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MedKoo Cat#: 529302 | Name: Licochalcone A
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Description:

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

Licochalcone A is a a P-glycoprotein inhibitor potentially for the treatment of skin irritation.

Chemical Structure

Licochalcone A
Licochalcone A
CAS#58749-22-7

Theoretical Analysis

MedKoo Cat#: 529302

Name: Licochalcone A

CAS#: 58749-22-7

Chemical Formula: C21H22O4

Exact Mass: 338.1518

Molecular Weight: 338.40

Elemental Analysis: C, 74.54; H, 6.55; O, 18.91

Price and Availability

Size Price Availability Quantity
50mg USD 300.00 2 Weeks
100mg USD 500.00 2 Weeks
250mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Licochalcone A; Licochalcone-A
IUPAC/Chemical Name
(E)-3-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
InChi Key
KAZSKMJFUPEHHW-DHZHZOJOSA-N
InChi Code
InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+
SMILES Code
O=C(C1=CC=C(O)C=C1)/C=C/C2=CC(C(C)(C)C=C)=C(O)C=C2OC
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Licochalcone A (LCA) displays broad-spectrum inhibition against UDP-glucuronosyltransferases (UGTs).
In vitro activity:
The effect of LA (licochalcone A) on cell proliferation was determined using MTT assay after 24 h or 48 h exposure, a significant concentration-dependent and time-dependent reduction in cell viability was observed, and the cell viability of 100 μM LA-treated BGC cells was decreased by 66.67% and 81.30% respectively (Fig. 2). These results indicated that LA significantly suppressed the viability of human gastric cancer cells, with significantly lower toxicity against normal human gastric cells, suggesting that LA is a specific and effective inhibition agent against proliferation of human gastric cancer cells. Reference: Sci Rep. 2015 May 18;5:10336. https://pubmed.ncbi.nlm.nih.gov/25981581/
In vivo activity:
This study found that the administration of LCA (licochalcone A) alone significantly inhibited the size of the solid tumours in CT-26 cell-inoculated Balb/c mice, without any detectable induction of nephrotoxicity, hepatotoxicity and oxidative stress. LCA also suppressed cell proliferation by reducing DNA synthesis of CT-26 murine colon cancer cells in a dose-dependent manner. Reference: Basic Clin Pharmacol Toxicol. 2008 Jul;103(1):48-54. https://pubmed.ncbi.nlm.nih.gov/18484961/
Solvent mg/mL mM comments
Solubility
DMF 25.0 73.88
DMSO 37.7 111.31
Ethanol 43.5 128.54
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 338.40 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
Formulation protocol:
1. Hao W, Yuan X, Yu L, Gao C, Sun X, Wang D, Zheng Q. Licochalcone A-induced human gastric cancer BGC-823 cells apoptosis by regulating ROS-mediated MAPKs and PI3K/AKT signaling pathways. Sci Rep. 2015 May 18;5:10336. doi: 10.1038/srep10336. PMID: 25981581; PMCID: PMC4434846. 2. Tsukiyama R, Katsura H, Tokuriki N, Kobayashi M. Antibacterial activity of licochalcone A against spore-forming bacteria. Antimicrob Agents Chemother. 2002 May;46(5):1226-30. doi: 10.1128/AAC.46.5.1226-1230.2002. PMID: 11959549; PMCID: PMC127195. 3. Lee CK, Son SH, Park KK, Park JH, Lim SS, Kim SH, Chung WY. Licochalcone A inhibits the growth of colon carcinoma and attenuates cisplatin-induced toxicity without a loss of chemotherapeutic efficacy in mice. Basic Clin Pharmacol Toxicol. 2008 Jul;103(1):48-54. doi: 10.1111/j.1742-7843.2008.00238.x. Epub 2008 Jul 1. PMID: 18484961. 4. Chen M, Christensen SB, Theander TG, Kharazmi A. Antileishmanial activity of licochalcone A in mice infected with Leishmania major and in hamsters infected with Leishmania donovani. Antimicrob Agents Chemother. 1994 Jun;38(6):1339-44. doi: 10.1128/AAC.38.6.1339. PMID: 8092835; PMCID: PMC188208.
