General Description
Colorless crystals. More intense vanilla odor and taste than vanillin.
Reactivity Profile
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.
Air & Water Reactions
Slightly water soluble .
Health Hazard
ACUTE/CHRONIC HAZARDS: Toxic. May cause irritation on contact.
Chemical Properties
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.
Chemical Properties
Its odor resembles that of vanillin but is
approximately three times as strong. Ethylvanillin can be prepared by method 2
as described for vanillin, using guethol instead of guaiacol as the starting material.
Chemical Properties
White or slightly yellowish crystals with a characteristic intense
vanilla odor and flavor.
Chemical Properties
WHITE TO OFF-WHITE FINE CRYSTALLINE POWDER
Occurrence
Not reported found in nature; it can be distinguished from vanillin because of the yellow color developed in
the presence of concentrated H2SO4.
Uses
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.
Uses
In flavoring and perfumery.
Definition
ChEBI: A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.
Preparation
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.
Production Methods
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.
Aroma threshold values
Detection: 100 ppb; recognition: 2 ppm
Taste threshold values
Taste characteristics at 50 ppm: sweet, creamy, vanilla, smooth and caramellic.
Flammability and Explosibility
Nonflammable
Pharmaceutical Applications
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.
Safety
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
storage
Store in a well-closed container, protected from light, in a cool, dry
place. See Vanillin for further information.
Incompatibilities
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.
Regulatory Status
GRAS listed. Included in the FDA Inactive Ingredients Database
(oral capsules, suspensions, and syrups). Included in nonparenteral
medicines licensed in the UK.
