Liquiritigenin | CAS#578-86-9 | flavonoid

MedKoo Cat#: 598974 | Name: Liquiritigenin

Featured

Description:

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

Liquiritigenin is a flavonoid present in Glycyrrhizae radix.

Chemical Structure

Liquiritigenin

CAS#578-86-9

Theoretical Analysis

MedKoo Cat#: 598974

Name: Liquiritigenin

CAS#: 578-86-9

Chemical Formula: C15H12O4

Exact Mass: 256.0736

Molecular Weight: 256.26

Elemental Analysis: C, 70.31; H, 4.72; O, 24.97

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

69097-97-8 (racemic mixture) 578-86-9

Synonym

Liquiritigenin; MF101; MF 101; MF-101; Menerba;

IUPAC/Chemical Name

(S)-7-hydroxy-2-(4-hydroxyphenyl)chroman-4-one

InChi Key

FURUXTVZLHCCNA-AWEZNQCLSA-N

InChi Code

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2/t14-/m0/s1

SMILES Code

O=C1C[C@@H](C2=CC=C(O)C=C2)OC3=CC(O)=CC=C13

Appearance

Solid powder

Purity

>97% (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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Liquiritigenin is a highly selective estrogen receptor β (ERβ) agonist with an EC50 of 36.5 nM for activation of the ERE tk-Luc.

In vitro activity:

Liquiritigenin-treated murine osteoblastic MC3T3-E1 cells showed an increased alkaline phosphatase activity and enhanced phosphorylation of Smad1/5 compared with untreated cells. Moreover, liquiritigenin inhibited osteoclast differentiation, its bone-resorption activity through slightly decreased the phosphorylation of extracellular signal-regulated kinase, c-Jun N-terminal kinase, and inhibitor of nuclear factor kappa Bα; however, the phosphorylation of Akt and p38 slightly increased in bone marrow-derived osteoclasts. Reference: Phytother Res. 2015 Nov;29(11):1714-21. https://pubmed.ncbi.nlm.nih.gov/26172226/

In vivo activity:

Enzyme-linked immunosorbent assay (ELISA) revealed that treatment with liquiritigenin significantly reduced the concentrations of pro-inflammatory cytokines including interleukin (IL)-6, IL-1β and tumor necrosis factor (TNF)-α in serum and hippocampus. Meanwhile, glucocorticoids (GC) content was reduced in the liquiritigenin group, which suggested that liquiritigenin exhibiting the ameliorative effect on activated hypothalamic-pituitary-adrenal (HPA) axis stimulated with UCMS. Mice treated with liquiritigenin showed restored levels of neurotransmitter norepinephrine (NE) and serotonin (5-HT). Reference: Behav Brain Res. 2016 Jul 15;308:177-86. https://pubmed.ncbi.nlm.nih.gov/27113683/

	Solvent	mg/mL	mM
Solubility
	DMSO	88.0	343.41

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 256.26 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

Formulation protocol:

1. Uchino K, Okamoto K, Sakai E, Yoneshima E, Iwatake M, Fukuma Y, Nishishita K, Tsukuba T. Dual Effects of Liquiritigenin on the Proliferation of Bone Cells: Promotion of Osteoblast Differentiation and Inhibition of Osteoclast Differentiation. Phytother Res. 2015 Nov;29(11):1714-21. doi: 10.1002/ptr.5416. Epub 2015 Jul 14. PMID: 26172226. 2. Suh KS, Rhee SY, Kim YS, Choi EM. Protective effect of liquiritigenin against methylglyoxal cytotoxicity in osteoblastic MC3T3-E1 cells. Food Funct. 2014 Jul 25;5(7):1432-40. doi: 10.1039/c4fo00127c. PMID: 24789098. 3. Tao W, Dong Y, Su Q, Wang H, Chen Y, Xue W, Chen C, Xia B, Duan J, Chen G. Liquiritigenin reverses depression-like behavior in unpredictable chronic mild stress-induced mice by regulating PI3K/Akt/mTOR mediated BDNF/TrkB pathway. Behav Brain Res. 2016 Jul 15;308:177-86. doi: 10.1016/j.bbr.2016.04.039. Epub 2016 Apr 22. PMID: 27113683. 4. Su Q, Tao W, Huang H, Du Y, Chu X, Chen G. Protective effect of liquiritigenin on depressive-like behavior in mice after lipopolysaccharide administration. Psychiatry Res. 2016 Jun 30;240:131-136. doi: 10.1016/j.psychres.2016.04.002. Epub 2016 Apr 14. PMID: 27107388.

