Furaneol 4-glucoside

Base Information

• Chemical Name: Furaneol 4-glucoside
• CAS No.: 121063-56-7
• Molecular Formula: C₁₂H₁₈O₈
• Molecular Weight: 290.27
• Wikidata: Q105370939
• Mol file: 121063-56-7.mol

Synonyms:Furaneol 4-glucoside;2,5-dimethyl-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyfuran-3-one;121063-56-7;2,5-dimethyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyfuran-3-one;2,5-dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside;Furaneol beta-D-glucopyranoside;CHEBI:169238;2,5-dimethyl-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyuran-3-one

Chemical Property of Furaneol 4-glucoside

Chemical Property:

• Melting Point: >47°C (dec.)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 290.10016753
• Heavy Atom Count: 20
• Complexity: 420

Purity/Quality:

99% ^*data from raw suppliers

2,5-Dimethyl-4-hydroxy-3(2H)-furanoneβ-D-Glucopyranoside(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(=O)C(=C(O1)C)OC2C(C(C(C(O2)CO)O)O)O
• Uses: 2,5-Dimethyl-4-hydroxy-3(2H)-furanone β-D-Glucopyranoside is the glucopyranoside analogue of 2,5-Dimethyl-4-hydroxy-3(2H)-furanone and a component of strawberry fruits.

Technology Process of Furaneol 4-glucoside

There total 5 articles about Furaneol 4-glucoside 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: 92.0%

glucofuraneol tetraacetate (121063-57-8) → furaneol (3658-77-3,192466-95-8) + 2,5-dimethyl-4-hydroxy-3(2H)-furanone β-D-glucopyranoside (121063-56-7)

Guidance literature:

With sodium methylate; In methanol; for 4h; Ambient temperature;

DOI:10.1016/0031-9422(89)80068-8

Reference yield: 50.0%

glucofuraneol tetraacetate (121063-57-8) → 2,5-dimethyl-4-hydroxy-3(2H)-furanone β-D-glucopyranoside (121063-56-7)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃; for 4h;

DOI:10.1081/CAR-120019010

Reference yield:

furaneol (3658-77-3,192466-95-8) → 2,5-dimethyl-4-hydroxy-3(2H)-furanone β-D-glucopyranoside (121063-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 19 percent / tetrabutylammonium bromide; aqueous sodium hydroxide / CH₂Cl₂ / 0.75 h / 35 °C

2: 50 percent / sodium carbonate / methanol / 4 h / 20 °C

With sodium hydroxide; tetrabutylammomium bromide; sodium carbonate; In methanol; dichloromethane;

DOI:10.1081/CAR-120019010

upstream raw materials:

glucofuraneol tetraacetate

furaneol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

Refernces

• 1、 Roscher, Rene,Herderich, Markus,Steffen, Jens-Peter,Schreier, Peter,Schwab, Wilfried. "2,5-dimethyl-4-hydroxy-3 [2H]-furanone 6'O-malonyl-β-D-glucopyranoside in strawberry fruits". . p. 155 - 159. Retrieved 1996.