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Ethyl cinnamate

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Ethyl cinnamate
Skeletal formula of ethyl cinnamate
Ball-and-stick model of ethyl cinnamate
Names
Preferred IUPAC name Ethyl (2E)-3-phenylprop-2-enoate
Other names Ethyl cinnamate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.822 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+Key: KBEBGUQPQBELIU-CMDGGOBGSA-N
  • 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/cm
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 cm/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Ethyl cinnamate is the ester of cinnamic acid and ethanol. It is present in the essential oil of cinnamon. Pure ethyl cinnamate has a "fruity and balsamic odor, reminiscent of cinnamon with an amber note".

The p-methoxy derivative is reported to be a monoamine oxidase inhibitor. 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

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.


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