Ethyl cinnamate

Ethyl cinnamate

Names
Preferred IUPAC name Ethyl (2E)-3-phenylprop-2-enoate
Other names Ethyl cinnamate
Identifiers
CAS Number	103-36-6  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL318196  Y
ChemSpider	553344  Y
PubChem CID	637758
UNII	C023P3M5JJ  Y
CompTox Dashboard (EPA)	DTXSID9022520
InChI InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+ Y Key: KBEBGUQPQBELIU-CMDGGOBGSA-N Y InChI=1/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+ Key: KBEBGUQPQBELIU-CMDGGOBGBD
SMILES CCOC(=O)/C=C/c1ccccc1
Properties
Chemical formula	C11H12O2
Molar mass	176.21 g/mol
Density	1.046 g/cm3
Melting point	6.5 to 8 °C (43.7 to 46.4 °F; 279.6 to 281.1 K)
Boiling point	271 °C (520 °F; 544 K)
Magnetic susceptibility (χ)	−107.5·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y  verify  (what is  YN ?) Infobox references

Ethyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon.^{[ citation needed ]} Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note". ^[1]

The p-methoxy derivative is reported to be a monoamine oxidase inhibitor. ^[2] It can be synthesized by the esterification reaction involving ethanol and cinnamic acid in the presence of sulfuric acid.

List of plants that contain the chemical

• Kaempferia galanga ^{[3] [4]}

References

1. Budavari, Susan (2001). "Merck Index 13th Ed". Merck & Co., Inc.
2. Noro T, Miyase T, Kuroyanagi M, Ueno A, Fukushima S (1983). "Monoamine oxidase inhibitor from the rhizomes of Kaempferia galanga L". Chem Pharm Bull. 31 (8): 2708–11. doi: 10.1248/cpb.31.2708 . PMID   6652816.
3. Wong, K. C.; et al. (2006). "Composition of the essential oil of rhizomes of kaempferia galanga L". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.
4. Othman, R.; et al. (2006). "Bioassay-guided isolation of a vasorelaxant active compound from Kaempferia galanga L". Phytomedicine. 13 (1–2): 61–66. doi:10.1016/j.phymed.2004.07.004. PMID   16360934.