Structure via PubChem · Public domain (PubChem)
(E)-cinnamaldehyde
Sign in to saveAlso known as cinnamic aldehyde, 3-phenylacrylaldehyde, (E)-Cinnamic aldehyde, (E)-3-Phenyl-2-propenal, trans-Cinnamic aldehyde, (E)-3-Phenylpropenal, 3-Phenylacrolein
Cinnamaldehyde is an organic compound with the formula or . 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. It is an found in high concentrations in cinanamon essential oil.
Chemical data
- Formula
- C9H8O
- Molecular weight
- 132.16 g/mol
- IUPAC name
- (E)-3-phenylprop-2-enal
- SMILES
- C1=CC=C(C=C1)/C=C/C=O
- InChIKey
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N
- XLogP
- 1.9
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
112 papers- Combination of synthetic acaricides with (E)-cinnamaldehyde to control Rhipicephalus microplus.Experimental & applied acarology · 2022
- Acaricidal activity of (E)-cinnamaldehyde and α-bisabolol on populations of Rhipicephalus microplus (Acari: Ixodidae) with different resistance profiles.Veterinary parasitology · 2020
- Enzyme-Based Antiviral Potential of Cinnamomum verum J. Presl. Essential Oil and Its Major Component (E)-Cinnamaldehyde.ACS omega · 2024
- Evaluation of Eugenol and (E)-Cinnamaldehyde Insecticidal Activity Against Larvae and Pupae of Musca domestica (Diptera: Muscidae).Journal of medical entomology · 2020
- Acaricidal activity of Cinnamomum cassia (Chinese cinnamon) against the tick Haemaphysalis longicornis is linked to its content of (E)-cinnamaldehyde.Parasites & vectors · 2021
via PubMed
Wikidata facts
- Mass
- 132.057515
Show 8 more facts
- Commons category
- Cinnamaldehyde
- chemical formula
- C₉H₈O
- isomeric SMILES
- C1=CC=C(C=C1)/C=C/C=O
- canonical SMILES
- C1=CC=C(C=C1)C=CC=O
- melting point
- -8
- boiling point
- 253
- flash point
- 120
- density
- 1.05
via Wikidata · CC0
~8 min read
Article
13 sectionsContents
- Structure and synthesis
- Biosynthesis
- Preparation
- Applications
- As a flavorant
- As an agrichemical
- Miscellaneous uses
- Derivatives
- Toxicology
- DNA repair
- Biological effects
- References
- External links
Cinnamaldehyde is an organic compound with the formula or . 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. It is an found in high concentrations in cinanamon essential oil.
==Structure and synthesis== Cinnamaldehyde was isolated from cinnamon essential oil in 1834 by Jean-Baptiste Dumas and Eugène-Melchior Péligot and synthesized in the laboratory by the Italian chemist Luigi Chiozza in 1854. Synonyms for Cinnamaldehyde include 3-Phenyl-2-propenal, Cinnamic aldehyde, trans-Cinnamaldehyde, Cinnamal, Cinnamyl aldehyde, Cassia aldehyde, 3-Phenylacrolein, and β-Phenylacrolein.