13190-34-6

Basic information

• Product Name: DL-GOITRIN
• Synonyms: DL-GOITRIN;(+/-)-GOITRIN;5-Vinyl-1,3-oxazolidine-2-thione;5-vinyloxazolidine-2-thione;5-Vinyloxazolidone-2-thione;DL-Goitrin, 98+%;5-Ethenyl-2-oxazolidinethione;2-Oxazolidinethione, 5-ethenyl-
• CAS NO: 13190-34-6
• Molecular Formula: C₅H₇NOS
• Molecular Weight: 129.18
• EINECS: 236-145-3
• Mol File: 13190-34-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 64-65°C
• Boiling Point: 150.6°Cat760mmHg
• Flash Point: 44.9°C
• Appearance: /
• Density: 1.19g/cm³
• PKA: 13.34±0.40(Predicted)
• Merck: 14,4513
• BRN: 80669
• CAS DataBase Reference: DL-GOITRIN(CAS DataBase Reference)
• NIST Chemistry Reference: DL-GOITRIN(13190-34-6)
• EPA Substance Registry System: DL-GOITRIN(13190-34-6)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 13190-34-6(Hazardous Substances Data)

Usage

Description

DL-GOITRIN is a sulfur-containing oxazolidine, a cyclic thiocarbamate, which is known for its ability to reduce the production of thyroid hormones such as thyroxine.

Uses

Used in Pharmaceutical Industry:
DL-GOITRIN is used as a pharmaceutical compound for its ability to inhibit the production of thyroid hormones, particularly thyroxine. This property makes it a potential candidate for the treatment of hyperthyroidism and other thyroid-related conditions.
Used in Research Applications:
In the field of research, DL-GOITRIN is utilized as a tool to study the effects of thyroid hormone production inhibition on various biological processes and to understand the underlying mechanisms of thyroid hormone regulation.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 4792, 1950 DOI: 10.1021/ja01166a126Journal of Heterocyclic Chemistry, 27, p. 811, 1990 DOI: 10.1002/jhet.5570270361

InChI:InChI=1/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)

Upstream product

• 75-15-0 carbon disulfide 
• 13269-47-1 4-amino-3-hydroxybut-1-ene 
• 63-68-3 L-methionine 

Downstream Products

• 1072-93-1 (5R)-5-vinyl-1,3-oxazolidine-2-thione 
• 500-12-9 goitrin 

Relevant articles and documents

Synthetic method of antiviral drug (R,S)-goitrine

The invention discloses a synthetic method of an antiviral drug (R,S)-goitrine. The synthesis method comprise the following steps: dissolving nitromethane in a proper solvent, adding acrolein, carrying out stirring at a set temperature for a period of time to obtain a solution A, dissolving triethylamine into residual nitromethane to obtain a solution B, dropwise adding the solution B into the solution A for a reaction, carrying out rotary evaporation to remove the solvent and unreacted nitromethane after the reaction is completed, and carrying out column chromatography separation on the obtained mixture to obtain 1-nitro-3-butenyl-2-ol; reducing nitro of the 1-nitro-3-butenyl-2-ol by an iron powder reduction method to obtain 1-amino-3-butenyl-2-ol; and further carrying out a cyclization reaction on the 1-amino-3-butenyl-2-ol with carbon disulfide to generate the (R,S)-goitrine. The synthetic method disclosed by the invention had the advantages of low cost, simple operation, safety andenvironmentally friendliness.

A high-purity 5 - vinyl oxazolidine -2 - thione preparation method

The invention discloses a preparation method of high-purity 5-vinyl oxazolidine-2-thioketone. The preparation method comprises the following steps: carrying out coordination on 1-amino-3-butene-2-alcohol taken as a starting material by using lead nitrate water solution, carrying out annulation on the raw material and CS2 in alkaline environment of potassium hydroxide solution, filtering the reaction liquid, extracting the reaction liquid by using ethyl acetate, carrying out liquid separation, drying and rotary evaporation to obtain a crude product, purifying the water solution containing the crude product through a preparative liquid chromatograph, receiving a mobile phase in the retention time period of a target product, and carrying out rotary evaporation and drying to obtain the product. According to the method, the steps are simple, the operation is convenient, the cost is low and the output is relatively high; and according to the method, the single-pass preparation amount can be up to 0.2-0.3g and the purity is 99.0-99.5%.

BIOSYNTHESIS OF 2-HYDROXY-3-BUTENYLGLUCOSINOLATE AND 3-BUTENYLGLUCOSINOLATE IN BRASSICA NAPUS

Desulpho-3-butenylglucosinolate is considered to be a potential late stage precursor in the biosynthesis of (R)-2-hydroxy-3-butenylglucosinolate (progoitrin) and 3-butenylglucosinolate (gluconapin) in Brassica.Chemically synthesized (β-D-glucopyranosyl)-4-pentenethiohydroxamic acid when administered to developing seedlings of Brassica napus cv Bienvenu was found to be well incorporated into both 2-hydroxy-3-butenylglucosinolate and 3-butenylglucosinolate, while feeding experiments with methionine have shown that de novo biosynthesis is slow.Analysis of seeds and developing seedlings has shown that levels of 2-hydroxy-3-butenylglucosinolate are maintained while 3-butenylglucosinolate levels are considerably reduced.