WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H122982
CAS#: 72944-19-5
Description: Artepillin C is a primary reference substance with assigned absolute purity. It possesses antitumour and chemopreventive activities and sensitizes LNCaP prostate cancer cells to TRAIL-induced apoptosis.
Hodoodo Cat#: H122982
Name: Artepillin C
CAS#: 72944-19-5
Chemical Formula: C19H24O3
Exact Mass: 300.17
Molecular Weight: 300.400
Elemental Analysis: C, 75.97; H, 8.05; O, 15.98
Synonym: Artepillin C; Artepillin-C; ArtepillinC
IUPAC/Chemical Name: (E)-3-(4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)acrylic acid
InChi Key: KABCFARPAMSXCC-JXMROGBWSA-N
InChi Code: InChI=1S/C19H24O3/c1-13(2)5-8-16-11-15(7-10-18(20)21)12-17(19(16)22)9-6-14(3)4/h5-7,10-12,22H,8-9H2,1-4H3,(H,20,21)/b10-7+
SMILES Code: C/C(C)=C\CC1=CC(/C=C/C(O)=O)=CC(C/C=C(C)\C)=C1O
Appearance: To be determined
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 300.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Shahinozzaman M, Basak B, Emran R, Rozario P, Obanda DN. Artepillin C: A comprehensive review of its chemistry, bioavailability, and pharmacological properties. Fitoterapia. 2020 Nov;147:104775. doi: 10.1016/j.fitote.2020.104775. Epub 2020 Nov 3. PMID: 33152464.
2: Beserra FP, Gushiken LFS, Hussni MF, Ribeiro VP, Bonamin F, Jackson CJ, Pellizzon CH, Bastos JK. Artepillin C as an outstanding phenolic compound of Brazilian green propolis for disease treatment: A review on pharmacological aspects. Phytother Res. 2020 Sep 15. doi: 10.1002/ptr.6875. Epub ahead of print. PMID: 32935428.
3: Kobal MB, Pazin WM, Bistaffa MJ, Constantino CJL, Toledo KA, Aoki PHB. Correlating Artepillin C cytotoxic activity on HEp-2 cells with bioinspired systems of plasma membranes. Mater Sci Eng C Mater Biol Appl. 2020 Jul;112:110943. doi: 10.1016/j.msec.2020.110943. Epub 2020 Apr 8. PMID: 32409089.
4: Hirata Y, Motoyama M, Kimura S, Takashima M, Ikawa T, Oh-Hashi K, Kamatari YO. Artepillin C, a major component of Brazilian green propolis, inhibits endoplasmic reticulum stress and protein aggregation. Eur J Pharmacol. 2021 Dec 5;912:174572. doi: 10.1016/j.ejphar.2021.174572. Epub 2021 Oct 14. PMID: 34656606.
5: Pazin WM, Vilanova N, Voets IK, Soares AEE, Ito AS. Effects of artepillin C on model membranes displaying liquid immiscibility. Braz J Med Biol Res. 2019 Mar 25;52(3):e8281. doi: 10.1590/1414-431X20198281. PMID: 30916221; PMCID: PMC6437936.
6: Pazin WM, Olivier DD, Vilanova N, Ramos AP, Voets IK, Soares AE, Ito AS. Interaction of Artepillin C with model membranes. Eur Biophys J. 2017 May;46(4):383-393. doi: 10.1007/s00249-016-1183-5. Epub 2016 Oct 26. PMID: 27785542.
7: Szliszka E, Zydowicz G, Mizgala E, Krol W. Artepillin C (3,5-diprenyl-4-hydroxycinnamic acid) sensitizes LNCaP prostate cancer cells to TRAIL-induced apoptosis. Int J Oncol. 2012 Sep;41(3):818-28. doi: 10.3892/ijo.2012.1527. Epub 2012 Jun 25. PMID: 22735465; PMCID: PMC3582787.
8: Souza RP, Bonfim-Mendonça PS, Damke GMZF, de-Assis Carvalho ARB, Ratti BA, Dembogurski DSO, da-Silva VRS, Silva SO, Da-Silva DB, Bruschi ML, Maria-Engler SS, Consolaro MEL. Artepillin C Induces Selective Oxidative Stress and Inhibits Migration and Invasion in a Comprehensive Panel of Human Cervical Cancer Cell Lines. Anticancer Agents Med Chem. 2018;18(12):1750-1760. doi: 10.2174/1871520618666180604092930. PMID: 29866020.
9: Pang S, Yee M, Saba Y, Chino T. Artepillin C as a targeting survivin molecule in oral squamous cell carcinoma cells in vitro: A preliminary study. J Oral Pathol Med. 2018 Jan;47(1):48-52. doi: 10.1111/jop.12624. Epub 2017 Oct 12. PMID: 28833597.
