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
Density	1.094 g/cm3
Melting point	38.5 °C (101.3 °F; 311.6 K)
Boiling point	258 °C (496 °F; 531 K)
Solubility in water	2470 mg/L
Hazards
Flash point	138 °C (280 °F)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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.

References

^ ^a ^b ^c Para-Acetanisole, The Good Scents Company
^ ^a ^b ^c Template:ChemID
^ ^a ^b Acetanisole at Sigma-Aldrich
^ Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine
^ 21 CFR 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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

[ChemIDplus-2] Template:ChemID

[Aldrich-3] Acetanisole at Sigma-Aldrich

[4] Tobacco Documents | Profiles | Additives | Acetanisole Archived April 11, 2008, at the Wayback Machine

[5] 21 CFR 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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