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==Occurrence and production== |
==Occurrence and production== |
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===Biosynthesis=== |
===Biosynthesis=== |
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Cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to [[lignin]] and [[lignocellulose]]), [[flavonoids]], [[isoflavonoids]], [[coumarin]]s, [[aurones]], [[stilbenes]], [[catechin]], and [[phenylpropanoid]]s. Its [[biosynthesis]] is performed by action of the [[enzyme]] [[phenylalanine ammonia-lyase]] (PAL) on [[phenylalanine]].<ref>{{cite journal|journal=Molecular Plant|year=2010|pages=2-20|doi=10.1093/mp/ssp106|title=Phenylpropanoid Biosynthesis|last=Vogt|first=T.}}</ref> |
Cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to [[lignin]] and [[lignocellulose]]), [[flavonoids]], [[isoflavonoids]], [[coumarin]]s, [[aurones]], [[stilbenes]], [[catechin]], and [[phenylpropanoid]]s. Its [[biosynthesis]] is performed by action of the [[enzyme]] [[phenylalanine ammonia-lyase]] (PAL) on [[phenylalanine]].<ref>{{cite journal|journal=Molecular Plant|year=2010||volume=3|issue=1|pages=2-20|doi=10.1093/mp/ssp106|title=Phenylpropanoid Biosynthesis|last=Vogt|first=T.}}</ref> |
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===Natural occurrence=== |
===Natural occurrence=== |
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===Production=== |
===Production=== |
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The original synthesis of cinnamic acid involves the [[Perkin reaction]], which entails the base-catalysed [[aldol condensation]] reaction between [[acetic anhydride]] and [[benzaldehyde]], with accompanying [[hydrolysis]] of the [[acid anhydride]] product: |
The original synthesis{{cn}}<!-- previous versions of this article says Claisen's was first --> of cinnamic acid involves the [[Perkin reaction]], which entails the base-catalysed [[aldol condensation]] reaction between [[acetic anhydride]] and [[benzaldehyde]], with accompanying [[hydrolysis]] of the [[acid anhydride]] product: |
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:[[File:Zimtsäure nach Perkin.svg|450px|center|thumb|Synthesis of cinnamic acid via the [[Perkin reaction]]]] |
:[[File:Zimtsäure nach Perkin.svg|450px|center|thumb|Synthesis of cinnamic acid via the [[Perkin reaction]]]] |
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==Uses== |
==Uses== |
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Cinnamic acid is used in flavorings, [[Indigo dye#Chemical synthesis|synthetic indigo]], and certain [[pharmaceutical]]s. A major use is as a precursor to produce [[methyl |
Cinnamic acid is used in flavorings, [[Indigo dye#Chemical synthesis|synthetic indigo]], and certain [[pharmaceutical]]s. A major use is as a precursor to produce [[methyl cinnamate]], [[ethyl cinnamate]], and [[benzyl cinnamate]] for the perfume industry.<ref name=Merck/> Cinnamic acid is a precursor to the sweetener [[aspartame]] via enzyme-catalysed amination to give [[phenylalanine]].<ref name=Ullmann/> Cinnamic acid can [[Dimer (chemistry)|dimerize]] in non-polar solvents resulting in different [[Free-energy relationship|linear free energy relationships]].<ref>{{cite journal | doi = 10.1186/s13065-015-0080-9 | pmid = 25798191 | pmc = 4369286 | title = Determination of Abraham model solute descriptors for the monomeric and dimeric forms of ''trans''-cinnamic acid using measured solubilities from the Open Notebook Science Challenge | journal = Chemistry Central Journal | volume = 9 | pages = 11 | year = 2015 | last1 = Bradley | first1 = J.-C. | last2 = Abraham | first2 = M. H. | last3 = Acree | first3 = W. E. | last4 = Lang | first4 = A. | last5 = Beck | first5 = S. N. | last6 = Bulger | first6 = D. A. | last7 = Clark | first7 = E. A. | last8 = Condron | first8 = L. N. | last9 = Costa | first9 = S. T. | last10 = Curtin | first10 = E. M. | last11 = Kurtu | first11 = S. B. | last12 = Mangir | first12 = M. I. | last13 = McBride | first13 = M. J. }}</ref> |
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==References== |
