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MedKoo Cat#: 540136 | Name: Flavokawain A
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Description:

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

Flavokawain A is found in Piper methysticum (kava plant). It suppresses expression of iNOS and COX-2 in macrophages, decreases expression of Ki67, XIAP and survivin in urothelial cell carcinoma cells, and inhibits degradation of NF-χB.

Chemical Structure

Flavokawain A
Flavokawain A
CAS# 37951-13-6

Theoretical Analysis

MedKoo Cat#: 540136

Name: Flavokawain A

CAS#: 37951-13-6

Chemical Formula: C18H18O5

Exact Mass: 314.1154

Molecular Weight: 314.33

Elemental Analysis: C, 68.78; H, 5.77; O, 25.45

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
1775-97-9 (Flavokawain B); 64680-84-8 37951-13-6
Synonym
Flavokawain A; Flavokavin A; 4-Methoxyflavokawain B; (E)-Flavokawain A; NSC-37445; NSC 37445; NSC37445
IUPAC/Chemical Name
(E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
InChi Key
CGIBCVBDFUTMPT-RMKNXTFCSA-N
InChi Code
InChI=1S/C18H18O5/c1-21-13-7-4-12(5-8-13)6-9-15(19)18-16(20)10-14(22-2)11-17(18)23-3/h4-11,20H,1-3H3/b9-6+
SMILES Code
O=C(C1=C(OC)C=C(OC)C=C1O)/C=C/C2=CC=C(OC)C=C2
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
>2 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 314.33 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: Abu N, Mohamed NE, Yeap SK, Lim KL, Akhtar MN, Zulfadli AJ, Kee BB, Abdullah MP, Omar AR, Alitheen NB. In Vivo Anti-Tumor Effects of Flavokawain A in 4T1 Breast Cancer Cell-Challenged Mice. Anticancer Agents Med Chem. 2015;15(7):905-15. PubMed PMID: 26179368. 2: Abu N, Mohameda NE, Tangarajoo N, Yeap SK, Akhtar MN, Abdullah MP, Omar AR, Alitheen NB. In vitro Toxicity and in vivo Immunomodulatory Effects of Flavokawain A and Flavokawain B in Balb/C Mice. Nat Prod Commun. 2015 Jul;10(7):1199-202. PubMed PMID: 26411010. 3: Li X, Yokoyama NN, Zhang S, Ding L, Liu HM, Lilly MB, Mercola D, Zi X. Flavokawain A induces deNEDDylation and Skp2 degradation leading to inhibition of tumorigenesis and cancer progression in the TRAMP transgenic mouse model. Oncotarget. 2015 Dec 8;6(39):41809-24. doi: 10.18632/oncotarget.6166. PubMed PMID: 26497688; PubMed Central PMCID: PMC4747190. 4: Kwon DJ, Ju SM, Youn GS, Choi SY, Park J. Suppression of iNOS and COX-2 expression by flavokawain A via blockade of NF-κB and AP-1 activation in RAW 264.7 macrophages. Food Chem Toxicol. 2013 Aug;58:479-86. doi: 10.1016/j.fct.2013.05.031. Epub 2013 May 28. PubMed PMID: 23727179. 5: Li X, Xu X, Ji T, Liu Z, Gu M, Hoang BH, Zi X. Dietary feeding of Flavokawain A, a Kava chalcone, exhibits a satisfactory safety profile and its association with enhancement of phase II enzymes in mice. Toxicol Rep. 2014;1:2-11. PubMed PMID: 25379458; PubMed Central PMCID: PMC4219529. 6: Niu L, Ding L, Lu C, Zuo F, Yao K, Xu S, Li W, Yang D, Xu X. Flavokawain A inhibits Cytochrome P450 in in vitro metabolic and inhibitory investigations. J Ethnopharmacol. 2016 Sep 15;191:350-9. doi: 10.1016/j.jep.2016.06.039. Epub 2016 Jun 16. PubMed PMID: 27318274. 7: Abu N, Akhtar MN, Yeap SK, Lim KL, Ho WY, Zulfadli AJ, Omar AR, Sulaiman MR, Abdullah MP, Alitheen NB. Flavokawain A induces apoptosis in MCF-7 and MDA-MB231 and inhibits the metastatic process in vitro. PLoS One. 2014 Oct 6;9(10):e105244. doi: 10.1371/journal.pone.0105244. eCollection 2014. PubMed PMID: 25286005; PubMed Central PMCID: PMC4186755. 8: Liu Z, Xu X, Li X, Liu S, Simoneau AR, He F, Wu XR, Zi X. Kava chalcone, flavokawain A, inhibits urothelial tumorigenesis in the UPII-SV40T transgenic mouse model. Cancer Prev Res (Phila). 