In vitro protocol:

In vivo protocol:

1. Tao W, Dong Y, Su Q, Wang H, Chen Y, Xue W, Chen C, Xia B, Duan J, Chen G. Liquiritigenin reverses depression-like behavior in unpredictable chronic mild stress-induced mice by regulating PI3K/Akt/mTOR mediated BDNF/TrkB pathway. Behav Brain Res. 2016 Jul 15;308:177-86. doi: 10.1016/j.bbr.2016.04.039. Epub 2016 Apr 22. PMID: 27113683. 2. Su Q, Tao W, Huang H, Du Y, Chu X, Chen G. Protective effect of liquiritigenin on depressive-like behavior in mice after lipopolysaccharide administration. Psychiatry Res. 2016 Jun 30;240:131-136. doi: 10.1016/j.psychres.2016.04.002. Epub 2016 Apr 14. PMID: 27107388.

1: Min JK, Lee CH, Jang SE, Park JW, Lim SJ, Kim DH, Bae H, Kim HJ, Cha JM. Amelioration of trinitrobenzene sulfonic acid-induced colitis in mice by liquiritigenin. J Gastroenterol Hepatol. 2015 May;30(5):858-65. doi: 10.1111/jgh.12812. PubMed PMID: 25311527. 2: Choi EM, Suh KS, Lee YS. Liquiritigenin restores osteoblast damage through regulating oxidative stress and mitochondrial dysfunction. Phytother Res. 2014 Jun;28(6):880-6. doi: 10.1002/ptr.5071. Epub 2013 Oct 3. PubMed PMID: 24123597. 3: Suh KS, Rhee SY, Kim YS, Choi EM. Protective effect of liquiritigenin against methylglyoxal cytotoxicity in osteoblastic MC3T3-E1 cells. Food Funct. 2014 Jul 25;5(7):1432-40. doi: 10.1039/c4fo00127c. PubMed PMID: 24789098. 4: Chen L, Chen W, Qian X, Fang Y, Zhu N. Liquiritigenin alleviates mechanical and cold hyperalgesia in a rat neuropathic pain model. Sci Rep. 2014 Jul 14;4:5676. doi: 10.1038/srep05676. PubMed PMID: 25022218; PubMed Central PMCID: PMC4097342. 5: Uchino K, Okamoto K, Sakai E, Yoneshima E, Iwatake M, Fukuma Y, Nishishita K, Tsukuba T. Dual Effects of Liquiritigenin on the Proliferation of Bone Cells: Promotion of Osteoblast Differentiation and Inhibition of Osteoclast Differentiation. Phytother Res. 2015 Nov;29(11):1714-21. doi: 10.1002/ptr.5416. Epub 2015 Jul 14. PubMed PMID: 26172226. 6: Hongyan L, Suling W, Weina Z, Yajie Z, Jie R. Antihyperuricemic effect of liquiritigenin in potassium oxonate-induced hyperuricemic rats. Biomed Pharmacother. 2016 Dec;84:1930-1936. doi: 10.1016/j.biopha.2016.11.009. Epub 2016 Nov 15. PubMed PMID: 27863839. 7: Wu W, Xia Q, Luo RJ, Lin ZQ, Xue P. In vitro Study of the Antagonistic Effect of Low-dose Liquiritigenin on Gemcitabine-induced Capillary Leak Syndrome in Pancreatic Adenocarcinoma via Inhibiting ROS- Mediated Signalling Pathways. Asian Pac J Cancer Prev. 2015;16(10):4369-76. PubMed PMID: 26028101. 8: Su Q, Tao W, Huang H, Du Y, Chu X, Chen G. Protective effect of liquiritigenin on depressive-like behavior in mice after lipopolysaccharide administration. Psychiatry Res. 2016 Jun 30;240:131-136. doi: 10.1016/j.psychres.2016.04.002. Epub 2016 Apr 14. PubMed PMID: 27107388. 9: Sayre CL, Hopkins M, Takemoto JK, Davies NM. Chiral analytical method development of liquiritigenin with application to a pharmacokinetic study. Biomed Chromatogr. 2013 Mar;27(3):404-6. doi: 10.1002/bmc.2787. Epub 2012 Jul 20. PubMed PMID: 22815238; PubMed Central PMCID: PMC4237312. 