104594-70-9

Basic information

• Product Name: Phenethyl caffeate
• Synonyms: Caffeic Acid 2-Phenylethyl Ester;CAFFEIC ACID PHENETHYLESTER (CAPE);CAPE,PhenethylCaffeate;CAFFEIC ACID PHENETHYL ESTER(CAPE)(P);KAFFEESUREPHENYLETHYLESTER;CAFFEICACIDPHENYLETHERESTER;3-(3,4-Dihydroxyphenyl)-2-propenoic acid 2-phenylethyl ester;Cafestol Acid Phenethyl Ester
• CAS NO: 104594-70-9
• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31
• EINECS: 1592732-453-0
• Product Categories: Miscellaneous Natural Products;Inhibitors;Tyrosine Kinase Inhibitors;Cytokine signaling;HIV/AIDS/Related Products;Apoptosis Inducers
• Mol File: 104594-70-9.mol
• Article Data: 22

Chemical Properties

• Melting Point: 127-129℃
• Boiling Point: 498.6 °C at 760 mmHg
• Flash Point: 185.1 °C
• Appearance: off-white/
• Density: 1.266 g/cm³
• Vapor Pressure: 1.45E-10mmHg at 25°C
• Refractive Index: 1.645
• Storage Temp.: Store at 0°C
• Solubility: Soluble in ethyl acetate at 50mg/ml. Soluble in DMSO and ethanol
• PKA: 8.46±0.20(Predicted)
• 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.
• CAS DataBase Reference: Phenethyl caffeate(CAS DataBase Reference)
• NIST Chemistry Reference: Phenethyl caffeate(104594-70-9)
• EPA Substance Registry System: Phenethyl caffeate(104594-70-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: UD3334375
• Hazardous Substances Data: 104594-70-9(Hazardous Substances Data)

Usage

Description

Phenethyl caffeate, also known as Phenylethyl 3,4-dihydroxycinnamate, is a naturally occurring compound found in propolis (bee glue) and poplar-bud secretions. It is an off-white solid with potent bioactive properties, making it a valuable compound for various applications in the pharmaceutical and healthcare industries.

Uses

Phenethyl caffeate is used as an anti-cancer agent for its cytotoxic effects against cancer cell lines. It inhibits the proliferation of transformed cells and induces apoptosis in transformed fibroblasts, making it a promising candidate for cancer treatment.
Used in Pharmaceutical Industry:
Phenethyl caffeate is used as an anti-inflammatory agent for its ability to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation. This property makes it a potential candidate for the development of new anti-inflammatory drugs.
Phenethyl caffeate is used as an immunomodulator for its potential to modulate the immune system, which can be beneficial in the treatment of various immune-related disorders.
Phenethyl caffeate is used as an NF-kB blocker for its ability to specifically inhibit the nuclear transcription factor, NF-kB, which plays a crucial role in various cellular processes, including inflammation and cancer.
Used in Anticancer Applications:
Phenethyl caffeate is employed as an antineoplastic agent, targeting various cancer cell lines and exhibiting cytotoxic effects. It also inhibits ornithine decarboxylase and protein tyrosine kinase, further contributing to its potential as a cancer treatment option.

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

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+

Upstream product

• 60-12-8 2-phenylethanol 
• 331-39-5 caffeic acid 
• 103-63-9 1-phenyl-2-bromoethane 
• 77201-71-9 (E)-3-(3,4-dihydroxyphenyl)acryloyl chloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 848598-50-5 malonic acid monophenethyl ester 
• 621-59-0 isovanillin 
• 103-82-2 phenylacetic acid 
• 88623-81-8 3,4-diacetoxycinnamic acid 
• 118971-54-3 (E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate 
• 92778-42-2 malonic acid di(2-phenylethyl) ester 
• 538-75-0 dicyclohexyl-carbodiimide 

Related news

Phenethyl caffeate (cas 104594-70-9) benzo[kl]xanthene lignan with DNA interacting properties induces DNA damage and apoptosis in colon cancer cells08/17/2019

AimsPhenethyl caffeate benzoxanthene lignan (PCBL) is a synthetic compound with DNA interacting, antiangiogenic, antiproliferative and tumor cell death inducing abilities. Though PCBL exhibits the qualities of a prospective antitumor agent, the basic mechanism of PCBL induced cell death remains ...detailed

Relevant articles and documents

Development of blood-brain barrier permeable nitrocatechol-based catechol O-methyltransferase inhibitors with reduced potential for hepatotoxicity

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

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

Caffeic acid phenethyl ester (CAPE)-derivatives act as selective inhibitors of acetylcholinesterase

Unexpected inhibitory effects against eeAChE could be found for a newly synthesized class of caffeic acid phenethyl ester (CAPE)derivatives. Thus, phenethyl-(E)-3-(3,5-dimethoxy-4-phenethoxyphenyl)-acrylate (Ki = 1.97 ± 0.38 μM, Ki′ = 2.44 ± 0.07 μM)and 4-(2-(((E)-3-(3,4-bis(benzyloxy)phenyl)acryloyl)oxy)ethyl)-1,2-phenylene (2E,2′E)-bis(3-(3,4-bis(benzyloxy)phenyl)acrylate)(Ki = 0.72 ± 0.31 μM, Ki′ = 1.80 ± 0.21 μM)showed very good inhibition of eeAChE, while being non cytotoxic for malignant human cancer cells and non-malignant mouse fibroblasts. Also, they are weak inhibitors for BChE (from equine serum).

Crystal form II of caffeic acid phenethyl ester, and preparation method and use thereof

The invention provides a crystal form II of caffeic acid phenethyl ester, and a preparation method and a use thereof. The caffeic acid phenethyl ester has a structure represented by formula I, and diffraction peaks represented by 2theta diffraction angles of 6.199 DEG, 18.439 DEG, 22.560 DEG, 26.481 DEG and 30.721 DEG exist in an X-ray powder diffraction map of the crystal form II radiated with CuKalpha. The novel crystal form has a better stability than other forms. The preparation method of the novel crystal form has the characteristics of simple process, high yield and good stability.