4-Anisaldehyde

4-Anisaldehyde^[1]

Ball-and-stick model of the anisaldehyde molecule

Names

IUPAC name

4-Methoxybenzaldehyde

Identifiers

CAS Number

123-11-5^Y

3D model (Jmol)

28984^Y
21105937

ECHA InfoCard

9PA5V6656V^Y

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

C₈H₈O₂

136.15 g/mol

1.119 g/cm³ at 15 °C

0 °C (32 °F; 273 K)

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 aniseed odor.

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

↑ Merck Index, 11th Edition, 693
1 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
↑ Stains for Developing TLC Plates

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