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Ethyl cinnamate

From Wikipedia, the free encyclopedia

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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.822 Edit this at Wikidata
UNII
  • InChI=1S/C11H12O2/c1-2-13-11(12)9-8-10-6-4-3-5-7-10/h3-9H,2H2,1H3/b9-8+ checkY
    Key: KBEBGUQPQBELIU-CMDGGOBGSA-N checkY
  • 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
  • CCOC(=O)/C=C/c1ccccc1
Properties
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)
-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).
checkY verify (what is checkY☒N ?)

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.

YouTube Encyclopedic

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  • 362L Stereoselective Wittig Reaction - Synthesis of Ethyl trans-Cinnamate (#7)

Transcription

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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This page was last edited on 16 August 2021, at 14:21
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