ChemicalBook > Product Catalog > Food Additives > Food flavorings > Artificial flavor > Ethyl maltol
Ethyl maltol Chemical Properties
- Melting point:85-95 °C (lit.)
- Boiling point:196.62°C (rough estimate)
- Density 1.1624 (rough estimate)
- refractive index 1.4850 (estimate)
- FEMA 3487 | ETHYL MALTOL
- storage temp. Sealed in dry,2-8°C
- form neat
- Merck 14,3824
- JECFA Number1481
- CAS DataBase Reference4940-11-8(CAS DataBase Reference)
- NIST Chemistry Reference4H-pyran-4-one, 2-ethyl-3-hydroxy-(4940-11-8)
- EPA Substance Registry System4H-Pyran-4-one, 2-ethyl-3-hydroxy- (4940-11-8)
Ethyl maltol Usage And Synthesis
- Chemical PropertiesWhite crystalline solid with characteristic, very sweet, caramel-like odor and taste. In dilute solution it possesses a sweet, fruitlike flavor and odor.
- Chemical PropertiesIt 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 PropertiesEthyl 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.
- OccurrenceHas apparently not been reported to occur in nature.
- UsesEthyl 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.
- UsesFlavor 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.
- PreparationSeveral 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 MethodsUnlike 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 valuesTaste characteristics at 70 ppm: sweet, burnt cotton, sugar candy-like with jamy, strawberry notes.
- Pharmaceutical ApplicationsEthyl 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 ProfileModerately toxic by ingestion and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
- SafetyIn 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 SynthesisFrom kojic acid
- MetabolismWhen 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).
- storageSolutions 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 StatusGRAS listed. Included in the FDA Inactive Ingredients Database (oral syrup).
Ethyl maltol Preparation Products And Raw materials
- Disodium nucleotide Vanillin ETHYL 2-(2-FORMYLAMINO-1,3-THIAZOL-4-YL)-2-OXOACETATE Sodium ethylxanthogenate Potassium ethylxanthate ETHYLMAGNESIUM BROMIDE ETHYL MALTOL (FOOD GRADE: >99%) ETHYL MALTOL/3-HYDROXY-2-ETHYL-4-PYRONE 3-Diethylaminophenol 2-AMINO-4-CYCLOHEXYL-6-(HYDROXYMETHYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-4-[4-(TERT-BUTYL)PHENYL]-6-(HYDROXYMETHYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-6-(HYDROXYMETHYL)-4-(1-NAPHTHYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-4-[4-(BENZYLOXY)PHENYL]-6-(HYDROXYMETHYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-6-(HYDROXYMETHYL)-8-OXO-4-(2-THIENYL)-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-4-(2-ETHOXYPHENYL)-6-(HYDROXYMETHYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-6-(HYDROXYMETHYL)-8-OXO-4-(4-PYRIDINYL)-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-4-(1,3-BENZODIOXOL-5-YL)-6-(HYDROXYMETHYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE 2-AMINO-6-(HYDROXYMETHYL)-4-(4-METHOXYPHENYL)-8-OXO-4,8-DIHYDROPYRANO[3,2-B]PYRAN-3-CARBONITRILE
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