==References== |
Revision as of 02:06, 2 September 2019
Names | |
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Preferred IUPAC name
(2E)-3-Phenylprop-2-enoic acid | |
Other names
Cinnamic acid
trans-Cinnamic acid Phenylacrylic acid[1] Cinnamylic acid 3-Phenylacrylic acid (E)-Cinnamic acid Benzenepropenoic acid Isocinnamic acid | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.908 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C9H8O2 | |
Molar mass | 148.161 g·mol−1 |
Appearance | White monoclinic crystals |
Density | 1.2475 g/cm3[2] |
Melting point | 133 °C (271 °F; 406 K)[2] |
Boiling point | 300 °C (572 °F; 573 K)[2] |
500 mg/L[2] | |
Acidity (pKa) | 4.44 |
−7.836×10−5 cm3/mol | |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | > 100 °C (212 °F; 373 K)[2] |
Related compounds | |
Related compounds
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Benzoic acid, Phenylacetic acid, Phenylpropanoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Cinnamic acid is an organic compound with the formula C6H5CH=CHCOOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents.[3] Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.[4]
Occurrence and production
Biosynthesis
Cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis is performed by action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine.[5]
Natural occurrence
It is obtained from oil of cinnamon, or from balsams such as storax.[3] It is also found in shea butter. Cinnamic acid has a honey-like odor;[6] it and its more volatile ethyl ester (ethyl cinnamate) are flavor components in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent.
Production
The original synthesis[citation needed] of cinnamic acid involves the Perkin reaction, which entails the base-catalysed aldol condensation reaction between acetic anhydride and benzaldehyde, with accompanying hydrolysis of the acid anhydride product:
In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate by the reaction of ethyl acetate with benzaldehyde using sodium to form the enolate of the ethyl acetate, the hydrolysis of which gives the acid.[7]
Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction.[8] The reactants for this are benzaldehyde and malonic acid in the presence of a weak base, followed by acid-catalyzed decarboxylation.
It can also be prepared from cinnamaldehyde and benzal chloride.[4][clarification needed]
Uses
Cinnamic acid is used in flavorings, synthetic indigo, and certain pharmaceuticals. A major use is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry.[3] Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to give phenylalanine.[4] Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships.[9]
References
- ^ Encyclopædia Britannica. Vol. 6 (11th ed.). 1911. p. 376. .
- ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b c Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123
- ^ a b c Garbe, Dorothea. "Cinnamic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_099. ISBN 978-3527306732.
- ^ Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3 (1): 2–20. doi:10.1093/mp/ssp106.
{{cite journal}}
: Cite has empty unknown parameter:|1=
(help) - ^ "Cinnamic acid". flavornet.org.
- ^ Claisen, L. (1890). "Zur Darstellung der Zimmtsäure und ihrer Homologen" [On the preparation of cinnamic acid and its homologues]. Berichte der deutschen chemischen Gesellschaft. 23: 976–978.
- ^ Tieze, L. (1988). Reactions and Synthesis in the Organic Chemistry Laboratory. Mill Vall, CA. p. 1988.
{{cite book}}
: CS1 maint: location missing publisher (link) - ^ Bradley, J.-C.; Abraham, M. H.; Acree, W. E.; Lang, A.; Beck, S. N.; Bulger, D. A.; Clark, E. A.; Condron, L. N.; Costa, S. T.; Curtin, E. M.; Kurtu, S. B.; Mangir, M. I.; McBride, M. J. (2015). "Determination of Abraham model solute descriptors for the monomeric and dimeric forms of trans-cinnamic acid using measured solubilities from the Open Notebook Science Challenge". Chemistry Central Journal. 9: 11. doi:10.1186/s13065-015-0080-9. PMC 4369286. PMID 25798191.
{{cite journal}}
: CS1 maint: unflagged free DOI (link)