DL-GOITRIN

Description

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

Identification

Computed Descriptors

Physical & Chemical Properties

Physical description & 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).

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)... .

Synonyms

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)-

Frequently Asked Questions

What are the CAS number and molecular formula of DL-GOITRIN?

CAS 500-12-9; molecular formula C5H7NOS; molecular weight — g/mol.

What other names is DL-GOITRIN known by?

Goitrin, 500-12-9, (S)-5-Vinyloxazolidine-2-thione, Goitrin, L-, Goitrin, l, 5-vinyl-2-thiooxazolidone.

What are the key physical properties of DL-GOITRIN?

Melting Point: 50 °C; Dissociation Constants: pKa = 10.5.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.