Етилмальтол

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.
- Type
- Складник
- Olfactive family
- Гурманські
- Source
- Purely synthetic; it can be made from kojic acid, furfural or maltol.
- Chemical class
- 4-pyrone
Запах
Докладно
Цікавий факт
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.
Отримання й хімія
Спосіб отримання
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.
- Формула
- C₇H₈O₃
- CAS
- 4940-11-8
- Зовнішній вигляд
- white crystalline powder
- Сила запаху
- Від середньої до сильної
- Синоніми
- 2-Ethyl-3-hydroxy-4H-pyran-4-one, 2-Ethyl pyromeconic acid, 3-Hydroxy-2-ethyl-4-pyrone
No IFRA Standard for the material itself (51st Amendment)
- Температура кипіння
- 289.00 to 290.00 °C. @ 760.00 mm Hg
- Температура плавлення
- 90 - 91 °C
У парфумерії
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.