Етилванілін

СинтетичнийПОПУЛЯРНІ Й НЕЗВИЧНІгурманський · солодкий · вершковий
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Етилванілін як парфумерна сировина
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Ethylvanillin is a synthetic vanilla flavouring agent and a homologue of vanillin. Its aroma is described as sweet, creamy, vanilla, caramellic and root beer.

СОЛОДКИЙ ВЕРШКОВИЙ ВАНІЛЬНИЙ КАРАМЕЛЬНИЙ
Ethyl vanillin, 3-ethoxy-4-hydroxybenzaldehyde, Bourbonal, Ethovan, Vanillal, Ethylprotal
Type
Складник
Olfactive family
Гурманські
Source
synthetic molecule
Chemical class
benzaldehyde, phenol, aromatic ether
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти
Країни-виробники
Сполучені Штати

Запах

The odour resembles that of vanillin but is approximately three times as strong. Crystals of the material have a characteristic intense vanilla odour. A root berry salicylate-like nuance accompanies the sweet, creamy vanilla character. The detection threshold is 100 ppb and the recognition threshold is 2 ppm.

Докладно

Chemistry

Ethylvanillin is the organic compound 3-ethoxy-4-hydroxybenzaldehyde, with the molecular formula C₉H₁₀O₃. The molecule is a benzene ring that carries a hydroxyl group at position 4, an ethoxy group at position 3 and a formyl group at position 1. Ethylvanillin is vanillin in which the methoxy group is replaced by an ethoxy group. It is a homologue of vanillin, differing at the 3 position. Ethylvanillin belongs to the class of benzaldehydes and is also a phenol and an aromatic ether.

Properties

Ethylvanillin appears as colorless crystals. The crystals can be slightly yellowish and occur as flakes or fine needles. Ethylvanillin is slightly soluble in water and soluble in ethanol, ether, benzene and chloroform. Its solubility in water is 2,822 mg/L at 25 °C, and in 95% alcohol it is about 1 g in 2 mL. The material dissolves freely in solutions of alkali hydroxides and is soluble in glycerol and propylene glycol. It is affected by light. In contact with iron or alkali, it shows a red colour and loses its flavouring power. Because less material is needed to produce an equivalent vanilla flavour, it may cause less discoloration to a formulation. An acceptable daily intake of up to 3 mg/kg body weight has been allocated.

Occurrence and comparison with vanillin

Vanillin and ethylvanillin are both used by the food industry; ethylvanillin is more expensive but has a stronger note.

Production

Reported production volume was 10,000,000 to under 25,000,000 pounds in each year from 2020 to 2023. For 2012, the reported national production volume was 1,000,000 to 10,000,000 pounds per year.

Safety

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Related: Almond · Benzoin · Butterscotch · Caramel · Chocolate · Cinnamon · Coffee · Coumarin

Цікавий факт

The harmony of a perfume of the 1920s was created when a perfumer poured a bottle of ethylvanillin into a bottle of a fragrance created in 1889. Reducing the benzaldehyde group of ethylvanillin to a methyl group gives a compound called Ultravanil, also named vanilla cresol.

Отримання й хімія

Спосіб отримання

Ethylvanillin is prepared from catechol, beginning with ethylation to give guaethol. The ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative, which by oxidation and decarboxylation gives ethylvanillin. It may also be prepared synthetically by the same methods as vanillin, using guethol instead of guaiacol as the starting material. Guaethol can also be condensed with chloral to give 3-ethoxy-4-hydroxyphenyl trichloromethyl carbinol, which is boiled with an alcoholic solution of KOH or NaOH, acidified and extracted with chloroform to yield ethyl vanillin. Another route runs from safrole by isomerization to isosafrole and oxidation to piperonal, followed by breaking the methylene linkage of piperonal with alcoholic KOH.

Формула
C₉H₁₀O₃
CAS
121-32-4
Зовнішній вигляд
white to off-white powder
Синоніми
Ethyl vanillin, 3-ethoxy-4-hydroxybenzaldehyde, Bourbonal, Ethovan, Vanillal, Ethylprotal
Статус IFRA
Див. примітку

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

Фізичні властивості
Температура кипіння
285.00 to 294.00 °C. @ 760.00 mm Hg
Температура плавлення
76.00 to 78.00 °C. @ 760.00 mm Hg
Температура спалаху
145 °C (293 °F), closed cup

У парфумерії

Ethylvanillin is used in flavouring and perfumery. It is used in perfumes, cosmetics, air fresheners and pharmaceuticals, as well as in the food industry. As a flavorant, it is about three times as potent as vanillin and is used in the production of chocolate. It is used in ice cream, beverages and baked goods. It enhances fruity and chocolate odour impression. Its addition is self-limiting, as too high a level may impart an unpleasant flavour in the product. It is used in tobacco flavor formulations. Ethylvanillin is involved in the synthesis of methyl dilantilis.

Роль у формулі
01фіксатор
02модифікатор
03кістяк
04фірмова нота
Форми випуску
синтетична речовина

Див. також

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