Etil-maltol

SintetičkaPOPULARNO I NEOBIČNOsladak · topao · gurmanski
Srednje note·Bazne notePiramida
3½/5Jačina
—Trajnost
—Poreklo
Uzorak
Etil-maltol kao sirovina za parfeme
Srednje i bazne note
Definicija

Ethyl maltol is a synthetic 4-pyrone that is related to maltol by replacement of the methyl group with an ethyl group. It is a white solid with a sweet smell that can be described as caramelized sugar or as caramelized fruit.

SLADAK GURMANSKI TOPAO KARAMELAST
2-Ethyl-3-hydroxy-4H-pyran-4-one, 2-Ethyl pyromeconic acid, 3-Hydroxy-2-ethyl-4-pyrone
Type
Sirovina
Olfactive family
Gurmanski
Source
Purely synthetic; it can be made from kojic acid, furfural or maltol.
Chemical class
4-pyrone
Instrumenti
Piramida
GGornje note
SSrednje note
BBazne note
3½/5Jačina
Srednje visoka
jačina mirisa

Miris

Its aroma is described as sweet, caramellic, jammy, strawberry, cotton candy, berry and sugar. Its odor character is similar to that of maltol but more intense and sweeter. Maltol has a more caramel-like odor, while ethylmaltol is fruitier.

Detaljno

What it is

The preferred IUPAC name of ethyl maltol is 2-ethyl-3-hydroxy-4H-pyran-4-one. It is a common flavourant in some confectioneries. It is a white crystalline powder with the formula C₇H₈O₃ and a molar mass of about 140.14 g/mol.

Natural and synthetic

Maltol is also produced during the roasting of malt and in the baking of bread. Maltol has the odor of caramel and is used to impart a pleasant aroma to foods and fragrances. Ethyl maltol itself is purely synthetic.

Chemistry

The conjugate base derived from ethyl maltol has a high affinity for iron, forming a red coordination complex. In such compounds, the heterocycle is a bidentate ligand. Ethyl maltol is sparingly soluble in water and soluble in propylene glycol. It is also soluble in ethanol.

Specification

The JECFA specification describes ethyl maltol as a white crystalline powder with a characteristic odour and requires an assay of not less than 98%. Its melting range is 89 to 93 °C. Water content may not exceed 0.5%, sulfated ash may not exceed 0.2%, and lead may not exceed 1 mg/kg. It carries the INS number 637 and the functional classes flavouring agent and flavour enhancer.

Uses and regulation

Ethyl maltol is used as an additive in a wide range of beverages, perfumes, ice cream, cakes, confections, e-liquids, cigarettes and oral medications. In the European Union it has the food additive code E 637. Because of its lack of toxicity, it is approved to be dosed quantum satis, which means as much as necessary. It has been evaluated by JECFA and EFSA. Typical concentrations in food range between 1 and 100 ppm, depending on the application.

Food and drink tests

Ten parts per million of ethyl maltol in grape juice greatly amplifies the natural sweet grape aroma, and pineapple juice flavor is pleasingly enhanced at 4 ppm. Sherry wine has an improved flavor at 5 ppm, an orange-type liqueur is sweetened at 10 ppm, and the fruit flavor of a low calorie orange drink is enhanced at 1 ppm. In chocolate bars it increases the richness of the chocolate flavor, creates a blended taste and lifts the aroma. Creme candies containing 20 ppm had significantly better flavors than candies without it. In a strawberry-flavored gelatin dessert, ethyl maltol at about one fifth to one half of the maltol level gives a more flavorful product than maltol does.

Comparison with maltol

In a patent test of dilute solutions, the sample containing 500 ppm of maltol had about the same odor intensity as the sample containing 100 ppm of ethyl maltol.

In e-liquids

Explore all seven extraits in the Discovery Set.

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Related: Acetyl Furan · Ambermax · Ambrofix · Egg · Flour · Furfural · Genepi · Gold

Zanimljivosti

Added alone to a perfume base solvent at 10 ppm, ethyl maltol gave a pleasant cotton-candy like aroma when sprayed into an area. Its aroma was found to be 6 times as strong as that of maltol. Maltol can replace four times its weight of coumarin as a flavor and aroma enhancer. Maltol takes its name from malt, in which it is produced during roasting.

Dobijanje i hemija

Način dobijanja

Numerous syntheses of ethylmaltol have been developed, most of which fall into two approaches based on their starting materials. One approach starts from a 4-pyrone such as kojic acid, which is readily available through fermentation. In one version, kojic acid is oxidized with molecular oxygen to comenic acid, which is then decarboxylated to yield pyromeconic acid. An aldol addition with acetaldehyde followed by reduction of the newly introduced secondary hydroxy group affords ethylmaltol in four steps overall. The second approach takes advantage of furfural. Furfural originates from the acid-catalyzed dehydration of agricultural biomass and is converted with an ethyl Grignard compound to an alcohol. Oxidation state adjustment of this alcohol through an Achmatowicz rearrangement, initiated by anodic oxidation, chlorine gas or tert-butyl hypochlorite, provides pyran-3-ones. Further oxidation and acid- or heat-induced rearrangement furnishes ethylmaltol. A route to ethylmaltol from naturally abundant maltol has also been disclosed. In the finalized procedure, maltol is deprotonated with sodium hydride and treated with TBSCl to give a silyl ether, which is deprotonated with LiHMDS and C-methylated with methyl iodide at 0 °C.

Formula
C₇H₈O₃
CAS
4940-11-8
Izgled
white crystalline powder
Jačina mirisa
Srednji do jak
Sinonimi
2-Ethyl-3-hydroxy-4H-pyran-4-one, 2-Ethyl pyromeconic acid, 3-Hydroxy-2-ethyl-4-pyrone
Status prema standardima IFRA
Pogledajte napomenu

No IFRA Standard for the material itself (51st Amendment)

Fizička svojstva
Tačka ključanja
289.00 to 290.00 °C. @ 760.00 mm Hg
Tačka topljenja
90 - 91 °C

U parfemima

Ethyl maltol is often used in perfumery to create gourmand scents. Dissolved in a floral base cologne at 4 to 250 ppm, ethyl maltol significantly enhanced the aromas of the perfumes. It bridges fruity and vanillic materials and extends sweetness, and it rounds and smooths fruity-lactonic blends.

Uloga u formuli
01modifikator
02graditelj volumena
03pojačivač difuzije
Oblici na tržištu
standardni oblik

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