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4940-11-8

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Identification

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

Melting point 
85-95 °C (lit.)
mp 
85-95 °C(lit.)

Boiling point 
196.62°C (rough estimate)
density 
1.1624 (rough estimate)
refractive index 
1.4850 (estimate)
FEMA 
3487
storage temp. 
Sealed in dry,2-8°C
form 
neat
pka
8.38±0.10(Predicted)
Merck 
3824
JECFA Number
1481
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

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)

Raw materials And Preparation Products

Hazard Information

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.
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
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
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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