205546

Caffeic Acid

A natural dietary compound reported to have anti-carcinogenic and anti-inflammatory properties.

• Synonym(s): Caffeic Acid, 3,4-Dihydroxycinnamic Acid
• Empirical Formula (Hill Notation): C₉H₈O₄
• CAS Number: 331-39-5
• Molecular Weight: 180.16
• UNSPSC Code: 12352106
• NACRES: NA.77
• MDL number: MFCD00004392
• Assay: ≥95% (HPLC)
• Form: crystalline solid
• Storage condition: OK to freeze

Properties

• Quality Segment: 100
• description: Merck USA index - 14, 1635
• assay: ≥95% (HPLC)
• form: crystalline solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: tan
• solubility: DMSO: 200 mg/mL, ethanol: 50 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: Oc1c(ccc(c1)\C=C/C(=O)O)O
• InChI: 1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2-
• InChI key: QAIPRVGONGVQAS-RQOWECAXSA-N

Description

General description

A cell-permeable natural dietary compound reported to have anti-carcinogenic and anti-inflammatory properties. A selective, non-competitive inhibitor of 5-lipoxygenase (ID₅₀ = 3.7 µM). Inhibits Cu²⁺-induced LDL oxidation in the initiation phase but acts as a prooxidant in the propagation phase. An effective irreversible inhibitor of glutathione S-transferases and a non-competitive inhibitor of xanthine oxidase.

A natural dietary compound reported to have anti-carcinogenic and anti-inflammatory properties. A cell-permeable, selective, non-competitive inhibitor of 5-lipoxygenase (ID₅₀ = 3.7 µM). Inhibits Cu²⁺-induced LDL oxidation in the initiation phase but acts as a prooxidant in the propagation phase. An irreversible inhibitor of glutathione S-transferases and a non-competitive inhibitor of xanthine oxidase.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
5-lipoxygenase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 3.7 µM against 5-lipoxygenase

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Yamanaka, N., et al. 1997. FEBS Lett.405, 186.
Chan, W.S., et al. 1995. Anticancer Res.15, 703.
Ploemen, J.H., et al. 1993. Food Chem. Toxicol.31, 475.
Koshihara, Y., et al. 1984. Biochim. Biophys. Acta792, 92.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Carcinogenic / Teratogenic (D)

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Codes: H351
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 2
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable