Ethylvanillin is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

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 betwee ...

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

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

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, differing on the 3 position.

Preparation

Ethylvanillin is prepared from

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

, 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. Th ...

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

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 extract of the vanilla bean. Synthetic vanillin is now used ...

and is used in the production of

chocolate Chocolate is a food made from roasted and ground cacao seed kernels that is available as a liquid, solid, or paste, either on its own or as a flavoring agent in other foods. Cacao has been consumed in some form since at least the Olmec civ ...

. The molecule revolutionized both the design and aesthetics of

olfactory art Olfactory art is an art form that uses scents as a medium. Olfactory art includes perfume as well as other applications of scent. The art form has been a recognized genre since at least 1980. Marcel Duchamp was one of the first artists who pioneer ...

; 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 Jicky is a perfume originally created by Aimé Guerlain in 1889 for French perfume and cosmetics house Guerlain. Introduced in 1889, it is the oldest continuously-produced perfume in the world. History Jicky was one of the first perfumes crea ...

(1889) perfume, creating the main accord for the perfume house's flagship fragrance,

Shalimar (perfume) Shalimar is a perfume originally created by Jacques Guerlain in 1921 for French perfume and cosmetics house Guerlain. In production continuously since 1925, Shalimar is currently a flagship product for Guerlain. History Shalimar was created b ...

(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