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Ethylvanillin

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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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.059 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3Key: CBOQJANXLMLOSS-UHFFFAOYSA-N
  • InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3Key: CBOQJANXLMLOSS-UHFFFAOYAD
SMILES
  • O=Cc1cc(OCC)c(O)cc1
Properties
Chemical formula C9H10O3
Molar mass 166.176 g·mol
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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).

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.

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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