Ethyl Vanillin

Product Name:

Ethyl vanillin

Synonyms:

AKOS BBS-00003203;AKOS B004185;FEMA 2464;FEMA 3107;ETHYLPROTAL;Ethyl protocatechualdehyde 3-ethyl ether;ETHYL PROTOCATECHUIC ALDEHYDE;ETHYL VANILLIN

CAS:

121-32-4

MF:

C9H10O3

MW:

166.17

EINECS:

204-464-7

Product Categories:

Pharmaceutical Raw Materials;Food and Feed Additive;Flavor;Food Additives;Food & Feed ADDITIVES;Aromatic Aldehydes & Derivatives (substituted)

Mol File:

121-32-4.mol

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)

Fp 

127°C

storage temp. 

Store below +30°C.

solubility 

2.82g/l

pka

7.91±0.18(Predicted)

form 

Fine Crystalline Powder

color 

White to off-white

Water Solubility 

slightly soluble

Sensitive 

Light Sensitive

Merck 

14,3859

JECFA Number

893

BRN 

1073761

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)

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)

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 vanil[1]lin. 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.

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.

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 alco[1]holic 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.

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

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.

Raw materials

Etanol-->Sodium hydroxide-->Chloroform-->Hexamethylenetetramine-->Pyrocatechol-->Chloral-->Potassium hydroxide solution-->Cupric oxide-->Glyoxylic acid-->Sodium 3-nitrobenzenesulphonate-->1,3-Benzodioxole-->ISOEUGENOL-->Safrole-->DIMETHYLANILINE-->Ethylsulphuric acid-->N,N-DIMETHYL-4-NITROSOANILINE-->PROPENYL GUAETHOL-->Hydrogen peroxide 30% water solution-->2-Ethoxyphenol