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Merck

C8221

Caffeic acid phenethyl ester

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

Caffeic acid phenethyl ester

Sinonimo/i:

CAPE

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Informazioni su questo articolo

Formula empirica (notazione di Hill):
C17H16O4
Numero CAS:
Peso molecolare:
284.31
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥97% (HPLC)
Form:
powder
Quality level:
Storage condition:
protect from light

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Nome del prodotto

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

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

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

Quality Level

Gene Information

human ... NFKB2(4791)

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Questo articolo
211200C9623D5794
CAPE A cell-permeable active component of propolis from honeybee hives.

Sigma-Aldrich

211200

CAPE

Sigma-Aldrich

Sigma-Aldrich

C9623

Chetomin

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, 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

Caffeic acid phenethyl ester is a specific inhibitor of the nuclear transcription factor NF-κB.
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.

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.

Classe di stoccaggio

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
M R Fesen et al.
Biochemical pharmacology, 48(3), 595-608 (1994-08-03)
The inhibition of HIV-1 integrase by flavones and related compounds was investigated biochemically and by means of structure-activity relationships. Purified enzyme and synthetic oligonucleotides were used to assay for three reactions catalysed by integrase: (1) processing of 3' termini by
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
G F Sud'ina et al.
FEBS letters, 329(1-2), 21-24 (1993-08-23)
Caffeic acid phenethyl ester, an active component of propolis extract, inhibits 5-lipoxygenase in the micromolar concentration range. The inhibition is of an uncompetitive type, i.e. the inhibitor binds to the enzyme-substrate complex but not to the free enzyme. Caffeic acid
Protective effect of caffeic acid phenethyl ester (CAPE) on amiodarone-induced pulmonary fibrosisin rat
Zaeemzadeh N, et al.
Iranian Journal of Pharmaceutical Research : IJPR, 10(2), 321-321 (2011)

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Chronic inflammation is an underlying factor in the development and progression of many of the chronic diseases of aging, such as arthritis, atherosclerosis, diabetes, and cancer.

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