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
CAS Number	100-06-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	7196 ;
ECHA InfoCard	100.002.560
PubChem CID	7476;
UNII	0IRH2BR587 ;
CompTox Dashboard (EPA)	DTXSID2044347 ;
	InChI InChI=1S/C9H10O2/c1-7(10)8-3-5-9(11-2)6-4-8/h3-6H,1-2H3;
	SMILES CC(=O)C1=CC=C(C=C1)OC;
Properties
Chemical formula	C9H10O2
Molar mass	150.177 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]
Solubility in water	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]

In the pharmaceutical sector, acetanisole is used in the synthesis of Benfurodil hemisuccinate.
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]
In the case of m-acetanisole, this regioisomer was used to synthesize oxyfedrine.
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.

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References

Para-Acetanisole, The Good Scents Company
Acetanisole in the ChemIDplus database
Acetanisole at Sigma-Aldrich
Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine
21 C.F.R. 172.515
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. PMC 3313118.

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[goodscents-1] Para-Acetanisole, The Good Scents Company

[ChemIDplus-2] Acetanisole in the ChemIDplus database

[Aldrich-3] Acetanisole at Sigma-Aldrich

[4] Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, 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. PMC 3313118.