Acetanisole

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
Properties
C9H10O2
Molar mass 150.18 g·mol−1
Appearance White to pale yellow crystals[1]
Density 1.094 g/cm3
Melting point 38.5 °C (101.3 °F; 311.6 K)[2]
Boiling point 258 °C (496 °F; 531 K)[2]
2470 mg/L[2]
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 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]

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]

  1. In the pharmaceutical sector, acetanisole is used in the synthesis of Benfurodil hemisuccinate.
  2. It can also be used to synthesize basic stimulant compounds such as methyl-synephrine and methyl-hordenine, which were detected in the energy supplement Meltdown®.[6]
  3. In the case of m-acetanisole, this regioisomer was used to synthesize oxyfedrine.
  4. Sulfarlem (Anethole trithione) for treating Parkinson's disease.

Appearance

At room temperature 4-Methoxyacetophenone is solid, and has a white crystal like structure. Once melted, the white crystals turn into a clear liquid.

References

  1. 1 2 3 Para-Acetanisole, The Good Scents Company
  2. 1 2 3 Acetanisole in the ChemIDplus database
  3. 1 2 Acetanisole at Sigma-Aldrich
  4. ↑ Tobacco Documents | Profiles | Additives | Acetanisole Archived 2008-04-11 at the Wayback Machine.
  5. ↑ 21 C.F.R. 172.515
  6. ↑ Hoffman, Jay R; Kang, Jie; Ratamess, Nicholas A; Rashti, Stefanie L; Tranchina, Christopher P; Faigenbaum, Avery D (2009). "Thermogenic effect of an acute ingestion of a weight loss supplement". Journal of the International Society of Sports Nutrition. 6 (1): 1. doi:10.1186/1550-2783-6-1. ISSN 1550-2783.
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