Acetophenone: Difference between revisions
mNo edit summary |
No edit summary |
||
| Line 116: | Line 116: | ||
===Odor fear conditioning in lab rats=== |
===Odor fear conditioning in lab rats=== |
||
Acetophenone has been used in experiments to examine the inheritance of parental traumatic exposure (odor [[fear conditioning]]). Acetophenone's odor activates an odorant receptor ([[Olfr151]]) and has been used to condition mice. An experiment by B. G. Dias and K. J. Ressler<ref>[http://www.nature.com/neuro/journal/vaop/ncurrent/full/nn.3594.html Dias, B. G. & Ressler, K. J. (2013). Parental olfactory experience influences behavior and neural structure in subsequent generations. ''Nature Neuroscience'', Dec 01, 2013. PMID 24292232]</ref> found that environmental information may be inherited transgenerationally at behavioral, neuroanatomical and epigenetic levels. |
Acetophenone has been used in experiments to examine the inheritance of parental traumatic exposure (odor [[fear conditioning]]). Acetophenone's odor activates an odorant receptor ([[Olfr151]]) and has been used to condition mice. An experiment by B. G. Dias and K. J. Ressler<ref>[http://www.nature.com/neuro/journal/vaop/ncurrent/full/nn.3594.html Dias, B. G. & Ressler, K. J. (2013). Parental olfactory experience influences behavior and neural structure in subsequent generations. ''Nature Neuroscience'', Dec 01, 2013. PMID 24292232 (Retrieved December 21, 2013]</ref> found that environmental information may be inherited transgenerationally at behavioral, neuroanatomical and epigenetic levels. |
||
== Natural occurrence == |
== Natural occurrence == |
||
Revision as of 00:15, 22 December 2013
| |||
| Names | |||
|---|---|---|---|
| IUPAC name
Acetophenone, 1-phenylethanone
| |||
| Other names
Phenyl methyl ketone, ACP, Phenylethanone
| |||
| Identifiers | |||
3D model (JSmol)
|
|||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.002.462 | ||
| KEGG | |||
PubChem CID
|
|||
| UNII | |||
CompTox Dashboard (EPA)
|
|||
| |||
| |||
| Properties | |||
| C8H8O | |||
| Molar mass | 120.151 g·mol−1 | ||
| Density | 1.028 g/cm³ | ||
| Melting point | 19–20 °C | ||
| Boiling point | 202 °C | ||
| 5.5 g/L at 25 °C 12.2 g/L at 80 °C | |||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 77 °C (171 °F; 350 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |||
Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances.[1]
Production
Acetophenone can be obtained by a variety of methods. In industry, acetophenone is recovered as a by-product of the oxidation of ethylbenzene, which mainly gives ethylbenzene hydroperoxide for use in the production of propylene oxide.[1]
Uses
Precursor to resins
Commercially significant resins are produced from treatment of acetophenone with formaldehyde and base. The resulting polymers are conventionally described with the formula [C6H5C(O)CH]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.[1] These modified resins are again found in coatings, inks, as well as adhesives.
Use in pharmaceutical and related areas
Acetophenone is a raw material for the synthesis of some pharmaceuticals, examples include dextropropoxyphene and phenylpropanolamine.[2] [3]
Niche uses
Acetophenone is an ingredient in fragrances that resemble almond, cherry, honeysuckle, jasmine, and strawberry. It is used in chewing gum.[4] It is also listed as an approved excipient by the U.S. FDA.[5] 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.[6]
Laboratory reagent
In instructional laboratories,[citation needed] acetophenone is converted to styrene in a two step process that illustrates the reduction of carbonyls and the dehydration of alcohols:[clarification needed]
- 4 C6H5C(O)CH3 + NaBH4 + 4 H2O → 4 C6H5CH(OH)CH3 + NaOH + B(OH)3
A similar process is used industrially but the hydrogenation step to 1-phenylethanol is done over a copper catalyst.[1]
- C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O
Being prochiral, acetophenone is also a popular test substrate for asymmetric transfer hydrogenation experiments.
Odor fear conditioning in lab rats
Acetophenone has been used in experiments to examine the inheritance of parental traumatic exposure (odor fear conditioning). Acetophenone's odor activates an odorant receptor (Olfr151) and has been used to condition mice. An experiment by B. G. Dias and K. J. Ressler[7] found that environmental information may be inherited transgenerationally at behavioral, neuroanatomical and epigenetic levels.
Natural occurrence
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.[8]
Pharmacology
In the late 19th and early 20th centuries, acetophenone was used in medicine.[9] It was marketed as a hypnotic and anticonvulsant under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters.[10] It was considered to have superior sedative effects to both paraldehyde and chloral hydrate.[11] In humans, acetophenone is metabolized to benzoic acid, carbonic acid, and acetone.[12] Hippuric acid occurs as an indirect metabolite and its quantity in urine may be used to confirm acetophenone exposure.[13]
Toxicity
The LD50 is 815 mg/kg (oral, rats).[1] Acetophenone is currently listed as a Group D carcinogen (Not Classifiable as to Human Carcinogenicity), indicating that it does not produce carcinogenic effects in humans, although no studies on humans have ever been conducted on acetophenones' carcinogenic potential. Studies have shown that acetophenone causes chromosomal damage in hamsters.[13]
References
- ^ a b c d e Hardo Siegel, Manfred Eggersdorfer “Ketones” in Ullmann’s Encyclopedia of Industrial Chemistry, Wiley-VCH, 2002, Wienheim. doi:10.1002/14356007.a15_077
- ^ Sittig, Marshall (1988). Pharmaceutical Manufacturing Encyclopedia. pp. 39, 177. ISBN 978-0-8155-1144-1.
- ^
Gadamasetti, Kumar (2007). Process Chemistry in the Pharmaceutical Industry, Volume 2. pp. 142–145. ISBN 978-0-8493-9051-7.
{{cite book}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^ Burdock, George A. (2005), Fenaroli's Handbook of Flavor Ingredients (5th ed.), CRC Press, p. 15, ISBN 0-8493-3034-3
{{citation}}: Cite has empty unknown parameters:|month=and|chapterurl=(help) - ^ http://www.accessdata.fda.gov/scripts/cder/iig/index.cfm
- ^ "What's in a cigarette?". Archived from the original on 23 May 2006. Retrieved 2006-05-31.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ Dias, B. G. & Ressler, K. J. (2013). Parental olfactory experience influences behavior and neural structure in subsequent generations. Nature Neuroscience, Dec 01, 2013. PMID 24292232 (Retrieved December 21, 2013
- ^ Pheromonal activity of single castoreum constituents in beaver,Castor canadensis., Müller-Schwarze, D and Houlihan, P.W., Journal of Chemical Ecology, April 1991, Volume 17, Number 4, Springer Netherlands, doi:10.1007/BF00994195
- ^ The Merck Index, 12th Edition
- ^ Bartholow, Roberts. "A Practical Treatise On Materia Medica And Therapeutics." Appleton & Co, 1908.
- ^ Norman, Conolly "Cases illustrating the sedative effects of aceto-phenone." Journal of Mental Science, Vol 32, p 519. 1887.
- ^ "Hypnone - The new hypnotic." J Am Med Assoc. Vol 5, p 632. 1885. doi:10.1001/jama.1885.02391220016006
- ^ a b "Acetophenone Compound Summary".