Ethyl vanillin Chemical 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

Flash point:

127°C

storage temp. 

Store below +30°C.

solubility 

2.82g/l

form 

Fine Crystalline Powder

pka

7.91±0.18(Predicted)

color 

White to off-white

Odor

at 10.00 % in dipropylene glycol. sweet creamy vanilla caramel

Odor Type

vanilla

Water Solubility 

slightly soluble

Sensitive 

Light Sensitive

Merck 

14,3859

JECFA Number

893

BRN 

1073761

Stability:

Hygroscopic

LogP

1.58 at 25℃

CAS DataBase Reference

121-32-4(CAS DataBase Reference)

NIST Chemistry Reference

3-Ethoxy-4-hydroxybenzadehyde(121-32-4)

EPA Substance Registry System

Ethyl vanillin (121-32-4)

Safety Information

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 Data

121-32-4(Hazardous Substances Data)

Toxicity

LD50 orally in rats: >2000 mg/kg, P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964)

MSDS

• Language:English Provider:3-Ethoxy-4-hydroxybenzaldehyde
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Ethyl vanillin Usage And Synthesis

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. 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&rsquo;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^[1].

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; 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.

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 used as a flavorant, which is about three times as potent as vanillin (V097500) and can be utilized in the production of chocolate. It has also shown to have antioxidant properties.

Uses

In flavoring and perfumery.

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.

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. It 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.

Aroma threshold values

Detection: 100 ppb; recognition: 2 ppm

Taste threshold values

Taste 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 Description

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

Air & Water Reactions

Slightly water soluble .

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.

Health Hazard

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

Fire Hazard

Combustible

Flammability and Explosibility

Non flammable

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 Profile

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.

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.

Ethyl vanillin(121-32-4)Related Product Information

• 2-Ethoxyethanol
• 3-Methoxysalicylaldehyde
• Veratraldehyde
• 3-Hydroxybenzaldehyde
• ISOXADIFEN-ETHYL
• Trinexapac-ethyl
• Ethoxyquin
• Ethylbenzene
• Ethylparaben
• 4-Hydroxybenzaldehyde
• Vanillin
• Cuminaldehyde
• 2-Nitrobenzaldehyde
• 4-Hydroxy-3-methylbenzaldehyde
• 4-Dimethylaminobenzaldehyde
• 2,3,4-Trihydroxybenzoic acid
• Ethyl formate
• Dimethyl ether