Caffeic acid phenethyl ester

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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
3D model (
JSmol
)
Abbreviations CAPE
ChEBI
ChemSpider
ECHA InfoCard
 100.155.538 Edit this at Wikidata
UNII
  • 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
  • O=C(OCCc1ccccc1)\C=C\c2cc(O)c(O)cc2
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).

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

honeybee hives.[1]

Potential pharmacology

A variety of

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. S2CID 21934712
    .
  2. PMID 8799159
    .
  3. S2CID 31950905
    .
  4. PMID 8625488
    .
  5. PMID 3139287
    .
  6. PMC 7390826
    . Retrieved January 13, 2023.
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