4940-11-8 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 4940-11-8 differently. You can refer to the following data:
1. White crystalline solid with characteristic, very sweet, caramel-like
odor and taste. In dilute solution it possesses a sweet, fruitlike flavor
and odor.
2. 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
3. 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.
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.
Uses
Different sources of media describe the Uses of 4940-11-8 differently. You can refer to the following data:
1. Ethyl Maltol is an extract from medicinal plants such as P. Incarnata and can be used as an anticonvulsant, acting as a depressant, and on motor activity.
2. 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.
3. 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
Different sources of media describe the Preparation of 4940-11-8 differently. You can refer to the following data:
1. 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.
2. Fermentation method. Kojic acid is obtained from starch fermentation, and then ethyl maltol is obtained by etherification, oxidation, debenzylation, decarboxylation, hydroxylation and reduction.
Pyrofuroic acid method. A solution of pyrofuroic acid and acetic acid at a temperature of 90°C was added dropwise to the ether solution of diacetyl peroxide within 1~2h, and then the mixture was raised to 2h within 2h. 110 ° C, so that the 2-position of pyrofuroic acid can be directly alkylated to obtain ethyl maltol.
furfuryl alcohol method. Furfuryl alcohol is chlorinated in methanol aqueous solution by introducing chlorine gas to generate 4-chloro-3-hydroxy-4H-ketone, and then heated and hydrolyzed to obtain pyrofuroic acid; under alkaline conditions, pyrofuroic acid is condensed with acetaldehyde to obtain hydroxyethyl Pyrofuroic acid, which is reduced to ethyl maltol with zinc powder in hydrochloric acid.
Furfural method. Furfural reacts with ethylmagnesium bromide to obtain ethylfurfuryl alcohol (α-furan alkanol), which is then oxidized by chlorine gas in methanol aqueous solution at 0°C, and then heated to 100°C for hydrolysis to obtain ethyl maltol.
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 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
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).
Check Digit Verification of cas no
The CAS Registry Mumber 4940-11-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,9,4 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 4940-11:
(6*4)+(5*9)+(4*4)+(3*0)+(2*1)+(1*1)=88
88 % 10 = 8
So 4940-11-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3
4940-11-8Relevant articles and documents
Method for preparing ethyl maltol from corn cobs with furfuryl alcohol process
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Paragraph 0011; 0012; 0013, (2017/08/28)
The invention discloses a method for preparing ethyl maltol from corn cobs with a furfuryl alcohol process in the technical field of chemical synthesis. The method comprises the steps as follows: preparing furfural from the corn cobs with a two-step method; generating of furfuryl alcohol from furfural through a reaction: furfural and a platinum-loaded nitrogen-doped graphene material are placed in a reaction device, distilled water is added, hydrogen is introduced, and the mixture reacts at 90-160 DEG C for 4-8 h and furfuryl alcohol is prepared; preparing pyromeconic acid from furfuryl alcohol through chlorination and isomerization reactions; preparing hydroxyethyl maltol through condensation; finally, preparing ethyl maltol through reduction: heating is performed continuously after reaction for distilling off an ethanol aqueous solution, the temperature is increased for distilling off crude ethyl maltol, chloroform is added to the crude ethyl maltol for dissolving the crude ethyl maltol, the solution is cooled to 0 DEG C for recrystallization, crystals are dried, and finished maltol is obtained. Pollution-free, green, environment-friendly and pure food-grade ethyl maltol which is high in yield and produces no wastewater basically is prepared with the preparation method; as the structure of the maltol is similar to that of the ethyl maltol, the preparation method can be general, and all that is required is to adjust other raw materials in the reactions.
A novel heterocyclic atom exchange reaction with Lawesson's reagent: A one-pot synthesis of dithiomaltol
Brayton, Daniel,Jacobsen, Faith E.,Cohen, Seth M.,Farmer, Patrick J.
, p. 206 - 208 (2008/02/07)
A one-pot reaction of maltol with Lawesson's reagent generates dithiomaltol, a thiopyran-4-thione, via an unusual heterocyclic atom exchange (HCAE) reaction; only pyrones with proton or aliphatic substituents undergo the HCAE substitution. The Royal Society of Chemistry 2006.
OXIDATIVE REARRANGEMENT OF FURYLCARBINOLS TO 6-HYDROXY-2H-PYRAN-3(6H)-ONES, A USEFUL SYNTHON FOR THE PREPARATION OF A VARIETY OF HETEROCYCLIC COMPOUNDS. A REVIEW
Georgiadis, Minas P.,Albizati, Kim F.,Georgiadis, Taxiarchis M.
, p. 95 - 118 (2007/10/03)
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