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.
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]
Applicationedit
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]
Referencesedit
^ abKarl-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.
January 01, 1970
ethylvanillin, organic, compound, with, formula, c2h5o, c6h3cho, this, colorless, solid, consists, benzene, ring, with, hydroxyl, ethoxy, formyl, groups, positions, respectively, homologue, vanillin, differing, position, names, preferred, iupac, name, ethoxy, . 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 Ethylvanillin Names Preferred IUPAC name 3 Ethoxy 4 hydroxybenzaldehyde Other names Bourbonal Identifiers CAS Number 121 32 4 Y 3D model JSmol Interactive image ChEBI CHEBI 48408 Y ChEMBL ChEMBL508676 Y ChemSpider 8154 Y ECHA InfoCard 100 004 059 KEGG D01086 Y PubChem CID 8467 UNII YC9ST449YJ Y 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 YKey CBOQJANXLMLOSS UHFFFAOYSA N YInChI 1 C9H10O3 c1 2 12 9 5 7 6 10 3 4 8 9 11 h3 6 11H 2H2 1H3Key CBOQJANXLMLOSS UHFFFAOYAD SMILES O Cc1cc OCC c O cc1 Properties Chemical formula C 9H 10O 3 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 210 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 Y verify what is Y N Infobox referencesPreparation editEthylvanillin 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 nbsp Application editAs 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 edit 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 Retrieved from https en wikipedia org w index php title Ethylvanillin amp oldid 1192551339, wikipedia, wiki, book, books, library,
