Ethylvanillin

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. It is a homologue of vanillin, differing on the 3 position.

Ethylvanillin

Names
Preferred IUPAC name 3-Ethoxy-4-hydroxybenzaldehyde
Other names Bourbonal
Identifiers
CAS Number	121-32-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48408 Y
ChEMBL	ChEMBL508676 Y
ChemSpider	8154 Y
KEGG	D01086 Y
PubChem CID	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	166.176 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
Occupational safety and health (OHS/OSH):
Main hazards	Harmful, irritant
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319, H402
Precautionary statements	P264, P273, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)	<imagemap> File:NFPA 704.svg|80px|alt=NFPA 704 four-colored diamond poly 150 150 300 300 150 450 0 300 Health 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroform poly 300 0 450 150 300 300 150 150 Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil poly 450 150 600 300 450 450 300 300 Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen poly 300 300 450 450 300 600 150 450 Special hazards (white): no code desc none </imagemap> 2 1 0
Flash point	145 °C (293 °F; 418.15K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Preparation

Ethylvanillin is prepared from catechol, beginning with ethylation to give guaethol (1). This ether condenses with glyoxylic acid to give the corresponding mandelic acid derivative (2), which by oxidation (3) and decarboxylation, gives ethylvanillin (4).

Application

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

The molecule revolutionized both the design and aesthetics of olfactory art; artist Jacques Guerlain added a large quantity of it to a bottle of Jicky (1889) perfume, creating the main accord for the perfume house's flagship fragrance, Shalimar (perfume) (1925). This is one of the earliest uses of synthetic molecules that freed scent artists from the limits of natural materials.