Liquiritin, a natural flavonoid extracted from licorice, is a potent and competitive AKR1C1 inhibitor (antagonist) with IC50s of 0.62 μM, 0.61 μM and 3.72 μM for AKR1C1, AKR1C2 and AKR1C3 respectively. Liquiritin potently inhibits AKR1C1-mediated progesterone metabolism in vivo. Liquiritin is an antioxidant with neuro-protective (neuro-protection), anticancer, and anti~inflammatory activities.

Physicochemical Properties

Molecular Formula	C21H22O9
Molecular Weight	418.39
Exact Mass	418.126
CAS #	551-15-5
PubChem CID	503737
Appearance	White to off-white solid powder
Density	1.5±0.1 g/cm3
Boiling Point	746.8±60.0 °C at 760 mmHg
Melting Point	212 °C
Flash Point	265.9±26.4 °C
Vapour Pressure	0.0±2.6 mmHg at 25°C
Index of Refraction	1.670
LogP	0.61
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	4
Heavy Atom Count	30
Complexity	593
Defined Atom Stereocenter Count	6
SMILES	C1[C@H](OC2=C(C1=O)C=CC(=C2)O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChi Key	DEMKZLAVQYISIA-ZRWXNEIDSA-N
InChi Code	InChI=1S/C21H22O9/c22-9-17-18(25)19(26)20(27)21(30-17)28-12-4-1-10(2-5-12)15-8-14(24)13-6-3-11(23)7-16(13)29-15/h1-7,15,17-23,25-27H,8-9H2/t15-,17+,18+,19-,20+,21+/m0/s1
Chemical Name	(S)-7-hydroxy-2-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)chroman-4-one
Synonyms	Liquiritoside Liquiritin Likviritin
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	The AKR1C1 residues Asn-56, Ala-27, Val-29, and Ala-25 can all be inhibited by liquidritin [1]. In HEC-1-B cells, liquidritin (50 μM; 6 hours) led to an 85.00% decrease in progesterone consumption, which was mediated by the activity of the enzyme aldehyde-keto reductase family 1 member C1 (AKR1C1) [1]. On B65 neuroblastoma tumor cells, liquidritin (100 μM) stimulates the expression of important 6-phosphate dehydrogenase [2].
References	[1]. Liquiritin, as a Natural Inhibitor of AKR1C1, Could Interfere With the Progesterone Metabolism. Front Physiol. 2019 Jul 3;10:833. [2]. Neuroprotective effect of liquiritin as an antioxidant via an increase in glucose-6-phosphate dehydrogenase expression on B65 neuroblastoma cells. Eur J Pharmacol. 2017 Nov 15;815:381-390.
Additional Infomation	Liquiritin is a flavanone glycoside that is liquiritigenin attached to a beta-D-glucopyranosyl residue at position 4' via a glycosidic linkage. It has a role as a plant metabolite, an anticoronaviral agent and an anti-inflammatory agent. It is a flavanone glycoside, a beta-D-glucoside, a monosaccharide derivative and a monohydroxyflavanone. It is functionally related to a liquiritigenin. Liquiritin has been reported in Glycyrrhiza uralensis, Glycyrrhiza aspera, and other organisms with data available. See also: Glycyrrhiza Glabra (part of); Glycyrrhiza uralensis Root (part of).

Solubility Data

Solubility (In Vitro)

DMSO : ~150 mg/mL (~358.52 mM) H2O : < 0.1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (5.98 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.98 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.3901 mL	11.9506 mL	23.9011 mL
	5 mM	0.4780 mL	2.3901 mL	4.7802 mL
	10 mM	0.2390 mL	1.1951 mL	2.3901 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.