File:Zimtsäure_-_Cinnamic_acid.svg · Wikimedia Commons · See Wikimedia Commons
(E)-cinnamic acid
Sign in to saveAlso 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.
In the Vinony graph
Vinony's link graph records 199 inbound references to (E)-cinnamic acid, and connects out to honey, sodium and medication.
It is catalogued under topics including Chembox having GHS data, ECHA InfoCard ID from Wikidata and Enoic acids.
Vinony links it to 44 Wikipedia language editions.
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 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
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
Wikidata facts
- Has part
- oxygen
- Mass
- 148.052
Show 11 more facts
- described by source
- New International Encyclopedia
- Commons category
- Cinnamic acid
- chemical formula
- C₉H₈O₂
- canonical SMILES
- C1=CC=C(C=C1)C=CC(=O)O
- isomeric SMILES
- C1=CC=C(C=C1)/C=C/C(=O)O
- melting point
- 135
- pKa
- 4.44
- density
- 1.2475
- boiling point
- 300
- flash point
- 160
- subject has role
- primary metabolite
via Wikidata · CC0
~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.