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MedKoo Cat#: 584847 | Name: Eupafolin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eupafolin, also known as Nepetin, is a flavonoid from Eupatorium ballotaefolium HBK with anti-inflammatory and anti-cancer properties.

Chemical Structure

Eupafolin
Eupafolin
CAS#520-11-6

Theoretical Analysis

MedKoo Cat#: 584847

Name: Eupafolin

CAS#: 520-11-6

Chemical Formula: C16H12O7

Exact Mass: 316.0583

Molecular Weight: 316.27

Elemental Analysis: C, 60.76; H, 3.82; O, 35.41

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Eupafolin; Nepetin
IUPAC/Chemical Name
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy- (9CI)
InChi Key
FHHSEFRSDKWJKJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H12O7/c1-22-16-11(20)6-13-14(15(16)21)10(19)5-12(23-13)7-2-3-8(17)9(18)4-7/h2-6,17-18,20-21H,1H3
SMILES Code
O=C1C=C(C2=CC=C(O)C(O)=C2)OC3=CC(O)=C(OC)C(O)=C13
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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

Preparing Stock Solutions

The following data is based on the product molecular weight 316.27 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.

Recalculate based on batch purity %
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
1: Chen X, Han R, Hao P, Wang L, Liu M, Jin M, Kong D, Li X. Nepetin inhibits IL-1β induced inflammation via NF-κB and MAPKs signaling pathways in ARPE-19 cells. Biomed Pharmacother. 2018 May;101:87-93. doi: 10.1016/j.biopha.2018.02.054. Epub 2018 Feb 23. PubMed PMID: 29477475. 2: Militão GC, Albuquerque MR, Pessoa OD, Pessoa C, Moraes ME, de Moraes MO, Costa-Lotufo LV. Cytotoxic activity of nepetin, a flavonoid from Eupatorium ballotaefolium HBK. Pharmazie. 2004 Dec;59(12):965-6. PubMed PMID: 15638088. 3: Jin XF, Lu YH, Wei DZ, Wang ZT. Chemical fingerprint and quantitative analysis of Salvia plebeia R.Br. by high-performance liquid chromatography. J Pharm Biomed Anal. 2008 Sep 10;48(1):100-4. doi: 10.1016/j.jpba.2008.05.027. Epub 2008 May 28. PubMed PMID: 18678457. 4: Jiang H, Wu D, Xu D, Yu H, Zhao Z, Ma D, Jin J. Eupafolin Exhibits Potent Anti-Angiogenic and Antitumor Activity in Hepatocellular Carcinoma. Int J Biol Sci. 2017 May 16;13(6):701-711. doi: 10.7150/ijbs.17534. eCollection 2017. PubMed PMID: 28655996; PubMed Central PMCID: PMC5485626. 5: Zhang H, Chen MK, Li K, Hu C, Lu MH, Situ J. Eupafolin nanoparticle improves acute renal injury induced by LPS through inhibiting ROS and inflammation. Biomed Pharmacother. 2017 Jan;85:704-711. doi: 10.1016/j.biopha.2016.11.083. Epub 2016 Dec 4. PubMed PMID: 27923689. 6: Li J, Zhang X, Yu Q, Fu X, Wang W. One-step separation of four flavonoids from Herba Salviae Plbeiae by HSCCC. J Chromatogr Sci. 2014 Nov-Dec;52(10):1288-93. doi: 10.1093/chromsci/bmu007. Epub 2014 Mar 9. PubMed PMID: 24615721. 7: Thitilertdecha P, Guy RH, Rowan MG. Characterisation of polyphenolic compounds in Clerodendrum petasites S. Moore and their potential for topical delivery through the skin. J Ethnopharmacol. 2014 Jun 11;154(2):400-7. doi: 10.1016/j.jep.2014.04.021. Epub 2014 Apr 18. PubMed PMID: 24747028. 8: Thitilertdecha P, Rowan MG, Guy RH. Topical formulation and dermal delivery of active phenolic compounds in the Thai medicinal plant--Clerodendrum petasites S. Moore. Int J Pharm. 2015 Jan 15;478(1):39-45. doi: 10.1016/j.ijpharm.2014.11.004. Epub 2014 Nov 6. PubMed PMID: 25445977. 9: Naß J, Efferth T. The activity of Artemisia spp. and their constituents against Trypanosomiasis. Phytomedicine. 2018 Aug 1;47:184-191. doi: 10.1016/j.phymed.2018.06.002. Epub 2018 Jun 9. Review. PubMed PMID: 30166103. 