Ethyl Maltol
2-ETHYL-3-HYDROXY-4-PYRONE · 2-ETHYL-3-HYDROXY-4H-PYRAN-4-ONE · FEMA 3487 · 6-ETHYL-3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE · ETHYL HYDROXYPYRONE · 3-HYDROXY-2-ETHYL-4-PYRONE · 2-ethyl-3-hydroxypyran-4-one · 2-ethyl-3-hydroxy-4-pyranone
Identifiers & Physical Properties
| CAS No. | 4940-11-8 |
|---|---|
| Molecular formula | C7H8O3 |
| Average molar mass | 140.14 g/mol |
| Monoisotopic mass | 140.04734412 g/mol |
| SMILES | CCc1occc(=O)c1O |
| InChIKey | YIKYNHJUKRTCJL-UHFFFAOYSA-N |
| PubChem CID | 21059 |
| ChEMBL | CHEMBL121557 |
| ChEBI | CHEBI:169105 |
| EC No. | 225-582-5 |
| DTXSID | DTXSID5041516 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 46.5 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 213 |
| Fragrances | Fragrance Ingredient (Ethyl maltol) -> IFRA transparency List |
| LogP (partition coefficient) | 0.630 |
| Food additives | COLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT, PROCESSING AID -> FDA Substance added to food |
| Flavoring agents | EU Flavoring substances |
| Solubility | Sparingly soluble in water, soluble in propylene glycolSoluble (in ethanol)Chloroform (Slightly), Methanol (Slightly)9.345g/L at 24℃ |
| Animal Drugs | Pharmaceuticals -> UK Veterinary Medicines Directorate List |
| Boiling point | 289.00 to 290.00 °C. @ 760.00 mm Hg196.62°C (rough estimate) |
| Melting point | 90 - 91 °C85-95 °C (lit.) |
| Physical Description | SolidWhite crystalline powderSweet fruit-like aroma |
| Density | 1.1624 (rough estimate) |
| Vapor pressure | 0.2Pa at 24℃ |
| Refractive index | 1.4850 (estimate) |
| FEMA | 3487 | ETHYL MALTOL |
| FLAVIS Number | 07.047 | Ethyl maltol |
| Storage conditions | 2-8°C |
| pKa (acidity coefficient) | 8.38±0.10(Predicted) |
| Physical state | Solid |
| Color | White to Pale Yellow |
| Odor | at 5.00 % in benzyl alcohol. sweet caramel jam strawberry cotton candy |
| Odor type | caramellic |
| Biological source | synthetic |
| Merck | 14,3824 |
| JECFA Number | 1481 |
| Major applications | cleaning productscosmeticsflavors and fragrancesfood and beveragespersonal care |
| Cosmetics Ingredients Functions | PERFUMINGFRAGRANCE |
| InChI | 1S/C7H8O3/c1-2-6-7(9)5(8)3-4-10-6/h3-4,9H,2H2,1H3 |
| InChIKey | YIKYNHJUKRTCJL-UHFFFAOYSA-N |
| SMILES | CCC1=C(O)C(=O)C=CO1 |
| LogP (partition coefficient) | 2.9 at 25℃ |
| CAS DataBase Reference | 4940-11-8(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | ETHYL MALTOL |
| FDA 21 CFR | 172.515 |
| EWG's Food Scores | 1 |
| FDA UNII | L6Q8K29L05 |
| NIST Chemistry Reference | 4H-pyran-4-one, 2-ethyl-3-hydroxy-(4940-11-8) |
| EPA Substance Registry System | 4H-Pyran-4-one, 2-ethyl-3-hydroxy- (4940-11-8) |
| UNSPSC Code | 85151701 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302 |
| GHS precautionary statements | P301+P312+P330 |
| Hazard symbols | Xn |
| Risk statements (R) | 22 |
| Safety statements (S) | 36 |
| Water hazard class (WGK) | 3 |
| RTECS number | UQ0840000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29329990 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 Oral |
| Toxicity | LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.3% (7 of 2365) of reports.WarningH302 (99.7%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2365 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: 4H-Pyran-4-one, 2-ethyl-3-hydroxy-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Active Update: 15-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/225494H-Pyran-4-one, 2-ethyl-3-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Acute Tox. 4 (99.7%) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | UQ0840000 |
| Customs code | 29329990 |
| Toxicity | LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla) |
| Risk statements (R) | 22 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H302 |
| REACH registrations | Active |
| Hazard class | Acute Tox. 4 Oral |
| GHS precautionary statements | P301+P312+P330 |
Applications & Uses
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.
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.
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.
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.
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.
Preparation & Synthesis
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.
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.