Product Name

  • Name

    Ethyl maltol

  • EINECS 225-582-5
  • CAS No. 4940-11-8
  • Article Data14
  • CAS DataBase
  • Density 1.261 g/cm3
  • Solubility 9.345g/L at 24℃
  • Melting Point 85-95 °C(lit.)
  • Formula C7H8O3
  • Boiling Point 290.3 °C at 760 mmHg
  • Molecular Weight 140.139
  • Flash Point 124.8 °C
  • Transport Information
  • Appearance White crystalline powder
  • Safety 36
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 4940-11-8 (Ethyl maltol)
  • Hazard Symbols HarmfulXn
  • Synonyms 2-Ethyl-3-hydroxy-4-pyrone;2-Ethyl-3-hydroxy-4H-pyran-4-one;2-Ethylpyromeconic acid;3-Hydroxy-2-ethyl-1,4-pyrone;3-Hydroxy-2-ethyl-4-pyrone;3-Hydroxy-2-ethyl-g-pyrone;
  • PSA 50.44000
  • LogP 0.90780

Synthetic route

ethylfurfuryl alcohol
4208-61-1, 119619-55-5, 127418-31-9, 128948-40-3

ethylfurfuryl alcohol

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
With chlorine In methanol; water 1.) -5 deg C; 2.) 90-95 deg C, 3.5 h;67%
With chlorine In methanol; water at 90 - 95℃; for 3.5h; Rearrangement;67%
Stage #1: ethylfurfuryl alcohol With oxygen In methanol at 93℃; Molecular sieve;
Stage #2: With oxygen In methanol at 20℃; for 2h;
Stage #3: With hydrogenchloride In water at 100℃; for 2h; pH=2.5 - 3; Solvent; Temperature;		66.8%
With tert-butylhypochlorite In acetic acid65%
hydroxyethyl maltol

hydroxyethyl maltol

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
With hydrogenchloride; zinc In ethanol at 55℃; for 3h; Temperature;
3-hydroxy-2-ethyl-4H-thiopyran-4-thione

3-hydroxy-2-ethyl-4H-thiopyran-4-thione

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
With Lawessons reagent In 1,4-dioxane for 1h; Heating;
furfural
98-01-1

furfural

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogen / water / 8 h / 90 °C / 15001.5 Torr
2: chlorine / water; methanol / -5 - 60 °C
3: sodium hydroxide / 3 h / 55 °C
4: zinc; hydrogenchloride / ethanol / 3 h / 55 °C
View Scheme
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: chlorine / water; methanol / -5 - 60 °C
2: sodium hydroxide / 3 h / 55 °C
3: zinc; hydrogenchloride / ethanol / 3 h / 55 °C
View Scheme
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

benzyl bromide
100-39-0

benzyl bromide

3-(benzyloxy)-2-ethyl-4H-pyran-4-one
111782-87-7

3-(benzyloxy)-2-ethyl-4H-pyran-4-one

Conditions
ConditionsYield
In acetone for 6h; Reflux;98%
Stage #1: 2-ethyl-3-hydroxy-4-pyranone With sodium hydroxide In methanol Heating;
Stage #2: benzyl bromide In methanol for 6h; Heating; Further stages.;		85%
With sodium hydroxide In ethanol Heating;80%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

benzenesulfonic acid
98-11-3

benzenesulfonic acid

3,4-dihydroxy-2-ethylpyrylium benzenesulfonate

3,4-dihydroxy-2-ethylpyrylium benzenesulfonate

Conditions
ConditionsYield
In methanol for 1h; Reflux;98%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

salicylic acid
69-72-7

salicylic acid

2-ethyl-3-hydroxy-4-pyrone/salicylic acid 1:1 cocrystals
1325228-63-4

2-ethyl-3-hydroxy-4-pyrone/salicylic acid 1:1 cocrystals

Conditions
ConditionsYield
In methanol at 64℃; for 1h;98%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

