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

MedKoo CAT#: 462026

CAS#: 500-62-9

Description: 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

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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: 258.273
Elemental Analysis: C, 69.76; H, 5.46; O, 24.78

Price and Availability

Size Price Availability Quantity
1.0mg USD 250.0 2 Weeks
5.0mg USD 520.0 2 Weeks
Bulk inquiry

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

Solubility Data

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

Preparing Stock Solutions

The following data is based on the product molecular weight 258.273 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

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Reconstitution Calculator

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1: Ferreira JV, Pierotte IC, Pianetti GA, César IC. Simultaneous quantitation of kavalactones in kava dry extracts: comparison of multi-standards and single standard validation approaches. Phytochem Anal. 2020 Dec 7. doi: 10.1002/pca.3019. Epub ahead of print. PMID: 33615586.

2: Wang ZY, Chu FH, Gu NN, Wang Y, Feng D, Zhao X, Meng XD, Zhang WT, Li CF, Chen Y, Wei SS, Ma ZQ, Lin RC, Zhao CJ, Zou DX. Integrated strategy of LC-MS and network pharmacology for predicting active constituents and pharmacological mechanisms of Ranunculus japonicus Thunb. for treating rheumatoid arthritis. J Ethnopharmacol. 2021 May 10;271:113818. doi: 10.1016/j.jep.2021.113818. Epub 2021 Jan 16. PMID: 33465444.

3: Planer S, Małecki P, Trzaskowski B, Kajetanowicz A, Grela K. Sterically Tuned N-Heterocyclic Carbene Ligands for the Efficient Formation of Hindered Products in Ru-Catalyzed Olefin Metathesis. ACS Catal. 2020 Oct 2;10(19):11394-11404. doi: 10.1021/acscatal.0c02770. Epub 2020 Sep 18. 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. J Org Chem. 2018 Apr 6;83(7):4279-4285. doi: 10.1021/acs.joc.8b00497. Epub 2018 Mar 9. PMID: 29509410.