19322-27-1

Basic information

• Product Name: 4-Hydroxy-5-methyl-3-furanone
• Synonyms: 4-Hydroxy-5-methyl-3-furanone 97%;4-hydroxy-5-methyl-3(2h)-furanon;4-HYDROXY-5-METHYL-3(2H)-FURANONE;4-Hydroxy-5-methyl-3-furanone;4-HYDROXY-5-METHYL-FURAN-3-ONE;4-HYROXY-5-METHYL-3-FURANONE;CHICORY FURANEOL;FEMA 3635
• CAS NO: 19322-27-1
• Molecular Formula: C₅H₆O₃
• Molecular Weight: 114.1
• EINECS: 242-961-0
• Product Categories: Furan&Benzofuran;Building Blocks;Furans;Heterocyclic Building Blocks;Building Blocks;C4 to C7;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 19322-27-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 129-133 °C(lit.)
• Boiling Point: 218.3 °C at 760 mmHg
• Flash Point: 97.5 °C
• Appearance: white to light yellow crystal powder
• Density: 1.382 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• PKA: 9.61±0.20(Predicted)
• CAS DataBase Reference: 4-Hydroxy-5-methyl-3-furanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-5-methyl-3-furanone(19322-27-1)
• EPA Substance Registry System: 4-Hydroxy-5-methyl-3-furanone(19322-27-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19322-27-1(Hazardous Substances Data)

Usage

Description

4-Hydroxy-5-methyl-3-furanone is a key flavor component found in beef broth, guava, raspberry, and shoyu (fermented soya hydrolysate). It is a member of the class of furans, specifically a 5-methyl-2,3-dihydrofuran with a hydroxy group at position 4 and a keto group at position 3. This organic compound has a fruity caramel or "burnt pineapple" aroma and appears as a white to light yellow crystal powder.

Uses

Used in Food Industry:
4-Hydroxy-5-methyl-3-furanone is used as a flavor enhancer for its unique fruity caramel or "burnt pineapple" aroma, contributing to the characteristic taste of beef broth and shoyu (soy sauce).
Used in Chemical Research:
4-Hydroxy-5-methyl-3-furanone is used as a chemical standard in the evaluation of oxidoreductase activity, playing a crucial role in oxidoreductase assay for the assessment of enzyme function and activity in various research applications.

Upstream product

• 553-90-2 Dimethyl oxalate 
• 685-73-4 D-galacturonic acid 
• 489-91-8 D-galacturonic acid 
• 108321-99-9 α,β-D-ribofuranose-5-phophate disodium salt 
• 2280-44-6 D-Glucose 
• 58-86-6 D-xylose 
• 87-72-9 D-Xylose 
• 56-40-6 glycine 
• 95-92-1 oxalic acid diethyl ester 

Downstream Products

• 3581-91-7 4,5-Dimethylthiazole 
• 74015-70-6 4,5-Dihydro-2-methylthiophen-3-(2H)-on 
• 20662-84-4 2,4,5-trimethyloxazole 
• 329769-49-5 5-methyl-4-(1-pyrrolidinyl)-3(2H)-furanone 
• 948557-12-8 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone 

Relevant articles and documents

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

D-galacturonic acid as a highly reactive compound in nonenzymatic browning. 1. Formation of browning active degradation products

Thermal treatment of an aqueous solution of d-galacturonic acid at pH 3, 5, and 8 led to rapid browning of the solution and to the formation of carbocyclic compounds such as reductic acid (2,3-dihydroxy-2-cyclopenten-1-one), DHCP (4,5-dihydroxy-2-cyclopenten-1-one), and furan-2-carbaldehyde, as degradation products in weak acidic solution. Studies on their formation revealed 2-ketoglutaraldehyde as their common key intermediate. Norfuraneol (4-hydroxy-5-methyl-3-(2H)-furanone) is a typical alkaline degradation product and formed after isomerization. Further model studies revealed reductic acid as an important and more browning active compound than furan-2-carbaldehyde, which led to a red color of the model solution. This red-brown color is also characteristic of thermally treated uronic acid solutions.

Analysis of furanone, pyranone, and new heterocyclic colored compounds from sugar-glycine model maillard systems

Aqueous sugar (xylose or glucose)-glycine model systems were refluxed for 2 h with the pH maintained at 5. Reverse-phase HPLC of the total reaction products gave two resolved peaks (one of which was colored) for the xylose system and five resolved peaks (two of which were colored) for the glucose system. The components responsible for these peaks were isolated from the ethyl acetate extracts by semipreparative HPLC. Using mainly NMR, the colored compound from the xylose system was identified as the new 2-acetyl-6- (hydroxymethyl)-5,6-dihydro-4H-pyridinone. The colored compounds from the glucose system were most likely to be two novel cis/trans ring isomers of the related new compound 2-acetyl-6-hydroxy-7-(hydroxymethyl)-1,5,6,7-tetrahydro- 4H-azepinone. These compounds are the first one-ring structures isolated from sugar-amino acid model systems that are reported to be colored. Two of the colorless components of the glucose system were identified, mainly by NMR experiments, as the related compounds 4-hydroxy-2-(hydroxymethyl)-5-methyl- 3(2H)-furanone and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyranone. The remaining compound from the glucose system and the colorless compound from the xylose system were identified as 5-(hydroxymethyl)furfural and 4-hydroxy- 5-methyl-3(2H)-furanone, respectively.