Acetophenone
Synthetic Ingredient For Perfumery
Acetophenone is a synthetic ingredient fundamental to perfumery, known for its aromatic ketone structure, C6H5C(O)CH3. This colorless, viscous liquid imparts a narcotic, synthetic odor with notes of leather polish, marzipan, and a heliotropin-like vanilla nuance. Naturally found in foods and beaver castoreum, it is also utilized in creating fragrances with almond, cherry, and floral tones, highlighting its versatility in scent composition
Synthetic Ingredient For Perfumery
Acetophenone is a synthetic ingredient fundamental to perfumery, known for its aromatic ketone structure, C6H5C(O)CH3. This colorless, viscous liquid imparts a narcotic, synthetic odor with notes of leather polish, marzipan, and a heliotropin-like vanilla nuance. Naturally found in foods and beaver castoreum, it is also utilized in creating fragrances with almond, cherry, and floral tones, highlighting its versatility in scent composition
Synthetic Ingredient For Perfumery
Acetophenone is a synthetic ingredient fundamental to perfumery, known for its aromatic ketone structure, C6H5C(O)CH3. This colorless, viscous liquid imparts a narcotic, synthetic odor with notes of leather polish, marzipan, and a heliotropin-like vanilla nuance. Naturally found in foods and beaver castoreum, it is also utilized in creating fragrances with almond, cherry, and floral tones, highlighting its versatility in scent composition
Acetophenone is the organic compound with the formula C6H5C(O)CH3 (also represented by the pseudoelement symbols PhAc or BzMe). It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Acetophenone is recovered as a by-product of the oxidation of ethylbenzene to ethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is an intermediate in the commercial production of propylene oxide via the propylene oxide - styrene co-product process. Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (ฮฑ-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone. Acetophenone is recovered or hydrogenated to 1-phenyl ethanol which is then dehydrated to produce styrene. Acetophenone occurs naturally in many foods including apple, cheese, apricot, banana, beef, and cauliflower. It is also a component of castoreum, the exudate from the castor sacs of the mature beaver.
Profile:
๐ CAS Nยฐ 98-86-2
โ๏ธ MW 120,15 g/mol
๐ Odor Type: Narcotic (literature says floral)
๐ Odor Strength: high
๐๐ผ Odor Profile: Narcotic, synthetic, leather polish. Plasticky, hawthorn floral facet. sweet, cherry pit, marzipan, and coumarinic. It has a slight almond nutty and heliotropin-like vanilla nuance.
๐ Flavor Profile: Powdery, bitter almond cherry pit-like with coumarinic and fruity nuances
โ๏ธ Uses: Commercially significant resins are produced from the treatment of acetophenone with formaldehyde and a base. The resulting copolymers are conventionally described with the formula [(C6H5COCH)x(CH2)x]n, resulting from aldol condensation. These substances are components of coatings and inks. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting polyol can be further crosslinked with diisocyanates. The modified resins are found in coatings, inks, and adhesives.
Niche use:
Acetophenone is an ingredient in fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry. It is used in chewing gum. It is also listed as an approved excipient by the U.S. FDA. In a 1994 report released by five top cigarette companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes.
Laboratory reagent:
In instructional laboratories, acetophenone is converted to styrene in a two-step process that illustrates the reduction of carbonyls using hydride and the dehydration of alcohols:4 C6H5C(O)CH3 + NaBH4 + 4 H2O โ 4 C6H5CH(OH)CH3 + NaOH + B(OH)3 โ C6H5CH=CH2A similar two-step process is used industrially, but reduction step is performed by hydrogenation over a copper catalyst.C6H5C(O)CH3 + H2 โ C6H5CH(OH)CH3Being prochiral, acetophenone is also a popular test substrate for asymmetric hydrogenation experiments.
Drugs:
Acetophenone is used for the synthesis of many pharmaceuticals. A Mannich reaction with dimethylamine and formaldehyde gives ฮฒ-dimethylamino propiophenone. Using diethylamine instead gives the diethylamino analog.
Sources:
National Center for Biotechnology Information (2020). PubChem Compound Summary for CID 7410, Acetophenone. Retrieved November 24, 2020 from https://pubchem.ncbi.nlm.nih.gov/compound/Acetophenone.
