Acetanisole

Acetanisole is an aromatic chemical compound with an aroma described as sweet, fruity, nutty, and similar to vanilla. In addition acetanisole can sometimes smell like butter or caramel.[3] Its chemical names are based on considering the structure as either an acetyl (methyl-ketone) analog of anisole. Other names It can also be seen as a methyl ether analog of acetophenone.

Acetanisole
Names
Preferred IUPAC name
1-(4-Methoxyphenyl)ethan-1-one
Other names
4-Acetylanisole; para-Acetanisole; 4-Methoxyacetophenone; Linarodin; Novatone; Vananote; Castoreum anisole; 4-Methoxyphenyl methyl ketone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.560
UNII
  • InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3
  • CC(=O)C1=CC=C(C=C1)OC
Properties
C9H10O2
Molar mass 150.177 g·mol−1
Appearance White to pale yellow crystals[1]
Density 1.094 g/cm3
Melting point 38.2 °C (100.8 °F; 311.3 K)[2]
Boiling point 254 °C (489 °F; 527 K)[2]
2470 mg/L[1]
Hazards
Flash point 138 °C (280 °F)[3]
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

Acetanisole is found naturally in castoreum, the glandular secretion of the beaver.[1]

Preparation

Acetanisole can be prepared synthetically by Friedel-Crafts acylation of anisole with acetyl chloride:

Application

It is used as a cigarette additive,[4] a fragrance,[1] and a flavoring in food.[5]

References
  1. Para-Acetanisole, The Good Scents Company
  2. 4'-Methoxyacetophenone from PubChem
  3. Acetanisole at Sigma-Aldrich
  4. Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine
  5. 21 CFR 172.515
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