{{Chembox | Watchedfields = changed | verifiedrevid = 443745711 | Name = Ethylvanillin | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = Ethylvanillin.svg | ImageSize = 170px | ImageAlt = Structural formula of ethylvanillin | ImageFile1 = Ethylvanillin 3D ball.png | ImageSize1 = 190px | ImageAlt1 = Ball-and-stick model of the ethylvanillin molecule | ImageName1 = Ball-and-stick model of the ethylvanillin molecule | ImageFile2 = Ethylvanilin.jpg | PIN = 3-Ethoxy-4-hydroxybenzaldehyde | OtherNames = Bourbonal | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8154 | PubChem = 8467 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = YC9ST449YJ | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D01086 | InChI = 1/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 48408 | SMILES = O=Cc1cc(OCC)c(O)cc1 | InChIKey = CBOQJANXLMLOSS-UHFFFAOYAD | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 508676 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = CBOQJANXLMLOSS-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 121-32-4 }} | Section2 = {{Chembox Properties | C=9|H=10|O=3 | Appearance = Colourless powder | Density = 1.186 g/mL | Solubility = Slightly soluble in water | MeltingPtC = 76 | BoilingPtC = 295.1 }} | Section3 = {{Chembox Hazards | MainHazards = Harmful, irritant | NFPA-H = 2 | NFPA-F = 1 | NFPA-I = 0 | NFPA-S = | GHSPictograms = {{GHS exclamation mark}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|319|402}} | PPhrases = {{P-phrases|264|273|280|305+351+338|337+313|501}} | FlashPt = 145 °C (293 °F; 418.15K) }} }}
'''Ethylvanillin''' is the organic compound with the formula (C<sub>2</sub>H<sub>5</sub>O)(HO)C<sub>6</sub>H<sub>3</sub>CHO. 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''').<ref name=Ullmann>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}}.</ref> :500px
== Application == As a flavorant, ethylvanillin is about three times as potent as vanillin and is used in the production of chocolate.<ref name=Ullmann/> Its aroma is described as "sweet, creamy, vanilla, caramellic, root beer".<ref>{{cite web |title=ethyl vanillin|url=https://scentsandflavors.com/database/9dbb4f46-3dc4-49b0-abbf-37bbe749f602|website=Scents and Flavors |publisher=Scents and Flavors |access-date=1 April 2026}}</ref>
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).<ref>{{Cite web |title=Духи Guerlain Shalimar - Парфюм Герлен Шалимар. |url=https://duhishalimar.ru/ |access-date=2025-04-03 |website=duhishalimar.ru}}</ref> This is one of the earliest uses of synthetic molecules that freed scent artists from the limits of natural materials.<ref>{{cite web | url = http://www.chm.bris.ac.uk/motm/vanillin/vanillinh.htm | title = Vanillin:Molecule of the Month | publisher = Bristol University}}</ref>{{POV statement|date=November 2025}}
== References == {{reflist}}
Category:Flavors Category:Phenol ethers Category:4-Hydroxybenzaldehyde derivatives Category:Perfume ingredients Category:Ethoxy compounds