Ethyl Maltol

HCID 21059CAS 4940-11-8

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

Ethyl maltol2-Ethyl-3-hydroxy-4H-pyran-4-one4940-11-82-Ethyl-3-hydroxy-4-pyroneEthylmaltolVeltol plus3-Hydroxy-2-ethyl-4-pyrone2-ethyl-3-hydroxypyran-4-one2-Ethylpyromeconic acid4H-PYRAN-4-ONE, 2-ETHYL-3-HYDROXY-2-Ethyl pyromeconic acidDTXSID5041516
Show more names
FEMA 34876-ETHYL-3-HYDROXY-2-METHYL-4H-PYRAN-4-ONE2-ethyl-3-hydroxy-4-pyranoneveltolplusethyl mantol
Ethyl HydroxypyroneFEMA No. 3487L6Q8K29L05NSC638851NSC-638851DTXCID3021516RefChem:138985225-582-5

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

Experimental & physicochemical properties

FragrancesFragrance Ingredient (Ethyl maltol) -> IFRA transparency List
LogP0.630
Food AdditivesCOLOR OR COLORING ADJUNCT, FLAVORING AGENT OR ADJUVANT, PROCESSING AID -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 2 items

Sparingly soluble in water, soluble in propylene glycol

Soluble (in ethanol)

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 4 items

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

Hazard Classes and CategoriesAcute Tox. 4 (99.7%)

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

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Household ProductsInformation on 92 consumer products that contain Ethyl Hydroxypyrone in the following categories is provided:
Use Classification · 3 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENTFood Additives -> FLAVOUR_ENHANCER; STABILIZER -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

General Manufacturing Information4H-Pyran-4-one, 2-ethyl-3-hydroxy-: ACTIVE
Applications · 6 items

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 · 2 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

Additional notes

DefinitionChEBI: Ethyl maltol is a pyranone.

Related reactions

26 records

Linked notes

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