Acetanisole is an

aromatic In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with an aroma described as sweet, fruity, nutty, and similar to vanilla. In addition acetanisole can sometimes smell like butter or caramel. Its chemical names are based on considering the structure as either an

acetyl In organic chemistry, an acetyl group is a functional group denoted by the chemical formula and the structure . It is sometimes represented by the symbol Ac (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl grou ...

(

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

) analog of

anisole Anisole, or methoxybenzene, is an organic compound with the formula . It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly ...

. Other names It can also be seen as a

methyl ether Methyl ether may refer to: * Any chemical compound of the ether class that includes a methyl group * Dimethyl ether, often simply called methyl ether See also *Methoxy group In organic chemistry, a methoxy group is the functional group consisti ...

analog of

acetophenone Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byproduct of the cumene ...

. Acetanisole is found naturally in

castoreum Castoreum is a yellowish exudate from the castor sacs of mature beavers used in combination with urine to territorial marking, scent mark their territory. Both beaver sexes have a pair of castor sacs and a pair of anal glands, located in two c ...

, the glandular secretion of the

beaver Beavers (genus ''Castor'') are large, semiaquatic rodents of the Northern Hemisphere. There are two existing species: the North American beaver (''Castor canadensis'') and the Eurasian beaver (''C. fiber''). Beavers are the second-large ...

Preparation

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

acetyl chloride Acetyl chloride () is an acyl chloride derived from acetic acid (). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On an ...

: :

Application

It is used as a cigarette additive, a

fragrance An aroma compound, also known as an odorant, aroma, fragrance, flavoring or flavor, is a chemical compound that has a smell or odor. For an individual chemical or class of chemical compounds to impart a smell or fragrance, it must be sufficien ...

, and a flavoring in

food Food is any substance consumed by an organism for Nutrient, nutritional support. Food is usually of plant, animal, or Fungus, fungal origin and contains essential nutrients such as carbohydrates, fats, protein (nutrient), proteins, vitamins, ...

Reactions

4-Methoxyacetophenone is a standard substrate or product of much research, such as

transfer hydrogenation In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular . It is applied in laboratory and industrial organic synthesis to saturate organic compounds and re ...

and directed arylations.

References

{{reflist Food additives Piceol ethers Sweet-smelling chemicals