View source for Caffeic acid phenethyl ester

{{Chembox
| ImageFile = Phenethyl caffeate.svg
| ImageSize = 200px
| PIN = 2-Phenylethyl (2''E'')-3-(3,4-dihydroxyphenyl)prop-2-enoate
| OtherNames = Phenylethyl caffeate; Phenethyl caffeate; Caffeic acid 2-phenylethyl ester; β-Phenylethyl caffeate
|Section1={{Chembox Identifiers
| Abbreviations = CAPE
| CASNo = 104594-70-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII =  G960R9S5SK
| PubChem = 5281787
| ChEBI = 8062
| ChemSpiderID = 4445100
| SMILES = O=C(OCCc1ccccc1)\C=C\c2cc(O)c(O)cc2
| 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+
| InChIKey = SWUARLUWKZWEBQ-VQHVLOKHBT
| StdInChI = 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+
| StdInChIKey = SWUARLUWKZWEBQ-VQHVLOKHSA-N
}}
|Section2={{Chembox Properties
| C=17 | H=16 | O=4
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
'''Caffeic acid phenethyl ester''' ('''CAPE''') is a [[natural phenol]]ic 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]] [[Beehive|hives]].<ref name="pmid18726924">{{cite journal |author=Demestre M |title=CAPE (caffeic acid phenethyl ester)-based propolis extract (Bio 30) suppresses the growth of human neurofibromatosis (NF) tumor xenografts in mice |journal=Phytother Res |volume= 23|issue= 2|pages= 226–30|date=August 2008 |pmid=18726924 |doi=10.1002/ptr.2594 |name-list-style=vanc|author2=Messerli SM |author3=Celli N |display-authors=3 |last4=Shahhossini |first4=M. |last5=Kluwe |first5=L. |last6=Mautner |first6=V. |last7=Maruta |first7=H.|s2cid=21934712 }}</ref>
== Potential pharmacology ==
A variety of ''[[in vitro]]'' pharmacology and effects in [[animal model]]s have been reported for CAPE, but their clinical significance is unknown.  It has [[mitosis|antimitogenic]], anticarcinogenic, [[anti-inflammatory]], and [[immunomodulator]]y properties ''in vitro''.<ref name="pmid8799159">{{cite journal |vauthors=Natarajan K, Singh S, Burke TR, Grunberger D, Aggarwal BB |title=Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B |journal=Proc. Natl. Acad. Sci. U.S.A. |volume=93 |issue=17 |pages=9090–5 |date=August 1996 |pmid=8799159 |pmc=38600 |doi= 10.1073/pnas.93.17.9090|bibcode=1996PNAS...93.9090N |doi-access=free }}</ref>  Another study also showed that CAPE suppresses [[acute (medical)|acute]] [[immune]] and [[inflammation|inflammatory]] responses ''in vitro''.<ref name="pmid10686520">{{cite journal |vauthors=Orban Z, Mitsiades N, Burke TR, Tsokos M, Chrousos GP |title=Caffeic acid phenethyl ester induces leukocyte apoptosis, modulates nuclear factor-kappa B and suppresses acute inflammation |journal=Neuroimmunomodulation |volume=7 |issue=2 |pages=99–105 |year=2000 |pmid=10686520 |doi= 10.1159/000026427|s2cid=31950905 |url=https://zenodo.org/record/1235309 }}</ref>
This anti-cancer effect was also seen when mice skin was treated with bee propolis and exposed to [[12-O-Tetradecanoylphorbol-13-acetate|TPA]], a chemical that induced skin [[papilloma]]s. CAPE significantly reduced the number of papillomas.<ref name="pmid8625488">{{cite journal |author=Huang MT |title=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 |journal=Carcinogenesis |volume=17 |issue=4 |pages=761–5 |date=April 1996 |pmid=8625488 |doi= 10.1093/carcin/17.4.761|name-list-style=vanc|author2=Ma W |author3=Yen P |display-authors=3 |last4=Xie |first4=Jian-Guo |last5=Han |first5=Jingkang |last6=Frenkel |first6=Krystyna |last7=Grunberger |first7=Dezider |last8=Conney |first8=Allan H.|doi-access=free }}</ref><ref name="pmid3139287">{{cite journal |vauthors=Huang MT, Smart RC, Wong CQ, Conney AH |title=Inhibitory effect of curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor promotion in mouse skin by 12-O-tetradecanoylphorbol-13-acetate |journal=Cancer Res. |volume=48 |issue=21 |pages=5941–6 |date=November 1988 |pmid=3139287 |url=http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=3139287}}</ref>
Recent study suggest that CAPE can also help in reducing oxidative stress caused by traumatic brain injury.<ref>{{cite journal
| last1 = Nasution
| first1 = Rizha Anshori
| last2 = Asadul Islam
| first2 = Andi
| last3 = Hatta
| first3 = Mochammad
| last4= (none)
| first4 = Prihantono
| last5 = Turchan
| first5 = Agus
| last6 = (none)
| first6 = Nasrullah
| last7= Faruk
| first7 = Muhammad
| date = September 2020
| title = Role of CAPE in reducing oxidative stress in animal models with traumatic brain injury
| journal = Annals of Medicine and Surgery
| volume = 57
| issue =
| pages = 118–122
| doi =10.1016/j.amsu.2020.07.036
| pmid = 32760580
| pmc = 7390826
}}</ref>
== References ==
{{reflist}}
{{Hydroxycinnamic acid}}
[[Category:Hydroxycinnamic acid esters]]