2013 Dec;6(12):1365-75. doi: 10.1158/1940-6207.CAPR-13-0219. Epub 2013 Oct 11. PubMed PMID: 24121102; PubMed Central PMCID: PMC3873822. 9: Abu N, Ho WY, Yeap SK, Akhtar MN, Abdullah MP, Omar AR, Alitheen NB. The flavokawains: uprising medicinal chalcones. Cancer Cell Int. 2013 Oct 22;13(1):102. doi: 10.1186/1475-2867-13-102. PubMed PMID: 24148263; PubMed Central PMCID: PMC4015927. 10: Zi X, Simoneau AR. Flavokawain A, a novel chalcone from kava extract, induces apoptosis in bladder cancer cells by involvement of Bax protein-dependent and mitochondria-dependent apoptotic pathway and suppresses tumor growth in mice. Cancer Res. 2005 Apr 15;65(8):3479-86. PubMed PMID: 15833884. 11: Ali NM, Akhtar MN, Ky H, Lim KL, Abu N, Zareen S, Ho WY, Alan-Ong HK, Tan SW, Alitheen NB, Ismail JB, Yeap SK, Kamarul T. Flavokawain derivative FLS induced G2/M arrest and apoptosis on breast cancer MCF-7 cell line. Drug Des Devel Ther. 2016 Jun 10;10:1897-907. doi: 10.2147/DDDT.S102164. eCollection 2016. PubMed PMID: 27358555; PubMed Central PMCID: PMC4912327. 12: Rücker H, Amslinger S. Identification of heme oxygenase-1 stimulators by a convenient ELISA-based bilirubin quantification assay. Free Radic Biol Med. 2015 Jan;78:135-46. doi: 10.1016/j.freeradbiomed.2014.10.506. Epub 2014 Oct 23. PubMed PMID: 25462643. 13: Lebot V, Do TK, Legendre L. Detection of flavokavins (A, B, C) in cultivars of kava (Piper methysticum) using high performance thin layer chromatography (HPTLC). Food Chem. 2014 May 15;151:554-60. doi: 10.1016/j.foodchem.2013.11.120. Epub 2013 Nov 27. PubMed PMID: 24423570. 14: Tang Y, Simoneau AR, Xie J, Shahandeh B, Zi X. Effects of the kava chalcone flavokawain A differ in bladder cancer cells with wild-type versus mutant p53. Cancer Prev Res (Phila). 2008 Nov;1(6):439-51. doi: 10.1158/1940-6207.CAPR-08-0165. PubMed PMID: 19138991; PubMed Central PMCID: PMC2830727. 15: Narayanapillai SC, Leitzman P, O'Sullivan MG, Xing C. Flavokawains a and B in kava, not dihydromethysticin, potentiate acetaminophen-induced hepatotoxicity in C57BL/6 mice. Chem Res Toxicol. 2014 Oct 20;27(10):1871-6. doi: 10.1021/tx5003194. Epub 2014 Sep 12. PubMed PMID: 25185080; PubMed Central PMCID: PMC4203398. 16: Zenger K, Agnolet S, Schneider B, Kraus B. Biotransformation of Flavokawains A, B, and C, Chalcones from Kava (Piper methysticum), by Human Liver Microsomes. J Agric Food Chem. 2015 Jul 22;63(28):6376-85. doi: 10.1021/acs.jafc.5b01858. Epub 2015 Jul 10. PubMed PMID: 26123050. 17: Jandial DD, Krill LS, Chen L, Wu C, Ke Y, Xie J, Hoang BH, Zi X. Induction of G2M Arrest by Flavokawain A, a Kava Chalcone, Increases the Responsiveness of HER2-Overexpressing Breast Cancer Cells to Herceptin. Molecules. 2017 Mar 14;22(3). pii: E462. doi: 10.3390/molecules22030462. PubMed PMID: 28335434. 18: Pinner KD, Wales CT, Gristock RA, Vo HT, So N, Jacobs AT. Flavokawains A and B from kava (Piper methysticum) activate heat shock and antioxidant responses and protect against hydrogen peroxide-induced cell death in HepG2 hepatocytes. Pharm Biol. 2016 Sep;54(9):1503-12. doi: 10.3109/13880209.2015.1107104. Epub 2016 Jan 20. PubMed PMID: 26789234; PubMed Central PMCID: PMC5040346. 19: Seidel V, Bailleul F, Waterman PG. (Rel)-1beta,2alpha-di-(2,4-dihydroxy-6-methoxybenzoyl)-3beta, 4alpha-di-(4-methoxyphenyl)-cyclobutane and other flavonoids from the aerial parts of Goniothalamus gardneri and Goniothalamus thwaitesii. Phytochemistry. 2000 Nov;55(5):439-46. PubMed PMID: 11140605. 20: Wu D, Yu L, Nair MG, DeWitt DL, Ramsewak RS. Cyclooxygenase enzyme inhibitory compounds with antioxidant activities from Piper methysticum (kava kava) roots. Phytomedicine. 2002 Jan;9(1):41-7. PubMed PMID: 11924763.