Cinnamic acid

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Cinnamic acid
trans-Cinnamic Acid
IUPAC name (E)-3-phenylprop-2-enoic acid
Other names Cinnamic Acid, trans-Cinnamic Acid
Identifiers
CAS number [140-10-3]
Properties
Molecular formula C6H5CHCHCOOH
Molar mass 148.17 g/mol
Appearance monoclinic crystals
Density 1.2475 g/cm3
Melting point

133 °C
Boiling point

300 °C
Solubility in water 0.4 g/L
Acidity (pKa) 4.44
Hazards
EU classification Irritant (Xi)
R-phrases R36
S-phrases S25
Flash point >110 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Cinnamic acid has the formula C6H5CHCHCOOH 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 balsams 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.

[edit] References

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Types of Phenylpropanoids
Phenylpropanoids


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