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

Chemical Properties

Different sources of media describe the Chemical Properties of 698-10-2 differently. You can refer to the following data:
1. light yellow liqui
2. Abhexone has been found in, for example, lovage and roasted coffee. It has a bouillon-like, coffee and lovage aroma, depending on its concentration. It can be prepared starting from alkyl 2-oxobutanoate either by self-condensation followed subsequently 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 . It is used for aromatization of food.
3. 5-Ethyl-3-hydroxy-4-methyl-2(5H)-furanone has a sweet, maple, caramel odor.

Occurrence

Reported found in coffee.

Taste threshold values

Taste characteristics at 50 ppm: sweet, fruity with brown maple note.

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.