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MedKoo Cat#: 563276 | Name: Licochalcone B

Description:

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

Licochalcone B is an inhibitor of phosphorylation of NF-kappaB p65 in LPS signaling pathway.

Chemical Structure

Licochalcone B
Licochalcone B
CAS#58749-23-8

Theoretical Analysis

MedKoo Cat#: 563276

Name: Licochalcone B

CAS#: 58749-23-8

Chemical Formula: C16H14O5

Exact Mass: 286.0841

Molecular Weight: 286.28

Elemental Analysis: C, 67.13; H, 4.93; O, 27.94

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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Synonym
Licochalcone B; Licochalcone-B; LicoB; Lico-B; Lico B;
IUPAC/Chemical Name
(E)-1-(3,4-dihydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
InChi Key
IOBDWJXFMVMVKI-XBXARRHUSA-N
InChi Code
InChI=1S/C16H14O5/c1-21-16-12(7-9-14(19)15(16)20)13(18)8-4-10-2-5-11(17)6-3-10/h2-9,17,19-20H,1H3/b8-4+
SMILES Code
OC1=CC=C(/C=C/C(C2=CC=C(O)C(O)=C2OC)=O)C=C1
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 286.28 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: Kang TH, Yoon G, Kang IA, Oh HN, Chae JI, Shim JH. Natural Compound Licochalcone B Induced Extrinsic and Intrinsic Apoptosis in Human Skin Melanoma (A375) and Squamous Cell Carcinoma (A431) Cells. Phytother Res. 2017 Dec;31(12):1858-1867. doi: 10.1002/ptr.5928. Epub 2017 Oct 13. PubMed PMID: 29027311. 2: Wang XX, Liu GY, Yang YF, Wu XW, Xu W, Yang XW. Intestinal Absorption of Triterpenoids and Flavonoids from Glycyrrhizae radix et rhizoma in the Human Caco-2 Monolayer Cell Model. Molecules. 2017 Sep 29;22(10). pii: E1627. doi: 10.3390/molecules22101627. PubMed PMID: 28961192. 3: Kuang Y, Lin Y, Li K, Song W, Ji S, Qiao X, Zhang Q, Ye M. Screening of hepatoprotective compounds from licorice against carbon tetrachloride and acetaminophen induced HepG2 cells injury. Phytomedicine. 2017 Oct 15;34:59-66. doi: 10.1016/j.phymed.2017.08.005. Epub 2017 Aug 7. PubMed PMID: 28899510. 4: Lin Y, Kuang Y, Li K, Wang S, Ji S, Chen K, Song W, Qiao X, Ye M. Nrf2 activators from Glycyrrhiza inflata and their hepatoprotective activities against CCl(4)-induced liver injury in mice. Bioorg Med Chem. 2017 Oct 15;25(20):5522-5530. doi: 10.1016/j.bmc.2017.08.018. Epub 2017 Aug 15. Erratum in: Bioorg Med Chem. 2018 Jun 11;:. PubMed PMID: 28835349. 5: Lin Y, Kuang Y, Li K, Wang S, Song W, Qiao X, Sabir G, Ye M. Screening for bioactive natural products from a 67-compound library of Glycyrrhiza inflata. Bioorg Med Chem. 2017 Jul 15;25(14):3706-3713. doi: 10.1016/j.bmc.2017.05.009. Epub 2017 May 6. PubMed PMID: 28522265. 6: Gao XP, Qian DW, Xie Z, Hui H. Protective role of licochalcone B against ethanol-induced hepatotoxicity through regulation of Erk signaling. Iran J Basic Med Sci. 2017 Feb;20(2):131-137. doi: 10.22038/ijbms.2017.8235. PubMed PMID: 28293388; PubMed Central PMCID: PMC5339652. 7: Teng H, Chen M, Zou A, Jiang H, Han J, Sun L, Feng C, Liu J. Hepatoprotective effects of licochalcone B on carbon tetrachloride-induced liver toxicity in mice. Iran J Basic Med Sci. 2016 Aug;19(8):910-915. PubMed PMID: 27746874; PubMed Central PMCID: PMC5048128. 8: Yu L, Ma J, Han J, Wang B, Chen X, Gao C, Li D, Zheng Q. Licochalcone B Arrests Cell Cycle Progression and Induces Apoptosis in Human Breast Cancer MCF-7 Cells. Recent Pat Anticancer Drug Discov. 