Cinnamic acid
926601
225435070
2008-07-13T18:01:46Z
Thijs!bot
1392310
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{{Chembox new
| Name = Cinnamic acid
| ImageFile = cinnamicacid2.png
| ImageSize = 250px
| ImageName = trans-Cinnamic Acid
| IUPACName = ([[entgegen|E]])-3-phenylprop-2-enoic acid
| OtherNames = Cinnamic Acid, ''trans''-Cinnamic Acid
| Section1 = {{Chembox Identifiers
| CASNo = 140-10-3
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>9</sub>H<sub>8</sub>O<sub>2</sub> / C<sub>6</sub>H<sub>5</sub>CHCHCOOH
| MolarMass = 148.17 g/mol
| Appearance = monoclinic crystals
| Solubility = 0.4 g/L
| Density = 1.2475 g/cm<sup>3</sup>
| MeltingPt = 133 °C
| BoilingPt = 300 °C
| pKa = 4.44
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS =
| EUClass = Irritant ('''Xi''')
| RPhrases = {{R36}}
| SPhrases = {{S25}}
| FlashPt = >110 °C
}}
}}
'''Cinnamic acid''' has the formula C<sub>6</sub>H<sub>5</sub>CHCHCOOH and is a white crystalline [[acid]], which is slightly [[soluble]] in water. It has a [[melting point]] of 133°C and a [[boiling point]] of 300°C.
It is obtained from oil of [[cinnamon]], or from [[balsam]]s such as [[storax]]. It is also found in [[shea butter]] and is the best indication of its environmental history and post-extraction conditions. It can also be made synthetically.
Cinnamic acid is used in flavours, synthetic indigo, and certain [[pharmaceuticals]], though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry. Cinnamic acid has a "honey, floral odor" (Merck Index); it and its more volatile ethyl [[ester]] ([[ethyl cinnamate]]) are flavour components in the essential oil of [[cinnamon]], in which related [[cinnamaldehyde]] is the major constituent. Cinnamic acid is also part of the biosynthetic [[shikimate]] and [[phenylpropanoid]] pathways. Its [[biosynthesis]] is performed by action of the [[enzyme]] [[phenylalanine ammonia-lyase]] (PAL) on [[phenylalanine]].
Cinnamic acid is soluble in [[diethyl ether]], insoluble in [[hexane]].
==References==
*[http://www.flavornet.org/info/140-10-3.html Flavornet.org]
*CRC Handbook
*[http://www.chemfinder.com Chemfinder]
*Katzer, G. [http://www.uni-graz.at/~katzer/engl/index.html Gernot Katzer's Spice Pages], accessed August 17, 2006.
*Budavari, Susan (Ed.) ''The Merck Index'', 13 Ed. Merck & Co., Inc, Whitehouse Station, NJ, USA, 2001.
{{Phenylpropanoids}}
[[Category:flavors]]
[[Category:Carboxylic acids]]
[[Category:Aromatic compounds]]
[[Category:Phenylpropanoids]]
{{aromatic-stub}}
[[bg:Канелена киселина]]
[[de:Zimtsäure]]
[[fr:Acide cinnamique]]
[[he:חומצת קינמון]]
[[lv:Kanēļskābe]]
[[lt:Cinamono rūgštis]]
[[hu:Fahéjsav]]
[[nl:Kaneelzuur]]
[[ja:ケイ皮酸]]
[[pl:Kwas cynamonowy]]
[[pt:Ácido cinâmico]]
[[ru:Коричная кислота]]
[[zh:肉桂酸]]