Furaneol

Base Information

• Chemical Name: Furaneol
• CAS No.: 3658-77-3
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• Hs Code.: 29321900
• European Community (EC) Number: 222-908-8
• UNII: 20PI8YZP7A
• DSSTox Substance ID: DTXSID0041517
• Nikkaji Number: J13.291H
• Wikipedia: Furaneol
• Wikidata: Q250455
• RXCUI: 1313733
• Metabolomics Workbench ID: 49104
• ChEMBL ID: CHEMBL3186302
• Mol file: 3658-77-3.mol

Synonyms:2,5-dimethyl-4-hydroxy-3(2H)-furanone;4-HDMF;4-hydroxy-2,5-dimethyl-3(2H)-furanone;alletone;furaneol;furaneol, (R)-isomer;furaneol, (S)-isomer

Chemical Property of Furaneol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.213mmHg at 25°C
• Melting Point: 73-77 °C(lit.)
• Refractive Index: n20/D 1.439
• Boiling Point: 215.5 °C at 760 mmHg
• PKA: 9.62±0.40(Predicted)
• Flash Point: 90.5 °C
• PSA: 46.53000
• Density: 1.249 g/cm³
• LogP: 0.76370
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 176g/L at 20℃
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxy-2- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(=O)C(=C(O1)C)O
• Description: Furaneol is a very important aroma chemical and is a key flavoring compound found in many kinds of fruits. It can be chemically formed through different carbohydrates during the Mainlard reaction. It can also be synthesized by yeast, bacteria and plants and play some physiological effects. Study has shown that it can suppress the phosphorylation of cAMP response element binding protein, underlying its potential role as an effective inhibitor of hyperpigmentation. It also has the potential to become an effective antimicrobial agent for human beings.
• Uses: 2,5-Dimethyl-4-hydroxy-3(2H)-furanone is a component of meat essence composition. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone is used in the flavor and perfume industry due to its sweet strawberry aroma.

Technology Process of Furaneol

There total 13 articles about Furaneol 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:

D-glucose (50-99-7) + glycine (56-40-6,18875-39-3,25718-94-9) → 5-hydroxymethyl-2-furfuraldehyde (67-47-0) + furaneol (3658-77-3,192466-95-8) + 5-hydroxymaltol (1073-96-7) + 2-hydroxymethyl-5-methylfuran (3857-25-8)

Guidance literature:

In water; at 95 ℃; for 120h; Product distribution; other reaction time, other temperature;

Reference yield:

2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (28564-83-2) → furaneol (3658-77-3,192466-95-8) + 5-hydroxymaltol (1073-96-7) + 2-methyltetrahydrofuran-3-one (3188-00-9) + 2,3-Pentanedione (600-14-6) + 2-hydroxy-3-methylcyclopent-2-en-1-one (80-71-7) + hydroxy-2-propanone (116-09-6)

Guidance literature:

With water; at 150 ℃; for 1h; also 2,3-dihydro-3,5-dihydroxy-6(¹³C)methyl-4(H)-pyran-4-one; var. temp., pH, and time; effect of 2,4-dihydroxy-2,5-dimethyl-3(2H)-furanone;

DOI:10.1021/jf950208h

upstream raw materials:

D-glucose

glycine

glucofuraneol tetraacetate

D-Xylose

Downstream raw materials:

2-(1-hydroxyethyl)-2,5-dimethyl-4-hydroxy-3-(2H)-furanone

(S)-(-)-2,5-dimethyl-4-hydroxy-3(2H)-furanone

(R)-(+)-2,5-dimethyl-4-hydroxy-3(2H)-furanone

LACTIC ACID

Refernces

• 1、 Fay, Laurent B.,Newton, Anthony,Simian, Herve,Robert, Fabien,Douce, David,Hancock, Peter,Green, Martin,Blank, Imre. "Potential of gas chromatography-orthogonal acceleration time-of-flight mass spectrometry (GC-oaTOFMS) in flavor research". . p. 2708 - 2713. Retrieved 2007/10/03.
• 2、 Bristow, Mark,Isaacs, Neil S.. "The effect of high pressure on the formation of volatile products in a model Maillard reaction". . p. 2213 - 2218. Retrieved 2007/10/03.