Caffeic_acid_phenethyl_ester
Caffeic acid phenethyl ester
Chemical compound
Caffeic acid phenethyl ester (CAPE) is a natural phenolic chemical compound. It is the ester of caffeic acid and phenethyl alcohol.
| Names | |
|---|---|
| Preferred IUPAC name
2-Phenylethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate | |
| Other names
Phenylethyl caffeate; Phenethyl caffeate; Caffeic acid 2-phenylethyl ester; β-Phenylethyl caffeate | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | CAPE |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.155.538  |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C17H16O4 | |
| Molar mass | 284.311 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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CAPE is found in a variety of plants. It is also a component of propolis from honeybee hives.[1]
A variety of in vitro pharmacology and effects in animal models have been reported for CAPE, but their clinical significance is unknown. It has antimitogenic, anticarcinogenic, anti-inflammatory, and immunomodulatory properties in vitro.[2] Another study also showed that CAPE suppresses acute immune and inflammatory responses in vitro.[3] This anti-cancer effect was also seen when mice skin was treated with bee propolis and exposed to TPA, a chemical that induced skin papillomas. CAPE significantly reduced the number of papillomas.[4][5]
Recent study suggest that CAPE can also help in reducing oxidative stress caused by traumatic brain injury.[6]
- Natarajan K, Singh S, Burke TR, Grunberger D, Aggarwal BB (August 1996). "Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B". Proc. Natl. Acad. Sci. U.S.A. 93 (17): 9090–5. Bibcode:1996PNAS...93.9090N. doi:10.1073/pnas.93.17.9090. PMC 38600. PMID 8799159.
- Orban Z, Mitsiades N, Burke TR, Tsokos M, Chrousos GP (2000). "Caffeic acid phenethyl ester induces leukocyte apoptosis, modulates nuclear factor-kappa B and suppresses acute inflammation". Neuroimmunomodulation. 7 (2): 99–105. doi:10.1159/000026427. PMID 10686520. S2CID 31950905.
- Huang MT, Ma W, Yen P, et al. (April 1996). "Inhibitory effects of caffeic acid phenethyl ester (CAPE) on 12-O-tetradecanoylphorbol-13-acetate-induced tumor promotion in mouse skin and the synthesis of DNA, RNA and protein in HeLa cells". Carcinogenesis. 17 (4): 761–5. doi:10.1093/carcin/17.4.761. PMID 8625488.
- Huang MT, Smart RC, Wong CQ, Conney AH (November 1988). "Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate". Cancer Res. 48 (21): 5941–6. PMID 3139287.
- Nasution, Rizha Anshori; Asadul Islam, Andi; Hatta, Mochammad; (none), Prihantono; Turchan, Agus; (none), Nasrullah; Faruk, Muhammad (September 2020). "Role of CAPE in reducing oxidative stress in animal models with traumatic brain injury". Annals of Medicine and Surgery. 57: 118–122. doi:10.1016/j.amsu.2020.07.036. PMC 7390826. Retrieved January 13, 2023.