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Caffeic acid phenethyl ester

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

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
  • 104594-70-9
3D model (JSmol)
  • Interactive image
Abbreviations CAPE
ChEBI
  • CHEBI:8062
ChemSpider
  • 4445100
ECHA InfoCard 100.155.538
  • 5281787
UNII
  • G960R9S5SK Y
  • DTXSID8040987
  • 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).

Natural occurrences edit

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

Potential pharmacology edit

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 edit

  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. Retrieved January 13, 2023.

caffeic, acid, phenethyl, ester, cape, natural, phenolic, chemical, compound, ester, caffeic, acid, phenethyl, alcohol, names, preferred, iupac, name, phenylethyl, dihydroxyphenyl, prop, enoate, other, names, phenylethyl, caffeate, phenethyl, caffeate, caffeic. Caffeic acid phenethyl ester CAPE is a natural phenolic chemical compound It is the ester of caffeic acid and phenethyl alcohol 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 b 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 PubChem CID 5281787 UNII G960R9S5SK Y CompTox Dashboard EPA DTXSID8040987 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 NInChI 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 C 17H 16O 4 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 referencesNatural occurrences editCAPE is found in a variety of plants It is also a component of propolis from honeybee hives 1 Potential pharmacology editA 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 edit 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 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 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 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 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 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 Retrieved January 13 2023 Retrieved from https en wikipedia org w index php title Caffeic acid phenethyl ester amp oldid 1195799477, wikipedia, wiki, book, books, library,

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