methyl iodide
74-88-4

methyl iodide

2-ethyl-3-methoxy-4Hpyran-4-one
50741-69-0

2-ethyl-3-methoxy-4Hpyran-4-one

Conditions
ConditionsYield
With potassium carbonate In acetone for 4h; Inert atmosphere; Reflux;97%
With potassium carbonate In acetone at 25℃; for 4h;93%
With potassium carbonate In acetone for 8h; Reflux;
dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

sodium methylate
124-41-4

sodium methylate

Rh(C5(CH3)5)Cl(C5H2O3C2H5)
173413-66-6

Rh(C5(CH3)5)Cl(C5H2O3C2H5)

Conditions
ConditionsYield
In methanol byproducts: NaCl; N2-atmosphere; stoich. amts., refluxing for 3 h; solvent removal, extn. into CH2Cl2, filtration (Celite), evapn., recrystn. (CH2Cl2/light petroleum);96%
...Expand
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

titanium tetrachloride
7550-45-0

titanium tetrachloride

bis-ethylmaltoldichloro-titanium(IV)

bis-ethylmaltoldichloro-titanium(IV)

Conditions
ConditionsYield
In tetrahydrofuran ethylmaltol stirred with anhyd. THF at room temp., TiCl4 added dropwise to soln., stirred at room. temp for 30 min; filtered, washed with Et2O, recrystd. from CH2Cl2-petroleum ether (1:1);95%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

{(η6-1,3,5-Me3C6H3)RuCl2}2

{(η6-1,3,5-Me3C6H3)RuCl2}2

sodium methylate
124-41-4

sodium methylate

(C6(CH3)3H3)RuCl(OOC5H2C2H5O)
151781-33-8

(C6(CH3)3H3)RuCl(OOC5H2C2H5O)

Conditions
ConditionsYield
In methanol; water byproducts: NaCl; Sodium methoxide and ethylmaltol are added to a suspn. of the Ru-compd. in CH3OH/H2O and the mixt. is refluxed for 2 h.; The solvent is removed. The residue is dissolved in CH2Cl2. After filtn. the solvent is evaporated, recrystn. from CH2Cl2/diethylether, elem. anal.;80%
...Expand
zinc(II) sulfate heptahydrate

zinc(II) sulfate heptahydrate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

C14H14O6Zn
98445-51-3

C14H14O6Zn

Conditions
ConditionsYield
Stage #1: 2-ethyl-3-hydroxy-4-pyranone With lithium hydroxide monohydrate In water at 20℃; for 0.5h;
Stage #2: zinc(II) sulfate heptahydrate In water at 20℃; for 5h;		77%
vanadyl sulfate trihydrate

vanadyl sulfate trihydrate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

bis(ethylmaltolato)(ethylmaltol)oxovanadium(IV) monohydrate

bis(ethylmaltolato)(ethylmaltol)oxovanadium(IV) monohydrate

Conditions
ConditionsYield
In water VOSO4*3H2O and ethylmaltol (molar ratio 1:2) suspended in water at 45°C; pptd. over 15-20 min; cooled to room temp.; filtered; ppt. air dried; elem. anal.;72%
oxovanadium(IV) sulfate

oxovanadium(IV) sulfate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

salicylaldehyde
90-02-8

salicylaldehyde

anthranilic acid hydrazide
1904-58-1

anthranilic acid hydrazide

C21H18N3O6V

C21H18N3O6V

Conditions
ConditionsYield
Stage #1: salicylaldehyde; anthranilic acid hydrazide In methanol for 0.5h;
Stage #2: oxovanadium(IV) sulfate; 2-ethyl-3-hydroxy-4-pyranone In methanol for 0.5h;		72%
...Expand
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

4-tert-Butylaniline
769-92-6

4-tert-Butylaniline

1-(4-(tert-butyl)phenyl)-2-ethyl-3-hydroxypyridin-4(1H)-one

1-(4-(tert-butyl)phenyl)-2-ethyl-3-hydroxypyridin-4(1H)-one

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 160℃; for 12h; pH=5; Autoclave;70%
lanthanum(III) nitrate hexahydrate

lanthanum(III) nitrate hexahydrate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

