2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

• ChemBase ID: 105695
• Molecular Formular: C17H16O4
• Molecular Mass: 284.30654
• Monoisotopic Mass: 284.10485899
• SMILES: Oc1c(O)cc(/C=C/C(=O)OCCc2ccccc2)cc1
• Canonical SMILES: O=C(/C=C/c1ccc(c(c1)O)O)OCCc1ccccc1
• InChI: 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
• InChIKey: SWUARLUWKZWEBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate; 2-phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• IUPAC Traditional name: 2-phenylethyl 3-(3,4-dihydroxyphenyl)prop-2-enoate; caffeic acid phenethyl ester
• Synonyms: Caffeic acid phenethyl ester(CAPE); 3-(3,4-Dihydroxyphenyl)-2-propenoic Acid 2-Phenylethyl Ester; Phenethyl caffeate; PHENYLETHYL CAFFEATE; CAPE; CAFFEIC ACID PHENETHYL ESTER; Caffeic acid phenethyl ester; Phenylethyl caffeate; Caffeic acid 2-phenylethyl ester; β-Phenylethyl caffeate; Phenethyl 3-(3,4-dihydroxyphenyl)acrylate

Database IDs

• CAS Number: 104594-70-9
• MDL Number: MFCD00866470
• PubChem SID: 162092374; 24278341
• PubChem CID: 5281787
• Chemspider ID: 4445100
• Wikipedia Title: Caffeic_acid_phenethyl_ester

CALCULATED PROPERTIES

• Acid pKa: 9.208643
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.921233
• LogD (pH = 7.4): 3.9146662
• Log P: 3.9213173
• Molar Refractivity: 81.1584 cm^3
• Polarizability: 30.931627 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: soluble; Ethanol; ethanol: soluble; Ethyl Acetate; ethyl acetate: soluble50 mg/mL
• Apperance: off-white powder; Off-White Solid

Safety Information

• Storage Condition: -20°C; 2-8°C; protect from light
• RTECS: UD3334375
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Target: NF-κB
• Gene Information: human ... NFKB2(4791)

Product Information

• Purity: ≥97%; ≥97% (HPLC); 98%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02193775

A cytotoxic agent to cancer cell lines. Acts as an inhibitor of protein tyrosine kinase and ornithine decarboxylase.

MP Biomedicals - 02195860

Purity: >97%
Active component of propolis from honeybee hives. Possesses anti-viral, anti-inflammatory and immunomodulary properties. Inhibits growth of several types of transformed cells and induces apoptosis in cloned rat embryo fibroblast (CREF) cells.

Sigma Aldrich - C8221

Biochem/physiol Actions
Caffeic acid phenethyl ester is a specific inhibitor of the nuclear transcription factor NF-κB.
Application
Caffeic acid phenethyl ester (CAPE) is the active component of propolis, a honeybee hive product.1 Caffeic acid phenethyl ester is a specific inhibitor of the nuclear transcription factor, NF-κB.2 CAPE has been shown to significantly suppress the lipoxygenase pathway of arachidonic acid metabolism during inflammation.3,4 Caffeic acid phenethyl ester inhibits HIV-1 integrase,5,6 and also inhibits proliferation of transformed cells.7,8 It induces apoptosis in transformed fibroblasts,9 and interferes with EGF signal transduction affecting both protein kinase C and ornithine decarboxylase activity.7

Toronto Research Chemicals - C080050

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 p

REFERENCES

• Rao, C.V., et al., Chem. Biol. Interactions , 84 : 277-90 (1992).
• Grunberger, D., et al.: Experientia, 44, 230 (1988)
• Fesen, M.R., et al.: Biochem. Pharmacol., 48, 595 (1988)
• Su, Z.Z., et al.: Cancer Res., 54, 1865 (1988)
• Zheng, Z.S., et al.: Oncol. Res., 7, 445 (1988)
• Mirzoeva, O.K. and Calder, P.C.: Essent. Fatty