yingweiwo

Liquiritoside

Alias: Liquiritoside Liquiritin Likviritin
Cat No.:V12766 Purity: ≥98%
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.
Liquiritoside
Liquiritoside Chemical Structure CAS No.: 551-15-5
Product category: AKR1C
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10mg
25mg
50mg
100mg
250mg
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Product Description
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.
Biological Activity I Assay Protocols (From Reference)
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).
These protocols are for reference only. InvivoChem does not independently validate these methods.
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)
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.

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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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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