Ethylvanillin

Ethylvanillin
Names
	Preferred IUPAC name 3-Ethoxy-4-hydroxybenzaldehyde
	Other names Bourbonal
Identifiers
CAS Number	121-32-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:48408 ;
ChEMBL	ChEMBL508676 ;
ChemSpider	8154 ;
ECHA InfoCard	100.004.059
KEGG	D01086 ;
PubChem CID	8467;
UNII	YC9ST449YJ ;
CompTox Dashboard (EPA)	DTXSID5021968 ;
	InChI InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 Key: CBOQJANXLMLOSS-UHFFFAOYSA-N ; InChI=1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 Key: CBOQJANXLMLOSS-UHFFFAOYAD;
	SMILES O=Cc1cc(OCC)c(O)cc1;
Properties
Chemical formula	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)
Solubility in water	Slightly soluble in water
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Harmful, irritant
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319, H402
Precautionary statements	P264, P273, P280, P305+P351+P338, P337+P313, P501
NFPA 704 (fire 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). verify (what is ?) 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. 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).^[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

^ ^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.
^ "Vanillin:Molecule of the Month". Bristol University.

[Ullmann-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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[2]