4-Anisaldehyde

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4-Anisaldehyde[1]
Skeletal formula of anisaldehyde
Ball-and-stick model of the anisaldehyde molecule
Names
IUPAC name
4-Methoxybenzaldehyde
Other names
  • p-Anisaldehyde
  • para-Anisaldehyde
  • Anisic aldehyde
  • Anise aldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.185
UNII
Properties
C8H8O2
Molar mass 136.15 g·mol−1
Density 1.119 g/cm3[2]
Melting point −1 °C (30 °F; 272 K)[2]
Boiling point 248 °C (478 °F; 521 K)[2]
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 (p-anisaldehyde, anisic aldehyde, or 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[edit]

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.[3]

Uses[edit]

Being structurally related to vanillin, anisaldehyde is a widely used in the fragrance and flavor industry.[3] 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.[4] Different chemical compounds on the plate can give different colors, allowing easy distinction.

Drugs[edit]

Drugs made from 4-Anisaldehyde include:

  1. PMA & PMMA
  2. 4-Hydroxyamfetamine
  3. Dasantafil
  4. Tomoxiprole
  5. Benzestrol
  6. Meobentine (via p-methoxybenzylamine made via reduction of the oxime).
  7. Ambucetamide
  8. Metostilenol

References[edit]

  1. ^ Merck Index, 11th Edition, 693
  2. ^ a b c "p-Anisaldehyde". Sigma-Aldrich. 
  3. ^ a b 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
  4. ^ Stains for Developing TLC Plates