3-этокси-4-гидроксибензальдегид

Химические свойства

Ethyl vanillin has an intense vanilla odor and sweet taste. The flavoring power is two to four times stronger than vanillin. Ethyl vanillin has been used in food since the 1930s; it enhances fruity and chocolate odor impression. Its addition is self-limiting, as too high a level may impart an unpleasant flavor in the product; the product is not stable. In contact with iron or alkali, it exhibits a red color and loses its flavoring power.

Вхождение

Not reported found in nature; it can be distinguished from vanillin because of the yellow color developed in the presence of concentrated H2SO4.

Использование

Ethyl Vanillin is a flavoring agent that is a synthetic vanilla flavor with approximately three and one-half times the flavoring power of vanillin. it has a solubility of 1 g in 100 ml of water at 50°c. it is used in ice cream, beverages, and baked goods.

Подготовка

From safrole by isomerization to isosafrole and subsequent oxidation to piperonal; the methylene linkage is then broken by heating piperonal in an alcoholic solution of KOH; finally the resulting protocatechualdehyde is reacted with ethyl alcohol. From guaethol by condensation with chloral to yield 3-ethoxy-4-hydroxyphenyl trichloromethyl carbinol; this is then boiled with an alcoholic solution of KOH or NaOH, acidified, and extracted with chloroform to yield ethyl vanillin.

Методы производства

Unlike vanillin, ethyl vanillin does not occur naturally. It may be prepared synthetically by the same methods as vanillin, using guethol instead of guaiacol as a starting material; see Vanillin.

Определение

ChEBI: A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.

Общее описание

Colorless crystals. More intense vanilla odor and taste than vanillin.

Реакции воздуха и воды

Slightly water soluble .

Профиль реактивности

Protect from light. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Угроза здоровью

ACUTE/CHRONIC HAZARDS: Toxic. May cause irritation on contact.

Пожароопасность

Combustible

Фармацевтические приложения

Ethyl vanillin is used as an alternative to vanillin, i.e. as a flavoring agent in foods, beverages, confectionery, and pharmaceuticals. It is also used in perfumery.
Ethyl vanillin possesses a flavor and odor approximately three times as intense as vanillin; hence the quantity of material necessary to produce an equivalent vanilla flavor may be reduced, causing less discoloration to a formulation and potential savings in material costs. However, exceeding certain concentration limits may impart an unpleasant, slightly bitter taste to a product due to the intensity of the ethyl vanillin flavor.

Профиль безопасности

Moderately toxic by ingestion, intraperitoneal, subcutaneous, and intravenous routes. A human skin irritant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES and ETHERS.

Безопасность

Ethyl vanillin is generally regarded as an essentially nontoxic and nonirritant material. However, cross-sensitization with other structurally similar molecules may occur.
The WHO has allocated an acceptable daily intake for ethyl vanillin of up to 3 mg/kg body-weight.
LD50 (guinea pig, IP): 1.14 g/kg
LD50 (mouse, IP): 0.75 g/kg
LD50 (rabbit, oral): 3 g/kg
LD50 (rabbit, SC): 2.5 g/kg
LD50 (rat, oral): 1.59 g/kg
LD50 (rat, SC): 3.5–4.0 g/kg

хранилище

Store in a well-closed container, protected from light, in a cool, dry place. See Vanillin for further information.

Несовместимости

Ethyl vanillin is unstable in contact with iron or steel, forming a redcolored, flavorless compound. In aqueous media with neomycin sulfate or succinylsulfathiazole, tablets of ethyl vanillin produced a yellow color. See Vanillin for other potential incompatibilities.

Регуляторный статус

GRAS listed. Included in the FDA Inactive Ingredients Database (oral capsules, suspensions, and syrups). Included in nonparenteral medicines licensed in the UK.