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{{Orphan|date=February 2009}}
{{chembox
{{chembox
| Verifiedfields = changed
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| verifiedrevid = 396298376
| Watchedfields = changed
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| ImageFile = Benzylacetone.png
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| verifiedrevid = 396299528
| ImageSize = 200px
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| ImageFile = Benzylacetone.png
| ImageName =
| ImageName =
| IUPACName = 4-Phenyl-2-butanone
| PIN = 4-Phenylbutan-2-one
| OtherNames = Methyl (2-phenyl)-ethyl ketone, 1-phenyl-3-butanone
| OtherNames = 4-Phenyl-2-butanone<br />Methyl 2-phenylethyl ketone
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16422
| ChemSpiderID = 16422
| InChI = 1/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
| InChI = 1/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
| InChIKey = AKGGYBADQZYZPD-UHFFFAOYAH
| InChIKey = AKGGYBADQZYZPD-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
| StdInChI = 1S/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AKGGYBADQZYZPD-UHFFFAOYSA-N
| StdInChIKey = AKGGYBADQZYZPD-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 2550-26-7
| CASNo = 2550-26-7
| UNII_Ref = {{fdacite|correct|FDA}}
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| SMILES = O=C(CCc1ccccc1)C
| UNII = UZM5QH16YW
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| SMILES = O=C(CCc1ccccc1)C
| PubChem = 17355
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=10|H=12|O=1
| C=10 | H=12 | O=1
| Density = 0.989 g/mL
| Density = 0.989 g/mL
| MeltingPtC = -13
| MeltingPt =
| BoilingPtC = 235
| BoilingPtC = 235
| Flash PointC = 98
| Appearance =
| Appearance =
}}
}}
| Section7 = {{Chembox Hazards
|Section7={{Chembox Hazards
| ExternalMSDS =
| FlashPtC = 98
| ExternalSDS =
}}
}}
}}
}}
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'''Benzylacetone''' (IUPAC name: 4-phenylbutan-2-one) is a liquid with a sweet, flowery smell that is considered to be the most abundant attractant compound in flowers (e.g. Coyote Tobacco, ''[[Nicotiana attenuata]]'')<ref>{{cite journal |author1=Kessler, D. |author2=Baldwin, I.T. |name-list-style=amp | title = Making sense of nectar scents: the effects of nectar secondary metabolites on floral visitors of ''Nicotiana attenuata'' | journal = The Plant Journal | volume = 49 | issue = 5 | pages = 840–854 | doi= 10.1111/j.1365-313X.2006.02995.x | pmid= 17316174 | year= 2007| doi-access= free }}</ref><ref>{{cite journal | author = Baldwin, I.T. | title = Patterns and Consequences of Benzyl Acetone Floral Emissions from ''Nicotiana attenuata'' Plants | journal = J. Chem. Ecol. | volume = 23 | issue = 100 | pages = 2327–2343 | display-authors = etal | doi = 10.1023/B:JOEC.0000006677.56380.cd | year = 1997 | s2cid = 25042144 }}</ref> and one of volatile components of [[Cocoa mass|cocoa]].<ref>Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe & Horst Surburg: ''Flavors and Fragrances'', Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, New York, 2003. Cited 28.8.2015.</ref>
'''Benzylacetone''' (IUPAC name: 4-phenyl-2-butanone) is a liquid with a sweet, flowery smell that is considered to be the most abundant attractant compound in flowers (e.g. Coyote Tobacco, ''[[Nicotiana attenuata]]'')<ref>{{cite journal | url= http://www3.interscience.wiley.com/journal/118488467/abstract?CRETRY=1&SRETRY=0
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| author =Kessler, D. and Baldwin, I.T. | title = Making sense of nectar scents: the effects of nectar secondary metabolites on floral visitors of ''Nicotiana attenuata'' | journal = The Plant Journal | volume = 49 | issue = 5 | pages = 840–854 | doi= 10.1111/j.1365-313X.2006.02995.x | pmid= 17316174 | year= 2007}}</ref><ref>{{cite journal | url= http://www.ingentaconnect.com/content/klu/joec/1997/00000023/00000010/00426077;jsessionid=4ckb78c6tfms6.alexandra| author =Baldwin, I.T., et al. | title = Patterns and Consequences of Benzyl Acetone Floral Emissions from ''Nicotiana attenuata'' Plants | journal = J. Of Chem. Eco. | volume = 23 | issue = 100 | pages = 2327–2343}}</ref> and one of volatile components of [[Cocoa mass|cocoa]].{{Fact|date=November 2008}}


It can be used as an attractant for melon flies (''[[Bactrocera]] cucurbitae''),<ref>{{citeweb|url=http://entomology.ifas.ufl.edu/creatures/fruit/tropical/melon_fly.htm|title=University of Florida Featured Creatures|accessdate=2008-11-18}}</ref><ref>{{citeweb|url=http://www.answers.com/topic/benzylacetone|title=Answers.com webpage|accessdate=2008-11-18}}</ref> in [[Aroma compound|perfume]],<ref>{{citeweb|url=http://www.thegoodscentscompany.com/data/rw1024231.html|title=The Goods Company webpage|accessdate=2008-11-18}}</ref> and as an odorant for soap.
It can be used as an attractant for melon flies (''[[Bactrocera]] cucurbitae''),<ref>{{cite web|url=http://entomology.ifas.ufl.edu/creatures/fruit/tropical/melon_fly.htm|title=University of Florida Featured Creatures|accessdate=2008-11-18}}</ref><ref>{{cite web|url=http://www.answers.com/topic/benzylacetone|title=Answers.com webpage|website=[[Answers.com]] |accessdate=2008-11-18}}</ref> in [[Aroma compound|perfume]],<ref>{{cite web|url=http://www.thegoodscentscompany.com/data/rw1024231.html|title=The Goods Company webpage|accessdate=2008-11-18}}</ref> and as an odorant for soap.


It can be prepared by the hydrogenation of [[benzylideneacetone]].
It can be prepared by the hydrogenation of [[benzylideneacetone]].

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==References==
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{{reflist}}


==See also==
==See also==
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* [[Pheromone]]
* [[Pheromone]]
* [[Fragrances]]
* [[Fragrances]]

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==References==
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{{reflist}}


==External links==
==External links==
* [http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/13150 Fluka 4-Phenyl-2-butanone]
* [https://archive.today/20130202152107/http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/13150 Fluka 4-Phenyl-2-butanone]
* [http://webbook.nist.gov/cgi/cbook.cgi?InChI=1/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3 NIST 4-Phenyl-2-butanone]
* [http://webbook.nist.gov/cgi/cbook.cgi?InChI=1/C10H12O/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3 NIST 4-Phenyl-2-butanone]


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[[Category:Flavors]]
[[Category:Flavors]]
[[Category:Perfume ingredients]]
[[Category:Perfume ingredients]]
[[Category:Phenyl compounds]]

[[Category:Benzyl compounds]]
[[de:Benzylaceton]]
[[Category:Sweet-smelling chemicals]]
[[nl:Benzylaceton]]
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