La(ethylmaltol(1-))3
960499-98-3

La(ethylmaltol(1-))3

Conditions
ConditionsYield
With triethylamine In ethanol Ln(NO3)*6H2O was added to soln. ligand in EtOH and heated until ligand completely dissolved, Et3N was added and stirred for 18-24 h; ppt. was filtered, washed with cold water and cold MeOH and dried in vacuo; elem. anal.;68%
bis(acetylacetonate)oxovanadium
3153-26-2

bis(acetylacetonate)oxovanadium

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

2-chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide

2-chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide

C23H20ClN2O7V

C23H20ClN2O7V

Conditions
ConditionsYield
Stage #1: bis(acetylacetonate)oxovanadium; 2-ethyl-3-hydroxy-4-pyranone; 2-chloro-N′-(3-ethoxy-2-hydroxybenzylidene)benzohydrazide In methanol at 20℃; for 0.5h;
Stage #2: With air In methanol		68%
...Expand
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

tin(II) n-butoxide
14254-05-8, 26306-46-7, 130287-64-8

tin(II) n-butoxide

Sn(ethylmaltol)2
361148-46-1

Sn(ethylmaltol)2

Conditions
ConditionsYield
In toluene a soln. of hydroxyketone in toluene was added a stirred soln. of Sn-compound in toluene under N2, the soln. was stirred for 2 h then left at room temp.; elem. anal.;66%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

2-ethyl-3-hydroxy-5-bromo-4H-pyran-4-one
95790-62-8

2-ethyl-3-hydroxy-5-bromo-4H-pyran-4-one

Conditions
ConditionsYield
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 95℃; for 18h; Inert atmosphere;66%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 95℃; Inert atmosphere; Schlenk technique;32%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 95℃; for 18h; Inert atmosphere; Schlenk technique;
oxovanadium(IV) sulfate

oxovanadium(IV) sulfate

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

2-hydroxy-3-bromobenzaldehyde
1829-34-1

2-hydroxy-3-bromobenzaldehyde

3-hydroxybenzoic hydrazide
5818-06-4

3-hydroxybenzoic hydrazide

C21H16BrN2O7V

C21H16BrN2O7V

Conditions
ConditionsYield
Stage #1: 2-hydroxy-3-bromobenzaldehyde; 3-hydroxybenzoic hydrazide In methanol for 0.5h;
Stage #2: oxovanadium(IV) sulfate; 2-ethyl-3-hydroxy-4-pyranone In methanol for 0.5h;		65%
...Expand
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

europium(III) nitrate hexahydrate

europium(III) nitrate hexahydrate

Eu(ethylmaltol(1-))3*2.5H2O

Eu(ethylmaltol(1-))3*2.5H2O

Conditions
ConditionsYield
With triethylamine In ethanol Ln(NO3)*6H2O was added to soln. ligand in EtOH and heated until ligand completely dissolved, Et3N was added and stirred for 18-24 h; ppt. was filtered, washed with cold water and cold MeOH and dried in vacuo; elem. anal.;64%
2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

benzyl chloride
100-44-7

benzyl chloride

ethanolamine
141-43-5

ethanolamine

3-Benzyloxy-1,2-diethyl-1H-pyridin-4-one

3-Benzyloxy-1,2-diethyl-1H-pyridin-4-one

Conditions
ConditionsYield
Stage #1: 2-ethyl-3-hydroxy-4-pyranone; benzyl chloride With sodium hydroxide In methanol; ethanol; water
Stage #2: ethanolamine With sodium hydroxide In methanol; ethanol; water		63%
Stage #1: 2-ethyl-3-hydroxy-4-pyranone; benzyl chloride With sodium hydroxide In methanol; water
Stage #2: ethanolamine With sodium hydroxide In ethanol; water		63%
...Expand
bis(acetylacetonate)oxovanadium
3153-26-2

