Ethylvanillin

Ethylvanillin

Structural formula of ethylvanillin
Ball-and-stick model of the ethylvanillin molecule Ball-and-stick model of the ethylvanillin molecule
File:Ethylvanilin.jpg
Names
Preferred IUPAC name 3-Ethoxy-4-hydroxybenzaldehyde
Other names Bourbonal
Identifiers
CAS Number	121-32-4 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:48408 checkY
ChEMBL	ChEMBL508676 checkY
ChemSpider	8154 checkY
ECHA InfoCard
E number
KEGG	D01086 checkY
PubChem CID	8467
UNII	YC9ST449YJ checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 checkY Key: CBOQJANXLMLOSS-UHFFFAOYSA-N checkY 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	GHS07: Exclamation mark
Signal word	Warning
Hazard statements	H319, H402
Precautionary statements	P264, P273, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)	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). checkY verify (what is checkY☒N ?) 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. It is a homologue of vanillin, differing on the 3 position.

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).

File:Synthesis Ethylvanillin.svg

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.