Cinnamic acid

Cinnamic acid
Names
	Preferred IUPAC name (2E)-3-Phenylprop-2-enoic acid
	Systematic IUPAC name Cinnamic acid
	Other names 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;
Beilstein Reference	1905952
ChEBI	CHEBI:35697 ;
ChEMBL	ChEMBL27246 ;
ChemSpider	392447 ;
ECHA InfoCard	100.004.908
EC Number	205-398-1;
Gmelin Reference	3731
IUPHAR/BPS	3203;
KEGG	C00423 ;
PubChem CID	444539;
UNII	U14A832J8D ;
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
Odor	Honey-like
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
Magnetic susceptibility (χ)	−7.836×10−5 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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)	1 1 0
Flash point	> 100 °C (212 °F; 373 K)
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). verify (what is ?) Infobox references

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. 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. The cis-isomer is called allocinnamic acid.

Names



Preferred IUPAC name (2E)-3-Phenylprop-2-enoic acid
Systematic IUPAC name Cinnamic acid
Other names trans-Cinnamic acid Phenylacrylic acid Cinnamylic acid 3-Phenylacrylic acid (E)-Cinnamic acid Benzenepropenoic acid Isocinnamic acid
Identifiers
CAS Number	140-10-3^Y
3D model (JSmol)	Interactive image
Beilstein Reference	1905952
ChEBI	CHEBI:35697^Y
ChEMBL	ChEMBL27246^Y
ChemSpider	392447^Y
ECHA InfoCard	100.004.908
EC Number	205-398-1
Gmelin Reference	3731
IUPHAR/BPS	3203
KEGG	C00423^Y
PubChem CID	444539
UNII	U14A832J8D^N
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+^Y Key: WBYWAXJHAXSJNI-VOTSOKGWSA-N^Y 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
Odor	Honey-like
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 (pK_a)	4.44
Magnetic susceptibility (χ)	−7.836×10⁻⁵ cm³/mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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)	1 1 0
Flash point	> 100 °C (212 °F; 373 K)
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). N verify (what is ^YN ?) Infobox references