Phenethyl caffeate Chemical Properties

Melting point:

127-129℃

Boiling point:

498.6±45.0 °C(Predicted)

Density 

1.266±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Soluble in ethyl acetate at 50mg/ml. Soluble in DMSO and ethanol.

form 

White to off-white solid

pka

8.46±0.20(Predicted)

color 

off-white

λmax

323nm(lit.)

Sensitive 

Light Sensitive

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.

InChIKey

SWUARLUWKZWEBQ-VQHVLOKHSA-N

LogP

3.734 (est)

CAS DataBase Reference

104594-70-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-38-37-36

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UD3334375

HS Code 

29182900

Phenethyl caffeate Usage And Synthesis

Description

Phenylethyl caffeate is one of the allergens of propolis (bee glue); also contained in poplar-bud secretions.

Chemical Properties

Off-White Solid

Uses

Phenylethyl 3,4-dihydroxycinnamate is a potent and specific inhibitor of nuclear transcription factor, NF-κB, activation. It has been shown to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation. It inhibits HIV-1 integrase and also inhibits proliferation of transformed cells. It induces apoptosis in transformed fibroblasts, and interferes with EGF signal transduction affecting both protein kinase C and ornithine decarboxylase activity.

Uses

antineoplastic, antiinflammatory, immunomodulator, NFkB blocker

Uses

Cytotoxic agent against cancer cell lines. Inhibitor of ornithine decarboxylase and protein tyrosine kinase. Found to be a specific inhibitor of the nuclear transcription factor, NF-kB. It has also been shown to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation.

Definition

ChEBI: Phenethyl caffeate is an alkyl caffeate ester in which 2-phenylethyl is the alkyl component. It has a role as an antineoplastic agent, an anti-inflammatory agent, an immunomodulator, a metabolite, an antioxidant, a neuroprotective agent, an antiviral agent and an antibacterial agent.

Biological Activity

Antioxidant, antimitogenic, anticarcinogenic, anti-inflammatory and antiviral. Specifically inhibits NF- κ B activation and inhibits the growth of transformed cells. Also suppresses lipid peroxidation and inhibits ornithine decarboxylase, protein tyrosine kinase and lipoxygenase activities.

Contact allergens

Capee is one of the allergens of propolis (bee glue). It is also contained in poplar bud secretions.

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.

Anticancer Research

Caffeic acid (3,4-dihydroxycinnamic acid) phenethyl ester (CAPE) is a natural phenolcompound and an active component of propolis from honeybee hives. Torkiet al. (2017)investigated the effect of phosphatidylinositol 3-kinase/AKT/mammaliantarget of rapamycin (PI3K/Akt/mTOR) signaling pathway dual inhibitor, NVP-BEZ235,and CAPE on TNBC cell line (MDA-MB-231), stimulated withtransforming growth factor (TGF)-β1 for 14 days. CAPE in combination with NVP-BEZ235synergistically inhibited cell growth and reduced CXCR4 expression.Also, treatment of MDA-MB-231 cells with CAPE and NVP-BEZ235 time-dependentlyinhibited the expression of p-Forkhead Box O3a (FOXO3a). In a nutshell,these results indicate that tumour metastasis and progression in TNBC cellscan be effectively reduced through the concurrent use of NVP-BEZ235 and CAPE(Torki et al. 2017).

storage

Store at -20°C

References

1) Sudine et al. (1993) Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties. FEBS Lett. 21 329 2) Natarajan et al. (1996) Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B. Proc. Natl. Acad. Sci. USA 93 9090 3) Chiao et al. (1995). Apoptosis and altered redox state induced by caffeic acid phenethyl ester (CAPE) in transformed rat fibroblast cells; Cancer Res. 55 3576 4) Orban et.al. (2000), Caffeic acid phenethyl ester induces leukocyte apoptosis, modulates nuclear factor-kappa B and suppresses acute inflammation; Neuroimmunomodulation, 7 99

Phenethyl caffeate(104594-70-9)Related Product Information

• Olibanum oil
• Diethyl phthalate
• Ethylparaben
• BUTYL OLEATE
• Caffeic acid
• Methyl acrylate
• PHENETHYL SALICYLATE
• Phenethyl phenylacetate
• 1-Phenylethyl propionate
• Ethyl 2-hydroxybenzoate
• Phenethyl isothiocyanate
• Styralyl acetate
• Ethyl phenylacetate
• Dimethyl succinate
• Tris(trimethylsilyl)phosphate
• METHYL CAFFEATE
• Benzocaine
• Phenethyl isocyanate