500-12-9

Basic information

• Product Name: DL-GOITRIN
• Synonyms: DL-GOITRIN;(+/-)-GOITRIN;(±)-Goitrin,98%;()-GOITRIN 98%;(5S)-5-Vinyloxazolidine-2-thione;(S)-5-Ethenyl-2-oxazolidinethione;Zinc05226611;Zinc05226613
• CAS NO: 500-12-9
• Molecular Formula: C₅H₇NOS
• Molecular Weight: 129.18
• Mol File: 500-12-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 50°
• Boiling Point: 150.6°Cat760mmHg
• Flash Point: 44.9°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 3.81mmHg at 25°C
• Refractive Index: 1.57
• PKA: 10.5(at 25℃)
• CAS DataBase Reference: DL-GOITRIN(CAS DataBase Reference)
• NIST Chemistry Reference: DL-GOITRIN(500-12-9)
• EPA Substance Registry System: DL-GOITRIN(500-12-9)

Safety Data

• Hazardous Substances Data: 500-12-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H7NOS/c1-2-4-3-6-5(8)7-4/h2,4H,1,3H2,(H,6,8)/t4-/m0/s1

Upstream product

• 63-68-3 L-methionine 
• 75-15-0 carbon disulfide 
• 13269-47-1 4-amino-3-hydroxybut-1-ene 
• 500-12-9 DL-5-vinyloxazolidine-2-thione (goitrin) 

Downstream Products

• 1072-93-1 (5R)-5-vinyl-1,3-oxazolidine-2-thione 

Relevant articles and documents

Antiviral activity of Isatidis Radix derived glucosinolate isomers and their breakdown products against influenza A in vitro/ovo and mechanism of action

Ethnopharmacological relevance: Isatidis Radix, the sun-dried roots of Isatis indigotica Fortune ex Lindl., is one of the most usually used traditional Chinese medicines. For centuries, the herb has been employed in clinical practice for treatment of virus infection and inflammation. However, its active ingredients remain unclear. Aim of the study: In the present study, the anti-influenza virus activity of epiprogoitrin, progoitrin, epigoitrin and goitrin, the Isatidis Radix derived glucosinolate isomers and their breakdown products, was firstly evaluated in vitro and in ovo and their mechanism of action was investigated. Materials and methods: Epiprogoitrin, progoitrin, epigoitrin and goitrin were isolated from Isatidis Radix by chiral separation. In vitro and in ovo evaluations were performed on Madin-Darby canine kidney (MDCK) cells and embryonated eggs respectively, both using protocols including prevention, treatment and virus neutralization. Hemagglutination (HA) and neuraminidase (NA) inhibition assays were performed for further understanding of the antiviral mechanism. Results: Isatidis Radix derived glucosinolate isomers and their breakdown products all exhibited dose-dependent inhibition effect against influenza A virus (H1N1) without toxicity. The antiviral potency of the components was in the order of progoitrin > goitrin > epigoitrin > epiprogoitrin. The attachment of the constituents to the viral envelope conduced to the mechanism of their antiviral action without disturbing viral adsorption or budding. Conclusion: Taken together, these results are promising for further development of Isatidis Radix and may contribute an adjunct to pharmacotherapy for influenza virus infection.

Preparation method of 5-vinyl-2-sulfo-oxazolidine

The invention discloses a preparation method of 5-vinyl-2-sulfo-oxazolidine. The preparation method comprises the following steps: (1) using acrolein and trimethylsilyl cyanide as raw materials for reaction under the catalysis of zinc iodide to obtain 2-[(trimethyorganosilyl)oxy]-3-butenenitrile; (2) in a toluene solution, using a red aluminum solution as a reducing agent and potassium carbonate and methanol as a desiliconizing agent, performing reduction and desiliconization on the 2-[(trimethyorganosilyl)oxy]-3-butenenitrile to obtain 1-amino-3-butene-2-alcohol; (3) enabling the 1-amino-3-butene-2-alcohol to react with carbon disulfide, and using hydrogen peroxide as a desulfurizing agent to obtain the 5-vinyl-2-sulfo-oxazolidine. The fatty chain cyanogroup used in the preparation methodis the red aluminum solution; compared with conventional lithium aluminum hydride, the red aluminum solution has simple operation conditions and is low in cost. In the reduction, methylbenzene, instead of traditional combustible liquid such as diethyl ether and the like, is used as a solvent, so that the reaction conditions are safer. In the annulations in the step (3), the hydrogen peroxide replaces original lead nitrate and serves as the desulfurizing agent, so that the pollution to the environment can be reduced, and the method is safe and environmentally-friendly.

The formation of 2-hydroxybut-3-enyl cyanide from (2s)-2-hydroxybut-3-enyl glucosinolate using immobilized myrosinase

Starting from (2S)-2-hydroxybut-3-enylglucosinolate (epiprogoitrin) isolated from Crambe abyssinica seeds the chiralic 2-hydroxy-3-butenyl cyanide was produced in pure form and acceptable yield, using immobilized myrosinase purified from Sinapis alba on a Nylon 6.6 membrane.