DL-GOITRIN

Public-database records for DL-GOITRIN (CAS 500-12-9), reproduced here for independent cross-checking.

Physical description and handling notes

• Solid; [Merck Index]
• Large prisms from ether
• Stable in alkali, but not in acid.
• Specific optical rotation at 31 °C for D (sodium) line = -70.5 deg (c=2 in methanol).

Reported physical properties

How this substance is indexed

Documented uses

• A thyroid toxin found in the seeds of various Brassica and Cruciferae species; [Merck Index]
• An antithyroid cmpd isolated from seeds of different species of Brassica, Cruciferae: Astwood et al., J. Biol. Chem. 181,121 (1949); Greer, J. Am. Chem. Soc., 78, 1260 (1956)
• Agents that are used to treat hyperthyroidism by reducing the excessive production of thyroid hormones.
• A total of six cows, divided into 3 groups, were fed various amounts of rape cake containing 6 g of goitrin/kg over a period of 7 days. The cows were milked twice a day ... . When rape cake was fed at 0.39, 1.9 and 3.9% resp. of the total feed this resulted in medium goitrin values of 37, 163 and 707 ug/l milk. These values correspond to a transfer of about 0.1% of the original progoitrin content in the feed. 12 h after the last rape feeding the amount of goitrin in the milk was below the detection limit of 7 ppb.
• A wide variety of chemicals, drugs, and other xenobiotics affect the second step in thyroid hormone biosynthesis. The stepwise binding of iodide to the tyrosyl residues in thyroglobulin requires oxidation of inorganic iodide (I2) to molecular (reactive) iodine (I2) by the thyroid peroxidase present in the luminal aspect (microvillar membranes) of follicular cells and adjacent colloid. Classes of chemicals that inhibit the organification of thyroglobulin include ... the thionamides (such as ... goitrin)... .

Names this substance appears under

Goitrin; 500-12-9; (S)-5-Vinyloxazolidine-2-thione; Goitrin, L-; Goitrin, l; 5-vinyl-2-thiooxazolidone; (5S)-5-ethenyl-1,3-oxazolidine-2-thione; (S)-5-Ethenyl-2-oxazolidinethione; (-)-5-Vinyl-2-oxazolidinethione; 7Q618OJ6K9; (5S)-5-Ethenyl-2-oxazolidinethione; 2-Oxazolidinethione, 5-ethenyl-, (S)-; L-5-Vinyl-2-thiooxazolidone; L-5-Vinyl-2-oxazolidinethione; DTXSID501032368; 2-Oxazolidinethione, 5-ethenyl-,(s)-

Computed molecular descriptors

Database abstract

DL-GOITRIN · CAS 500-12-9 · C5H7NOS. UNII 7Q618OJ6K9. 熔点: 50 °C; Dissociation Constants: pKa = 10.5.

Source: PubChem / Wikidata; the batch COA governs where values differ.