Progoitrin

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Progoitrin
Progoitrin.svg
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
Properties
C11H19NO10S2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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, brussels sprouts, kale, peanuts, mustard, rutabaga, kohlrabi, spinach, cauliflower, horseradish, and rapeseed oil. [1]

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Goitrin

Goitrin is a sulfur-containing oxazolidine, a cyclic thiocarbamate, that 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 derived from the latter glucosinolate spontaneously cyclizes to goitrin, because the hydroxy group is situated in proximity to the isothiocyanate group. Hence, the oxygen in the molecule stems from the hydroxy group of the original unstable isothiocyanate. Plants containing this specific glucosinolate 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.

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References

  1. Comprehensive Pharmacy Review, Leon Shargel, 6th edition, p1191.

Bibliography