Caffeic Acid Phenethyl Ester

Alias: CAPE, Phenylethyl Caffeate; CAPE; Caffeic Acid Phenethyl Ester; BAF-IN-C09; 2-Phenylethyl Caffeate; β-Phenylethyl Caffeate
Cat No.:V0766 Purity: ≥98%
Caffeic acid phenethyl ester (also called CAPE; BAF-IN-C09; 2-Phenylethyl Caffeate; β-Phenylethyl Caffeate), a naturally occuring compound isolated fromhoneybee hive propolis, is potent and specific inhibitor of NF-κB activation with antioxidant, anticancer, immunomodulatory and antiinflammatory activities.
Caffeic Acid Phenethyl Ester Chemical Structure CAS No.: 104594-70-9
Product category: NF-κB
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
50mg
100mg
250mg
Other Sizes

Other Forms of Caffeic Acid Phenethyl Ester:

  • Caffeic acid
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Caffeic acid phenethyl ester (also called CAPE; BAF-IN-C09; 2-Phenylethyl Caffeate; β-Phenylethyl Caffeate), a naturally occurring substance isolated from honeybee hive propolis, is a potent and specific inhibitor of NF-κB activation with antioxidant, anticancer, immunomodulatory, and antiinflammatory activities. Caffeic acid phenethyl ester prevents TNF-dependent activation of NF-κB in U937 cells in a dose-dependent manner.

Biological Activity I Assay Protocols (From Reference)
Targets
NF-κB
ln Vitro
By preventing the translocation of the p65 subunit of NF-κB to the nucleus, caffeine acid phenethyl ester inhibits NF-κB activation brought on by phorbol ester, ceramide, okadaic acid, and hydrogen peroxide. [1] In a series of tumor cell lines, Caffeic acid phenethyl ester exhibits promising antiproliferative activity with EC50 values of 1.76, 3.16, 13.7, and 44.0 μM against murine colon 26-L5, murine B16-BL6 melanoma, human HT-1080 fibrosarcoma, and human lung A549 adenocarcinoma cell lines, respectively. [2] By preventing ROS formation and repressing caspase activity, caffeine acid phenethyl ester, a potent antioxidant, prevents apoptosis in cerebellar granule cells. [3] Additionally, Caffeic acid phenethyl ester inhibits NF-κB signaling, which reduces the pro-inflammatory phenotype of LPS-stimulated HSCs and the sensitivity of LPS-induced HSCs to fibrogenic cytokines.[4]
ln Vivo
In vivo, Caffeic acid phenethyl ester (10 mg/kg, i.p.) inhibits the development and angiogenesis of primary tumors in C57BL/6 and BALB/c mice inoculated with Lewis lung carcinoma, colon carcinoma, and melanoma cells. [5] By reducing thymus weight and/or cellularity of the thymus and spleen, caffeine phenethyl ester (5, 10, 20 mg/kg) also exhibits immunomodulatory effects in vivo. [6]
Enzyme Assay
LNCaP 104-R1 cells are treated with 0, 10, 20, or 40 μM Caffeic acid phenethyl ester (CAPE) for 96 h. Three biological replicates of cells are lysed in SDS lysis buffer (240 mM Tris-acetate, 1% SDS, 1% glycerol, 5 mM EDTA pH 8.0) with DTT, protease inhibitors, and a cocktail of phosphatase inhibitors. Micro-Western Arrays are performed to measure protein expression and phosphorylation status modification.
Cell Assay
In EMEM medium supplemented with 10% FCS, 0.1% sodium bicarbonate, and 2 mM glutamine, murine B16-BL6 melanoma cell lines, human HT-1080 fibrosarcoma, human lung A549 adenocarcinoma, and are all kept alive. On the other hand, the same supplements found in EMEM are also present in the RPMI medium used to maintain the murine colon 26-L5 carcinoma cell line. With the exception of A-549 carcinoma, all of these cell lines are highly metastatic. The MTT assay, which is widely used, is used to assess cellular viability. A 100 μl cell suspension containing 2000 cells is plated in 96-well microtiter plates after exponentially growing cells are harvested. The cells are treated with varying concentrations of test samples in medium (100 μl) and incubated for 72 hours at 37°C with 5% CO2 after a 24-hour period of incubation to allow for cell attachment. Utilizing a Perkin Elmer HTS-7000 plate reader, spectrophotometric measurements of the formazan formation are made at 550 nm three hours after the addition of MTT. The test samples are first dissolved in DMSO, and then the DMSO is diluted with medium until the DMSO concentration is less than 0.25 percent. The amount of DMSO in normal was identical. Using the average values of the data from four wells, the EC50 values of 5-fluorouracil (5-FU) and doxorubicin HCl are calculated.
Animal Protocol
At 6 to 8 weeks of age, 5×105 LNCaP 104-R1 cells suspended in 0.5 mL of Matrigel are subcutaneously injected into male Balb/c nu/nu mice in both flanks to induce tumor development. The typical tumor volume exceeds 150 mm3 after 14 weeks. The mice are next divided into two groups: control group and group receiving caffeic acid phenethyl ester (CAPE) treatment. Caffeic acid phenethyl ester treatment group has 6 mice and 9 tumors, compared to control group's 6 mice and 8 tumors. After the 14th week of cancer cell injection, caffeic acid phenethyl ester (10 mg/kg/day in sesame oil) or the vehicle (sesame oil) is given by gavage. Volume is calculated using the formula volume=length×width×height×0.52 for tumor volume and body weight of mice carrying 104-R1 xenografts.
References

[1]. Proc Natl Acad Sci U S A . 1996 Aug 20;93(17):9090-5.

[2]. J Ethnopharmacol . 2002 Apr;80(1):67-73.

[3]. Int J Dev Neurosci . 2003 Nov;21(7):379-89

[4]. Int J Mol Med . 2014 Mar;33(3):687-94.

[5]. J Mol Med (Berl) . 2013 Feb;91(2):271-82.

[6]. Int Immunopharmacol . 2004 Mar;4(3):429-36.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H16O4
Molecular Weight
284.31
Exact Mass
284.10
Elemental Analysis
C, 71.82; H, 5.67; O, 22.51
CAS #
104594-70-9
Related CAS #
Caffeic acid;331-39-5
Appearance
Solid powder
SMILES
C1=CC=C(C=C1)CCOC(=O)/C=C/C2=CC(=C(C=C2)O)O
InChi Key
SWUARLUWKZWEBQ-VQHVLOKHSA-N
InChi Code
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+
Chemical Name
2-phenylethyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms
CAPE, Phenylethyl Caffeate; CAPE; Caffeic Acid Phenethyl Ester; BAF-IN-C09; 2-Phenylethyl Caffeate; β-Phenylethyl Caffeate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: ~57 mg/mL (~200.5 mM)
Water: <1 mg/mL
Ethanol:~57 mg/mL (~200.5 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.5173 mL 17.5864 mL 35.1729 mL
5 mM 0.7035 mL 3.5173 mL 7.0346 mL
10 mM 0.3517 mL 1.7586 mL 3.5173 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02744703 Completed Drug: CAPE-T
Drug: CAPE-S
Matrix Metalloproteinase Inhibitors
Composite Resins
Ege University April 2013 Not Applicable
Biological Data
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