| Identification | More | [Name]
Ethyl maltol | [CAS]
4940-11-8 | [Synonyms]
2-ETHYL-3-HYDROXY-4H-PYRAN-4-ONE
2-ETHYL-3-HYDROXY-4-PYRONE
3-HYDROXY-2-ETHYL-4-PYRONE
6-ETHYL-3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE
ETHYL MALTOL
FEMA 3487
2-ethyl-3-hydroxy-4h-pyran-4-on
2-ethylpyromeconicacid
4H-Pyran-4-one,2-ethyl-3-hydroxy-
veltolplus
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
2-Ethyl-3-hydroxy-4H-pyran-4-one, Ethyl maltol
3-hydrox~2-ethyl-4-pyrone
ethyl mantol
3-Hydroxy-2-ethyl-4H-pyran-4-one | [EINECS(EC#)]
225-582-5 | [Molecular Formula]
C8H10O3 | [MDL Number]
MFCD00059795 | [Molecular Weight]
154.16 | [MOL File]
4940-11-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
85-95 °C (lit.) | [Boiling point ]
196.62°C (rough estimate) | [density ]
1.1624 (rough estimate) | [vapor pressure ]
0.2Pa at 24℃ | [FEMA ]
3487 | [refractive index ]
1.4850 (estimate) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [pka]
8.38±0.10(Predicted) | [color ]
White to Pale Yellow | [Odor]
at 5.00 % in benzyl alcohol. sweet caramel jam strawberry cotton candy | [Odor Type]
caramellic | [Water Solubility ]
9.345g/L at 24℃ | [JECFA Number]
1481 | [Merck ]
3824 | [LogP]
2.9 at 25℃ | [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. | [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]
4940-11-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
UQ0840000
| [HS Code ]
29329990 | [Safety Profile]
Moderately toxic by
ingestion and subcutaneous routes.
Mutation data reported. When heated to decomposition it emits acrid smoke and
irritating fumes. | [Toxicity]
LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla) |
| Hazard Information | Back Directory | [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). |
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