- Melting point:76 °C
- Boiling point:285°C
- Density 1.1097 (rough estimate)
- vapor pressure <0.01 mm Hg ( 25 °C)
- FEMA 2464 | ETHYL VANILLIN
- refractive index 1.4500 (estimate)
- Flash point:127°C
- storage temp. Store below +30°C.
- solubility 2.82g/l
- form Fine Crystalline Powder
- color White to off-white
- Water Solubility slightly soluble
- Sensitive Light Sensitive
- Merck 14,3859
- JECFA Number893
- BRN 1073761
- CAS DataBase Reference121-32-4(CAS DataBase Reference)
- NIST Chemistry Reference3-Ethoxy-4-hydroxybenzadehyde(121-32-4)
- EPA Substance Registry SystemEthyl vanillin (121-32-4)
- Hazard Codes Xn,Xi
- Risk Statements 22-36/37/38
- Safety Statements 26-36
- WGK Germany 1
- RTECS CU6125000
- Hazard Note Harmful/Irritant/Light Sensitive
- TSCA Yes
- HS Code 29124200
- Hazardous Substances Data121-32-4(Hazardous Substances Data)
- ToxicityLD50 orally in rats: >2000 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964)
Vanillin (4-hydroxy-3-methoxybenzaldehyde) 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. It 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 it 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.
- Chemical PropertiesWHITE TO OFF-WHITE FINE CRYSTALLINE POWDER
- Chemical PropertiesWhite or slightly yellowish crystals with a characteristic intense vanilla odor and flavor.
- Chemical PropertiesIts 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 PropertiesEthyl 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.
- OccurrenceNot reported found in nature; it can be distinguished from vanillin because of the yellow color developed in the presence of concentrated H2SO4.
- UsesEthyl 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.
- UsesIn flavoring and perfumery.
- DefinitionChEBI: A member of the class of benzaldehydes that is vanillin in which the methoxy group is replaced by an ethoxy group.
- Production MethodsUnlike 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.
- PreparationFrom 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.
- Aroma threshold valuesDetection: 100 ppb; recognition: 2 ppm
- Taste threshold valuesTaste characteristics at 50 ppm: sweet, creamy, vanilla, smooth and caramellic.
- Synthesis Reference(s)The Journal of Organic Chemistry, 44, p. 3305, 1979 DOI: 10.1021/jo01333a006
- General DescriptionColorless crystals. More intense vanilla odor and taste than vanillin.
- Air & Water ReactionsSlightly water soluble .
- Reactivity ProfileProtect 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.
- Health HazardACUTE/CHRONIC HAZARDS: Toxic. May cause irritation on contact.
- Fire HazardCombustible
- Pharmaceutical ApplicationsEthyl 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 ProfileModerately 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.
- SafetyEthyl 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
- storageStore in a well-closed container, protected from light, in a cool, dry place. See Vanillin for further information.
- IncompatibilitiesEthyl 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 StatusGRAS listed. Included in the FDA Inactive Ingredients Database (oral capsules, suspensions, and syrups). Included in nonparenteral medicines licensed in the UK.
- Raw materialsEtanolSodium hydroxideChloroformHexamethylenetetraminePyrocatecholChloralPotassium hydroxide solutionCupric oxideGlyoxylic acidSodium 3-nitrobenzenesulphonate1,3-BenzodioxoleISOEUGENOLSafroleDIMETHYLANILINEEthylsulphuric acidN,N-DIMETHYL-4-NITROSOANILINEPROPENYL GUAETHOLHydrogen peroxide 30% water solution2-Ethoxyphenol
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