Yangonin | CAS#500-62-9 | Kavalactone

MedKoo Cat#: 462026 | Name: Yangonin

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Description:

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

Yangonin is an analytical reference standard categorized as a kavalactone. This product is intended for analytical forensic applications. This product is also available as a general research tool.

Chemical Structure

Yangonin

CAS#500-62-9

Theoretical Analysis

MedKoo Cat#: 462026

Name: Yangonin

CAS#: 500-62-9

Chemical Formula: C15H14O4

Exact Mass: 258.0892

Molecular Weight: 258.27

Elemental Analysis: C, 69.76; H, 5.46; O, 24.78

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 750.00	2 Weeks

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Related CAS #

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Synonym

Yangonin; CCRIS 9372; CCRIS9372; CCRIS-9372; NSC 212502; NSC212502; NSC-212502;

IUPAC/Chemical Name

2H-Pyran-2-one, 4-methoxy-6-(2-(4-methoxyphenyl)ethenyl)-, (E)- (9CI)

InChi Key

XLHIYUYCSMZCCC-VMPITWQZSA-N

InChi Code

InChI=1S/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+

SMILES Code

O=C1C=C(OC)C=C(/C=C/C2=CC=C(OC)C=C2)O1

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	19.36
	DMSO	5.0	19.36
	DMSO:PBS (pH 7.2) (1:2)	0.3	1.16

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 258.27 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.

