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MedKoo Cat#: 584612 | Name: Licoricidin

Description:

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

Licoricidin is a lysoPAF acetyltransferase inhibitor isolated from licorice root.

Chemical Structure

Licoricidin
Licoricidin
CAS#30508-27-1

Theoretical Analysis

MedKoo Cat#: 584612

Name: Licoricidin

CAS#: 30508-27-1

Chemical Formula: C26H30O5

Exact Mass: 422.2093

Molecular Weight: 422.52

Elemental Analysis: C, 73.91; H, 7.16; O, 18.93

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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Related CAS #
No Data
Synonym
Licoricidin
IUPAC/Chemical Name
4-((R)-7-Hydroxy-5-methoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl)-2-((E)-3-methyl-but-2-enyl)-benzene-1,3-diol
InChi Key
UKCISAPCNFSMTG-AREMUKBSSA-N
InChi Code
InChI=1S/C26H30O5/c1-15(2)6-8-19-22(27)11-10-18(25(19)29)17-12-21-24(31-14-17)13-23(28)20(26(21)30-5)9-7-16(3)4/h6-7,10-14,26-29H,8-9H2,1-5H3/t26-/m1/s1
SMILES Code
OC1=CC=C(C2=COC3=CC(O)=C(C/C=C(C)\C)[C@@H](OC)C3=C2)C(O)=C1C/C=C(C)\C
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 422.52 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: Park SY, Kwon SJ, Lim SS, Kim JK, Lee KW, Park JH. Licoricidin, an Active Compound in the Hexane/Ethanol Extract of Glycyrrhiza uralensis, Inhibits Lung Metastasis of 4T1 Murine Mammary Carcinoma Cells. Int J Mol Sci. 2016 Jun 14;17(6). pii: E934. doi: 10.3390/ijms17060934. PubMed PMID: 27314329; PubMed Central PMCID: PMC4926467. 2: Tanabe S, Desjardins J, Bergeron C, Gafner S, Villinski JR, Grenier D. Reduction of bacterial volatile sulfur compound production by licoricidin and licorisoflavan A from licorice. J Breath Res. 2012 Mar;6(1):016006. doi: 10.1088/1752-7155/6/1/016006. Epub 2012 Feb 27. PubMed PMID: 22368239. 3: La VD, Tanabe S, Bergeron C, Gafner S, Grenier D. Modulation of matrix metalloproteinase and cytokine production by licorice isolates licoricidin and licorisoflavan A: potential therapeutic approach for periodontitis. J Periodontol. 2011 Jan;82(1):122-8. doi: 10.1902/jop.2010.100342. Epub 2010 Aug 19. PubMed PMID: 20722535. 4: Park SY, Lim SS, Kim JK, Kang IJ, Kim JS, Lee C, Kim J, Park JH. Hexane-ethanol extract of Glycyrrhiza uralensis containing licoricidin inhibits the metastatic capacity of DU145 human prostate cancer cells. Br J Nutr. 2010 Nov;104(9):1272-82. doi: 10.1017/S0007114510002114. Epub 2010 May 21. PubMed PMID: 20487583. 5: Villinski JR, Bergeron C, Cannistra JC, Gloer JB, Coleman CM, Ferreira D, Azelmat J, Grenier D, Gafner S. Pyrano-isoflavans from Glycyrrhiza uralensis with antibacterial activity against Streptococcus mutans and Porphyromonas gingivalis. J Nat Prod. 2014 Mar 28;77(3):521-6. doi: 10.1021/np400788r. Epub 2014 Jan 30. PubMed PMID: 24479468. 6: Kırmızıbekmez H, Uysal GB, Masullo M, Demirci F, Bağcı Y, Kan Y, Piacente S. Prenylated polyphenolic compounds from Glycyrrhiza iconica and their antimicrobial and antioxidant activities. Fitoterapia. 2015 Jun;103:289-93. doi: 10.1016/j.fitote.2015.05.003. Epub 2015 May 8. PubMed PMID: 25963162. 7: Shibata S, Saito T. The chemical studies on the oriental plant drugs. XIX. Some new constituents of licorice root. 1. The structure of licoricidin. Chem Pharm Bull (Tokyo). 1968 Oct;16(10):1932-6. PubMed PMID: 5710927. 8: Nagumo S, Fukuju A, Takayama M, Nagai M, Yanoshita R, Samejima Y. Inhibition of lysoPAF acetyltransferase activity by components of licorice root. Biol Pharm Bull. 1999 Oct;22(10):1144-6. PubMed PMID: 10549875. 