DL-Goitrin

Base Information

• Chemical Name: DL-Goitrin
• CAS No.: 500-12-9
• Molecular Formula: C5H7 N O S
• Molecular Weight: 129.18
• European Community (EC) Number: 236-145-3
• UNII: O8KVD7J2P5
• DSSTox Substance ID: DTXSID10274235
• Nikkaji Number: J213.733J
• Wikipedia: Goitrin
• Wikidata: Q5577929
• Metabolomics Workbench ID: 140647
• ChEMBL ID: CHEMBL508652
• Mol file: 500-12-9.mol

Synonyms:5-vinyl-2-thiooxazolidone;5-vinyloxazolidin-2-thione;5-vinyloxazolidine-2-thione;epigoitrin;goitrin;goitrin, (+-)-isomer;goitrin, (R)-isomer;goitrin, (S)-isomer

Chemical Property of DL-Goitrin

Chemical Property:

• Vapor Pressure: 3.81mmHg at 25°C
• Melting Point: 50°
• Boiling Point: 150.6°Cat760mmHg
• PKA: 10.5(at 25℃)
• Flash Point: 44.9°C
• PSA: 53.35000
• Density: 1.19g/cm³
• LogP: 0.77450
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 129.02483502
• Heavy Atom Count: 8
• Complexity: 124

Purity/Quality:

≥98% ^*data from raw suppliers

GOITRIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C=CC1CNC(=S)O1

Technology Process of DL-Goitrin

There total 7 articles about DL-Goitrin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

carbon disulfide (75-15-0,12122-00-8) + 4-amino-3-hydroxybut-1-ene (13269-47-1) → DL-5-vinyloxazolidine-2-thione (goitrin) (500-12-9,1072-93-1,13190-34-6,13997-13-2)

Guidance literature:

carbon disulfide; 4-amino-3-hydroxybut-1-ene; With triethylamine; In methanol; at 20 ℃; for 0.5h;

With dihydrogen peroxide; In methanol;

Reference yield:

epi-progoitrin → DL-5-vinyloxazolidine-2-thione (goitrin) (500-12-9,1072-93-1,13190-34-6,13997-13-2) + (-)-2-hydroxybut-3-enyl cyanide

Guidance literature:

With 4-morpholineethanesulfonic acid; rac-cysteine; immobilized myrosinase (nylon 6.6 membrane); iron(II) sulfate; at 37 ℃; for 1h; Yield given; acidic pH;

DOI:10.1016/S0040-4039(00)61525-3

Reference yield:

L-methionine (63-68-3,26062-47-5,58576-49-1) → DL-5-vinyloxazolidine-2-thione (goitrin) (500-12-9,1072-93-1,13190-34-6,13997-13-2)

Guidance literature:

With ammonium hydroxide; Multistep reaction; 1) feeding of seedlings of Brassica napus cv Bienvenu, 25 deg C, 48 h, 2) water, Na-Pi buffer, myrosinase, 3 h, 3) water, room temperature, 48 h;

DOI:10.1016/0031-9422(90)85177-H

upstream raw materials:

DL-5-vinyloxazolidine-2-thione (goitrin)

carbon disulfide

4-amino-3-hydroxybut-1-ene

L-methionine

Downstream raw materials:

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

Refernces

• 1、 -. "Synthetic method of antiviral drug (R,S)-goitrine". Paragraph 0016; 0030; 0034; 0039; 0044; 0049. . Retrieved 2019/04/26.
• 2、 -. "A high-purity 5 - vinyl oxazolidine -2 - thione preparation method". Paragraph 0033-0048. . Retrieved 2017/08/24.