Structure via PubChem · Public domain (PubChem)
trans-caffeic acid
Sign in to saveAlso known as 3,4-Dihydroxybenzeneacrylic acid, Cichoric acid, 3,4-Dihydroxycinnamic acid, Caffeic acid, 3,4-Dihydroxy-trans-cinnamate, caffeic acid (trans from), 3,4-Dihydroxycinnamic Acid
chemical compound
Chemical data
- Formula
- C9H8O4
- Molecular weight
- 180.16 g/mol
- IUPAC name
- (E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
- SMILES
- C1=CC(=C(C=C1/C=C/C(=O)O)O)O
- InChIKey
- QAIPRVGONGVQAS-DUXPYHPUSA-N
- XLogP
- 1.2
- Polar surface area
- 77.8 Ų
- H-bond donors
- 3
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
9,993 papers- Caffeic Acid and Diseases-Mechanisms of Action.International journal of molecular sciences · 2022
- Caffeic acid.IARC monographs on the evaluation of carcinogenic risks to humans · 1993
- Caffeic Acid: Numerous Chemoprotective Effects are Mediated via Hormesis.Journal of dietary supplements · 2024
- Caffeic Acid and Its Derivatives: Antimicrobial Drugs toward Microbial Pathogens.Journal of agricultural and food chemistry · 2021
- Caffeic Acid and Cyclen-Based Hydrogel for Synergistic Antibacterial Therapy.ACS applied materials & interfaces · 2024
via PubMed
Wikidata facts
- Mass
- 180.042
Show 4 more facts
- Commons category
- Caffeic acid
- chemical formula
- C₉H₈O₄
- canonical SMILES
- C1=CC(=C(C=C1C=CC(=O)O)O)O
- isomeric SMILES
- O=C(O)/C=C/c1ccc(O)c(O)c1
via Wikidata · CC0
~8 min read
Article
Caffeic acid is an organic compound with the formula (HO)2C6H3CH=CHCO2H. It plays a key role in scavenging reactive oxygen species (ROS) generated in energy metabolism. Caffeic acid is also responsible for maintaining normal levels of nitric oxide (NO) within cells. Caffeic acid is a yellow, solid chemical compound that is structurally classified as a hydroxycinnamic acid, and the molecule consists of both phenolic and acrylic functional groups. Caffeic acid is found in all plants as an intermediate in the biosynthesis of lignin, a naturally occurring complex carbohydrate representing the principal components of biomass and its residues. It is chemically unrelated to caffeine; instead, the shared name is related to its presence in coffee.
Natural occurrences