Caffeic acid phenethyl ester

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
ECHA InfoCard 100.155.538 Edit this at Wikidata
PubChem CID
  • 5281787
UNII
  • G960R9S5SK checkY
CompTox Dashboard (EPA)
  • DTXSID80861176 DTXSID8040987, DTXSID80861176 Edit this at Wikidata
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
  • 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
Chemical compound

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. S2CID 21934712.
  2. ^ 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.
  3. ^ 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.
  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. ^ 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.
  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. PMID 32760580.
  • v
  • t
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Aglycones
Precursor
Monohydroxycinnamic acids
(Coumaric acids)
  • p-Coumaric acid
  • o-Coumaric acid
  • m-Coumaric acid
Dihydroxycinnamic acids
Trihydroxycinnamic acids
O-methylated forms
others
Esters
glycoside-likes
Esters of
caffeic acid
with cyclitols
esters of
quinic acid
  • Chlorogenic acid (3-caffeoylquinic acid)
  • Cryptochlorogenic acid (4-O-caffeoylquinic acid)
  • Neochlorogenic acid (5-O-Caffeoylquinic acid)
  • Cynarine (1,5-dicaffeoylquinic acid)
  • 3,4-dicaffeoylquinic acid
  • 3,5-dicaffeoylquinic acid
esters of
shikimic acid
Glycosides
  • Ferulic acid glucoside
  • p-Coumaric acid glucoside
  • 1-Sinapoyl-D-glucose
Tartaric acid esters
Other esters
with caffeic acid
Caffeoyl phenylethanoid
glycoside (CPG)
  • Echinacoside
  • Calceolarioside A, B, C, F
  • Chiritoside A, B, C
  • Cistanoside A, B, C, D, E, F, G, H
  • Conandroside
  • Myconoside
  • Pauoifloside
  • Plantainoside A
  • Plantamajoside
  • Tubuloside B
  • Verbascoside (Isoverbascoside, 2′-Acetylverbascoside)
Oligomeric forms
Dimers
Trimers
Tetramers
  • Tetraferulic acids
Conjugates with
coenzyme A (CoA)