104594-70-9 Usage
Description
Phenylethyl caffeate is one of the allergens of propolis
(bee glue); also contained in poplar-bud secretions.
Chemical Properties
Off-White Solid
Uses
Different sources of media describe the Uses of 104594-70-9 differently. You can refer to the following data:
1. 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.
2. antineoplastic, antiinflammatory, immunomodulator, NFkB blocker
3. 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.
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).
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
Check Digit Verification of cas no
The CAS Registry Mumber 104594-70-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,4,5,9 and 4 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 104594-70:
(8*1)+(7*0)+(6*4)+(5*5)+(4*9)+(3*4)+(2*7)+(1*0)=119
119 % 10 = 9
So 104594-70-9 is a valid CAS Registry Number.
InChI:InChI=1/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+
104594-70-9Relevant articles and documents
Development of blood-brain barrier permeable nitrocatechol-based catechol O-methyltransferase inhibitors with reduced potential for hepatotoxicity
Silva, Tiago,Mohamed, Tarek,Shakeri, Arash,Rao, Praveen P.N.,Martínez-Gonzalez, Loreto,Pérez, Daniel I.,Martínez, Ana,Valente, Maria Jo?o,Garrido, Jorge,Uriarte, Eugenio,Serr?o, Paula,Soares-Da-silva, Patrício,Remi?o, Fernando,Borges, Fernanda
, p. 7584 - 7597 (2016)
Recent efforts have been focused on the development of centrally active COMT inhibitors, which can be valuable assets for neurological disorders such as Parkinson's disease, due to the severe hepatotoxicity risk associated with tolcapone. New nitrocatechol COMT inhibitors based on naturally occurring caffeic acid and caffeic acid phenethyl ester were developed. All nitrocatechol derivatives displayed potent inhibition of peripheral and cerebral COMT within the nanomolar range. Druglike derivatives 13, 15, and 16 were predicted to cross the blood-brain barrier in vitro and were significantly less toxic than tolcapone and entacapone when incubated at 50 μM with rat primary hepatocytes. Moreover, their unique acidity and electrochemical properties decreased the chances of formation of reactive quinone-imines and, as such, the potential for hepatotoxicity. The binding mode of 16 confirmed that the major interactions with COMT were established via the nitrocatechol ring, allowing derivatization of the side chain for future lead optimization efforts.
Caffeic acid phenethyl ester (CAPE): Synthesis and X-ray crystallographic analysis
Son,Lobkowsky,Lewis
, p. 236 - 238 (2001)
The structure of caffeic acid phenethyl ester [2-propenoic acid, 3-(3,4-dihydroxyphenyl)-, 2-phenethyl ester] (1), C17H16O4·1/2C6H 6, synthesized by base-catalyzed alkylation of caffeic acid salt with
Synthesis of Diverse Hydroxycinnamoyl Phenylethanoid Esters Using Escherichia coli
Song, Min Kyung,Cho, A Ra,Sim, Geunyoung,Ahn, Joong-Hoon
, p. 2028 - 2035 (2019/02/26)
Caffeic acid phenethyl ester (CAPE) is an ester of a hydroxycinnamic acid (phenylpropanoid) and a phenylethanoid (2-phenylethanol; 2-PE), which has long been used in traditional medicine. Here, we synthesized 54 hydroxycinnamic acid-phenylethanoid esters by feeding 64 combinations of hydroxycinnamic acids and phenylethanols to Escherichia coli harboring the rice genes OsPMT and Os4CL. The same approach was applied for ester synthesis with caffeic acid and eight different phenyl alcohols. Two hydroxycinnamoyl phenethyl esters, p-coumaroyl tyrosol and CAPE, were also synthesized from glucose using engineered E. coli by introducing genes for the synthesis of substrates. Consequently, we synthesized approximately 393.4 mg/L p-coumaroyl tyrosol and 23.8 mg/L CAPE with this approach. Overall, these findings demonstrate that the rice PMT and 4CL proteins can be used for the synthesis of diverse hydroxycinnamoyl phenylethanoid esters owing to their promiscuity and that further exploration of the biological activities of these compounds is warranted.
Antiproliferative activity and SARs of caffeic acid esters with mono-substituted phenylethanols moiety
Xie, Jin,Yang, Fengzhi,Zhang, Man,Lam, Celine,Qiao, Yixue,Xiao, Jia,Zhang, Dongdong,Ge, Yuxuan,Fu, Lei,Xie, Dongsheng
supporting information, p. 131 - 134 (2016/12/27)
A series of CAPE derivatives with mono-substituted phenylethanols moiety were synthesized and evaluated by MTT assay on growth of 4 human cancer cell lines (Hela, DU-145, MCF-7 and ECA-109). The substituent effects on the antiproliferative activity were systematically investigated for the first time. It was found that electron-donating and hydrophobic substituents at 2′-position of phenylethanol moiety could significantly enhance CAPE's antiproliferative activity. 2′-Propoxyl derivative, as a novel caffeic acid ester, exhibited exquisite potency (IC50?=?0.4?±?0.02 & 0.6?±?0.03?μM against Hela and DU-145 respectively).
