Chemistry:Ethylvanillin
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]
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Application
As a flavorant, ethylvanillin is about three times as potent as vanillin and is used in the production of chocolate.[1] Its aroma is described as "sweet, creamy, vanilla, caramellic, root beer".[2] Besides its applications in the food industry, ethylvanillin is also widely used in perfumes, cosmetics, air fresheners, and pharmaceuticals.[3]
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).[4] This is one of the earliest uses of synthetic molecules that freed scent artists from the limits of natural materials.[5][neutrality is disputed]
Ethylvanillin [121-32-4] is involved in the synthesis of methyl dilantilis.[6]
Reduction of the benzaldehyde group in ethylvanillin to a methyl group yields a compound called Ultravanil (vanilla cresol) [2563-07-7].
References
- ↑ 1.0 1.1 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.
- ↑ "ethyl vanillin". Scents and Flavors. https://scentsandflavors.com/database/9dbb4f46-3dc4-49b0-abbf-37bbe749f602.
- ↑ "Buy Bulk - Ethyl Vanillin | Manufacturer-Supplier" (in en-GB). 2025-04-18. https://sinofoodsupply.com/food-supplier-manufacturer/ethyl-vanillin/.
- ↑ "Духи Guerlain Shalimar - Парфюм Герлен Шалимар.". https://duhishalimar.ru/.
- ↑ "Vanillin:Molecule of the Month". Bristol University. http://www.chm.bris.ac.uk/motm/vanillin/vanillinh.htm.
- ↑ "Synthesis of Methyl Diantilis, a Commercially Important Fragrance". Journal of Chemical Education 83 (2): 285. February 2006. doi:10.1021/ed083p285. https://pubs.acs.org/doi/abs/10.1021/ed083p285.
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