Cinnamaldehyde

Cinnamaldehyde
Names
	Preferred IUPAC name (2E)-3-Phenylprop-2-enal
	Other names Cihinnamaldehyde; Cinnamal; Cinnamic aldehyde; trans-Cinnamaldehyde;
Identifiers
CAS Number	14371-10-9 ;
3D model (JSmol)	Interactive image;
3DMet	B00198;
Beilstein Reference	1071571
ChEBI	CHEBI:16731 ;
ChEMBL	ChEMBL293492 ;
ChemSpider	553117 ;
DrugBank	DB14184;
ECHA InfoCard	100.111.079
EC Number	203-213-9;
IUPHAR/BPS	2423;
KEGG	C00903 ;
PubChem CID	637511;
RTECS number	GD6475000;
UNII	SR60A3XG0F ;
CompTox Dashboard (EPA)	DTXSID6024834 ;
	InChI InChI=1S/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+ Key: KJPRLNWUNMBNBZ-QPJJXVBHSA-N ; InChI=1/C9H8O/c10-8-4-7-9-5-2-1-3-6-9/h1-8H/b7-4+ Key: KJPRLNWUNMBNBZ-QPJJXVBHBH;
	SMILES c1ccc(cc1)/C=C/C=O;
Properties
Chemical formula	C9H8O
Molar mass	132.16 g/mol
Appearance	Yellow oil
Odor	Pungent, cinnamon-like
Density	1.0497 g/mL
Melting point	−7.5 °C (18.5 °F; 265.6 K)
Boiling point	248 °C (478 °F; 521 K)
Solubility in water	Slightly soluble
Solubility	Soluble in ether, chloroform; Insoluble in petroleum ether; Miscible with alcohol, oils;
Magnetic susceptibility (χ)	−7.48×10−5 cm3/mol
Refractive index (nD)	1.6195
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H319, H335
Precautionary statements	P261, P264, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501
NFPA 704 (fire diamond)	2 2 0
Flash point	71 °C (160 °F; 344 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	3400 mg/kg (rat, oral)
Related compounds
Related compounds	Cinnamic 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

Cinnamaldehyde is an organic compound with the formula ${\ce {C9H8O}}$ or C₆H₅CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

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