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C8221

Caffeic acid phenethyl ester

synthetic, ≥97% (HPLC), Nuclear transcription factor NF-κB inhibitor, powder

Caffeic acid phenethyl ester

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

Key Documents

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Product Name

Caffeic acid phenethyl ester, ≥97% (HPLC), powder

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)

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This Item
211200C9623D5794
Caffeic acid phenethyl ester ≥97% (HPLC), powder

Sigma-Aldrich

C8221

Caffeic acid phenethyl ester

CAPE A cell-permeable active component of propolis from honeybee hives.

Sigma-Aldrich

211200

CAPE

Sigma-Aldrich

Sigma-Aldrich

C9623

Chetomin

Diacylglycerol Kinase Inhibitor II solid

Sigma-Aldrich

D5794

Diacylglycerol Kinase Inhibitor II

form

powder

form

solid

form

powder

form

solid

assay

≥97% (HPLC)

assay

≥97% (HPLC)

assay

≥98% (HPLC)

assay

≥97% (HPLC)

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage condition

protect from light

storage condition

OK to freeze, protect from light

storage condition

-

storage condition

-

solubility

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

solubility

DMSO: 200 mg/mL, ethanol: 50 mg/mL

solubility

DMSO: soluble, acetone: soluble, ethyl acetate: soluble

solubility

0.1 M HCl: slightly soluble, 0.1 M NaOH: slightly soluble, DMSO: soluble, H2O: insoluble, ethanol: soluble, ethyl acetate: soluble

Application

Caffeic acid phenethyl ester (CAPE) has been used to determine the effect of CAPE in hyperthyroidism,[1] as a component of culture media to measure the cytotoxicity of breast cancer cell line MDA-MB-231,[2] to study its effects on amiodarone-induced pulmonary fibrosis in rats.[3]

Biochem/physiol Actions

CAPE exhibits several properties such as anticarcinogenic, immunomodulatory activities, antioxidant, antiviral, anti-inflammatory, hypoglycaemic effect, cardioprotective and inhibits gastric secretion.[1] It also has an inhibitory effect on fibroblasts growth factor type 2 (FGF-2), a tumor growth factor in breast cancer.[2]
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM2256
BCCC6847
BCBV6787
BCBR2913V
BCBQ5475V

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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
M R Fesen et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(6), 2399-2403 (1993-03-15)
In an effort to further extend the number of targets for development of antiretroviral agents, we have used an in vitro integrase assay to investigate a variety of chemicals, including topoisomerase inhibitors, antimalarial agents, DNA binders, naphthoquinones, the flavone quercetin
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
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
D Grunberger et al.
Experientia, 44(3), 230-232 (1988-03-15)
The honeybee hive product, propolis, is a folk medicine employed for treating various ailments. Many important pharmaceutical properties have been ascribed to propolis, including anti-inflammatory, antiviral, immunostimulatory and carcinostatic activities. Propolis extracts have provided an active component identified as caffeic
View All Related Papers

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NF-κB and Inflammation

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