10: Galeotti F, Capitani F, Maccari F, Mantovani V, Volpi N. Capillary Electrophoresis Separation of Artepillin C: Determination in Brazilian Green Propolis. J Chromatogr Sci. 2021 Oct 29;59(10):994-1003. doi: 10.1093/chromsci/bmab015. PMID: 33604611.
11: Ding J, Matsumiya T, Hayakari R, Shiba Y, Kawaguchi S, Seya K, Ueno K, Imaizumi T. Daily Brazilian green propolis intake elevates blood artepillin C levels in humans. J Sci Food Agric. 2021 Aug 30;101(11):4855-4861. doi: 10.1002/jsfa.11132. Epub 2021 Feb 16. PMID: 33543484.
12: Pazin WM, Ruiz GCM, Oliveira ON Jr, Constantino CJL. Interaction of Artepillin C with model membranes: Effects of pH and ionic strength. Biochim Biophys Acta Biomembr. 2019 Feb 1;1861(2):410-417. doi: 10.1016/j.bbamem.2018.11.008. Epub 2018 Nov 20. PMID: 30468729.
13: Cornara L, Biagi M, Xiao J, Burlando B. Therapeutic Properties of Bioactive Compounds from Different Honeybee Products. Front Pharmacol. 2017 Jun 28;8:412. doi: 10.3389/fphar.2017.00412. PMID: 28701955; PMCID: PMC5487425.
14: Choi SS, Cha BY, Iida K, Lee YS, Yonezawa T, Teruya T, Nagai K, Woo JT. Artepillin C, as a PPARγ ligand, enhances adipocyte differentiation and glucose uptake in 3T3-L1 cells. Biochem Pharmacol. 2011 Apr 1;81(7):925-33. doi: 10.1016/j.bcp.2011.01.002. Epub 2011 Jan 8. PMID: 21219874.
15: Hata T, Tazawa S, Ohta S, Rhyu MR, Misaka T, Ichihara K. Artepillin C, a major ingredient of Brazilian propolis, induces a pungent taste by activating TRPA1 channels. PLoS One. 2012;7(11):e48072. doi: 10.1371/journal.pone.0048072. Epub 2012 Nov 2. PMID: 23133611; PMCID: PMC3487895.
16: Martins NS, de Campos Fraga-Silva TF, Correa GF, Boko MMM, Ramalho LNZ, Rodrigues DM, Hori JI, Costa DL, Bastos JK, Bonato VLD. Artepillin C Reduces Allergic Airway Inflammation by Induction of Monocytic Myeloid-Derived Suppressor Cells. Pharmaceutics. 2021 Oct 22;13(11):1763. doi: 10.3390/pharmaceutics13111763. PMID: 34834178; PMCID: PMC8625726.
17: Nishikawa S, Hydo T, Aoyama H, Miyata R, Kumazawa S, Tsuda T. Artepillin C, a Key Component of Brazilian Propolis, Induces Thermogenesis in Inguinal White Adipose Tissue of Mice through a Creatine-Metabolism-Related Thermogenic Pathway. J Agric Food Chem. 2020 Jan 29;68(4):1007-1014. doi: 10.1021/acs.jafc.9b07080. Epub 2020 Jan 21. Erratum in: J Agric Food Chem. 2020 Feb 26;68(8):2606. PMID: 31914311.
18: Uto Y, Ae S, Koyama D, Sakakibara M, Otomo N, Otsuki M, Nagasawa H, Kirk KL, Hori H. Artepillin C isoprenomics: design and synthesis of artepillin C isoprene analogues as lipid peroxidation inhibitor having low mitochondrial toxicity. Bioorg Med Chem. 2006 Aug 15;14(16):5721-8. doi: 10.1016/j.bmc.2006.04.015. Epub 2006 May 11. PMID: 16697207.
19: Kano Y, Horie N, Doi S, Aramaki F, Maeda H, Hiragami F, Kawamura K, Motoda H, Koike Y, Akiyama J, Eguchi S, Hashimoto K. Artepillin C derived from propolis induces neurite outgrowth in PC12m3 cells via ERK and p38 MAPK pathways. Neurochem Res. 2008 Sep;33(9):1795-803. doi: 10.1007/s11064-008-9633-9. Epub 2008 Mar 13. PMID: 18338254.
20: Pazin WM, Furini LN, Solovyeva V, Lemma T, Rubira RJG, Jørgensen B, Constantino CJL, Brewer JR. Vibrational Spectroscopic Characterization and Coherent Anti-Stokes Raman Spectroscopy (CARS) Imaging of Artepillin C. Appl Spectrosc. 2020 Jul;74(7):751-757. doi: 10.1177/0003702820904456. Epub 2020 Apr 30. PMID: 32031016.
