GOITRINE

Base Information

• Chemical Name: GOITRINE
• CAS No.: 1072-93-1
• Molecular Formula: C5H7NOS
• Molecular Weight: 129.18
• Hs Code.: 29349990
• UNII: 2N815D740R
• DSSTox Substance ID: DTXSID501318342
• Nikkaji Number: J65.711E
• Wikipedia: Goitrin
• Wikidata: Q27255092
• Metabolomics Workbench ID: 134077
• ChEMBL ID: CHEMBL442589
• Mol file: 1072-93-1.mol

Synonyms:2-Oxazolidinethione,5-ethenyl-, (R)-;2-Oxazolidinethione, 5-vinyl-, (R)- (8CI);(+)-5-Vinyl-2-oxazolidinethione;(R)-5-Vinyloxazolidine-2-thione;(R)-Goitrin;Ba 51-090278;epi-Goitrin;Epigoitrin;

Chemical Property of GOITRINE

Chemical Property:

• Vapor Pressure: 3.81mmHg at 25°C
• Melting Point: 50oC
• Refractive Index: 1.57
• Boiling Point: 150.599 °C at 760 mmHg
• PKA: 13.34±0.40(Predicted)
• Flash Point: 44.881 °C
• PSA: 53.35000
• Density: 1.198 g/cm³
• LogP: 0.77450
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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%,99%, ^*data from raw suppliers

Epigoitrin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: C=CC1CNC(=S)O1
• Isomeric SMILES: C=C[C@@H]1CNC(=S)O1
• Uses: Goitrine is a cyclic thiocarbamate that is seen reducing production of thyroid hormones.

Technology Process of GOITRINE

There total 15 articles about GOITRINE 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: 90.0%

epi-progoitrin → (5R)-5-vinyl-1,3-oxazolidine-2-thione (1072-93-1)

Guidance literature:

In water; at 37 ℃; enzymatic by myrosinase, pH 6.5;

DOI:10.1016/0957-4166(94)80145-2

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

upstream raw materials:

(R)-5-(2-hydroxyethyl)oxazolidine-2-thione

(R)-5-(2-iodoethyl)oxazolidine-2-thione

(R)-ethyl 2-(2-thioxooxazolidin-5-yl)acetate

(R)-1-amino-but-3-en-2-ol

Downstream raw materials:

(R)-2-Benzylsulfanyl-5-vinyl-4,5-dihydro-oxazole

Refernces

• 1、 Leoni, Onofrio,Marot, Christophe,Rollin, Patrick,Palmieri, Sandro. "Preparation of (5R)-5-Vinyloxazolidine-2-thione from Natural Epi-Progoitrin Using Immobilized Myrosinase". . p. 1157 - 1160. Retrieved 1994.
• 2、 Dai, Zhong,Ma, Shuang-cheng,Nie, Li-xing,Wu, Yan-lin. "Antiviral activity of Isatidis Radix derived glucosinolate isomers and their breakdown products against influenza A in vitro/ovo and mechanism of action". . . Retrieved 2020.
• 3、 MacLeod, Alexander J.,Rossiter, John T.. "Degradation of 2-Hydroxybut-3-enylglucosinolate (Progoitrin)". . p. 669 - 674. Retrieved 1987.
• 4、 Rossiter, J. T.,James, D. C.,Atkins, N.. "BIOSYNTHESIS OF 2-HYDROXY-3-BUTENYLGLUCOSINOLATE AND 3-BUTENYLGLUCOSINOLATE IN BRASSICA NAPUS". . p. 2509 - 2512. Retrieved 1990.
• 5、 Leoni,Felluga,Palmieri. "The formation of 2-hydroxybut-3-enyl cyanide from (2s)-2-hydroxybut-3-enyl glucosinolate using immobilized myrosinase". . p. 7967 - 7970. Retrieved 1993.
• 6、 -. "Preparation method of 5-vinyl-2-sulfo-oxazolidine". Paragraph 0023; 0026; 0027; 0030; 0031; 0034. . Retrieved 2019/05/08.