Phenethyl caffeate

Bezeichnung:Phenethyl caffeate

CAS-Nr104594-70-9

Englisch Name:Phenethyl caffeate

CBNumberCB2438898

SummenformelC17H16O4

Molgewicht284.31

MOL-Datei104594-70-9.mol

Phenethyl caffeate physikalisch-chemischer Eigenschaften

Schmelzpunkt	127-129℃
Siedepunkt	498.6±45.0 °C(Predicted)
Dichte	1.266±0.06 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	Soluble in ethyl acetate at 50mg/ml. Soluble in DMSO and ethanol.
pka	8.46±0.20(Predicted)
Aggregatzustand	White to off-white solid
Farbe	off-white
maximale Wellenlänge (λmax)	323nm(lit.)
Sensitive	Light Sensitive
Stabilität	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 Datenbank	104594-70-9(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-38-37-36
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	UD3334375
HS Code	29182900

Gefahreninformationscode (GHS)

Phenethyl caffeate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Phenylethyl caffeate is one of the allergens of propolis (bee glue); also contained in poplar-bud secretions.
Chemische Eigenschaften
Off-White Solid
Verwenden
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.
Verwenden
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.
Verwenden
antineoplastic, antiinflammatory, immunomodulator, NFkB blocker
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.
Biologische Aktivität
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.
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.
Kontakt-Allergie
Capee is one of the allergens of propolis (bee glue). It is also contained in poplar bud secretions.
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).
Lager
Store at -20°C
Einzelnachweise
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

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