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

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PMID: 33123411; PMCID: PMC7587146. 4: Dong R, Wang X, Wang L, Wang C, Huang K, Fu T, Liu K, Wu J, Sun H, Meng Q. Yangonin inhibits ethanol-induced hepatocyte senescence via miR-194/FXR axis. Eur J Pharmacol. 2021 Jan 5;890:173653. doi: 10.1016/j.ejphar.2020.173653. Epub 2020 Oct 15. PMID: 33068587. 5: Celentano A, Yiannis C, Paolini R, Zhang P, Farah CS, Cirillo N, Yap T, McCullough M. Kava constituents exert selective anticancer effects in oral squamous cell carcinoma cells in vitro. Sci Rep. 2020 Sep 28;10(1):15904. doi: 10.1038/s41598-020-73058-4. PMID: 32985597; PMCID: PMC7522996. 6: Yiannis C, Huang K, Tran AN, Zeng C, Dao E, Baselyous O, Mithwani MA, Paolini R, Cirillo N, Yap T, McCullough M, Celentano A. Protective effect of kava constituents in an in vitro model of oral mucositis. J Cancer Res Clin Oncol. 2020 Jul;146(7):1801-1811. doi: 10.1007/s00432-020-03253-3. Epub 2020 May 20. PMID: 32435894. 7: Herath HMPD, Taki AC, Nguyen N, Garcia-Bustos J, Hofmann A, Wang T, Ma G, Chang BCH, Jabbar A, Sleebs BE, Gasser RB. Synthetic Kavalactone Analogues with Increased Potency and Selective Anthelmintic Activity against Larvae of Haemonchus contortus In Vitro. Molecules. 2020 Apr 24;25(8):2004. doi: 10.3390/molecules25082004. PMID: 32344703; PMCID: PMC7221733. 8: Prinsloo D, van Dyk S, Petzer A, Petzer JP. Monoamine Oxidase Inhibition by Kavalactones from Kava (Piper Methysticum). Planta Med. 2019 Oct;85(14-15):1136-1142. doi: 10.1055/a-1008-9491. Epub 2019 Sep 20. PMID: 31539917. 9: Wang X, Fu T, Wang J, Wang C, Liu K, Wu J, Sun H, Ma X, Sun P, Meng Q. Hepatoprotection of yangonin against hepatic fibrosis in mice via farnesoid X receptor activation. Int Immunopharmacol. 2019 Oct;75:105833. doi: 10.1016/j.intimp.2019.105833. Epub 2019 Aug 23. PMID: 31450152. 10: Chambers MI, Osborne AM, Musah RA. Rapid detection and validated quantification of psychoactive compounds in complex plant matrices by direct analysis in real time-high resolution mass spectrometry - Application to "Kava" psychoactive pepper products. Rapid Commun Mass Spectrom. 2019 Dec 30;33(24):1915-1925. doi: 10.1002/rcm.8532. PMID: 31323704. 11: Berry J, Gilbert A, Grodnitzky J. Cases of Kava Impairment in Iowa Drivers. J Forensic Sci. 2019 Nov;64(6):1943-1949. doi: 10.1111/1556-4029.14130. Epub 2019 Jul 15. PMID: 31305953. 12: Dong R, Wang J, Gao X, Wang C, Liu K, Wu J, Liu Z, Sun H, Ma X, Meng Q. Yangonin protects against estrogen-induced cholestasis in a farnesoid X receptor-dependent manner. Eur J Pharmacol. 2019 Aug 15;857:172461. doi: 10.1016/j.ejphar.2019.172461. Epub 2019 Jun 17. PMID: 31220436. 13: Hegazy NH, Breitinger HG, Breitinger U. Kavalactones from Kava (Piper methysticum) root extract as modulators of recombinant human glycine receptors. Biol Chem. 2019 Aug 27;400(9):1205-1215. doi: 10.1515/hsz-2019-0112. PMID: 31141476. 14: Tang Y, Fields C. A UHPLC-UV Method Development and Validation for Determining Kavalactones and Flavokavains in Piper methysticum (Kava). Molecules. 2019 Mar 30;24(7):1245. doi: 10.3390/molecules24071245. PMID: 30934989; PMCID: PMC6479543. 15: Herath HMPD, Preston S, Jabbar A, Garcia-Bustos J, Addison RS, Hayes S, Rali T, Wang T, Koehler AV, Chang BCH, Hofmann A, Davis RA, Gasser RB. Selected α-pyrones from the plants Cryptocarya novoguineensis (Lauraceae) and Piper methysticum (Piperaceae) with activity against Haemonchus contortus in vitro. Int J Parasitol Drugs Drug Resist. 2019 Apr;9:72-79. doi: 10.1016/j.ijpddr.2018.12.006. Epub 2019 Jan 4. PMID: 30739078; PMCID: PMC6369141. 16: Dong R, Yang X, Wang C, Liu K, Liu Z, Ma X, Sun H, Huo X, Fu T, Meng Q. Yangonin protects against non-alcoholic fatty liver disease through farnesoid X receptor. Phytomedicine. 2019 Feb;53:134-142. doi: 10.1016/j.phymed.2018.09.006. Epub 2018 Sep 5. PMID: 30668392. 17: Van TM, Xuan TD, Minh TN, Quan NV. Isolation and Purification of Potent Growth Inhibitors from Piper methysticum Root. Molecules. 2018 Jul 31;23(8):1907. doi: 10.3390/molecules23081907. PMID: 30065174; PMCID: PMC6222926. 18: Liu Y, Lund JA, Murch SJ, Brown PN. Single-Lab Validation for Determination of Kavalactones and Flavokavains in Piper methysticum (Kava). Planta Med. 2018 Nov;84(16):1213-1218. doi: 10.1055/a-0637-2400. Epub 2018 Jun 25. PMID: 29940660. 19: Gao X, Fu T, Wang C, Ning C, Liu K, Liu Z, Sun H, Ma X, Huo X, Yang X, Zou M, Meng Q. Yangonin protects against cholestasis and hepatotoxity via activation of farnesoid X receptor in vivo and in vitro. Toxicol Appl Pharmacol. 2018 Jun 1;348:105-116. doi: 10.1016/j.taap.2018.04.015. Epub 2018 Apr 14. PMID: 29660435. 20: Akagawa K, Kudo K. Iterative Polyketide Synthesis via a Consecutive Carbonyl-Protecting Strategy. 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