Cinnamic acid

Last updated
Cinnamic acid
Zimtsaure - Cinnamic acid.svg
Cinnamic acid 3D ball.png
Cinnamic acid.jpg
Names
Preferred IUPAC name
(2E)-3-Phenylprop-2-enoic acid
Systematic IUPAC name
Cinnamic acid
Other names
trans-Cinnamic acid
Phenylacrylic acid [1]
Cinnamylic acid
3-Phenylacrylic acid
(E)-Cinnamic acid
Benzenepropenoic acid
Isocinnamic acid
Identifiers
3D model (JSmol)
3DMet
1905952
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.908 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-398-1
3731
KEGG
PubChem CID
UNII
  • InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ Yes check.svgY
    Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N Yes check.svgY
  • InChI=1/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
    Key: WBYWAXJHAXSJNI-VOTSOKGWBT
  • O=C(O)\C=C\c1ccccc1
Properties
C9H8O2
Molar mass 148.161 g·mol−1
AppearanceWhite monoclinic crystals
Odor Honey-like [2]
Density 1.2475 g/cm3 [3]
Melting point 133 °C (271 °F; 406 K) [3]
Boiling point 300 °C (572 °F; 573 K) [3]
500 mg/L [3]
Acidity (pKa)4.44
−7.836×10−5 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Flash point >100 °C (212 °F; 373 K) [3]
Related compounds
Related compounds
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. [4] 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. [5]

Contents

Occurrence and production

Biosynthesis

Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine. [6]

Natural occurrence

It is obtained from oil of cinnamon, or from balsams such as storax. [4] It is also found in shea butter.[ citation needed ] Cinnamic acid has a honey-like odor; [2] and its more volatile ethyl ester, ethyl cinnamate, is a flavor component in the essential oil of cinnamon, in which related cinnamaldehyde is the major constituent. It is also found in wood from many diverse tree species. [7]

Synthesis

Cinnamic acid was first synthesized by the base-catalysed condensation of acetyl chloride and benzaldehyde, followed by hydrolysis of the acid chloride product. [5] In 1890, Rainer Ludwig Claisen described the synthesis of ethyl cinnamate via the reaction of ethyl acetate with benzaldehyde in the presence of sodium as base. [8] Another way of preparing cinnamic acid is by the Knoevenagel condensation reaction. [9] 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 by oxidation of cinnamaldehyde, condensation of benzal chloride and sodium acetate (followed by acid hydrolysis), and the Perkin reaction. The oldest commercially used route to cinnamic acid involves the Perkin reaction, which is given in the following scheme [5]

Synthesis of cinnamic acid via the Perkin reaction. Zimtsaure nach Perkin.svg
Synthesis of cinnamic acid via the Perkin reaction.

Metabolism

Cinnamic acid, obtained from autoxidation of cinnamaldehyde, is metabolized into sodium benzoate in the liver. [11]

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. [4] Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination with phenylalanine. [5] Cinnamic acid can dimerize in non-polar solvents resulting in different linear free energy relationships. [12]

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a functional group derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

Hydrolysis is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

<span class="mw-page-title-main">Cinnamaldehyde</span> Chemical compound

Cinnamaldehyde is an organic compound with the formula or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. It is an essential oil. The bark of cinnamon tree contains high concentrations of cinnamaldehyde.

The Perkin reaction is an organic reaction developed by English chemist William Henry Perkin that is used to make cinnamic acids. It gives an α,β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence of an alkali salt of the acid. The alkali salt acts as a base catalyst, and other bases can be used instead.

The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide. The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction.

<span class="mw-page-title-main">Mandelic acid</span> Chemical compound

Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C6H5CH(OH)CO2H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. The molecule is chiral. The racemic mixture is known as paramandelic acid.

<span class="mw-page-title-main">Dibenzylideneacetone</span> Chemical compound

Dibenzylideneacetone or dibenzalacetone, often abbreviated dba, is an organic compound with the formula C17H14O. It is a pale-yellow solid insoluble in water, but soluble in ethanol.

<span class="mw-page-title-main">Phenylpropanoid</span>

The phenylpropanoids are a diverse family of organic compounds that are biosynthesized by plants from the amino acids phenylalanine and tyrosine in the shikimic acid pathway. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

<span class="mw-page-title-main">Flavones</span> Class of flavonoid chemical compounds

Flavones are a class of flavonoids based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).

<span class="mw-page-title-main">Erlenmeyer–Plöchl azlactone and amino-acid synthesis</span>

The Erlenmeyer–Plöchl azlactone and amino acid synthesis, named after Friedrich Gustav Carl Emil Erlenmeyer who partly discovered the reaction, is a series of chemical reactions which transform an N-acyl glycine to various other amino acids via an oxazolone.

In enzymology, a trans-cinnamate 4-monooxygenase (EC 1.14.14.91) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Phenylalanine ammonia-lyase</span>

The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalyzes the conversion of L-phenylalanine to ammonia and trans-cinnamic acid.:

<span class="mw-page-title-main">Rosavin</span> Chemical compound

Rosavin are a family of cinnamyl mono- and diglycosides that are key ingredients of Rhodiola rosea L.,. R. rosea is an important medicinal plant commonly used throughout Europe, Asia, and North America, that has been recognized as a botanical adaptogen by the European Medicines Agency. Rosavin production is specific to R. rosea and R. sachalinenis, and the biosynthesis of these glycosides occurs spontaneously in Rhodiola roots and rhizomes. The production of rosavins increases in plants as they get older, and the amount of the cinnamyl alcohol glycosides depends on the place of origin of the plant.

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.

<span class="mw-page-title-main">Biosynthesis of cocaine</span>

The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.

α-Phenylcinnamic acid Chemical compound

α-Phenylcinnamic acid is a phenylpropanoid, or, more specifically, a derivative of cinnamic acid. It has the formula C15H12O2 and appears as an off-white crystalline solid.

The biosynthesis of phenylpropanoids involves a number of enzymes.

References

  1. "Cinnamic Acid"  . Encyclopædia Britannica . Vol. 6 (11th ed.). 1911. p. 376.
  2. 1 2 "Cinnamic acid". flavornet.org.
  3. 1 2 3 4 5 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. 1 2 3 Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN   0911910123
  5. 1 2 3 4 Garbe, Dorothea (2012). "Cinnamic Acid". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_099. ISBN   978-3527306732.
  6. Vogt, T. (2010). "Phenylpropanoid Biosynthesis". Molecular Plant. 3 (1): 2–20. doi: 10.1093/mp/ssp106 . PMID   20035037.
  7. Oldach, Laurel (February 22, 2023). "Forensic researchers use mass spectrometry to identify smuggled wood". Chemical and Engineering News. American Chemical Society.
  8. 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. doi:10.1002/cber.189002301156.
  9. Tieze, L. (1988). Reactions and Synthesis in the Organic Chemistry Laboratory. Mill Vall, CA. p. 1988.{{cite book}}: CS1 maint: location missing publisher (link)
  10. F. K. Thayer (1925). "m-Nitrocinnamic Acid". Organic Syntheses. 5: 83. doi:10.15227/orgsyn.005.0083.
  11. Jana A, Modi KK, Roy A, Anderson JA, van Breemen RB, Pahan K (June 2013). "Up-regulation of neurotrophic factors by cinnamon and its metabolite sodium benzoate: therapeutic implications for neurodegenerative disorders". Journal of Neuroimmune Pharmacology . 8 (3): 739–55. doi:10.1007/s11481-013-9447-7. PMC   3663914 . PMID   23475543.
  12. 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.