Caffeic acid phenethyl ester

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

CAS Number

* 104594-70-9

3D model (JSmol)

* Interactive image

Abbreviations  | CAPE
ChEBI |

* CHEBI:8062

ChemSpider |

* 4445100

PubChem CID

* 5281787

UNII |

* G960R9S5SK Y

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/b9-7+

Key: SWUARLUWKZWEBQ-VQHVLOKHSA-N

* 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+

Key: SWUARLUWKZWEBQ-VQHVLOKHBT

SMILES

* O=C(OCCc1ccccc1)\C=C\c2cc(O)c(O)cc2

Properties

Chemical formula

| 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).

Infobox references

Tracking categories (test):

* SizeSet

Caffeic acid phenethyl ester (CAPE) is a natural phenolic chemical compound. It is the ester of caffeic acid and phenethyl alcohol.

## Natural occurrences

CAPE is found in a variety of plants. It is also a component of propolis from honeybee hives.[1]

## Potential pharmacology

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]

## References

1. ↑ Demestre M; Messerli SM; Celli N et al. (August 2008). "CAPE (caffeic acid phenethyl ester)-based propolis extract (Bio 30) suppresses the growth of human neurofibromatosis (NF) tumor xenografts in mice". Phytother Res 23 (2): 226–30. doi:10.1002/ptr.2594. PMID 18726924.
2. ↑ "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. August 1996. doi:10.1073/pnas.93.17.9090. PMID 8799159. Bibcode: 1996PNAS...93.9090N.
3. ↑ "Caffeic acid phenethyl ester induces leukocyte apoptosis, modulates nuclear factor-kappa B and suppresses acute inflammation". Neuroimmunomodulation 7 (2): 99–105. 2000. doi:10.1159/000026427. PMID 10686520. https://zenodo.org/record/1235309.
4. ↑ 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.
5. ↑ "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. November 1988. PMID 3139287. http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=3139287.
6. ↑ 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. https://www.sciencedirect.com/science/article/pii/S2049080120302181. Retrieved January 13, 2023.

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*[CID]: Compound ID