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205546

Sigma-Aldrich

Caffeic Acid

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

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Synonym(s):
Caffeic Acid, 3,4-Dihydroxycinnamic Acid
Empirical Formula (Hill Notation):
C9H8O4
CAS Number:
Molecular Weight:
180.16
MDL number:
UNSPSC Code:
12352106
NACRES:
NA.77

Quality Level

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

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

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

Warning

Toxicity: Carcinogenic / Teratogenic (D)

Reconstitution

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

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

Carc. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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