In vitro protocol:
1. Hao W, Yuan X, Yu L, Gao C, Sun X, Wang D, Zheng Q. Licochalcone A-induced human gastric cancer BGC-823 cells apoptosis by regulating ROS-mediated MAPKs and PI3K/AKT signaling pathways. Sci Rep. 2015 May 18;5:10336. doi: 10.1038/srep10336. PMID: 25981581; PMCID: PMC4434846. 2. Tsukiyama R, Katsura H, Tokuriki N, Kobayashi M. Antibacterial activity of licochalcone A against spore-forming bacteria. Antimicrob Agents Chemother. 2002 May;46(5):1226-30. doi: 10.1128/AAC.46.5.1226-1230.2002. PMID: 11959549; PMCID: PMC127195.
In vivo protocol:
1. Lee CK, Son SH, Park KK, Park JH, Lim SS, Kim SH, Chung WY. Licochalcone A inhibits the growth of colon carcinoma and attenuates cisplatin-induced toxicity without a loss of chemotherapeutic efficacy in mice. Basic Clin Pharmacol Toxicol. 2008 Jul;103(1):48-54. doi: 10.1111/j.1742-7843.2008.00238.x. Epub 2008 Jul 1. PMID: 18484961. 2. Chen M, Christensen SB, Theander TG, Kharazmi A. Antileishmanial activity of licochalcone A in mice infected with Leishmania major and in hamsters infected with Leishmania donovani. Antimicrob Agents Chemother. 1994 Jun;38(6):1339-44. doi: 10.1128/AAC.38.6.1339. PMID: 8092835; PMCID: PMC188208.
1: Park MR, Kim SG, Cho IA, Oh D, Kang KR, Lee SY, Moon SM, Cho SS, Yoon G, Kim CS, Oh JS, You JS, Kim DK, Seo YS, Im HJ, Kim JS. Licochalcone-A induces intrinsic and extrinsic apoptosis via ERK1/2 and p38 phosphorylation-mediated TRAIL expression in head and neck squamous carcinoma FaDu cells. Food Chem Toxicol. 2015 Mar;77:34-43. doi: 10.1016/j.fct.2014.12.013. PubMed PMID: 25572524; PubMed Central PMCID: PMC4522946. 2: Kim SH, Yang M, Xu JG, Yu X, Qian XJ. Role of licochalcone A on thymic stromal lymphopoietin expression: implications for asthma. Exp Biol Med (Maywood). 2015 Jan;240(1):26-33. doi: 10.1177/1535370214545020. PubMed PMID: 25055998; PubMed Central PMCID: PMC4935181. 3: Choi JS, Choi JS, Choi DH. Effects of licochalcone A on the bioavailability and pharmacokinetics of nifedipine in rats: possible role of intestinal CYP3A4 and P-gp inhibition by licochalcone A. Biopharm Drug Dispos. 2014 Oct;35(7):382-90. doi: 10.1002/bdd.1905. PubMed PMID: 24903704. 4: Shen H, Zeng G, Tang G, Cai X, Bi L, Huang C, Yang Y. Antimetastatic effects of licochalcone A on oral cancer via regulating metastasis-associated proteases. Tumour Biol. 2014 Aug;35(8):7467-74. doi: 10.1007/s13277-014-1985-y. PubMed PMID: 24789273. 5: Zeng G, Shen H, Yang Y, Cai X, Xun W. Licochalcone A as a potent antitumor agent suppresses growth of human oral cancer SCC-25 cells in vitro via caspase-3 dependent pathways. Tumour Biol. 2014 Jul;35(7):6549-55. doi: 10.1007/s13277-014-1877-1. PubMed PMID: 24691971. 6: Yao K, Chen H, Lee MH, Li H, Ma W, Peng C, Song NR, Lee KW, Bode AM, Dong Z, Dong Z. Licochalcone A, a natural inhibitor of c-Jun N-terminal kinase 1. Cancer Prev Res (Phila). 2014 Jan;7(1):139-49. doi: 10.1158/1940-6207.CAPR-13-0117. PubMed PMID: 24253317. 7: Sulzberger M, Worthmann AC, Holtzmann U, Buck B, Jung KA, Schoelermann AM, Rippke F, Stäb F, Wenck H, Neufang G, Grönniger E. Effective treatment for sensitive skin: 4-t-butylcyclohexanol and licochalcone A. J Eur Acad Dermatol Venereol. 2016 Feb;30 Suppl 1:9-17. doi: 10.1111/jdv.13529. PubMed PMID: 26805417. 