Cinnamic acid

Cinnamic acid
Names
	IUPAC name (E)-3-phenylprop-2-enoic acid
	Other names Cinnamic Acid; trans-Cinnamic Acid; Phenylacrylic acid; Cinnamylic acid; 3-Phenylacrylic acid; (E)-Cinnamic acid; Benzenepropenoic acid; Isocinnamic acid
Identifiers
CAS Number	140-10-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:35697 ;
ChEMBL	ChEMBL27246 ;
ChemSpider	392447 ;
ECHA InfoCard	100.004.908
KEGG	C00423 ;
PubChem CID	444539;
CompTox Dashboard (EPA)	DTXSID5022489 ;
	InChI InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+ Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N ; 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;
	SMILES O=C(O)\C=C\c1ccccc1;
Properties
Chemical formula	C9H8O2
Molar mass	148.161 g·mol−1
Appearance	White monoclinic crystals
Density	1.2475 g/cm3
Melting point	133 °C (271 °F; 406 K)
Boiling point	300 °C (572 °F; 573 K)
Solubility in water	500 mg/L
Acidity (pKa)	4.44
Hazards
Flash point	>100 °C (212 °F)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cinnamic acid is a white crystalline organic acid, which is slightly soluble in water.

It is obtained from oil of cinnamon, or from balsams such as storax.^[2] 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 flavors, synthetic indigo, and certain pharmaceuticals, though its primary use is in the manufacturing of the methyl, ethyl, and benzyl esters for the perfume industry.^[2] Cinnamic acid has a honey-like odor;^[3] 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.

Cinnamic acid is freely soluble in benzene, diethyl ether, acetone, and acetic acid;^[2] it is insoluble in hexane.

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

Chemical synthesis

Rainer Ludwig Claisen (1851–1930), German chemist, described for the first time in 1890 the synthesis of cinnamates by reacting aromatic aldehydes with esters. The reaction is known as the Claisen reaction.

References

^ ^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
^ Cinnamic acid, flavornet.org

[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[Merck-2] Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123

[3] Cinnamic acid, flavornet.org

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