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Ethyl vanillin is a synthetic organic compound (3-ethoxy-4-hydroxybenzaldehyde) used as a flavoring and fragrance agent.
Ethyl vanillin is an artificial analog of natural vanillin, possessing a sweet, creamy vanilla aroma that is roughly 3 to 4 times stronger than standard vanillin.
Ethyl vanillin is a synthetic aromatic aldehyde widely utilized across the food, beverage, fragrance, and pharmaceutical industries.
CAS No.121-32-4
Chemical Name:Ethyl vanillin
CBNumber:CB7852934
Molecular Formula:C9H10O3
Molecular Weight:166.17
MDL Number:MFCD00006944
MOL File:121-32-4.mol
Synonyms : 3-ETHOXY-4-HYDROXYBENZALDEHYDE, ETHYL VANILIN, Benzaldehyde, 3-ethoxy-4-hydroxy-, Vanirom, FEMA 2464, Rhodiarome, VANILLAL, FEMA 3107, BOURBONAL, Vanbeenol
General Description
Colorless crystals.
More intense vanilla odor and taste than vanillin.
Overview
Vanillin (4-hydroxy-3-methoxybenzaldehyde) (121-32-4) is the primary chemical component of the extract of vanilla bean.
Natural vanilla extract is a mixture of several hundred compounds in addition to vanillin.
Artificial vanilla flavoring solution of pure vanillin, is usually of synthetic origin.
Synthetic vanillin and ethyl vanillin are used as flavoring agents in foods, beverages, and pharmaceuticals.
Ethyl vanillin (3-ethoxy-4-hydroxybenzaldehyde; EVA, Fig. 1) is more expensive and has a stronger flavor.
Compared to vanillin, ethyl vanillin has an ethoxy group (-O-CH2CH3) rather than a methoxy group (-O-CH3).
The largest single use of ethyl vanillin is for flavoring.
Ethyl vanillin is first synthesized from eugenol found in oil of clove and afterward synthesized from lignincontaining sulfite liquor, a by-product of wood pulp processing in paper manufacture.
While some ethyl vanillin is still made from lignin waste, today most synthetic vanillin is synthesized in a two-step process from the petrochemical precursors: vanillin, ethyl vanillin, and guaiacol and, glyoxylic acid.
Vanilla, being the world’s most popular flavoring materials, finds extensive applications in food, beverages, perfumery and pharmaceutical industry.
With the high demand and limited supply of vanilla pods and the continuing increase in their cost, numerous efforts of blending and adulteration in natural vanilla extracts have been reported.
Ethyl vanillin and vanillin, the major phenolic constituents in vanilla products, are widely used as flavoring agents in foods and beverages.
Ethyl vanillin, also used as a synthetic compound, is 2.5 times stronger in flavor than vanillin and used to substitute a large amount of vanillin, since Ethyl vanillin is less expensive and keeps better in storage and transport.
Ethyl vanillin is converted to 3-ethoxy4-hydroxybenzaldehyde and 3-ethoxy-4-hydroxymandelic acid after dietary intake.
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.
Uses
Ethyl Vanillin, is used as a flavorant, which is about three times as potent as vanillin (V097500) and can be utilized in the production of chocolate.
Ethyl vanillin has also shown to have antioxidant properties.
In flavoring and perfumery.
Ethyl Vanillin is a flavoring agent that is a synthetic vanilla flavor with approximately three and one-half times the flavoring power of vanillin.
Ethyl vanillin has a solubility of 1g in 100 ml of water at 50°c.
Ethyl vanillin is used in ice cream, beverages, and baked goods.
Pharmaceutical Applications
Ethyl vanillin is used as an alternative to vanillin, i.e. as a flavoring agent in foods, beverages, confectionery, and pharmaceuticals.
Ethyl Vanillin 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.
Chemical Properties
WHITE TO OFF-WHITE FINE CRYSTALLINE POWDER
Chemical Properties
White or slightly yellowish crystals with a characteristic intense vanilla odor and flavor.
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
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; Ethyl vanillin 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, Ethyl vanillin exhibits a red color and loses its flavoring power.
Occurrence
Not reported found in nature; Ethyl vanillin can be distinguished from vanillin because of the yellow color developed in the presence of concentrated H2SO4.
Definition
ChEBI: A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.
Production Methods
Unlike vanillin, ethyl vanillin does not occur naturally.
Ethyl vanillin may be prepared synthetically by the same methods as vanillin, using guethol instead of guaiacol as a starting material; see Vanillin.
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.
Properties:
Melting point: 74-77 °C (lit.)
Boiling point: 285 °C
Density: 1.1097 (rough estimate)
Vapor pressure: <0.01 mm Hg (25 °C)
Refractive index: 1.4500 (estimate)
FEMA: 2464 | ETHYL VANILLIN
FLAVIS Number: 05.019 | Ethyl vanillin
Flash point: 127 °C
Storage temp.: Store below +30°C.
Solubility: 2.82 g/l
pKa: 7.91±0.18 (Predicted)
Form: Fine Crystalline Powder
Color: White to off-white
Odor: at 10.00 % in dipropylene glycol. sweet creamy vanilla caramel
Odor Type: vanilla
Biological source: synthetic
Water Solubility: slightly soluble
Sensitive: Light Sensitive
Merck: 14,3859
JECFA Number: 893
BRN: 1073761
Henry's Law Constant: 1.2×104 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: Hygroscopic
Major Application:
cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care
Cosmetics Ingredients Functions: SOOTHING, FRAGRANCE
InChI: 1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3
InChIKey: CBOQJANXLMLOSS-UHFFFAOYSA-N
SMILES: [H]C(=O)c1ccc(O)c(OCC)c1
LogP: 1.58 at 25℃
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.
Stability and Storage
Light Sensitivity: Exposure to light can cause oxidation and discoloration.
Incompatibility: Reacts with alkaline substances and iron ions, turning yellow or brown and losing flavor. Avoid direct contact with iron containers.
Storage Temperature: Store in a cool, dry place below 30°C away from direct light.