8: Hao H, Hui W, Liu P, Lv Q, Zeng X, Jiang H, Wang Y, Zheng X, Zheng Y, Li J, Zhou X, Jiang Y. Effect of licochalcone A on growth and properties of Streptococcus suis. PLoS One. 2013 Jul 23;8(7):e67728. doi: 10.1371/journal.pone.0067728. Erratum in: PLoS One. 2013;8(7). doi:10.1371/annotation/59a7568c-915d-4d9c-b912-f93af72acdcb. PubMed PMID: 23935843; PubMed Central PMCID: PMC3720849. 9: Yang P, Tuo L, Wu Q, Cao X. Licochalcone-A sensitizes human esophageal carcinoma cells to TRAIL-mediated apoptosis by proteasomal degradation of XIAP. Hepatogastroenterology. 2014 Jul-Aug;61(133):1229-34. PubMed PMID: 25436288. 10: Kim SN, Bae SJ, Kwak HB, Min YK, Jung SH, Kim CH, Kim SH. In vitro and in vivo osteogenic activity of licochalcone A. Amino Acids. 2012 Apr;42(4):1455-65. doi: 10.1007/s00726-011-0901-7. PubMed PMID: 21468757. 11: Kim YJ, Jung EB, Myung SC, Kim W, Lee CS. Licochalcone A enhances geldanamycin-induced apoptosis through reactive oxygen species-mediated caspase activation. Pharmacology. 2013;92(1-2):49-59. doi: 10.1159/000351846. PubMed PMID: 23921841. 12: Messier C, Grenier D. Effect of licorice compounds licochalcone A, glabridin and glycyrrhizic acid on growth and virulence properties of Candida albicans. Mycoses. 2011 Nov;54(6):e801-6. doi: 10.1111/j.1439-0507.2011.02028.x. PubMed PMID: 21615543. 13: Feldman M, Grenier D. Cranberry proanthocyanidins act in synergy with licochalcone A to reduce Porphyromonas gingivalis growth and virulence properties, and to suppress cytokine secretion by macrophages. J Appl Microbiol. 2012 Aug;113(2):438-47. doi: 10.1111/j.1365-2672.2012.05329.x. PubMed PMID: 22563853. 14: Shang F, Ming L, Zhou Z, Yu Y, Sun J, Ding Y, Jin Y. The effect of licochalcone A on cell-aggregates ECM secretion and osteogenic differentiation during bone formation in metaphyseal defects in ovariectomized rats. Biomaterials. 2014 Mar;35(9):2789-97. doi: 10.1016/j.biomaterials.2013.12.061. PubMed PMID: 24439395. 15: Egler J, Lang F. Licochalcone A Induced Suicidal Death of Human Erythrocytes. Cell Physiol Biochem. 2015;37(5):2060-70. doi: 10.1159/000438565. PubMed PMID: 26584303. 16: Tsai JP, Lee CH, Ying TH, Lin CL, Lin CL, Hsueh JT, Hsieh YH. Licochalcone A induces autophagy through PI3K/Akt/mTOR inactivation and autophagy suppression enhances Licochalcone A-induced apoptosis of human cervical cancer cells. Oncotarget. 2015 Oct 6;6(30):28851-66. doi: 10.18632/oncotarget.4767. PubMed PMID: 26311737; PubMed Central PMCID: PMC4745696. 17: Funakoshi-Tago M, Nakamura K, Tsuruya R, Hatanaka M, Mashino T, Sonoda Y, Kasahara T. The fixed structure of Licochalcone A by alpha, beta-unsaturated ketone is necessary for anti-inflammatory activity through the inhibition of NF-kappaB activation. Int Immunopharmacol. 2010 May;10(5):562-71. doi: 10.1016/j.intimp.2010.02.003. PubMed PMID: 20153843. 18: Lee CS, Kwak SW, Kim YJ, Lee SA, Park ES, Myung SC, Kim W, Lee MS, Lee JJ. Guanylate cyclase activator YC-1 potentiates apoptotic effect of licochalcone A on human epithelial ovarian carcinoma cells via activation of death receptor and mitochondrial pathways. Eur J Pharmacol. 2012 May 15;683(1-3):54-62. doi: 10.1016/j.ejphar.2012.03.024. PubMed PMID: 22465181. 19: Xin H, Qi XY, Wu JJ, Wang XX, Li Y, Hong JY, He W, Xu W, Ge GB, Yang L. Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases. Food Chem Toxicol. 2016 Apr;90:112-22. doi: 10.1016/j.fct.2016.02.007. PubMed PMID: 26875642. 20: Hu J, Liu J. Licochalcone A Attenuates Lipopolysaccharide-Induced Acute Kidney Injury by Inhibiting NF-κB Activation. Inflammation. 2016 Apr;39(2):569-74. doi: 10.1007/s10753-015-0281-3. PubMed PMID: 26552405.

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