Basic information
- Standard SMILES
CCc1occc(=O)c1O- InChIKey
YIKYNHJUKRTCJL-UHFFFAOYSA-N- Molecular formula
- C7H8O3
- Average molar mass
- 140.14 g/mol
- Monoisotopic mass
- 140.04734412
Overview
Ethyl maltol is a pyranone.
Names & identifiers
- Preferred name
- Ethyl Maltol
- IUPAC
- 2-ethyl-3-hydroxypyran-4-one
- English name
- Ethyl maltol
- Molecular formula
- C7H8O3
- Molecular weight
- 140.14
Names & synonyms
Show more names
Database identifiers
- CAS
4940-11-8- PubChem CID
- 21059
- DTXSID
DTXSID5041516- ChEMBL
CHEMBL121557- ChEBI
CHEBI:169105- UNII
- L6Q8K29L05
- EC Number
- 225-582-5
- Nikkaji
- J35.389B
Properties
Computed structural properties
- XLogP
- 0.8
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 213
Experimental & physicochemical properties
Solubility
Sparingly soluble in water, soluble in propylene glycol
Soluble (in ethanol)
Physical Description
Solid
White crystalline powder; Sweet fruit-like aroma
Physicochemical properties
- Melting point
- 85 · 85-95 °C (lit.)
- Boiling point
- 196.62 °C · 196.62°C (rough estimate)
- Density
- 1.1624 · 1.1624 (rough estimate)
- vapor pressure
- 0.2 Pa · 0.2Pa at 24℃
- refractive index
- 1.485 · 1.4850 (estimate)
- FEMA
- 3487 · 3487 | ETHYL MALTOL
- FLAVIS Number
- 7.047 · 07.047 | Ethyl maltol
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 8.38 · 8.38±0.10(Predicted)
- form
- Solid
- color
- White to Pale Yellow
- Odor
- 5 % · at 5.00 % in benzyl alcohol. sweet caramel jam strawberry cotton candy
- Odor Type
- caramellic
- biological source
- synthetic
- Water Solubility
- 9.345 g/L · 9.345g/L at 24℃
- Merck
- 14 · 14,3824
- JECFA Number
- 1481 · 1481
- Major Application
- 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
- 2.9 at · 2.9 at 25℃
- CAS DataBase Reference
- 4940 · 4940-11-8(CAS DataBase Reference)
- Substances Added to Food (formerly EAFUS)
- ETHYL MALTOL
- FDA 21 CFR
- 172.515 · 172.515
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 Q8K29L05 · L6Q8K29L05
- NIST Chemistry Reference
- 4 H-pyran-4-one, · 4H-pyran-4-one, 2-ethyl-3-hydroxy-(4940-11-8)
- EPA Substance Registry System
- 4 H-Pyran-4-one, · 4H-Pyran-4-one, 2-ethyl-3-hydroxy- (4940-11-8)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 36 · 36
- WGK Germany
- 3 · 3
- RTECS
- 840000 · UQ0840000
- TSCA
- TSCA listed
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 50 orally · LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla)
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.3% (7 of 2365) of reports.
Warning
H302 (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.
Hazard information
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/22549
4H-Pyran-4-one, 2-ethyl-3-hydroxy-: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- UQ0840000
- hs_code
- 29329990
- Toxicity
- LD50 orally in male mice, male rats, female rats, chicks (mg/kg): 780, 1150, 1200, 1270 (Gralla)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
Uses & manufacturing
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENTFood Additives -> FLAVOUR_ENHANCER; STABILIZER -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Applications
OccurrenceHas apparently not been reported to occur in nature.
HistoryIn 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.
UsesFlavor 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.
UsesEthyl 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.
UsesEthyl 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 DescriptionEthyl 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 methods
PreparationSeveral 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.
PreparationFermentation 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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
DefinitionChEBI: Ethyl maltol is a pyranone.
Related reactions
Linked notes
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