698-10-2

Basic information

• Product Name: 3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone
• Synonyms: MAPLE FURANONE;Emoxyfurone;ETHYL FENUGREEK LACTONE;FEMA 3153;3-hydroxy-4-methyl-5-ethyl-2(5h)furanone;3-HYDROXY-4-METHYL-5-ETHYL-2-FURANONE;5-ETHYL-4-METHYL-3-HYDROXYFURANONE;5-ETHYL-3-HYDROXY-4-METHYL-2(5H)-FURANONE
• CAS NO: 698-10-2
• Molecular Formula: C₇H₁₀O₃
• Molecular Weight: 142.15
• EINECS: 211-811-6
• Product Categories: Alphabetical Listings;E-F;Flavors and Fragrances;food additive
• Mol File: 698-10-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 31-35 °C(lit.)
• Boiling Point: 83-86 °C0.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: light yellow liquid
• Density: 1.1643 (rough estimate)
• Vapor Pressure: 0.00387mmHg at 25°C
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: 2-8°C
• PKA: 9.28±0.40(Predicted)
• CAS DataBase Reference: 3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone(698-10-2)
• EPA Substance Registry System: 3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone(698-10-2)

Safety Data

• Safety Statements: 24/25
• RIDADR: UN 3335
• WGK Germany: 3
• Hazardous Substances Data: 698-10-2(Hazardous Substances Data)

Usage

Description

3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone, also known as Abhexone, is a light yellow liquid with a sweet, fruity taste and brown maple note. It is found in coffee and has a bouillon-like, coffee, and lovage aroma, depending on its concentration. It can be prepared starting from alkyl 2-oxobutanoate through self-condensation followed by decarbomethoxylation or by condensation with propionaldehyde and subsequent cyclization. Alkyl 2-oxobutanoate is available from acrylaldehyde and sodium cyanide via alkyl 2-hydroxy-3-butenoate or by reaction of dialkyloxalate with ethyl magnesium bromide.
Usage:
Used in Food Industry:
3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone is used as a flavoring agent for its sweet, maple, caramel odor and aroma, enhancing the taste and aroma of various food products.
Used in Aromatization of Food:
3-Hydroxy-4-methyl-5-ethyl-2(5H)furanone is used for aromatization of food, providing a unique and pleasant flavor profile to food products, particularly those with coffee, maple, or caramel notes.

InChI:InChI=1/C7H10O3/c1-3-5-4(2)6(8)7(9)10-5/h4-5H,3H2,1-2H3/t4-,5-/m0/s1

Synthetic route

2-ethyl-4-hydroxy-3-methyl-5-oxo-2,5-dihydrofuran-2-carboxylic acid → 5-ethyl-3-hydroxy-4-methyl-(5H)-furan-2-one (698-10-2)

Conditions	Yield
at 150℃; for 10h;	86%

2-hydroxy-4-(methoxycarbonyl)-3-methyl-2-hexen-4-olid (112026-00-3) → 5-ethyl-3-hydroxy-4-methyl-(5H)-furan-2-one (698-10-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / H2O / 1 h / 20 °C 2: 86 percent / 10 h / 150 °C View Scheme

5-ethyl-3-hydroxy-4-methyl-(5H)-furan-2-one (698-10-2) → 5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone (144831-61-8) + (R)-5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one (144831-60-7)

Conditions	Yield
With CHIRALPAK IA In ethyl acetate; isopropyl alcohol at 25℃; Resolution of racemate; optical yield given as %ee;

Upstream product

• 112026-00-3 2-hydroxy-4-(methoxycarbonyl)-3-methyl-2-hexen-4-olid 

Relevant articles and documents

Method for synthesizing ethyl cucurbituride lactone spice

Compared with the existing similar products, the method comprises the following steps: preparing 2 -oxobutyric acid ethyl ester by Grignard reaction under the condition of absolute ethyl acetate as a starting raw material and carrying out Grignard reaction on potassium carbonate. After the needed carbon skeleton is cyclized under the action of acetaldehyde, ethylcucurbituric acid lactone is obtained, and the technological process is reduced. The reaction solvent and the extractant are recycled, so that the cost is reduced, the purity of the product is 98.36% through gas chromatography, and higher reaction yield is ensured.