The acetophenone is an organic compound derived from chicory. It is used primarily as a flavoring agent in foods and perfumes. It is also used as a solvent for plastics and resins. This compound is part of the 599 additives present in cigarettes.
Its chemical formula is C 6 H 5 C (O) CH 3 and belongs to the group of ketones, chemical compounds characterized by having a carbonyl group. Acetophenone is the simplest aromatic ketone.
Structure of acetophenone
Acetophenone is denser than water, so it is slightly soluble and sinks in 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 o C, while its melting point is 20 o 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 by-product 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 benzine.
Pharmaceutical and general uses
During the 20th century, acetophenone was used as a hypnotic agent. For this, the compound was synthesized and packaged under the name Sypnone to induce sleep.
In today's 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 the diseased tissue. Acetophenone is generally used to treat psoriasis and some types of neoplasms.
Also, acetophenone is widely used to sweeten foods and beverages. Thanks to its fruity smell, 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 high levels, contact between steam and tissue can result in corneal injury. When this exposure is constant, the vapor can reduce the light sensitivity of the eye.
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 hematological effects.
The United States Environmental Protection Agency has classified acetophenone in Group D, called unclassifiable 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. US National Library of Medicine.
- Brown, W. (2015). Ketone. Encyclopedia Britannica. Encyclopeia Britannica Inc.
- Chemical Book (2017). CAS Database list: Acetophenone.
- United States Environmental Protection Agency (2016). Acetophenone.
- The Green Book (2012). Acetophenone and its uses.
- US 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.