Goitrin is a sulfur-containing

oxazolidine An oxazolidine is a five-membered ring compound consisting of three carbon atoms, a nitrogen atom and an oxygen atom. The O atom and NH group are the 1 and 3 positions, respectively. In oxazolidine derivatives, there is always a carbon atom bet ...

, a cyclic

thiocarbamate In organic chemistry, thiocarbamates (thiourethanes) are a family of organosulfur compounds. As the prefix ''thio-'' suggests, they are sulfur analogues of carbamates. There are two isomeric forms of thiocarbamates: ''O''-thiocarbamates, (este ...

, that reduces the production of

thyroid hormone File:Thyroid_system.svg, upright=1.5, The thyroid system of the thyroid hormones T3 and T4 rect 376 268 820 433 Thyroid-stimulating hormone rect 411 200 849 266 Thyrotropin-releasing hormone rect 297 168 502 200 Hypothalamus rect 66 216 38 ...

s such as

thyroxine File:Thyroid_system.svg, upright=1.5, The thyroid system of the thyroid hormones T3 and T4 rect 376 268 820 433 Thyroid-stimulating hormone rect 411 200 849 266 Thyrotropin-releasing hormone rect 297 168 502 200 Hypothalamus rect 66 216 38 ...

. It is found in cruciferous vegetables such as cabbage,

brussels sprout The Brussels sprout is a member of the Gemmifera cultivar group of cabbages (''Brassica oleracea''), grown for its edible buds. The leaf vegetables are typically 1.5–4.0 cm (0.6–1.6 in) in diameter and resemble miniature cabbage ...

s and

rapeseed oil Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historically, ...

, and is formed by the hydrolysis of a

glucosinolate Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damage ...

progoitrin Progoitrin is a biochemical from the glucosinolate family that is found in some food, which is inactive but after ingestion is converted to goitrin. Goitrin decreases the thyroid hormone production. Progoitrin has been isolated in cabbage, bruss ...

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 Glucobrassicin is a type of glucosinolate that can be found in almost all cruciferous plants, such as cabbages, broccoli, mustards, and woad. As for other glucosinolates, degradation by the enzyme myrosinase is expected to produce an isothiocy ...

and

sinalbin Sinalbin is a glucosinolate found in the seeds of white mustard, '' Sinapis alba'', and in many wild plant species. In contrast to mustard from black mustard (''Brassica nigra ''Brassica nigra'', or black mustard, is an annual plant cultivated ...

which liberate

thiocyanate ion Thiocyanate (also known as rhodanide) is the anion . It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Mercury(II) thiocyanate was formerly used in pyrot ...

) have

goitrogen Goitrogens are substances that disrupt the production of thyroid hormones. This triggers the pituitary to release thyroid-stimulating hormone (TSH), which then promotes the growth of thyroid tissue, eventually leading to goiter. Goitrogenic dru ...

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.

References

{{Cruciferous Biochemistry Oxazolidines Thiocarbamates Vinyl compounds

See also

References