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:

95%-98% ^*data from raw suppliers

Sinigrin hydrate ^*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
• General Description: Sinigrin is a naturally occurring glucosinolate found in the Cruciferae family, and its practical synthesis has been optimized for large-scale production. The improved method involves the formation of hydroxamoyl chloride followed by condensation with 1-mercaptoglucose, utilizing modified conditions such as an ethyl ether solution of HCl and strict water exclusion to enhance yield and purity. The final product, sinigrin monohydrate, was obtained in 42% yield and confirmed to match natural sinigrin through spectral and analytical data. This synthesis provides a reliable route for producing sinigrin, a compound of interest due to its presence in cruciferous vegetables and potential bioactive properties.

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

Practical synthesis of sinigrin

10.1080/07328309608005429

The study presents a practical synthesis of sinigrin, a naturally occurring glucosinolate found in the Cruciferae plant family, suitable for preparation on a ten-gram scale. The key step involves the preparation of hydroxamoyl chloride, followed by condensation with 1-mercaptoglucose. The authors modified existing methods to improve yield, using an ethyl ether solution of HCl instead of gaseous HCl and avoiding water in subsequent steps to prevent contamination. The final product, sinigrin monohydrate, was obtained with an overall yield of 42%, and its spectral and analytical data matched those of natural sinigrin. The chemicals involved include 4-nitrobut-1-ene, sodium methoxide, ethyl ether, thiol (1-mercaptoglucose), sulfuric acid, pyridine, sulfur trioxide, potassium bicarbonate, methanolic ammonia, and activated charcoal, each playing specific roles in the synthesis, such as reagents for functional group transformations and catalysts for reactions.

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