10: Akram M, Syed AS, Kim KA, Lee JS, Chang SY, Kim CY, Bae ON. Heme oxygenase 1-mediated novel anti-inflammatory activities of Salvia plebeia and its active components. J Ethnopharmacol. 2015 Nov 4;174:322-30. doi: 10.1016/j.jep.2015.08.028. Epub 2015 Aug 28. PubMed PMID: 26319962. 11: Han MA, Min KJ, Woo SM, Seo BR, Kwon TK. Eupafolin enhances TRAIL-mediated apoptosis through cathepsin S-induced down-regulation of Mcl-1 expression and AMPK-mediated Bim up-regulation in renal carcinoma Caki cells. Oncotarget. 2016 Oct 4;7(40):65707-65720. doi: 10.18632/oncotarget.11604. PubMed PMID: 27582546; PubMed Central PMCID: PMC5323186. 12: Chen CC, Lin MW, Liang CJ, Wang SH. The Anti-Inflammatory Effects and Mechanisms of Eupafolin in Lipopolysaccharide-Induced Inflammatory Responses in RAW264.7 Macrophages. PLoS One. 2016 Jul 14;11(7):e0158662. doi: 10.1371/journal.pone.0158662. eCollection 2016. PubMed PMID: 27414646; PubMed Central PMCID: PMC4945065. 13: Lee CW, Lin ZC, Hsu LF, Fang JY, Chiang YC, Tsai MH, Lee MH, Li SY, Hu SC, Lee IT, Yen FL. Eupafolin ameliorates COX-2 expression and PGE2 production in particulate pollutants-exposed human keratinocytes through ROS/MAPKs pathways. J Ethnopharmacol. 2016 Aug 2;189:300-9. doi: 10.1016/j.jep.2016.05.002. Epub 2016 May 13. PubMed PMID: 27180879. 14: Lin ZC, Lee CW, Tsai MH, Ko HH, Fang JY, Chiang YC, Liang CJ, Hsu LF, Hu SC, Yen FL. Eupafolin nanoparticles protect HaCaT keratinocytes from particulate matter-induced inflammation and oxidative stress. Int J Nanomedicine. 2016 Aug 11;11:3907-26. doi: 10.2147/IJN.S109062. eCollection 2016. PubMed PMID: 27570454; PubMed Central PMCID: PMC4986973. 15: Sung HC, Liang CJ, Lee CW, Yen FL, Hsiao CY, Wang SH, Jiang-Shieh YF, Tsai JS, Chen YL. The protective effect of eupafolin against TNF-α-induced lung inflammation via the reduction of intercellular cell adhesion molecule-1 expression. J Ethnopharmacol. 2015 Jul 21;170:136-47. doi: 10.1016/j.jep.2015.04.058. Epub 2015 May 11. PubMed PMID: 25975517. 16: Ko HH, Chiang YC, Tsai MH, Liang CJ, Hsu LF, Li SY, Wang MC, Yen FL, Lee CW. Eupafolin, a skin whitening flavonoid isolated from Phyla nodiflora, downregulated melanogenesis: Role of MAPK and Akt pathways. J Ethnopharmacol. 2014;151(1):386-93. doi: 10.1016/j.jep.2013.10.054. Epub 2013 Nov 7. PubMed PMID: 24212072. 17: Tsai MH, Lin ZC, Liang CJ, Yen FL, Chiang YC, Lee CW. Eupafolin inhibits PGE2 production and COX2 expression in LPS-stimulated human dermal fibroblasts by blocking JNK/AP-1 and Nox2/p47(phox) pathway. Toxicol Appl Pharmacol. 2014 Sep 1;279(2):240-51. doi: 10.1016/j.taap.2014.06.012. Epub 2014 Jun 23. PubMed PMID: 24967690. 18: Sanz MJ, Ferrandiz ML, Cejudo M, Terencio MC, Gil B, Bustos G, Ubeda A, Gunasegaran R, Alcaraz MJ. Influence of a series of natural flavonoids on free radical generating systems and oxidative stress. Xenobiotica. 1994 Jul;24(7):689-99. PubMed PMID: 7975732. 19: Kim JK, Kim WJ, Hyun JM, Lee JS, Kwon JG, Seo C, Song MJ, Choi CW, Hong SS, Park K, Kim P, Sung H, Lee JK, Choi Y. Salvia plebeia Extract Inhibits Xanthine Oxidase Activity In Vitro and Reduces Serum Uric Acid in an Animal Model of Hyperuricemia. Planta Med. 2017 Nov;83(17):1335-1341. doi: 10.1055/s-0043-111012. Epub 2017 May 18. PubMed PMID: 28521370. 20: Uehara A, Kitajima J, Kokubugata G, Iwashina T. Further characterization of foliar flavonoids in Crossostephium chinense and their geographic variation. Nat Prod Commun. 2014 Feb;9(2):163-4. PubMed PMID: 24689280.

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