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
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 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.

Read other articles:

Artyom Zhmakin

Artikel ini sebatang kara, artinya tidak ada artikel lain yang memiliki pranala balik ke halaman ini.Bantulah menambah pranala ke artikel ini dari artikel yang berhubungan atau coba peralatan pencari pranala.Tag ini diberikan pada November 2022. Artyom ZhmakinInformasi pribadiNama lengkap Artyom Ivanovich ZhmakinTanggal lahir 10 September 1995 (umur 28)Tinggi 1,74 m (5 ft 8+1⁄2 in)Posisi bermain GelandangInformasi klubKlub saat ini FC Avangard KurskKarier senior*Tahu...

 

Daftar Wakil Bupati Bantul

Wakil Bupati BantulHamemayu Hayuning Bawana (Jawa) Memperindah keindahan duniaPetahanaJoko B. Purnomosejak 26 Februari 2021Masa jabatan5 tahunDibentuk1999Pejabat pertamaH. Totok SudartoSitus webbantulkab.go.id Berikut ini adalah daftar Wakil Bupati Bantul dari masa ke masa. No Wakil Bupati Mulai Jabatan Akhir Jabatan Prd. Ket. Bupati 1 H.Totok Sudarto 1999 2004 1   Drs. H.Mohammad Idham Samawi Jabatan kosong 2004 2005 -   Drs.Mujono N.A.(Penjabat) 2 Drs. H.SumarnoPrs. 2005 2010...

 

نادي البحري

نادي البحري الرياضي شعار نادي البحري الرياضي الاسم الكامل النادي البحري الرياضي تأسس عام 1976 الملعب ملعب النادي البحري البلد العراق  الدوري دوري الدرجة الأولى موسم 2013- 2014 الثامن الإدارة الرئيس علاء صابر المدرب عبد اليمة ورور الطقم الرسمي الطقم الأساسي الطقم الاحتياطي ت...

Olympic Stadium (Athens)

Part of the Athens Olympic Sports Complex Olympic Stadium of AthensΟλυμπιακό Στάδιο της ΑθήναςUEFA Full nameCentral Olympic Stadium of O.A.C.A. Spyros LouisFormer namesSpyros Louis StadiumLocationMarousi, Athens, GreecePublic transit EiriniOwnerHellenic Olympic CommitteeOperatorOAKA S.A.Executive suites17Capacity69,618 (regulated capacity)[1]75,000 (total capacity)Field size105 x 68 m[1]SurfaceGrass, trackConstructionBroke ground1979[1]Opened8 S...

 

Lev Zadov

Ukrainian counter-intelligence agent (1893–1938) Lev Zadovלעוו זאדאווOtaman of the KontrrazvedkaIn officeMarch 1919 – August 1921 Personal detailsBornLevko Mykolaiovych Zadov(1893-04-11)11 April 1893Veselaya Yevreyka, Yuzivka, Katerynoslav, Russian EmpireDied25 September 1938(1938-09-25) (aged 45)Kyiv, Ukrainian SSR, Soviet UnionCause of deathExecution by firing squadResting placeBykivnia, Darnytsia, Kyiv, UkraineCitizenshipRussian Empire (1893-1917)State...

 

Lonely Gourmet

Artikel ini sebatang kara, artinya tidak ada artikel lain yang memiliki pranala balik ke halaman ini.Bantulah menambah pranala ke artikel ini dari artikel yang berhubungan atau coba peralatan pencari pranala.Tag ini diberikan pada Oktober 2022. Lonely Gourmet adalah sebuah seri drama Tiongkok tahun 2015. Seri tersebut disiarkan dari 28 Mei sampai 13 Agustus 2015 dan terdiri dari 12 episode. Seri tersebut berdasarkan pada manga Jepang Kodoku no Gourmet karya Masayuki Kusumi.[1][2&#...

Aktivitas air

Aktivitas air (singkatan: aw) adalah intensitas air di dalam unsur-unsur bukan air atau benda padat. Secara sederhana, aktivitas air adalah ukuran status energi air dalam suatu sistem. Hal ini didefinisikan sebagai tekanan uap dari cairan yang dibagi dengan air murni pada suhu yang sama, karena itu, air suling murni memiliki aw tepat satu. Semakin tinggi suhu biasanya aw juga akan naik, kecuali untuk benda yang mengkristal seperti garam atau gula. Semakin tinggi aw dalam sebuah benda, semakin...

