Ethylvanillin

Ethylvanillin

Names
Other names 3-ethoxy-4-hydroxybenzaldehyde, bourbonal
Identifiers
CAS Number	121-32-4 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:48408 Y
ChEMBL	ChEMBL508676 Y
ChemSpider	8154 Y
ECHA InfoCard	100.004.059
KEGG	D01086 Y
PubChem	8467
UNII	YC9ST449YJ Y
InChI InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 Y Key: CBOQJANXLMLOSS-UHFFFAOYSA-N Y InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 Key: CBOQJANXLMLOSS-UHFFFAOYAD
SMILES O=Cc1cc(OCC)c(O)cc1
Properties
Chemical formula	C9H10O3
Molar mass	166.18 g·mol−1
Appearance	colourless powder
Density	1.186 g/mL
Melting point	76 °C (169 °F; 349 K)
Boiling point	295.1 °C (563.2 °F; 568.2 K)
Solubility in water	slightly soluble in water
Hazards
Main hazards	Harmful, Irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ethylvanillin is the organic compound with the formula (C₂H₅O)(HO)C₆H₃CHO. This colorless solid consists of a benzene ring with hydroxyl, ethoxy, and formyl groups on the 4, 3, and 1 positions, respectively.

Preparation

Ethylvanillin is a synthetic molecule, not found in nature. It is prepared via several steps from catechol, beginning with ethylation to give "guethol" (1). This ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative (2), which via oxidation (3) and decarboxylation gives ethylvanillin (4).^[1]

Application

As a flavorant, ethylvanillin is about three times as potent as vanillin and is used in the production of chocolate.^[1]

The molecule revolutionized both the design and aesthetics of olfactory art; artist Aimé Guerlain used it in "Jicky" (1889), one of the earliest uses of the synthetic molecules that freed scent artists from the limits of natural materials.^[2]

References