5-Vinyl-1,3-oxazolidine-2-thione
31:
22:
349:(at 25 °C , 100 kPa).
394:classified as a derivative of
1:
560:10.1016/S0009-2797(96)03745-3
874:
747:Fluorescein isothiocyanate
490:10.1177/096032718600500104
339:129.18 g/mol
799:
343:
308:
288:
253:
64:
56:
44:
39:
30:
21:
821:Cruciferous Biochemistry
759:Phenethyl isothiocyanate
608:Cruciferous biochemistry
810:Cruciferous vegetables
779:Bioactive metabolites
753:Phenyl isothiocyanate
741:Benzyl isothiocyanate
735:Methyl isothiocyanate
392:organosulfur compound
729:Allyl isothiocyanate
548:Chem. Biol. Interact
46:Preferred IUPAC name
621:Phenylthiocarbamide
18:
614:Types of compounds
525:10.1007/BF01952381
376:Infobox references
16:
835:
834:
791:Indole-3-carbinol
384:Chemical compound
382:
381:
222:CompTox Dashboard
106:Interactive image
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602:
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588:
579:
572:
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416:brussels sprouts
404:thyroid hormones
398:and as a cyclic
366:
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316:Chemical formula
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128:
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84:
35:
26:
19:
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858:Vinyl compounds
838:
837:
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795:
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705:Isothiocyanates
699:
680:Glucotropaeolin
675:Gluconasturtiin
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609:
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441:thiocyanate ion
439:which liberate
385:
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372:
371: ?)
362:
358:
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328:
324:
318:
304:
301:
300:S=C1OC(\C=C)CN1
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5:
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853:Thiocarbamates
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660:Glucobrassicin
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652:Glucosinolates
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519:(5): 452–453.
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459:
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433:glucobrassicin
383:
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352:
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347:standard state
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239:DTXSID10274235
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2:
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827:
826:genera (list)
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670:Glucoraphanin
668:
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665:Glucocapparin
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554:(2): 79–129.
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424:glucosinolate
421:
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409:
405:
401:
400:thiocarbamate
397:
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158:ECHA InfoCard
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848:Oxazolidines
806:Brassicaceae
804:
785:
718:Sulforaphane
709:mustard oils
627:Thiocyanates
551:
547:
541:
516:
512:
506:
484:(1): 15–19.
481:
477:
471:
420:rapeseed oil
387:
386:
126:CHEBI:183226
65:Identifiers
57:Other names
642:Gibberellin
513:Experientia
478:Hum Toxicol
445:goitrogenic
396:oxazolidine
309:Properties
164:100.032.845
842:Categories
685:Progoitrin
463:References
428:progoitrin
335:Molar mass
329:NOS
210:O8KVD7J2P5
137:ChemSpider
93:3D model (
82:13190-34-6
72:CAS Number
623:(PTC/PTU)
457:Goitrogen
408:thyroxine
816:Brassica
724:Raphanin
695:Sinalbin
690:Sinigrin
632:Nitriles
451:See also
437:sinalbin
406:such as
17:Goitrin
786:Goitrin
761:(PEITC)
637:Indoles
568:9055870
533:6723906
498:2419242
443:) have
412:cabbage
388:Goitrin
369:what is
367: (
190:3034683
177:PubChem
146:2299106
59:Goitrin
770:Erucin
765:6-MITC
755:(PITC)
749:(FITC)
743:(BITC)
737:(MITC)
731:(AITC)
707:(ITC,
566:
531:
496:
390:is an
364:verify
361:
293:SMILES
40:Names
720:(SFN)
258:InChI
117:ChEBI
95:JSmol
564:PMID
529:PMID
494:PMID
435:and
418:and
201:UNII
556:doi
552:103
521:doi
486:doi
227:EPA
180:CID
844::
814::
562:.
550:.
527:.
517:40
515:.
492:.
480:.
426::
414:,
812:)
808:(
711:)
601:e
594:t
587:v
570:.
558::
535:.
523::
500:.
488::
482:5
359:N
327:7
325:H
323:5
321:C
229:)
225:(
97:)
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