2016;11(4):444-452. PubMed PMID: 27719653. 9: Oh H, Yoon G, Shin JC, Park SM, Cho SS, Cho JH, Lee MH, Liu K, Cho YS, Chae JI, Shim JH. Licochalcone B induces apoptosis of human oral squamous cell carcinoma through the extrinsic- and intrinsic-signaling pathways. Int J Oncol. 2016 Apr;48(4):1749-57. doi: 10.3892/ijo.2016.3365. Epub 2016 Feb 1. PubMed PMID: 26847145. 10: Park JH, Jun JG, Kim JK. (E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-(2,4-dihydroxyphenyl)prop-2-en-1-one, a novel licochalcone B derivative compound, suppresses lipopolysaccharide-stimulated inflammatory reactions in RAW264.7 cells and endotoxin shock in mice. Chem Biol Interact. 2014 Dec 5;224:142-8. doi: 10.1016/j.cbi.2014.10.024. Epub 2014 Oct 29. PubMed PMID: 25451593. 11: Han J, Wang D, Yu B, Wang Y, Ren H, Zhang B, Wang Y, Zheng Q. Cardioprotection against ischemia/reperfusion by licochalcone B in isolated rat hearts. Oxid Med Cell Longev. 2014;2014:134862. doi: 10.1155/2014/134862. Epub 2014 Aug 21. PubMed PMID: 25215172; PubMed Central PMCID: PMC4158311. 12: Zhao H, Yuan X, Jiang J, Wang P, Sun X, Wang D, Zheng Q. Antimetastatic effects of licochalcone B on human bladder carcinoma T24 by inhibition of matrix metalloproteinases-9 and NF-кB activity. Basic Clin Pharmacol Toxicol. 2014 Dec;115(6):527-33. doi: 10.1111/bcpt.12273. Epub 2014 Jul 1. PubMed PMID: 25099010. 13: Yuan X, Li T, Xiao E, Zhao H, Li Y, Fu S, Gan L, Wang Z, Zheng Q, Wang Z. Licochalcone B inhibits growth of bladder cancer cells by arresting cell cycle progression and inducing apoptosis. Food Chem Toxicol. 2014 Mar;65:242-51. doi: 10.1016/j.fct.2013.12.030. Epub 2013 Dec 31. PubMed PMID: 24384411. 14: Kim SJ, Kim CG, Yun SR, Kim JK, Jun JG. Synthesis of licochalcone analogues with increased anti-inflammatory activity. Bioorg Med Chem Lett. 2014 Jan 1;24(1):181-5. doi: 10.1016/j.bmcl.2013.11.044. Epub 2013 Nov 26. PubMed PMID: 24316124. 15: Fu Y, Chen J, Li YJ, Zheng YF, Li P. Antioxidant and anti-inflammatory activities of six flavonoids separated from licorice. Food Chem. 2013 Nov 15;141(2):1063-71. doi: 10.1016/j.foodchem.2013.03.089. Epub 2013 Apr 13. PubMed PMID: 23790887. 16: Zeng P, Zhang Y, Pan C, Jia Q, Guo FJ, Zhu WL, Li YM, Chen KX. [Phenolic constituents from Lysimachia patungensis]. Yao Xue Xue Bao. 2013 Mar;48(3):377-82. Chinese. PubMed PMID: 23724651. 17: Furusawa J, Funakoshi-Tago M, Mashino T, Tago K, Inoue H, Sonoda Y, Kasahara T. Glycyrrhiza inflata-derived chalcones, Licochalcone A, Licochalcone B and Licochalcone D, inhibit phosphorylation of NF-kappaB p65 in LPS signaling pathway. Int Immunopharmacol. 2009 Apr;9(4):499-507. PubMed PMID: 19291859. 18: Nakagawa T, Yokozawa T, Kim YA, Kang KS, Tanaka T. Activity of wen-pi-tang, and purified constituents of rhei rhizoma and glycyrrhizae radix against glucose-mediated protein damage. Am J Chin Med. 2005;33(5):817-29. PubMed PMID: 16265994. 19: Hatano T, Yasuhara T, Fukuda T, Noro T, Okuda T. Phenolic constituents of licorice. II. Structures of licopyranocoumarin, licoarylcoumarin and glisoflavone, and inhibitory effects of licorice phenolics on xanthine oxidase. Chem Pharm Bull (Tokyo). 1989 Nov;37(11):3005-9. PubMed PMID: 2632045.