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C8221

Sigma-Aldrich

Caffeic acid phenethyl ester

≥97% (HPLC), powder

Synonym(s):

CAPE

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About This Item

Empirical Formula (Hill Notation):
C17H16O4
CAS Number:
104594-70-9
Molecular Weight:
284.31
MDL number:
MFCD00866470
UNSPSC Code:
12352108
PubChem Substance ID:
24278341
NACRES:
NA.77

biological source

synthetic

Assay

≥97% (HPLC)

form

powder

storage condition

protect from light

color

off-white

solubility

ethyl acetate: 50 mg/mL
DMSO: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

Oc1ccc(\C=C\C(=O)OCCc2ccccc2)cc1O

InChI

1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7+

InChI key

SWUARLUWKZWEBQ-VQHVLOKHSA-N

Gene Information

human ... NFKB2(4791)

Application

Caffeic acid phenethyl ester (CAPE) has been used to determine the effect of CAPE in hyperthyroidism, as a component of culture media to measure the cytotoxicity of breast cancer cell line MDA-MB-231, to study its effects on amiodarone-induced pulmonary fibrosis in rats.

Biochem/physiol Actions

CAPE exhibits several properties such as anticarcinogenic, immunomodulatory activities, antioxidant, antiviral, anti-inflammatory, hypoglycaemic effect, cardioprotective and inhibits gastric secretion. It also has an inhibitory effect on fibroblasts growth factor type 2 (FGF-2), a tumor growth factor in breast cancer.
Caffeic acid phenethyl ester is a specific inhibitor of the nuclear transcription factor NF-κB.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Attenuation of oxidative stress in plasma and tissues of rats with experimentally induced hyperthyroidism by caffeic acid phenylethyl ester
Mohamadin AM, et al.
Basic and Clinical Pharmacology and Toxicology, 100(2), 84-90 (2007)
M T Hansen et al.
Oncogene, 34(4), 424-435 (2014-01-29)
S100A4 is implicated in metastasis and chronic inflammation, but its function remains uncertain. Here we establish an S100A4-dependent link between inflammation and metastatic tumor progression. We found that the acute-phase response proteins serum amyloid A (SAA) 1 and SAA3 are
K Natarajan et al.
Proceedings of the National Academy of Sciences of the United States of America, 93(17), 9090-9095 (1996-08-20)
Caffeic acid phenethyl ester (CAPE), an active component of propolis from honeybee hives, is known to have antimitogenic, anticarcinogenic, antiinflammatory, and immunomodulatory properties. The molecular basis for these diverse properties is not known. Since the role of the nuclear factor
O K Mirzoeva et al.
Prostaglandins, leukotrienes, and essential fatty acids, 55(6), 441-449 (1996-12-01)
To investigate the possible mechanism of the therapeutic action of propolis, we studied: (a) the effect of propolis, its components, caffeic acid phenethyl ester (CAPE), caffeic acid (CA), quercetin and naringenin, as well as the synthetic compounds indomethacin (IM) and
Z S Zheng et al.
Oncology research, 7(9), 445-452 (1995-01-01)
Caffeic acid phenethyl ester (CAPE) was evaluated for its potential in regulating keratinocyte proliferation. CAPE inhibited the proliferation of SV40 transformed keratinocytes (Z114) in a concentration- and time-dependent manner. Inhibition by CAPE was seen with 0.5 to 5.0 micrograms/ml at
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