4-Anisaldehyde

4-Anisaldehyde^[1]

Names
IUPAC name 4-Methoxybenzaldehyde
Identifiers
CAS Number	123-11-5
ChEMBL	ChEMBL161598
ChemSpider	28984 21105937
Jmol interactive 3D	Image
PubChem	31244
UNII	9PA5V6656V
InChI InChI=1S/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 Key: ZRSNZINYAWTAHE-UHFFFAOYSA-N InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3 Key: ZRSNZINYAWTAHE-UHFFFAOYAA
SMILES COc1ccc(C=O)cc1
Properties
Chemical formula	C8H8O2
Molar mass	136.15 g/mol
Density	1.119 g/cm^3 at 15 °C
Melting point	0 °C (32 °F; 273 K)
Boiling point	248 °C (478 °F; 521 K)
Hazards
Flash point	108 °C (226 °F; 381 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

4-Anisaldehyde (also: p-anisaldehyde, anisic aldehyde, anise aldehyde) is an organic compound that is commonly encountered in fragrances, both synthetic and natural. The compound consists of a benzene ring with an aldehyde and a methoxy group. It is a clear liquid with a strong aroma. Two related isomers, ortho-anisaldehyde and meta-anisaldehyde, are also known but less commonly encountered. It provides sweet, floral and strong almond odor. Atul Ltd, India is the largest manufacturer of Anisaldehyde in the world.

Production

Anisaldehyde is prepared commercially by oxidation of methoxytoluene (p-cresyl methyl ether) using manganese dioxide. It can also be produced by oxidation of anethole, a related fragrance that is found in some alcoholic beverages.^[2]

Uses

Being structurally related to vanillin, anisaldehyde is a widely used in the fragrance and flavor industry.^[2] Anisaldehyde is used as an intermediate in the synthesis of other compounds important in pharmaceuticals and perfumery. ortho-Anisaldehyde has a scent of licorice.

A solution of para-anisaldehyde in acid and ethanol is a useful stain in thin layer chromatography.^[3] Different chemical compounds on the plate can give different colors, allowing easy distinction.

References

1. Merck Index, 11th Edition, 693
2. 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
3. Stains for Developing TLC Plates