Veratraldehyde

Veratraldehyde

Names
Preferred IUPAC name 3,4-Dimethoxybenzaldehyde
Systematic IUPAC name 3,4-Dimethoxybenzenecarbaldehyde
Other names Methylvanillin; Veratric aldehyde; Veratral; Veratryl aldehyde; Veratrum aldehyde; Vanillin methyl ether
Identifiers
CAS Number	120-14-9  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17098  Y
ChEMBL	ChEMBL1088937  Y
ChemSpider	21106008  Y
ECHA InfoCard	100.003.976
PubChem CID	8419
UNII	UI88P68JZD  Y
CompTox Dashboard (EPA)	DTXSID7026285
InChI InChI=1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3 Y Key: WJUFSDZVCOTFON-UHFFFAOYSA-N Y InChI=1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3 InChI=1S/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3 Key: WJUFSDZVCOTFON-UHFFFAOYSA-N
SMILES COc1cc(ccc1OC)C=O
Properties
Chemical formula	C9H10O3
Molar mass	166.176 g·mol−1
Appearance	Peach coloured crystals
Density	1.114 g/mL
Melting point	40 to 43 °C (104 to 109 °F; 313 to 316 K)
Boiling point	281 °C (538 °F; 554 K)
Solubility in water	organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

Veratraldehyde (3,4-dimethoxybenzaldehyde) is an organic compound with the formula (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. ^[1] It can be obtained by chemical degradation of lignin. ^[2]

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 ]}

See also

• 3,4,5-Trimethoxybenzaldehyde

References

1. 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
2. Rahimi, Alireza; Azarpira, Ali; Kim, Hoon; Ralph, John; Stahl, Shannon S. (2013). "Chemoselective Metal-Free Aerobic Alcohol Oxidation in Lignin". Journal of the American Chemical Society. 135 (17): 6415–6418. Bibcode:2013JAChS.135.6415R. doi:10.1021/ja401793n. PMID   23570328.