Ethylvanillin

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Ethylvanillin
Structural formula of ethylvanillin
Ball-and-stick model of the ethylvanillin molecule
Names
Other names
3-ethoxy-4-hydroxybenzaldehyde, bourbonal
Identifiers
121-32-4 YesY
ChEBI CHEBI:48408 YesY
ChEMBL ChEMBL508676 YesY
ChemSpider 8154 YesY
Jmol-3D images Image
KEGG D01086 YesY
PubChem 8467
UNII YC9ST449YJ YesY
Properties
C9H10O3
Molar mass 166.17 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
Main hazards Harmful, Irritant
Except where noted otherwise, data is 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[edit]

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]

Synthesis Ethylvanillin.svg

Application[edit]

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[edit]

  1. ^ a b 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.