Ethylvanillin is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

(C₂H₅O)(HO)C₆H₃CHO. This colorless solid consists of a

benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...

ring with

hydroxyl In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

, ethoxy, and formyl groups on the 4, 3, and 1 positions, respectively. It is a homologue of

vanillin Vanillin is an organic compound with the molecular formula . It is a phenolic aldehyde. Its functional groups include aldehyde, hydroxyl, and ether. It is the primary component of the ethanolic extract of the vanilla bean. Synthetic vanillin ...

, differing on the 3 position.

Preparation

Ethylvanillin is prepared from

catechol Catechol ( or ), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula . It is the ''ortho'' isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It ...

, beginning with ethylation to give guaethol (1). This ether condenses with

glyoxylic acid Glyoxylic acid or oxoacetic acid is an organic compound. Together with acetic acid, glycolic acid, and oxalic acid, glyoxylic acid is one of the C2 carboxylic acids. It is a colourless solid that occurs naturally and is useful industrially. Str ...

to give the corresponding

mandelic acid Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The ...

derivative (2), which by oxidation (3) and decarboxylation, gives ethylvanillin (4).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; . : Synthesis Ethylvanillin

Application

As a flavorant, ethylvanillin is about three times as potent as

and is used in the production of

chocolate Chocolate is a food made from roasted and ground cocoa beans that can be a liquid, solid, or paste, either by itself or to flavoring, flavor other foods. Cocoa beans are the processed seeds of the cacao tree (''Theobroma cacao''); unprocesse ...

. The molecule revolutionized both the design and aesthetics of olfactory art; artist

Jacques Guerlain Jacques Edouard Guerlain (; 7 October 1874 – 2 May 1963) was a French perfumer, the third and most famous of the Guerlain family. One of the most prolific and influential perfumers of the 20th century, over eighty of Guerlain's perfumes remain ...

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

{{reflist Flavors Phenol ethers Hydroxybenzaldehydes Perfume ingredients Ethoxy compounds