The acetophenone is an organic compound derived from chicory. It is mainly used as a flavoring agent in foods and perfumes.
Acetophenone is also used as a solvent for plastics and resins. This compound is part of the 599 additives present in cigarettes.
Chemical and physical characteristics of acetophenone
The chemical formula of acetophenone is C 6 H 5 C (O) CH 3 . Acetophenone belongs to the group of ketones, chemical compounds characterized by having a carbonyl group. Acetophenone is the simplest aromatic ketone.
Acetophenone is more dense than water, so it is slightly soluble and sinks into it. In cold conditions, acetophenone freezes. At room temperature, acetophenone is a clear liquid with a sweet and spicy taste.
Its boiling point is 202 or C, while its melting point is 20 or C. Its smell resembles the smell of oranges.
Acetophenone is moderately reactive. Chemical reactions between acetophenone and bases or acids release high amounts of flammable gas and heat.
Reactions between acetophenone and alkali metals, hydrides, or nitrides also release gases and heat, which is sufficient to start a fire. Acetophenone does not react with isocyanates, aldehydes, peroxides and carbides.
Synthesis
Acetophenone can be synthesized in several ways. It can be purchased as a byproduct of isopropylbensene, also called cumene. In nature, cumene is found in cinnamon and ginger oil. Acetophenone can also be produced by the oxidation of ethyl benzene.
Pharmaceutical and general uses
During the 20th century, acetophenone was used as a hypnotic agent. To do this, the compound was synthesized and packed under the name Sypnone to induce sleep.
In the current pharmaceutical industry, acetophenone is used as a photosensitizing agent.
These drugs are inactive until they come in contact with ultraviolet light or sunlight.
Once in contact with light, a reaction is initiated in human tissue to heal diseased tissue. Acetophenone is generally used to treat psoriasis and some types of neoplasms.
In addition, acetophenone is widely used to sweeten foods and beverages. Thanks to its fruity scent, it is also used for fragrances found in lotions, perfumes, soaps and detergents.
Risks
At high levels, acetophenone vapor is a narcotic. This vapor is capable of moderately irritating the skin and eyes.
At elevated levels, contact between vapor and tissue can result in corneal injury. When this exposure is constant the vapor can reduce the sensitivity to the light of the view.
Inhaling this vapor can also cause congestion in the lungs, liver and kidneys. When acetophenone is consumed orally it can weaken the human pulse and cause sedative, hypnotic and haematological effects.
The US Environmental Protection Agency has classified acetophenone in group D, called non-classifiable as to human carcinogenicity.
Compounds assigned to group D do not demonstrate sufficient evidence to support or refute human carcinogenicity.
References
- National Center for Biotechnology Information. PubChem Compound Database; CID = 7410 National Center for Biotechnology Information (2017). PubChem Compound Database; CID = 7410, Acetophenone. U.S. National Library of Medicine.
- Brown, W. (2015). Ketone. Encyclopedia Britannica. Encyclopedia Britannica Inc.
- Chemical Book (2017). CAS Database list: Acetophenone.
- United States Environmental Protection Agency (2016). Acetophenone.
- The Green Book (2012). Acetophenone and its uses.
- U.S. Department of Health and Human Services (1993). Hazardous Substances Data Bank (HSDB, online database). National Toxicology Information Program, National Library of Medicine, Bethesda, MD.
- Sittig, M. (1985). Handbook of Toxic and Hazardous Chemicals and Carcinogens. 2nd edition.