bis(acetylacetonate)oxovanadium

2-ethyl-3-hydroxy-4-pyranone
4940-11-8

2-ethyl-3-hydroxy-4-pyranone

N′-(3-ethoxy-2-hydroxybenzylidene)pivalohydrazide

N′-(3-ethoxy-2-hydroxybenzylidene)pivalohydrazide

C21H25N2O7V

C21H25N2O7V

Conditions
ConditionsYield
In methanol at 20℃; for 0.5h;62%
...Expand

Ethyl Maltol Chemical Properties

The Molecular Structure of Ethyl maltol (CAS NO.4940-11-8) :

Empirical Formula: C7H8O3
Molecular Weight: 140.1366 
IUPAC Name: IUPAC: 2-ethyl-3-hydroxypyran-4-one 
Nominal Mass: 140 Da
Average Mass: 140.1366 Da
Monoisotopic Mass: 140.047344 Da 
Index of Refraction: 1.54
Molar Refractivity: 34.91 cm3
Molar Volume: 111.1 cm3
Surface Tension: 47 dyne/cm
Density: 1.261 g/cm3
Flash Point: 124.8 °C
Enthalpy of Vaporization: 61.46 kJ/mol
Boiling Point: 290.3 °C at 760 mmHg 
Melting Point: 85-95 °C
Vapour Pressure: 0.000228 mmHg at 25°C 
InChI
InChI=1/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3
Smiles
c1(c(ccoc1CC)=O)O 
Synonyms: 5-18-01-00135 (Beilstein Handbook Reference) ; BRN 1618110 ; EINECS 225-582-5 ; FEMA No. 3487 ; UNII-L6Q8K29L05   
It is a stable white crystalline powder at room temperature and easily dissolves in many polar liquids. Ethyl Maltol (CAS NO.4940-11-8) has a sweet odor that can be described as caramalized sugar and cooked fruit. Ethyl Maltol  (CAS NO.4940-11-8) can be easily detected by the human, with as little as 10 parts per million perceivable in air.

Ethyl Maltol Uses

  Ethyl Maltol (CAS NO.4940-11-8) is an important flavourant for the food, beverage, and fragrance industry. It is a sweet, synergistic agent used in TOBACCO, food, wines,beverages, essences,  cosmetics and other consumables, It has a remarkable effect on improving and increasing the flavor of foods and it enhances the sweetness of foods.

Ethyl Maltol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 oral 1270mg/kg (1270mg/kg)   Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.
 
mouse LD50 oral 780mg/kg (780mg/kg)   Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.
 
mouse LD50 subcutaneous 910mg/kg (910mg/kg)   Chemical and Pharmaceutical Bulletin. Vol. 22, Pg. 1008, 1974.
 
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Food and Cosmetics Toxicology. Vol. 13, Pg. 805, 1975.
rat LD50 oral 1150mg/kg (1150mg/kg)   Toxicology and Applied Pharmacology. Vol. 15, Pg. 604, 1969.
 

Ethyl Maltol Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22
R22: Harmful if swallowed
Safety Statements: 36 
S36: Wear suitable protective clothing

Ethyl Maltol Specification

 Ethyl maltol (CAS NO.4940-11-8) is also called as 2-Ethyl pyromeconic acid ; 2-Ethyl-3-hydroxy-4H-pyran-4-one ; 2-Ethylpyromeconic acid ; 3-Hydroxy-2-ethyl-1,4-pyrone ; 3-Hydroxy-2-ethyl-4-pyrone ; 3-Hydroxy-2-ethyl-4H-pyran-4-one ; 3-Hydroxy-2-ethyl-gamma-pyrone ; 4H-Pyran-4-one, 2-ethyl-3-hydroxy- ; Veltol plus ; 2-Ethyl-3-hydroxy-4-pyrone ; 4H-Pyran-4-one, 2-ethyl-3-hydroxy- .

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