(E)-cinnamic acid

Also known as (2E)-3-phenyl-2-propenoic acid, Phenylacrylic acid, trans-b-Carboxystyrene, trans-beta-carboxystyrene, (E)-3-phenyl-2-propenoic acid, trans-3-Phenylacrylate, trans-3-Phenyl-2-propenoic acid, (2E)-3-Phenyl-2-propenoate

chemical compound

OverviewAI-generated

(E)-cinnamic acid is a chemical compound with the formula C₉H₈O₂. Its IUPAC name is (E)-3-phenylprop-2-enoic acid. The substance has a mass of 148.052 and a density of 1.2475. It exhibits a melting point of 135 and a boiling point of 300. The flash point is recorded at 160, and the pKa value is 4.44.

Chemical properties include an xlogp of 2.1 and a topological polar surface area of 37.3. The molecule contains one hydrogen bond donor and two hydrogen bond acceptors, with a net charge of 0. The canonical SMILES notation is C1=CC=C(C=C1)C=CC(=O)O, while the isomeric SMILES is C1=CC=C(C=C1)/C=C/C(=O)O.

Literature references for (E)-cinnamic acid number 4995. The compound is referenced by 199 other encyclopedia articles.

Synthesized by Vinony from 24 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Chemical data

Formula: C9H8O2
Molecular weight: 148.16 g/mol
IUPAC name: (E)-3-phenylprop-2-enoic acid
SMILES: C1=CC=C(C=C1)/C=C/C(=O)O
InChIKey: WBYWAXJHAXSJNI-VOTSOKGWSA-N
XLogP: 2.1
Polar surface area: 37.3 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

4,995 papers

Methyl Esters of (E)-Cinnamic Acid: Activity against the Plant-Parasitic Nematode Meloidogyne incognita and In Silico Interaction with Histone Deacetylase.Journal of agricultural and food chemistry · 2022
Metabolic pathways of cinnamic acid derivatives in Brazilian green propolis in rats.Bioscience, biotechnology, and biochemistry · 2022
Cinnamic acid mitigates methotrexate-induced lung fibrosis in rats: comparative study with pirfenidone.Naunyn-Schmiedeberg's archives of pharmacology · 2024
Cinnamic acid hybrids as anticancer agents: A mini-review.Archiv der Pharmazie · 2022
A Review of Cinnamic Acid's Skeleton Modification: Features for Antibacterial-Agent-Guided Derivatives.Molecules (Basel, Switzerland) · 2024

via PubMed

~4 min read

Encyclopedic overview

Cinnamic acid is an organic compound with the formula C6H5−CH=CH−COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common. The cis-isomer is called allocinnamic acid.

Occurrence and production

Excerpted from Wikipedia’s “(E)-cinnamic acid” article, available under the CC BY-SA 4.0 licence.