3420-59-5

Basic information

• Product Name: 1-(3-hydroxy-2-furyl)ethanone
• Synonyms: 1-(3-hydroxy-2-furyl)ethanone;3-Hydroxy-2-furyl methyl ketone;3-Hydroxy-2-furyl(methyl) ketone;Isomaltol;1-(3-hydroxyfuran-2-yl)ethanone
• CAS NO: 3420-59-5
• Molecular Formula: C₆H₆O₃
• Molecular Weight: 126.11
• Mol File: 3420-59-5.mol

Chemical Properties

• Melting Point: 98-103°
• Boiling Point: 207.3°Cat760mmHg
• Flash Point: 79.2°C
• Appearance: white crystal
• Density: 1.234g/cm³
• Vapor Pressure: 0.158mmHg at 25°C
• Refractive Index: 1.508
• PKA: 9.57±0.10(Predicted)
• CAS DataBase Reference: 1-(3-hydroxy-2-furyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-hydroxy-2-furyl)ethanone(3420-59-5)
• EPA Substance Registry System: 1-(3-hydroxy-2-furyl)ethanone(3420-59-5)

Safety Data

• Hazardous Substances Data: 3420-59-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
1-(3-Hydroxy-2-furyl)ethanone is used as a flavoring agent for its sweet and fruity aroma in food products such as beverages, confectionery, and baked goods.
Used in Food Industry:
1-(3-Hydroxy-2-furyl)ethanone is used as an antioxidant and antimicrobial agent in the food industry, potentially enhancing the shelf life and safety of food products.
Used in Pharmaceutical Industry:
1-(3-Hydroxy-2-furyl)ethanone is used for its potential health benefits, including its ability to modulate glucose metabolism and its role as a chemopreventive agent.

InChI:InChI=1/C6H6O3/c1-4(7)6-5(8)2-3-9-6/h2-3,8H,1H3

Upstream product

• 87251-66-9 1-(N-L-triptophanyl)-1-deoxy-D-fructose 
• 69-79-4 D-maltose 

Downstream Products

• 105399-03-9 (E)-2-<1-(3-hydroxy-2-furanyl)ethylidene>-(2H)-furan-3-one 
• 30652-13-2 3-hydroxy-2-methyl-1-propyl-4(1H)-pyridinone 
• 30652-12-1 CP21 
• 30652-11-0 deferiprone 

Relevant articles and documents

Formation of Reactive Intermediates, Color, and Antioxidant Activity in the Maillard Reaction of Maltose in Comparison to d -Glucose

In this study, the Maillard reaction of maltose and d-glucose in the presence of l-alanine was investigated in aqueous solution at 130 °C and pH 5. The reactivity of both carbohydrates was compared in regards of their degradation, browning, and antioxidant activity. In order to identify relevant differences in the reaction pathways, the concentrations of selected intermediates such as 1,2-dicarbonyl compounds, furans, furanones, and pyranones were determined. It was found, that the degradation of maltose predominantly yields 1,2-dicarbonyls that still carry a glucosyl moiety and thus subsequent reactions to HMF, furfural, and 2-acetylfuran are favored due to the elimination of d-glucose, which is an excellent leaving group in aqueous solution. Consequently, higher amounts of these heterocycles are formed from maltose. 3-deoxyglucosone and 3-deoxygalactosone represent the only relevant C6-1,2-dicarbonyls in maltose incubations and are produced in nearly equimolar amounts during the first 60 min of heating as byproducts of the HMF formation.

Effect of pressure on processes modelling the Maillard reaction

The Maillard reaction between tryptophan and glucose or xylose was studied as a function of pressure. Using model reactions, volumes of activation for the formation of the intermediate imine and the Amadori rearrangement and for the decomposition of the aminoketose were measured as -14, 8 and 17 cm3mol-1, respectively. Pressure therefore accelerates the initial reactions but retards the formation of the final heterocyclic products and melanoidins. Oxygen was found to accelerate the latter reaction.