 

Dariush Forouhar

Iranian pan-Iranist politician (1928–1998) Dariush ForouharMinister of LabourIn office13 February 1979 – 29 September 1979Prime MinisterMehdi BazarganPreceded byManouchehr AryanaSucceeded byAli EspahbodiMinister without Portfoliofor Provincial Inspection[1]In office29 September 1979 – 6 November 1979Prime MinisterMehdi Bazargan Personal detailsBorn18 August 1928Isfahan, IranDied22 November 1998(1998-11-22) (aged 70)Tehran, IranPolitical partyNation Party o...

 

Croatie au Concours Eurovision de la chanson 2016

Cet article est une ébauche concernant le Concours Eurovision de la chanson et la Croatie. Vous pouvez partager vos connaissances en l’améliorant (comment ?) ; pour plus d’indications, visitez le projet Eurovision. Croatieau Concours Eurovision 2016 Données clés Pays  Croatie Chanson Lighthouse Interprète Nina Kraljić Langue Anglais Sélection nationale Type de sélection Sélection interne Date 24 février 2016 (artiste)9 mars 2016 (chanson) Concours Eurovision de l...

Son of Manjeet Singh

2018 Indian filmSon of Manjeet SinghTheatrical release posterDirected byVikram GroverScreenplay byDheeraj RattanSurmeet MaaviProduced byKapil SharmaSumeet SinghStarringGurpreet GhuggiB.N. SharmaKaramjit AnmolJapji KhairaTaniaCinematographyVineet MalhotraEdited byAjay SharmaMusic bySurender SodhiDarshan UmangProductioncompaniesK9 FilmsSeven Color Motion PicturesRelease date 12 October 2018 (2018-10-12) (India) CountryIndiaLanguagePunjabi Son of Manjeet Singh is a 2018 India...

 

Northern Ireland (European Parliament constituency)

Former European Parliament constituency Northern IrelandEuropean Parliament constituencyLocation among the 2014 constituenciesMember stateUnited KingdomCreated1979Dissolved31 January 2020MEPs3Sources[2][3] Northern Ireland (Irish: Tuaisceart Éireann [ˈt̪ˠuəʃcəɾˠt̪ˠ ˈeːɾʲən̪ˠ] ⓘ;[1] Ulster-Scots: Norlin Airlann) was a constituency of the European Parliament from 1979 until the UK exit from the European Union on 31 January 2020. It elected three MEPs using th...

 

Otto Hahn Peace Medal

German peace prize This article is about the prize awarded by the United Nations Association of Germany. For the prize awarded by the Max Planck Society, see Otto Hahn Medal. AwardOtto Hahn Peace Medal in GoldAwarded forOutstanding services to peace, tolerance and international understandingPresented byUnited Nations Association of Germany, LV Berlin-Brandenburg (DGVN)Websitehttps://www.dgvn.berlin/ohfm/  The Otto Hahn Peace Medal in Gold is named after the German nuclear chemist and 194...

Mamoré–Guaporé linguistic area

Linguistic area of South America Map of the locations of the indigenous settlements of Bolivia The Mamoré–Guaporé linguistic area is a linguistic area that includes over a dozen South American language families and isolates of the Mamoré–Guaporé region of eastern lowland Bolivia (the Llanos de Moxos and Chiquitania regions) and Brazil (Rondonia[1] and Mato Grosso states).[2] Languages Crevels and van der Voort (2008) propose a Mamoré–Guaporé linguistic area in east...

 

West Side Story (2021 film)

2021 film by Steven Spielberg West Side StoryTheatrical release posterDirected bySteven SpielbergScreenplay byTony KushnerBased onWest Side Storyby Jerome Robbins Leonard Bernstein Stephen Sondheim Arthur LaurentsProduced by Steven Spielberg Kristie Macosko Krieger Kevin McCollum Starring Ansel Elgort Ariana DeBose David Alvarez Mike Faist Rita Moreno Rachel Zegler CinematographyJanusz KamińskiEdited by Michael Kahn Sarah Broshar Music byLeonard BernsteinProductioncompanies Amblin Entertainm...

