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(±)-Licarin A ((±)-trans-Dehydrodiisoeugenol)

Cat No.:V52934 Purity: ≥98%
(±)-Licarin A ((±)-trans-Dehydrodiisoeugenol) is a dihydrobenzofuran neolignan, the product of the oxidative coupling reaction of isoeugenol with horseradish peroxidase (HRP).
(±)-Licarin A ((±)-trans-Dehydrodiisoeugenol)
(±)-Licarin A ((±)-trans-Dehydrodiisoeugenol) Chemical Structure CAS No.: 23518-30-1
Product category: Parasite
This product is for research use only, not for human use. We do not sell to patients.
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1mg
5mg
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Product Description
(±)-Licarin A ((±)-trans-Dehydrodiisoeugenol) is a dihydrobenzofuran neolignan, the product of the oxidative coupling reaction of isoeugenol with horseradish peroxidase (HRP). (±)-Licarin A exhibited 58.7% parasite lysis with IC50 of 100.8 µM against trypanosomes. (±)-Licarin A shows 100% parasite mortality at 200 µM.
(±)-Licarin A (CAS# 23518-30-1), also known as (±)-trans-Dehydrodiisoeugenol, is a dihydrobenzofuran neolignan that is the result of an oxidative coupling reaction of isoeugenol and horseradish peroxidase (HRP) enzyme. With a molecular formula of C20H22O4 and a molecular weight of 326.39, this natural neolignan is derived from plants such as licorice. It possesses various pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, and anticancer properties. It has also shown activity against Trypanosoma.
Biological Activity I Assay Protocols (From Reference)
Targets
(±)-Licarin A targets multiple biological pathways due to its diverse pharmacological activities. It exhibits trypanocidal activity, showing 58.7% parasite lysis against Trypanosoma with an IC50 of 100.8 µM. Its antioxidant, anti-inflammatory, antimicrobial, and anticancer properties suggest it interacts with various cellular targets, including those involved in oxidative stress, inflammation, and cell proliferation. However, its precise molecular targets are still being elucidated.
ln Vitro
In vitro, (±)-Licarin A demonstrates significant biological activity. It exhibits trypanocidal activity, showing 58.7% parasite lysis against Trypanosoma with an IC50 of 100.8 µM. It also possesses antioxidant, anti-inflammatory, antimicrobial, and anticancer properties. The compound's activity is typically assessed in cell-based assays measuring cell viability, parasite lysis, or the inhibition of inflammatory markers. These diverse in vitro activities highlight its potential as a lead compound for various therapeutic applications.
ln Vivo
In vivo studies for (±)-Licarin A are not extensively detailed in the provided literature. As a natural neolignan with promising in vitro activities, it has potential for in vivo applications in the treatment of parasitic infections, inflammation, and cancer. Studies in appropriate animal models would be needed to evaluate its in vivo efficacy, pharmacokinetics, and safety profile. Its activity against Trypanosoma suggests potential for in vivo efficacy studies in models of Chagas disease.
Enzyme Assay
For non-cellular enzyme/receptor binding studies, (±)-Licarin A's activity can be evaluated in biochemical assays targeting specific enzymes or receptors. Its antioxidant activity can be assessed using standard in vitro assays such as DPPH or ABTS radical scavenging. Its anti-inflammatory activity can be evaluated in enzyme inhibition assays targeting COX or LOX. However, specific biochemical targets for its diverse activities are not fully detailed in the provided sources.
Cell Assay
For in vitro cellular experiments, appropriate cell lines or parasites are cultured and treated with (±)-Licarin A at various concentrations. For trypanocidal activity, Trypanosoma cultures are treated with the compound, and parasite lysis is assessed. For anticancer studies, cancer cell lines are treated, and cell viability is measured using MTT or similar assays. For anti-inflammatory studies, immune cells are treated, and cytokine production is measured by ELISA.
Animal Protocol
In vivo animal studies for (±)-Licarin A are not extensively documented. However, its potential for in vivo applications is suggested by its in vitro activities against Trypanosoma and its anti-inflammatory and anticancer properties. Studies in animal models of Chagas disease, inflammation, or cancer would be needed to evaluate its in vivo efficacy. The compound could be administered orally or intraperitoneally.
ADME/Pharmacokinetics
Pharmacokinetic properties of (±)-Licarin A are not extensively detailed in the provided sources. It has a molecular weight of 326.39 and a density of 1.160 g/cm3 (predicted). The powder should be stored at -20°C for 3 years. In solvent, it is stable for 1 year at -80°C. Comprehensive pharmacokinetic studies including bioavailability, half-life, and tissue distribution are needed to fully understand its ADME properties.
Toxicity/Toxicokinetics
The toxicity profile of (±)-Licarin A is not explicitly detailed in the provided sources. As a naturally occurring neolignan, it may have a favorable safety profile, but standard laboratory safety precautions should be followed when handling it. It is intended for research use only and is not for human therapeutic applications. Comprehensive toxicological studies are needed to fully evaluate its safety.
References
[1]. Meleti VR, et al. (±)-licarin A and its semi-synthetic derivatives: in vitro and in silico evaluation of trypanocidaland schistosomicidal activities. Acta Trop. 2019 Oct 29:105248.
Additional Infomation
Licarin A is a benzofuran compound. 2-Methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol has been reported in Sinapis alba, Viburnum cylindricalum, and other organisms for which data are available.
(±)-Licarin A is a dihydrobenzofuran neolignan with a molecular formula of C20H22O4 and a molecular weight of 326.39. It is derived from plants such as licorice and possesses antioxidant, anti-inflammatory, antimicrobial, and anticancer properties. It exhibits trypanocidal activity with an IC50 of 100.8 µM. This research compound is for laboratory use only and has not been approved for clinical applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H22O4
Molecular Weight
326.39
Exact Mass
326.151
CAS #
23518-30-1
PubChem CID
5281836
Appearance
Typically exists as solid at room temperature
Density
1.2±0.1 g/cm3
Boiling Point
452.0±45.0 °C at 760 mmHg
Flash Point
227.2±28.7 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.596
LogP
4.19
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
24
Complexity
437
Defined Atom Stereocenter Count
2
SMILES
O1C2C(=C([H])C(/C(/[H])=C(\[H])/C([H])([H])[H])=C([H])C=2[C@@]([H])(C([H])([H])[H])[C@]1([H])C1C([H])=C([H])C(=C(C=1[H])OC([H])([H])[H])O[H])OC([H])([H])[H]
InChi Key
ITDOFWOJEDZPCF-FNINDUDTSA-N
InChi Code
InChI=1S/C20H22O4/c1-5-6-13-9-15-12(2)19(24-20(15)18(10-13)23-4)14-7-8-16(21)17(11-14)22-3/h5-12,19,21H,1-4H3/b6-5+/t12-,19-/m0/s1
Chemical Name
2-methoxy-4-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]phenol
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 : 100 mg/mL (306.38 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (7.66 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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 (7.66 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 (7.66 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 3.0638 mL 15.3191 mL 30.6382 mL
5 mM 0.6128 mL 3.0638 mL 6.1276 mL
10 mM 0.3064 mL 1.5319 mL 3.0638 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 is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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