C8221
Caffeic acid phenethyl ester
≥97% (HPLC), powder
Synonym(s):
CAPE
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About This Item
Empirical Formula (Hill Notation):
C17H16O4
CAS Number:
Molecular Weight:
284.31
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
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)
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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
Z Z Su et al.
Anticancer research, 15(5B), 1841-1848 (1995-09-01)
The active component of the folk medicine propolis, caffeic acid phenethyl ester (CAPE), displays selective toxicity toward cloned rat embryo fibroblast (CREF) cells transformed by a spectrum of diverse acting oncogenes. Identification of the mode of action of CAPE should
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