2. Membrane Transporter/Ion Channel Immunology/Inflammation NF-κB Apoptosis
  3. Potassium Channel Toll-like Receptor (TLR) NF-κB Apoptosis Caspase
  4. (±)-Naringenin

(±)-Naringenin is an orally available anti-inflammatory agent that can regulate both acute and chronic inflammation responses, while also showing antioxidant, neuroprotective, liver-protective, and anti-cancer effects. (±)-Naringenin promotes vasodilation in endothelial cells by activating BKCa channels in muscle cells. It also exerts protective effects against experimental colitis by inhibiting Toll-like receptor 4/NF-κB signaling, making it useful in studies related to sepsis, fulminant hepatitis, fibrosis, and cancer research.

For research use only. We do not sell to patients.

(±)-Naringenin Chemical Structure

(±)-Naringenin Chemical Structure

CAS No. : 67604-48-2

Size Price Stock Quantity
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in DMSO
ready for reconstitution
 In-stock
Solution
10 mM * 1 mL in DMSO In-stock
Solid
100 mg In-stock
200 mg   Get quote  
500 mg   Get quote  

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Customer Review

Based on 3 publication(s) in Google Scholar

Other Forms of (±)-Naringenin:

(±)-Naringenin Related Antibodies

Top Publications Citing Use of Products

View All Toll-like Receptor (TLR) Isoform Specific Products:

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TLR3 TLR8 TLR9 TLR2 TLR4 TLR7 TLR1 TLR6

View All NF-κB Isoform Specific Products:

View All Isoforms
NF-κB NF-κB1/p50 RelA/p65 RelB c-Rel

View All Caspase Isoform Specific Products:

View All Isoforms
Caspase 1 Caspase 2 Caspase 3 Caspase 4 Caspase 5 Caspase 6 Caspase 7 Caspase 8 Caspase 9 Caspase 10 Caspase 12 Caspase Caspase 11 Caspase-13

  • Biological Activity

  • Purity & Documentation

  • References

  • Customer Review

Description

(±)-Naringenin is an orally available anti-inflammatory agent that can regulate both acute and chronic inflammation responses, while also showing antioxidant, neuroprotective, liver-protective, and anti-cancer effects. (±)-Naringenin promotes vasodilation in endothelial cells by activating BKCa channels in muscle cells. It also exerts protective effects against experimental colitis by inhibiting Toll-like receptor 4/NF-κB signaling, making it useful in studies related to sepsis, fulminant hepatitis, fibrosis, and cancer research[1][2][3].

IC50 & Target

NF-κB

 

Caspase 9

 

Cellular Effect
Cell Line Type Value Description References
HCT-116 IC50
36.75 μM
Compound: (+/-)-Naringenin
Cytotoxicity against human HCT116 cells after 7 days by crystal violet staining based clonogenic assay
Cytotoxicity against human HCT116 cells after 7 days by crystal violet staining based clonogenic assay
[PMID: 23177257]
Neutrophil IC50
31 μM
Compound: 5a
Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of superoxide anion radical-induced lucigenin oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of superoxide anion radical-induced lucigenin oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
[PMID: 23871908]
Neutrophil IC50
51.4 μM
Compound: 5a
Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of ROS-induced luminol oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
Inhibition of oxidative burst in PMA-stimulated human neutrophils assessed as inhibition of ROS-induced luminol oxidation incubated for 5 mins prior to PMA challenge by chemiluminescence assay
[PMID: 23871908]
In Vitro

(±)-Naringenin induces concentration-dependent relaxation in endothelium-denuded aortic rings from rats pre-contracted with 20 mM KCl or norepinephrine, with pIC50 values of 4.74 and 4.68 respectively[1].
(±)-Naringenin increases large conductance calcium-activated potassium (BKCa) current in rat tail artery smooth muscle cells in a concentration-dependent manner[1].
(±)-Naringenin (1-25 μmol/L, 2 h) significantly inhibits TNF-α induced NF-κB luciferase expression in HT29 cells[2].
(±)-Naringenin (25 μmol/L, 2 h) blocks LPS-induced NF-κB p65 nuclear translocation in mouse macrophage RAW264.7 cells[2].
(±)-Naringenin induces apoptosis through both intrinsic (mitochondrial) and extrinsic pathways, upregulating pro-apoptotic genes such as P18, P21, p38, and Bcl-2-associated X protein (Bax), which stimulates mitochondrial cytochrome c release and forms apoptosomes including pro-caspase-9 and apoptosis protease-activating factor 1 (Apaf-1), thereby enhancing caspase-9 expression[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

