beta-D-Glucopyranose, 1-[N-(sulfooxy)-3-butenimidate], monopotassium salt

Base Information

• Chemical Name: beta-D-Glucopyranose, 1-[N-(sulfooxy)-3-butenimidate], monopotassium salt
• CAS No.: 3952-98-5
• Molecular Formula: C10H17 N O9 S2 . K
• Molecular Weight: 397.469
• Hs Code.: 29389090
• NSC Number: 407279,90774
• Wikipedia: Sinigrin
• Mol file: 3952-98-5.mol

Synonyms:myronate;sinigrin;sinigrin, monopotassium salt

Chemical Property of beta-D-Glucopyranose, 1-[N-(sulfooxy)-3-butenimidate], monopotassium salt

Chemical Property:

• Appearance/Colour: white to beige Crystalline powder
• Melting Point: 128 (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 202.62000
• Density: g/cm³
• LogP: -1.03330
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: almost transparency
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 7
• Exact Mass: 359.03447347
• Heavy Atom Count: 22
• Complexity: 503

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sinigrin 98% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCC(=NOS(=O)(=O)O)SC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: C=CC/C(=N\OS(=O)(=O)O)/SC1C(C(C(C(O1)CO)O)O)O
• Uses: Sinigrine, is a glucosinolate which is found naturally in Cruciferae including the genus Brassica. When enzymatically hydrolysed, Sinigrine yields isothiocyanates and give a pungent taste. Both Sinigrine, and isothiocyanates, have been shown to have anticancer activity as well as antifungal and antibacterial properties. Sinigrin, a glucosinolate, is used as a systrate to identify, differentiate and characterize myrosinase(s)/thioglucoside glucohydrolase(s)/thioglucosidase(s). Sinigrin is used as a reference material in procedures for the isolation and identification of glucosinolates.

Technology Process of beta-D-Glucopyranose, 1-[N-(sulfooxy)-3-butenimidate], monopotassium salt

There total 2 articles about beta-D-Glucopyranose, 1-[N-(sulfooxy)-3-butenimidate], monopotassium salt 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: 83.0%

potassium S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-but-3'-ene-thio-O-sulfoximate → sinigrin (3952-98-5)

Guidance literature:

With ammonia; In methanol; for 24h;

DOI:10.1080/07328309608005429

Reference yield:

methanol (67-56-1) + ammonia (7664-41-7) + tetra-O-acetyl-S-((Z)-N-sulfooxy-but-3-eneimidoyl)-1-thio-β-D-glucopyranose; potassium (5019-27-2) → sinigrin (3952-98-5)

Guidance literature:

Rate constant;

DOI:10.1002/ardp.19552881108

Reference yield:

sinigrin (3952-98-5) → but-3-enoic acid (625-38-7) + hydroxylamine (7803-49-8)

Guidance literature:

DOI:10.1021/ja01597a090

upstream raw materials:

methanol

ammonia

tetra-O-acetyl-S-((Z)-N-sulfooxy-but-3-eneimidoyl)-1-thio-β-D-glucopyranose; potassium

Downstream raw materials:

but-3-enenitrile

desulphosinigrin

4,5-epithiopentanenitrile

allyl thiocyanate

Refernces