Veratraldehyde

{{Chembox

| Watchedfields = changed

| verifiedrevid = 470629641

| ImageFile = Veratrumaldehyd.svg

| ImageSize = 150px

| PIN= 3,4-Dimethoxybenzaldehyde

| SystematicName = 3,4-Dimethoxybenzenecarbaldehyde

| OtherNames = Methylvanillin; Veratric aldehyde; Veratral; Veratryl aldehyde; Veratrum aldehyde; Vanillin methyl ether

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UI88P68JZD

| InChI = 1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3

| InChIKey1 = WJUFSDZVCOTFON-UHFFFAOYSA-N

| InChI1 = 1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 120-14-9

| PubChem = 8419

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 21106008

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17098

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WJUFSDZVCOTFON-UHFFFAOYSA-N

| SMILES = COc1cc(ccc1OC)C=O

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1088937

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3

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|Section2={{Chembox Properties

| C=9 | H=10 | O=3

| Appearance = Peach coloured crystals

| Density = 1.114 g/mL

| MeltingPtC = 40 to 43

| BoilingPtC = 281

| Solubility = organic solvents

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|Section3={{Chembox Hazards

| MainHazards = Harmful

| FlashPt =

| AutoignitionPt =

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Veratraldehyde (3,4-dimethoxybenzaldehyde) is an organic compound with the formula {{chem2|(CH3O)2C6H3CHO}}. Several isomers are known. The compound is widely used as a flavorant and odorant. The compound is structurally related to benzaldehyde, with two methoxy groups.

This compound is popular commercially because of its pleasant woody fragrance. It is derivative of vanillin, from which it is prepared by methylation.Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe and Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2003. {{doi|10.1002/14356007.a11_141}} It can be obtained by chemical degradation of lignin.{{cite journal |doi=10.1021/ja401793n |title=Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin |date=2013 |last1=Rahimi |first1=Alireza |last2=Azarpira |first2=Ali |last3=Kim |first3=Hoon |last4=Ralph |first4=John |last5=Stahl |first5=Shannon S. |journal=Journal of the American Chemical Society |volume=135 |issue=17 |pages=6415–6418 |pmid=23570328 |bibcode=2013JAChS.135.6415R }}

Uses

Veratraldehyde can be used as an intermediate in the synthesis of some pharmaceutical drugs including amiquinsin, hoquizil, piquizil, prazosin, quinazoline, tiapamil, toborinone, verazide, and vetrabutine.{{citation needed|date=October 2018}}

See also

References