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
Structural formula of ethylvanillin
Ball-and-stick model of the ethylvanillin molecule
Names
Preferred IUPAC name
3-Ethoxy-4-hydroxybenzaldehyde
Other names
Bourbonal
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.059
KEGG
UNII
  • 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
  • O=Cc1cc(OCC)c(O)cc1
Properties
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)
Slightly soluble in water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Harmful, irritant
GHS labelling:
GHS07: Exclamation mark
Warning
H319, H402
P264, P273, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored 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

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).[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 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.[2]

References
  1. Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; doi:10.1002/14356007.a11_141.
  2. "Vanillin:Molecule of the Month". Bristol University.
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