Cinnamic acid
Names | |
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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 ) |
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3DMet | |
1905952 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.004.908 |
EC Number |
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3731 | |
IUPHAR/BPS |
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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 |
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: | |
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) | |
Flash point | > 100 °C (212 °F; 373 K)[3] |
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).
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Cinnamic acid is an
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]
Occurrence and production
Biosynthesis
Cinnamic acid is a central intermediate in the biosynthesis of a myriad of natural products including lignols (precursors to
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
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 all species of trees.[7]
Synthesis
Cinnamic acid was first synthesized by the base-catalysed condensation of
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]
Metabolism
Cinnamic acid, obtained from autoxidation of cinnamaldehyde, is metabolized into sodium benzoate in the liver.[11]
Uses
Cinnamic acid is used in flavorings,
dimerize in non-polar solvents resulting in different linear free energy relationships.[12]
References
- ^ Encyclopædia Britannica. Vol. 6 (11th ed.). 1911. p. 376. .
- ^ a b "Cinnamic acid". flavornet.org.
- ^ a b c d e Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ ISBN 0911910123
- ^ ISBN 978-3527306732.
- PMID 20035037.
- ^ Oldach, Laurel (February 22, 2023). "Forensic researchers use mass spectrometry to identify smuggled wood". Chemical and Engineering News. American Chemical Society.
- .
- ^ Tieze, L. (1988). Reactions and Synthesis in the Organic Chemistry Laboratory. Mill Vall, CA. p. 1988.
{{cite book}}
: CS1 maint: location missing publisher (link) - .
- PMID 23475543.
- PMID 25798191.