4166-20-5

Basic information

• Product Name: Furaneol acetate
• Synonyms: 4-ACETOXY-2,5-DIMETHYL-3(2H)-FURANONE;4-ACETOXY-2,5-DIMETHYLFURAN-3(2H)-ONE;ACETOXY DIMETHYL FURANONE;2,5-DIMETHYL-4-OXO-4,5-DIHYDROFUR-3-YL ACETATE;FRAISION ACETATE;FURANEOL ACETATE;FEMA 3797;caramel acetate
• CAS NO: 4166-20-5
• Molecular Formula: C8H10O4
• Molecular Weight: 170.16
• Product Categories: Furan&Benzofuran;A-B;Alphabetical Listings;Flavors and Fragrances
• Mol File: 4166-20-5.mol

Chemical Properties

• Boiling Point: 243 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to light yellow liquid
• Density: 1.167 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.605mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Furaneol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Furaneol acetate(4166-20-5)
• EPA Substance Registry System: Furaneol acetate(4166-20-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4166-20-5(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
Furaneol acetate is used as a flavor enhancer for its ability to enhance the profile of brown flavors, including caramel, butterscotch, molasses, brown sugar, chocolate mocha, coffee, and toffee. It adds sweet caramelic notes to browned butter, custard, dulce de leche, strawberry and other fruit jams, BBQ, fried eggs, roasted meat and nuts, and soy sauce flavors.
Used in Nanotechnology Industry:
Furaneol acetate is used as a growth regulator in the manufacturing method of silver nanowire. It reacts with silver salt in a polyol in the presence of a halide salt and a specific furanone derivative to produce silver nanowires with unique properties and applications.

Identification

▼▲ CAS.No.:? 4166-20-5? FL.No.:? 13.099 FEMA.No.:? 3797 NAS.No.:? n/a? CoE.No.:? n/a? EINECS.No.:? n/a? JECFA.No.:? 1456

Regulatory Status

CoE: n/a FDA: n/a FDA (other): n/a JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2004).

Natural occurrence

Reported present in strawberry (0.001–0.01).

Biochem/physiol Actions

Taste at 20-40ppm

Synthesis

Synthesized from furaneol and acetic acid

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

Synthetic route

furaneol (3658-77-3) + acetyl chloride (75-36-5) → 2,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl acetate (4166-20-5)

Conditions	Yield
With dmap In pyridine; dichloromethane at 0 - 20℃;
at 80℃; for 3h;

Upstream product

• 3658-77-3 furaneol 
• 75-36-5 acetyl chloride 

Relevant articles and documents

Antioxidant Properties of Heterocyclic Intermediates of the Maillard Reaction and Structurally Related Compounds

It is well established that a wide range of reductones is formed in the course of the Maillard reaction and that these substances contribute to the oxidative stability of food. The aim of this study was to analyze 12 important heterocyclic intermediates with and without reductone structure as well as structurally related substances under equal conditions to compare their antioxidant properties in detail. For this purpose, five methods were selected including photometrical methods such as the trolox equivalent antioxidant capacity assay and an electron paramagnetic resonance spectroscopic method. Reductones with furan-3-one structure and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one were reducing in all assays, whereas isomaltol and maltol did not react in assays based on the reduction of metal ions because of their complexing abilities. The introduction of protecting groups to the free hydroxyl functions of selected reductones could nearly eliminate their reducing abilities. In addition, the oxidation products of the different reductive heterocycles were compared after treatment with iodine. Mainly short-chained organic acids such as lactic, glycolic, and glyceric acid are formed as result of the degradation, which indicates 1,3-dicarbonyl cleavage reactions of corresponding tricarbonyl compounds as intermediates of the oxidation.

Synthesis of 4-Hydroxy-3(2H)-furanone Acyl Derivatives and Their Anti-cataract Effect on Spontaneous Cataract Rats (ICR/f)

4-Hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF) and 2(or 5)-ethyl-4-hydroxy-5(or 2)-methyl-3(2H)-furanone (EHMF) are known to inhibit cataract development in spontaneous cataract rats (ICR/f). Forty-five acylated hydroxyfuranone derivatives were designed and synthesized for an anti-cataract test, and their hydrophobic constants were also tested. Among these derivatives, 2,5-dimethyl-4-pivaloyloxy-3(2H)-furanone (HDMF pivalate) exerted a marked protective effect against the development of cataract in a galactose-induced model using cultured rat lens (in vitro). When tested on an ICR/f cataract model (in vivo), HDMF pivalate showed more significant inhibition of cataract development than parent compound HDMF. This derivative is more lipophilic than HDMF, so that HDMF pivalate can penetrate the cornea more easily than HDMF. The inhibition of cataract development by HDMF converted from HDMF pivalate is supported by the fact that HDMF was observed in the lens of ICR/f rats treated with HDMF pivalate.