Ethyl Maltol

Product Name:

Ethyl maltol

Synonyms:

2-ethyl-3-hydroxy-4-pyranone;6-ETHYL-3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE;3-HYDROXY-2-ETHYL-4-PYRONE;Ethylmaltol (Subject To Patent Free);3-Hydroxy-2-ethyl-4-pyrone,ethyl maltol;ETHYL MALTOL 99+% FCC;ETHYLMALTOL FCCIV;PYRAN-4-ONE,3-HYDROXY-2-METHYL-,2-ETHYLESTER

CAS:

4940-11-8

MF:

C7H8O3

MW:

140.14

EINECS:

225-582-5

Product Categories:

Food and Feed Additive;Food & Feed ADDITIVES;Food & Flavor Additives;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Pyrans;Food Additives

Mol File:

4940-11-8.mol

Melting point 

85-95 °C(lit.)

Boiling point 

196.62°C (rough estimate)

density 

1.1624 (rough estimate)

FEMA 

3487 | ETHYL MALTOL

refractive index 

1.4850 (estimate)

pka

8.38±0.10(Predicted)

form 

neat

JECFA Number

1481

Merck 

14,3824

CAS DataBase Reference

4940-11-8(CAS DataBase Reference)

NIST Chemistry Reference

4H-pyran-4-one, 2-ethyl-3-hydroxy-(4940-11-8)

EPA Substance Registry System

4H-Pyran-4-one, 2-ethyl-3-hydroxy- (4940-11-8)

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

RTECS 

UQ0840000

HS Code 

29329990

Toxicity

LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla)

Chemical Properties

White crystalline solid with characteristic, very sweet, caramel-like odor and taste. In dilute solution it possesses a sweet, fruitlike flavor and odor.

Chemical Properties

It forms white crystals (mp 90–91°C) with very sweet caramel-like odor, four to six times more potent than maltol. Several syntheses have been developed for its preparation. In a one-pot process, for example, ??-ethylfurfuryl alcohol is treated with halogen to give 4-halo- 6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which need not be isolated and can be converted to ethylmaltol by aqueous hydrolysis

Chemical Properties

Ethyl maltol has a very sweet, fruit-like odor of immense tenacity and sweet, fruity taste with initial bitter-tart flavor; rapid loss of flavor per se. It is four to six times more potent than maltol.

Uses

Ethyl Maltol is a flavoring agent that is a white, crystalline powder. it has a unique odor and a sweet taste that resembles fruit. the melt- ing point is 90°c. it is sparingly soluble in water and propylene gly- col and soluble in alcohol and chloroform. it is obtained by chemical synthesis.

Uses

Flavor and fragrance enhancer in foods, especially baked goods, beverages, and synthetic berry and citrus flavorings; minimizes undesirable flavors in tobacco products, cough syrup, vitamins, cosmetics, and saccharin-containing products.

Preparation

Several syntheses have been developed for its preparation. In a one-pot process, for example, ??-ethylfurfuryl alcohol is treated with halogen to give 4-halo- 6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which need not be isolated and can be converted to ethylmaltol by aqueous hydrolysis.

Production Methods

Unlike maltol, ethyl maltol does not occur naturally. It may be prepared by treating a-ethylfurfuryl alcohol with a halogen to produce 4-halo-6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which is converted to ethyl maltol by hydrolysis.

Taste threshold values

Taste characteristics at 70 ppm: sweet, burnt cotton, sugar candy-like with jamy, strawberry notes.

Pharmaceutical Applications

Ethyl maltol is used in pharmaceutical formulations and food products as a flavoring agent or flavor enhancer in applications similar to maltol. It has a flavor and odor 4–6 times as intense asmaltol. Ethyl maltol is used in oral syrups at concentrations of about 0.004% w/v and also at low levels in perfumery.

Safety Profile

Moderately toxic by ingestion and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Safety

In animal feeding studies, ethyl maltol has been shown to be well tolerated with no adverse toxic, reproductive, or embryogenic effects. It has been reported that while the acute toxicity of ethyl maltol, in animal studies, is slightly greater than maltol, with repeated dosing the opposite is true. The WHO has set an acceptable daily intake for ethyl maltol at up to 2 mg/kg bodyweight.
LD50 (chicken, oral): 1.27 g/kg
LD50 (rat, oral): 1.15 g/kg
LD50 (mouse, oral): 0.78 g/kg
LD50 (mouse, SC): 0.91 g/kg

Chemical Synthesis

From kojic acid

storage

Solutions may be stored in glass or plastic containers. The bulk material should be stored in a well-closed container, protected from light, in a cool, dry place.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (oral syrup).

Raw materials

Diethyl ether-->Ammonium chloride-->Chlorine-->Benzyl chloride-->Manganese dioxide-->Bromoethane-->Sodium chlorate-->CHLOROETHANE-->Furfural-->Furfuryl alcohol-->2-Furoic acid-->CARAMEL-->Benzyl ether-->Kojic acid-->Pyromeconic acid