Ethylvanillin

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Ethylvanillin
Skeletal structure
Ball-and-stick model
Identifiers
CAS number121-32-4 YesY
PubChem8467
ChemSpider8154 YesY
UNIIYC9ST449YJ YesY
KEGGD01086 YesY
ChEBICHEBI:48408 YesY
ChEMBLCHEMBL508676 YesY
Jmol-3D imagesImage 1
Properties
Molecular formulaC9H10O3
Molar mass166.17 g mol−1
Appearancecolourless powder
Density1.186 g/mL
Melting point76 °C (169 °F; 349 K)
Boiling point295.1 °C (563.2 °F; 568.2 K)
Solubility in waterslightly soluble in water
Hazards
Main hazardsHarmful, Irritant
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references
 
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Ethylvanillin
Skeletal structure
Ball-and-stick model
Identifiers
CAS number121-32-4 YesY
PubChem8467
ChemSpider8154 YesY
UNIIYC9ST449YJ YesY
KEGGD01086 YesY
ChEBICHEBI:48408 YesY
ChEMBLCHEMBL508676 YesY
Jmol-3D imagesImage 1
Properties
Molecular formulaC9H10O3
Molar mass166.17 g mol−1
Appearancecolourless powder
Density1.186 g/mL
Melting point76 °C (169 °F; 349 K)
Boiling point295.1 °C (563.2 °F; 568.2 K)
Solubility in waterslightly soluble in water
Hazards
Main hazardsHarmful, Irritant
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/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.

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.