Cinnamic acid

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Cinnamic acid
Zimtsäure - Cinnamic acid.svg
Identifiers
CAS number 140-10-3 YesY
PubChem 444539
ChemSpider 392447 YesY
KEGG C00423 YesY
ChEBI CHEBI:35697 YesY
ChEMBL CHEMBL27246 YesY
Jmol-3D images Image 1
Properties
Molecular formula C9H8O2
Molar mass 148.16 g mol−1
Appearance White monoclinic crystals
Density 1.2475 g/cm3[1]
Melting point 133 °C (271 °F; 406 K)[1]
Boiling point 300 °C (572 °F; 573 K)[1]
Solubility in water 500 mg/L[1]
Acidity (pKa) 4.44
Hazards
EU classification Irritant (Xi)
R-phrases R36
S-phrases S25
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point > 100 °C (212 °F; 373 K)[1]
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Cinnamic acid is an organic compound with the formula C6H5CHCHCO2H. It is a white crystalline compound that is slightly soluble in water. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It is freely soluble in many organic solvents.[2] It exists as both a cis and a trans isomer, although the latter is more common.[3]

Occurrence and production[edit]

Natural occurrence[edit]

It is obtained from oil of cinnamon, or from balsams such as storax.[4] It is also found in shea butter and is the best indication of its environmental history and post-extraction conditions. Cinnamic acid has a honey-like odor;[5] 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. 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.

Production[edit]

The original synthesis of cinnamic acid involves the Perkin reaction, which entails the base-catalysed condensation of acetic anhydride and benzaldehyde. Rainer Ludwig Claisen (1851–1930) described the synthesis of cinnamate esters by the reaction of benzaldehyde and esters. The reaction is known as the Claisen condensation. It can also be prepared from cinnamaldehyde and benzal chloride.[3]

Synthesis of cinnamic acid via Perkin reaction

Uses[edit]

Cinnamic acid is used in flavors, synthetic indigo, and certain pharmaceuticals. A major use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.[4] Cinnamic acid is a precursor to the sweetener aspartame via enzyme-catalysed amination to phenylalanine.[3]

Cinnamic acid is also a kind of self-inhibitor produced by fungal spore to prevent germination.

References[edit]

  1. ^ a b c d e Record in the GESTIS Substance Database from the IFA
  2. ^ [lxsrv7.oru.edu/~alang/onsc/solubility/allsolvents.php?solute=cinnamic+acid ONSC: Solubility of trans-cinnamic acid. ] doi:10.1038/npre.2010.4243.3
  3. ^ a b c Dorothea Garbe "Cinnamic Acid" in Ullmann's Encyclopedia of Industrial Chemistry, 2000, Wiley-VCH, Weinheim. doi:10.1002/14356007.a07_099
  4. ^ a b Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123 
  5. ^ Cinnamic acid, flavornet.org