Denatonium (benzoate) [3734-33-6]

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Denatonium benzoate (THS-839) is known as the most bitter compound and is commonly used as a deterrent (bittering agent) to activate different types of bitter taste receptors (TAS2Rs) with oral activity. Denatonium benzoate can enhance insulin secretion, has anti-inflammatory effects, and promotes allergy susceptibility .

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

Denatonium benzoate Chemical Structure

Denatonium benzoate Chemical Structure

CAS No. : 3734-33-6

This product is a controlled substance and not for sale in your territory.

Based on 1 publication(s) in Google Scholar

Other Forms of Denatonium benzoate:

  • Denatonium (benzoate) (Standard) Get quote
Description

Denatonium benzoate (THS-839) is known as the most bitter compound and is commonly used as a deterrent (bittering agent) to activate different types of bitter taste receptors (TAS2Rs) with oral activity. Denatonium benzoate can enhance insulin secretion, has anti-inflammatory effects, and promotes allergy susceptibility[1] [2] [3][4].

IC50 & Target

TAS2Rs

In Vitro

Denatonium benzoate (15 μM, 5 min) reduces the spontaneous contraction activity of rat gastric smooth muscle strips[1].
Denatonium benzoate (10 μM, 24h) increases the release of β-hexosaminidase and the mobilization of Ca2+ in IgE-mediated activated RBL-2H3 and KU812 cells[2].
Denatonium benzoate (10 μM, 30 min) enhances the expression of FcεRIα on the surface of RBL-2H3 and KU812 cells[2].
Denatonium benzoate (0-25 mM, 24 h) inhibits the proliferation of RBL-2H3 and KU812 cells when above 0.1 mM[2].

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

Cell Viability Assay[2]

Cell Line: RBL-2H3, KU812
Concentration: 0, 0.01, 0.05, 0.1, 0.5, 1, 2, 2.5, 4, 5, 10, 25 mM
Incubation Time: 24 h
Result: Showed that 0.1 mM caused significant inhibition of cell viability in RBL-2H3 and KU812 cells in a dose-dependent manner.

Western Blot Analysis[2]

Cell Line: RBL-2H3, KU812
Concentration: 10 mM
Incubation Time: 30 min
Result: Promoted the expression of FcεRIα on the surface of mast cells.
In Vivo

Denatonium benzoate (15mg/kg, intraperitoneal injection, single dose) can reduce the initial stage of foot inflammation in rats induced by histamine[1].
Denatonium benzoate (5 mg/kg, i.g., single dose) promotes allergy susceptibility in mice[2].

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

Animal Model: Rat plantar edema model[1]
Dosage: 15 mg/kg, single dose
Administration: Intraperitoneal injection (i.p.)
Result: Reduced foot volume and had anti-inflammatory effects.
Animal Model: BLAB/c mice induced by OVA[2]
Dosage: 5 mg/kg, every other day, 20 days
Administration: i.g.
Result: Caused more severe allergic reactions and promoted allergic susceptibility in mice. Acute diarrhea began after three to four intragastric stimulations, mucus accumulation in the jejunum, β-hex and histamine levels were significantly increased, and ova in serum Specific IgE levels are also elevated.
Clinical Trial
Molecular Weight

446.58

Formula

C28H34N2O3

CAS No.

3734-33-6

Appearance

Solid

Color

White to light yellow

SMILES

CC[N+](CC)(CC(NC1=C(C)C=CC=C1C)=O)CC2=CC=CC=C2.O=C([O-])C3=CC=CC=C3

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, sealed storage, away from moisture

*In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

Solvent & Solubility
In Vitro: 

H2O : 20 mg/mL (44.78 mM; Need ultrasonic)

DMSO : 20 mg/mL (44.78 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 2.2392 mL 11.1962 mL 22.3924 mL
5 mM 0.4478 mL 2.2392 mL 4.4785 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 (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

  • Molarity Calculator

  • Dilution Calculator

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

Mass
=
Concentration
×
Volume
×
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

×
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: ≥ 2 mg/mL (4.48 mM); Clear solution

    This protocol yields a clear solution of ≥ 2 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.0 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.

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
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:  PBS

    Solubility: 33.33 mg/mL (74.63 mM); Clear solution; Need ultrasonic

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.
Calculation results:
Working solution concentration: mg/mL
This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
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).
Purity & Documentation

Purity: 99.90%

References
  • [1]. Plamen I Zagorchev, et al. Denatonium benzoate decreases the effect of histamine in vitro and in rats. Tropical Journal of Pharmaceutical Research September.2020; 19 (9): 1879-1885.

    [2]. Huaping Xu, et al. Denatonium Benzoate Exposure Promotes IgE-Mediated Mast Cell Degranulation and Allergy By Upregulating FcεRIα Expression.Hypothesis. posted 29 Sep, 2021

    [3]. DALEE. KAUKEINEN, et al. Evaluation of aversive agents to increase the selectivity of rodenticides with emphasis on denatonium benzoate (Bitrex) bittering agent. eScholarship. Proceedings of the Vertebrate Pest Conference, 15(15)

    [4]. Weikun Huang, et al. Effects of a bitter substance, denatonium benzoate, on pancreatic hormone secretion. Am J Physiol Endocrinol Metab. 2024 Apr 1;326(4):E537-E544.  [Content Brief]

  • [1]. Plamen I Zagorchev, et al. Denatonium benzoate decreases the effect of histamine in vitro and in rats. Tropical Journal of Pharmaceutical Research September.2020; 19 (9): 1879-1885.

    [2]. Huaping Xu, et al. Denatonium Benzoate Exposure Promotes IgE-Mediated Mast Cell Degranulation and Allergy By Upregulating FcεRIα Expression.Hypothesis. posted 29 Sep, 2021

    [3]. DALEE. KAUKEINEN, et al. Evaluation of aversive agents to increase the selectivity of rodenticides with emphasis on denatonium benzoate (Bitrex) bittering agent. eScholarship. Proceedings of the Vertebrate Pest Conference, 15(15)

    [4]. Weikun Huang, et al. Effects of a bitter substance, denatonium benzoate, on pancreatic hormone secretion. Am J Physiol Endocrinol Metab. 2024 Apr 1;326(4):E537-E544.

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 (sealed storage, away from moisture). 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
H2O / DMSO 1 mM 2.2392 mL 11.1962 mL 22.3924 mL 55.9810 mL
5 mM 0.4478 mL 2.2392 mL 4.4785 mL 11.1962 mL
10 mM 0.2239 mL 1.1196 mL 2.2392 mL 5.5981 mL
15 mM 0.1493 mL 0.7464 mL 1.4928 mL 3.7321 mL
20 mM 0.1120 mL 0.5598 mL 1.1196 mL 2.7991 mL
25 mM 0.0896 mL 0.4478 mL 0.8957 mL 2.2392 mL
30 mM 0.0746 mL 0.3732 mL 0.7464 mL 1.8660 mL
40 mM 0.0560 mL 0.2799 mL 0.5598 mL 1.3995 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Denatonium benzoate Related Classifications

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Keywords:

Denatonium3734-33-6THS-839THS839THS 839OthersAnti-inflammatoryAllergy susceptibilityBitter agentInhibitorinhibitorinhibit

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