10: Tao W, Dong Y, Su Q, Wang H, Chen Y, Xue W, Chen C, Xia B, Duan J, Chen G. Liquiritigenin reverses depression-like behavior in unpredictable chronic mild stress-induced mice by regulating PI3K/Akt/mTOR mediated BDNF/TrkB pathway. Behav Brain Res. 2016 Jul 15;308:177-86. doi: 10.1016/j.bbr.2016.04.039. Epub 2016 Apr 22. PubMed PMID: 27113683. 11: Zeng HJ, Yang R, You J, Qu LB, Sun YJ. Spectroscopic and Docking Studies on the Binding of Liquiritigenin with Hyaluronidase for Antiallergic Mechanism. Scientifica (Cairo). 2016;2016:9178097. doi: 10.1155/2016/9178097. Epub 2016 May 26. PubMed PMID: 27313960; PubMed Central PMCID: PMC4899609. 12: Alrushaid S, Davies NM, Martinez SE, Sayre CL. Pharmacological characterization of liquiritigenin, a chiral flavonoid in licorice. Res Pharm Sci. 2016 Oct;11(5):355-365. PubMed PMID: 27920817; PubMed Central PMCID: PMC5122824. 13: Zhang Y, He Y, Yu H, Ma F, Wu J, Zhang X. Liquiritigenin Protects Rats from Carbon Tetrachloride Induced Hepatic Injury through PGC-1α Pathway. Evid Based Complement Alternat Med. 2015;2015:649568. doi: 10.1155/2015/649568. Epub 2015 Jun 25. PubMed PMID: 26199636; PubMed Central PMCID: PMC4496487. 14: Yang EJ, Park GH, Song KS. Neuroprotective effects of liquiritigenin isolated from licorice roots on glutamate-induced apoptosis in hippocampal neuronal cells. Neurotoxicology. 2013 Dec;39:114-23. doi: 10.1016/j.neuro.2013.08.012. Epub 2013 Sep 5. PubMed PMID: 24012889. 15: Kim SJ, Kwon SS, Jeon SH, Yu ER, Park SN. Enhanced skin delivery of liquiritigenin and liquiritin-loaded liposome-in-hydrogel complex system. Int J Cosmet Sci. 2014 Dec;36(6):553-60. doi: 10.1111/ics.12156. Epub 2014 Oct 20. PubMed PMID: 25074560. 16: Yu JY, Ha JY, Kim KM, Jung YS, Jung JC, Oh S. Anti-Inflammatory activities of licorice extract and its active compounds, glycyrrhizic acid, liquiritin and liquiritigenin, in BV2 cells and mice liver. Molecules. 2015 Jul 20;20(7):13041-54. doi: 10.3390/molecules200713041. PubMed PMID: 26205049. 17: Dai XH, Li HE, Lu CJ, Wang JF, Dong J, Wei JY, Zhang Y, Wang X, Tan W, Deng XM, Zhao SH, Zhang MJ. Liquiritigenin prevents Staphylococcus aureus-mediated lung cell injury via inhibiting the production of α-hemolysin. J Asian Nat Prod Res. 2013;15(4):390-9. doi: 10.1080/10286020.2013.771344. Epub 2013 Mar 6. PubMed PMID: 23464667. 18: Shi H, Wu Y, Wang Y, Zhou M, Yan S, Chen Z, Gu D, Cai Y. Liquiritigenin Potentiates the Inhibitory Effects of Cisplatin on Invasion and Metastasis Via Downregulation MMP-2/9 and PI3 K/AKT Signaling Pathway in B16F10 Melanoma Cells and Mice Model. Nutr Cancer. 2015;67(5):761-70. doi: 10.1080/01635581.2015.1037962. Epub 2015 May 15. PubMed PMID: 25978595. 19: Jo DS, Shin DW, Park SJ, Bae JE, Kim JB, Park NY, Kim JS, Oh JS, Shin JW, Cho DH. Attenuation of Aβ toxicity by promotion of mitochondrial fusion in neuroblastoma cells by liquiritigenin. Arch Pharm Res. 2016 Aug;39(8):1137-43. doi: 10.1007/s12272-016-0780-2. Epub 2016 Aug 12. Erratum in: Arch Pharm Res. 2016 Sep;39(9):1337. PubMed PMID: 27515055. 20: Wang D, Wong HK, Feng YB, Zhang ZJ. Liquiritigenin exhibits antitumour action in pituitary adenoma cells via Ras/ERKs and ROS-dependent mitochondrial signalling pathways. J Pharm Pharmacol. 2014 Mar;66(3):408-17. doi: 10.1111/jphp.12170. Epub 2013 Nov 6. PubMed PMID: 24491032.