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121-32-4

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121-32-4 Usage

Overview

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[1].

Chemical Properties

Different sources of media describe the Chemical Properties of 121-32-4 differently. You can refer to the following data:
1. WHITE TO OFF-WHITE FINE CRYSTALLINE POWDER
2. White or slightly yellowish crystals with a characteristic intense vanilla odor and flavor.
3. 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.
4. 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

Different sources of media describe the Uses of 121-32-4 differently. You can refer to the following data:
1. 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.
2. 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.
3. 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 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

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 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.

Check Digit Verification of cas no

The CAS Registry Mumber 121-32-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 121-32:
(5*1)+(4*2)+(3*1)+(2*3)+(1*2)=24
24 % 10 = 4
So 121-32-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3

121-32-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A19478)  3-Ethoxy-4-hydroxybenzaldehyde, 98%   

  • 121-32-4

  • 25g

  • 191.0CNY

  • Detail
  • Alfa Aesar

  • (A19478)  3-Ethoxy-4-hydroxybenzaldehyde, 98%   

  • 121-32-4

  • 100g

  • 350.0CNY

  • Detail
  • Alfa Aesar

  • (A19478)  3-Ethoxy-4-hydroxybenzaldehyde, 98%   

  • 121-32-4

  • 500g

  • 1482.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1268)  Ethylvanillin  pharaceutical secondary standard; traceable to USP

  • 121-32-4

  • PHR1268-1G

  • 732.19CNY

  • Detail
  • USP

  • (1267500)  Ethylvanillin  United States Pharmacopeia (USP) Reference Standard

  • 121-32-4

  • 1267500-200MG

  • 4,326.66CNY

  • Detail

121-32-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl vanillin

1.2 Other means of identification

Product number -
Other names burbonal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fragrances
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:121-32-4 SDS

121-32-4Related news

Effect of vanillin and Ethyl vanillin (cas 121-32-4) on cytochrome P450 activity in vitro and in vivo09/07/2019

Food safety is of extreme importance to human health. Vanillin and ethyl vanillin are the widely used food additives and spices in foods, beverages, cosmetics and drugs. The objective of the present work was to evaluate the impact of vanillin and ethyl vanillin on the activities of CYP2C9, CYP2E...detailed

Corrigendum J. Chem. Thermodynamics 105 (2017) 345–351 “Solid–liquid phase equilibrium and dissolution properties of Ethyl vanillin (cas 121-32-4) in pure solvents”09/06/2019

Errors are discovered regarding the published equation coefficients of Wu and co-workers {J. Chem. Thermodynamics 105 (2017) 345–351} for mathematically describing the solubility behaviour of ethyl vanillin in neat solvents using the λh equation. The calculated values using the published equat...detailed

Control of undeclared flavoring of cocoa powders by the determination of vanillin and Ethyl vanillin (cas 121-32-4) by HPLC09/05/2019

A simple protocol for the extraction of vanillin and ethyl vanillin in cocoa powders, followed by analyte quantification using HPLC, has been proposed in this work. After optimizing both, extraction and separation conditions, both analytes were determined in less than 4 min, with relative standa...detailed

Solid–liquid phase equilibrium and dissolution properties of Ethyl vanillin (cas 121-32-4) in pure solvents09/04/2019

The solubility of ethyl vanillin (EVA) in eight pure solvents were determined in different temperature ranges from (273.15 to 318.15) K by a static analytical method. In the temperature ranges investigated, it was found that the solubility of EVA in all the selected solvents increased with the r...detailed

121-32-4Relevant articles and documents

Significant lability of guaiacylglycerol β-phenacyl ether under alkaline conditions

Imai, Alko,Yokoyama, Tomoya,Matsumoto, Yuji,Meshitsuka, Gyosuke

, p. 9043 - 9046 (2007)

It was observed that the β-O-4 bond cleavage of a dimeric phenolic lignin model compound with an α-carbonyl group at the B-ring, 2-(2-ethoxy-4-formylphenoxy)-1-(4-hydroxy-3-methoxyphenyl)propane-1,3-diol (I), is extremely fast in a mild anaerobic alkaline treatment (0.45 mol/L NaOH, 95°C, 0.8 MPa of N2). This phenomenon significantly contrasts with the case of a common dimeric phenolic lignin model compound without any specific functional group, 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy) propane-1,3-diol (II). The most plausible mechanism is the migration of the B-ring from the β- to the α-position following the SNAr mechanism. Because this migration affords the alkaline labile phenolic α-O-4-type compound (XI), the formation of the quinone methide as well as the cleavage of the originally alkaline very stable alkyl-aryl ether bond is promoted. This promotion of the quinone methide formation explains why a relatively large amount of 4-hydroxy-3-methoxybenzaldehyde (IV) is produced from I in an oxygen-alkali treatment.

Method for continuously preparing vanillin and syringaldehyde

-

Paragraph 0023-0031; 0032; 0033; 0034, (2020/01/08)

The invention relates to the technical field of organic synthesis, in particular to a method for continuously preparing vanillin and syringaldehyde. According to the method for continuously preparingthe vanillin and the syringaldehyde, the vanillin and the syringaldehyde are continuously synthesized and produced by taking the p-hydroxy benzaldehyde as the raw material, and the vanillin and the syringaldehyde are obtained by directly etherifying brominated products without refining in the process, so that the aims of shortening the process, improving the yield, reducing the cost, being safe and environment-friendly and easily realizing industrial production are achieved.

Magnetic nano-structured cobalt-cobalt oxide/nitrogen-doped carbon material as an efficient catalyst for aerobic oxidation of p-cresols

Liang, Cheng,Li, Xuefeng,Su, Diefeng,Ma, Qiyi,Mao, Jianyong,Chen, Zhirong,Wang, Yong,Yao, Jia,Li, Haoran

, p. 121 - 131 (2018/05/22)

Efficient aerobic oxidation has been developed for the selective preparation of a sequence of valuable p-hydroxybenzaldehydes from corresponding p-cresols, using a new magnetically separable catalyst of nano-structured cobalt-cobalt oxide/nitrogen-doped carbon (CoOx@CN) material. CoOx@CN showed high activity for the 2-methoxy-4-cresol oxidation to vanillin, giving great yield (90%) and with good turnover number (210), as well as other p-cresols in good to great yields. The catalytic performance was investigated and related to the structural, chemical and magnetic properties which determined by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), Fourier-transform infrared spectroscopy (FT-IR) and vibrating sample magnetometer (VSM). The effects of base to substrate molar ratio, catalyst concentration, temperature, and solvent on the conversion and selectivity patterns also have been studied. The investigation revealed that remarkable catalytic properties of CoOx@CN could be ascribed to the active species cobalt oxide, doped nitrogen and porous carbon with large surface area. The size of the catalyst is a key factor for catalyst performance. The ferromagnetic property of catalyst enables to recycle easily by an external magnetic field and reuse six successive times without significant activity loss.

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