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.
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
White crystalline solid with characteristic, very sweet, caramel-like
odor and taste. In dilute solution it possesses a sweet, fruitlike flavor
and odor.
Occurrence
Has apparently not been reported to occur in nature.
History
In 1891, Bernhardi first discovered synthesis, and its derivatives are used for therapeutic purposes and can be prepared in industrial experiments. As war ammunition, it was first used by France in fortress warfare, and was prepared before the war. In October 1914, the French used it as a gas grenade, planned for the fortress battle. On January 7, 1915, it was actually used in the forest of Argonnen on the western front of France.
Definition
ChEBI: Ethyl maltol is a pyranone.
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.
General Description
Ethyl maltol is a synthetic homologue of maltol, often found as flavor enhancers and it contributes to the fragrance of commercials products such as cereals, breads, malt beverages, coffee, soybeans and chocolate milk.
Flammability and Explosibility
Notclassified
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
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
Synthesis
From kojic acid
Metabolism
When orally administered, ethyl maltol was rapidly and extensively absorbed. Elimination was also extensive and rapid, involving conjugation as the glucuronide and ethereal sulphate, and excretion in the urine to the extent of 65-70% within 24 hr. Rate studies after iv dosage indicated that the bulk (86%) of the recovered conjugates was excreted within 6 hr (Rennhard, 1971).
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).
