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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.059 Edit this at Wikidata
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
Main hazards Harmful, irritant
Except where otherwise noted, data are 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[]

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]

Synthesis Ethylvanillin.svg

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. ^ 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.
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