(±)-Naringenin Related Antibodies

Western Blot Analysis[2]

Cell Line: RAW264.7
Concentration: 25 μmol/L
Incubation Time: 2 h
Result: Inhibited NF-κB p65 nuclear translocation.
In Vivo

(±)-Naringenin (50 mg/kg, orally, once a day for ten days) significantly reduces the severity of DSS-induced colitis in mice and downregulats pro-inflammatory mediators (iNOS, ICAM-1, MCP-1, Cox2, TNF-α, and IL-6 mRNA) in the colonic mucosa[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: C57BL/6[2]
Dosage: 50 mg/kg
Administration: Oral; daily; 10 days
Result: Reduced the severity of DSS-induced colitis in mice, downregulated pro-inflammatory mediators (iNOS, ICAM-1, MCP-1, Cox2, TNF-α, and IL-6 mRNA) in the colonic mucosa, inhibited the increase in TLR4 mRNA and protein levels, and reduced the phosphorylated NF-κB p65 protein level.
Molecular Weight

272.26

Formula

C15H12O5
CAS No.
Appearance

Solid

Color

Off-white to light yellow

SMILES

O=C1CC(C2=CC=C(O)C=C2)OC3=CC(O)=CC(O)=C13
Structure Classification
Initial Source
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
Solvent & Solubility
In Vitro: 

DMSO : 120 mg/mL (440.76 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

H2O : < 0.1 mg/mL (insoluble)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.6730 mL 18.3651 mL 36.7301 mL
5 mM 0.7346 mL 3.6730 mL 7.3460 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
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Concentration
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Volume
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Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

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Volume (final)

V2

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 3 mg/mL (11.02 mM); Clear solution

    This protocol yields a clear solution of ≥ 3 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (30.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 3 mg/mL (11.02 mM); Clear solution

    This protocol yields a clear solution of ≥ 3 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (30.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
% 
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 98.88%

SDS (393 KB)

COA (247 KB) RP-HPLC (243 KB) LCMS (95 KB)

Handling Instructions (2659 KB)
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 3.6730 mL 18.3651 mL 36.7301 mL 91.8253 mL
5 mM 0.7346 mL 3.6730 mL 7.3460 mL 18.3651 mL
10 mM 0.3673 mL 1.8365 mL 3.6730 mL 9.1825 mL
15 mM 0.2449 mL 1.2243 mL 2.4487 mL 6.1217 mL
20 mM 0.1837 mL 0.9183 mL 1.8365 mL 4.5913 mL
25 mM 0.1469 mL 0.7346 mL 1.4692 mL 3.6730 mL
30 mM 0.1224 mL 0.6122 mL 1.2243 mL 3.0608 mL
40 mM 0.0918 mL 0.4591 mL 0.9183 mL 2.2956 mL
50 mM 0.0735 mL 0.3673 mL 0.7346 mL 1.8365 mL
60 mM 0.0612 mL 0.3061 mL 0.6122 mL 1.5304 mL
80 mM 0.0459 mL 0.2296 mL 0.4591 mL 1.1478 mL
100 mM 0.0367 mL 0.1837 mL 0.3673 mL 0.9183 mL
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(±)-Naringenin Related Classifications

Help & FAQs
  • Do most proteins show cross-species activity?

    Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

(±)-Naringenin67604-48-2Potassium ChannelToll-like Receptor (TLR)NF-κBApoptosisCaspaseKcsANuclear factor-κBNuclear factor-kappaBvasorelaxantmyocytesTNF-αIL-6miceRAW264.7Inhibitorinhibitorinhibit

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