 

Kosmos 13

Soviet reconnaissance satellite (Zenit 2-8) Kosmos 13A Zenit reentry capsuleNamesZenit 2-8Mission typeOptical imaging reconnaissanceRadiationOperatorSoviet space programCOSPAR ID1963-006A SATCAT no.554Mission duration8 days Spacecraft propertiesSpacecraft typeZenit-2ManufacturerOKB-1Launch mass4730 kg[1] Start of missionLaunch date21 March 1963, 08:24:00 GMTRocketVostok-2Launch siteBaikonur 1/5ContractorOKB-1 End of missionDisposalRecoveredLanding date29 March 1963Landing siteSteppe i...

Ian Iqbal Rashid

British film director and poet Ian Iqbal RashidIan Iqbal Rashid in London in October 2021Born1968 (age 55–56)Dar es Salaam, TanzaniaOccupationsFilmmakerpoetscreenwriter Ian Iqbal Rashid (born in Dar es Salaam, Tanzania) is a poet, screenwriter and filmmaker known in particular for his volumes of poetry, for the TV series Sort Of and This Life and the feature films Touch of Pink and How She Move. Life Of Indian ancestry and raised in the Ismaili Muslim faith, Rashid's family lived i...

 

Meiliana Jauhari

Meiliana JauhariInformasi pribadiKebangsaan IndonesiaLahir7 Mei 1984 (umur 40)Jakarta, IndonesiaPeganganKananGanda PutriPeringkat tertinggi5 bersama Greysia Polii (15 Mei 2011) Meiliana Jauhari (lahir 7 Mei 1984) adalah salah satu pemain bulu tangkis ganda Putri Indonesia berpasangan dengan Greysia Polii. Prestasi Ganda Putri 2006: Juara 2006 XXI Brazil International Coris Corporate (bersama Purwati) 2007: Juara INDONESIA-SURABAYA CHALLENGE 2007 (bersama Shendy Puspa Irawati) 2...

 

Germanic mythology

Body of mythology associated with historical Germanic paganism Mythology Mythologies Albanian Arabian Armenian Aboriginal Australian Berber Baltic (Latvian - Lithuanian - Prussian) Basque Bantu Brazilian Buddhist Catalan Cantabrian Celtic Breton Cornish Irish Scottish Welsh Chinese Efik Egyptian English Estonian Etruscan Finnish French Georgian Germanic Frankish Continental Germanic Norse Anglo-Saxon Gothic Greek Guanche Hindu Hittite Hungarian Indonesian Italian Japanese Kongo Korean Lugbara...

Andi Sofyan Hasdam

Andi Sofyan Hasdam dr. H. Andi Sofyan Hasdam, Sp.S. (lahir 4 Februari 1956) adalah seorang politikus Indonesia kelahiran Makassar. Ayahnya adalah Haji Andi Sewang Daeng Muntu (Hasdam). Ia sempat tergabung dalam organisasi Pelajar Islam Indonesia (PII). Ia menempuh pendidikan di Fakultas Kedokteran Universitas Airlangga (Unair) Surabaya. Ia kemudian bekerja sebagai dokter spesialis saraf. Ia menjabat sebagai Wali Kota Bontang dari 2006 sampai 2011.[1] Ia mula-mula tergabung dalam Parta...

 

Ghana ai XXIII Giochi olimpici invernali

Ghana ai XXIII Giochi olimpici invernaliPyeongchang 2018 Codice CIOGHA Comitato nazionaleComitato Olimpico Ghanese Atleti partecipanti1 in 1 disciplina Di cui uomini/donne1 - 0 PortabandieraAkwasi Frimpong Medagliere Posizione - 0 0 0 0 Cronologia olimpica (sommario)Giochi olimpici estivi 1952* · 1956 · 1960 · 1964 · 1968 · 1972 · 1976 · 1980 · 1984 · 1988 · 1992 · 1996 · 2000 · 2004 · 2008&...