9: Gafner S, Bergeron C, Villinski JR, Godejohann M, Kessler P, Cardellina JH, Ferreira D, Feghali K, Grenier D. Isoflavonoids and coumarins from Glycyrrhiza uralensis: antibacterial activity against oral pathogens and conversion of isoflavans into isoflavan-quinones during purification. J Nat Prod. 2011 Dec 27;74(12):2514-9. doi: 10.1021/np2004775. Epub 2011 Nov 10. PubMed PMID: 22074222. 10: Li G, Nikolic D, van Breemen RB. Identification and Chemical Standardization of Licorice Raw Materials and Dietary Supplements Using UHPLC-MS/MS. J Agric Food Chem. 2016 Oct 4. [Epub ahead of print] PubMed PMID: 27696846; PubMed Central PMCID: PMC5378676. 11: Kim KJ, Xuan SH, Park SN. Licoricidin, an isoflavonoid isolated from Glycyrrhiza uralensis Fisher, prevents UVA-induced photoaging of human dermal fibroblasts. Int J Cosmet Sci. 2017 Apr;39(2):133-140. doi: 10.1111/ics.12357. Epub 2016 Sep 8. PubMed PMID: 27502959. 12: Tanaka Y, Kikuzaki H, Fukuda S, Nakatani N. Antibacterial compounds of licorice against upper airway respiratory tract pathogens. J Nutr Sci Vitaminol (Tokyo). 2001 Jun;47(3):270-3. PubMed PMID: 11575586. 13: Wang Q, Qian Y, Wang Q, Yang YF, Ji S, Song W, Qiao X, Guo DA, Liang H, Ye M. Metabolites identification of bioactive licorice compounds in rats. J Pharm Biomed Anal. 2015 Nov 10;115:515-22. doi: 10.1016/j.jpba.2015.08.013. Epub 2015 Aug 17. PubMed PMID: 26311472. 14: Messier C, Epifano F, Genovese S, Grenier D. Licorice and its potential beneficial effects in common oro-dental diseases. Oral Dis. 2012 Jan;18(1):32-9. doi: 10.1111/j.1601-0825.2011.01842.x. Epub 2011 Aug 18. Review. PubMed PMID: 21851508. 15: Eerdunbayaer, Orabi MA, Aoyama H, Kuroda T, Hatano T. Structures of new phenolics isolated from licorice, and the effectiveness of licorice phenolics on vancomycin-resistant Enterococci. Molecules. 2014 Aug 25;19(9):13027-41. doi: 10.3390/molecules190913027. PubMed PMID: 25157467. 16: Wang Y, Wang S, Liu J, Lu Y, Li D. Licoricidin enhances gemcitabine-induced cytotoxicity in osteosarcoma cells by suppressing the Akt and NF-κB signal pathways. Chem Biol Interact. 2018 Jun 25;290:44-51. doi: 10.1016/j.cbi.2018.05.007. Epub 2018 May 18. PubMed PMID: 29782821. 17: Lee HH, Lee S, Shin YS, Cho M, Kang H, Cho H. Anti-Cancer Effect of Quercetin in Xenograft Models with EBV-Associated Human Gastric Carcinoma. Molecules. 2016 Sep 26;21(10). pii: E1286. PubMed PMID: 27681719. 18: Kusano A, Nikaido T, Kuge T, Ohmoto T, Delle Monache G, Botta B, Botta M, Saitoh T. Inhibition of adenosine 3',5'-cyclic monophosphate phosphodiesterase by flavonoids from licorice roots and 4-arylcoumarins. Chem Pharm Bull (Tokyo). 1991 Apr;39(4):930-3. PubMed PMID: 1654220. 19: Hatano T, Kusuda M, Inada K, Ogawa TO, Shiota S, Tsuchiya T, Yoshida T. Effects of tannins and related polyphenols on methicillin-resistant Staphylococcus aureus. Phytochemistry. 2005 Sep;66(17):2047-55. Review. PubMed PMID: 16153408. 20: Ji S, Tang S, Li K, Li Z, Liang W, Qiao X, Wang Q, Yu S, Ye M. Licoricidin inhibits the growth of SW480 human colorectal adenocarcinoma cells in vitro and in vivo by inducing cycle arrest, apoptosis and autophagy. Toxicol Appl Pharmacol. 2017 Jul 1;326:25-33. doi: 10.1016/j.taap.2017.04.015. Epub 2017 Apr 14. PubMed PMID: 28416456.

View History

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