Ethyl maltol
- Iupac Name：2-ethyl-3-hydroxypyran-4-one
- CAS No.: 4940-11-8
- Molecular Weight：140.138
- Modify Date.: 2022-11-25 02:22
- Introduction:
Ethyl maltol (2-Ethyl-3-hydroxy-4H-pyran-4-one) is an odor-active (OA) compound[1].
DryPowder; Liquid|Solid
Ethyl maltol is a pyranone.
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1. Names and Identifiers
- 1.1 Name
- Ethyl maltol
- 1.2 Synonyms
2-Ethyl pyromeconic acid 2-Ethyl-3-hydroxy-4H-pyran-4-one 2-Ethyl-3-hydroxy-4H-pyran-4-one, Ethyl maltol 2-Ethyl-3-hydroxy-4-pyrone 3-HYDROXY-2-ETHYL-4-PYRONE 3-Hydroxy-2-ethyl-4-pyrone,ethyl maltol 4H-Pyran-4-one, 2-ethyl-3-hydroxy- 6-ETHYL-3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE EINECS 225-582-5 Ethylmaltol (Subject To Patent Free) ETHYLMALTOL FCCIV MFCD00059795 PYRAN-4-ONE,3-HYDROXY-2-METHYL-,2-ETHYLESTER Veltol plus
- 1.3 CAS No.
- 4940-11-8
- 1.4 CID
- 21059
- 1.5 EINECS(EC#)
- 225-582-5
- 1.6 Molecular Formula
- C7H8O3 (isomer)
- 1.7 Inchi
- InChI=1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3
- 1.8 InChkey
- YIKYNHJUKRTCJL-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CCC1=C(C(=O)C=CO1)O
- 1.10 Isomers Smiles
- CCC1=C(C(=O)C=CO1)O
2. Properties
- 2.1 Density
- 1.261
- 2.1 Melting point
- 85-95℃
- 2.1 Boiling point
- 290.3 oCat 760 mmHg
- 2.1 Refractive index
- 1.4850 (estimate)
- 2.1 Flash Point
- 124.8 oC
- 2.1 Precise Quality
- 140.04700
- 2.1 PSA
- 50.44000
- 2.1 logP
- 0.90780
- 2.1 Appearance
- DryPowder; Liquid
- 2.2 Storage
- Solutions may be stored in glass or plastic containers. The bulkmaterial should be stored in a well-closed container, protected fromlight, in a cool, dry place.
- 2.3 Chemical Properties
- White crystalline solid with characteristic, very sweet, caramel-likeodor and taste. In dilute solution it possesses a sweet, fruitlike flavorand odor.
- 2.4 Physical
- Solid
- 2.5 pKa
- 8.38±0.10(Predicted)
- 2.6 Water Solubility
- Sparingly soluble in water, soluble in propylene glycol
- 2.7 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 GHS Classification
- Signal: Warning
GHS Hazard StatementsAggregated GHS information provided by 1419 companies from 7 notifications to the ECHA C&L Inventory.
Reported as not meeting GHS hazard criteria by 5 of 1419 companies. For more detailed information, please visit
ECHA C&L websiteOf the 6 notification(s) provided by 1414 of 1419 companies with hazard statement code(s):
H302 (100%): Harmful if swallowed [
Warning Acute toxicity, oral]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501
- 3.2 Produe Method
- Unlike maltol, ethyl maltol does not occur naturally. It may beprepared by treating a-ethylfurfuryl alcohol with a halogen toproduce 4-halo-6-hydroxy-2-ethyl-2H-pyran-3(6H)-one, which isconverted to ethyl maltol by hydrolysis.
4. Safety and Handling
- 4.1 Symbol
- GHS07
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R22
- 4.1 Safety Statements
- S36
- 4.1 Hazard Declaration
- H302
- 4.1 RIDADR
- 25kgs
- 4.1 Safety Profile
- Moderately toxic by ingestion and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
- 4.2 Caution Statement
- P301 + P312 + P330
- 4.2 WGK Germany
- 3
- 4.2 RTECS
- UQ0840000
- 4.2 Safety
-
Hazard Codes:?
Xn
Risk Statements:?22
R22: Harmful if swallowed
Safety Statements:?36?
S36: Wear suitable protective clothing
- 4.3 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- .
- 4.4 Toxicity
- LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla)
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
4940-11-8Total: 1 Synthesis Route
9. Other Information
- 9.0 Mesh Entry Terms
- 3-hydroxy-2-ethyl-4-pyrone
- 9.1 Production
- 100,000 - 500,000 lb
- 9.2 Manufacturing Info
- All other chemical product and preparation manufacturing|4H-Pyran-4-one, 2-ethyl-3-hydroxy-: ACTIVE
- 9.3 Use Classification
- Food additives -> Flavoring Agents
- 9.4 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.
- 9.5 Preparation
- 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.
- 9.6 Flammability and Explosibility
- Notclassified
- 9.7 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.
- 9.8 Safety Profile
- Moderately toxic by ingestion and subcutaneous routes. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
- 9.9 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
- 9.10 Synthesis
- From kojic acid
- 9.11 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).
- 9.12 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.
- 9.13 Regulatory Status
- GRAS listed. Included in the FDA Inactive Ingredients Database (oral syrup).
- 9.14 Merck
- 14,3824
- 9.15 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.
- 9.16 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
- 9.17 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.
- 9.18 Occurrence
- Has apparently not been reported to occur in nature.
- 9.19 Uses
- 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.
- 9.20 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.
- 9.21 Uses
- 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.
- 9.22 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.
- 9.23 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.
- 9.24 Taste threshold values
- Taste characteristics at 70 ppm: sweet, burnt cotton, sugar candy-like with jamy, strawberry notes.
- 9.25 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.
10. Computational chemical data
- Molecular Weight: 140.138g/mol
- Molecular Formula: C7H8O3
- Compound Is Canonicalized: True
- XLogP3-AA: 0.8
- Exact Mass: 140.047344113
- Monoisotopic Mass: 140.047344113
- Complexity: 213
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 3
- Topological Polar Surface Area: 46.5
- Heavy Atom Count: 10
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAgAAAAAAAAAAAAAAAAGgAACAAACASggAICAAAABgCIAKBSAAIACAAgIAAICABAAEgAAAAAAAAAQAAAQAAIAYIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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