Art. -Nr.: HY-W010451

1,2,4-Trihydroxybenzene

(Synonyms: Hydroxyhydroquinone)

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1,2,4-Trihydroxybenzene (Hydroxyhydroquinone) is an ER stress inducer that targets proteins such as PKR-like ER kinase PERK to induce cytotoxicity. 1,2,4-Trihydroxybenzene selectively activates eIF2α phosphorylation, activates the PERK-eIF2α signaling pathway and induces stress granule formation. 1,2,4-Trihydroxybenzene subsequently exacerbates oxidative stress and causes DNA double-strand breaks, destroying organelles such as mitochondria and ER, and inducing cell death. 1,2,4-Trihydroxybenzene also has the potential to exhibit anti-tumor effect, increase blood pressure, and relieve spasm.

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Reinheit: 99.56%
CAS. Nr.: 533-73-3
Formel: C₆H₆O₃
Molecular Weight:126.11

Speicherung:

Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month

1,2,4-Trihydroxybenzene Chemical Structure

CAS. Nr.: 533-73-3

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Biologische Aktivität
- Beschreibung
- IC₅₀ & Target
- In Vitro
- In Vivo
Chemical Information
Lösungsmittel & Löslichkeit
- In Vitro
- In Vivo
Reinheit & Dokumentation
Verweise
Help & FAQs
Classifications
Bioz

Biologische Aktivität

Beschreibung

IC₅₀ & Target

eIF2-α

In Vitro

1,2,4-Trihydroxybenzene (HHQ) (10-100 μM; 2-4 h) increases intracellular Ca²⁺ concentration, induces membrane potential hyperpolarization and activates Ca²⁺-dependent K⁺ channels in rat thymic lymphocyte experiments^[1].
1,2,4-Trihydroxybenzene (THB) (50-800 μM; 24 h) dose-dependently reduces the cell viability of human keratinocytes (HaCaT) and induces stress granule formation and eIF2α/PERK phosphorylation. Continued treatment with 1,2,4-Trihydroxybenzene (THB) (50-800 μM; 1 h, followed by 24 h recovery) leads to DNA damage and apoptosis^[2].
1,2,4-Trihydroxybenzene (20-40 μg/mL; 6-24 h) significantly inhibits the cell viability of HeLa [Chang liver] (human Chang liver cells), induces G2/M phase arrest, and non-apoptotic cell death, accompanied by mitochondrial structural destruction and increasing ROS levels^[3].

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

Apoptosis Analysis^[3]

Cell Line:

HeLa Chang liver cells
Concentration:

20, 40 μg/mL
Incubation Time:

6, 12, 24 h
Result:

Resulted G2/M phase arrest (40% cell accumulation) at 40 μg/mL.
Showed mitochondrial swelling, cristae disruption, and ER volume reduction.

In Vivo

1,2,4-Trihydroxybenzene (1-10 mg/kg; intravenous injection; single dose) increases blood pressure and enhances catecholamine production in anesthetized dogs^[4].

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

Chemical Information

CAS. Nr. 533-73-3
Appearance Solid
Molecular Weight 126.11
Formel C₆H₆O₃
Color Brown to gray
SMILES

OC1=CC=C(O)C=C1O
Synonyms

Hydroxyhydroquinone
Structure Classification
- Phenols
- Polyphenols
Initial Source
- Microorganisms
Phanerochaete chrysosporium
Versand

Room temperature in continental US; may vary elsewhere.

Speicherung

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Lösungsmittel & Löslichkeit

In Vitro:

DMSO : 50 mg/mL (396.48 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

View the Complete Stock Solution Preparation Table

Preparing Stock Solutions

View the Complete Stock Solution Preparation Table

Concentration Solvent Mass

1 mg

5 mg

10 mg

Concentration

Solvent

Mass

1 mM

7.9296 mL

39.6479 mL

79.2959 mL

5 mM

1.5859 mL

7.9296 mL

15.8592 mL

10 mM

0.7930 mL

3.9648 mL

7.9296 mL

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.

Molaritätsrechner

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

Mass Mass

Konzentration Konzentration

Volumen Volumen

Molecular Weight Molecular Weight

Verdünnungsrechner

Konzentration _{(Stammlösung)} × Volumen _{(Stammlösung)} = Konzentration _{(Ziellösung)} × Volumen _{(Ziellösung)}

Konzentration _{(Stammlösung)} Konzentration _{(Stammlösung)}

Volumen _{(Stammlösung)} Volumen _{(Stammlösung)}

Konzentration _{(Ziellösung)} Konzentration _{(Ziellösung)}

Volumen _{(Ziellösung)} Volumen _{(Ziellösung)}

In Vivo:

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

Stock Solution Working Solution

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: 2.5 mg/mL (19.82 mM); Suspended solution; Need ultrasonic

This protocol yields a suspended solution of 2.5 mg/mL. Suspended solution can be used for oral and intraperitoneal injection.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 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.

Protocol 2

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

Solubility: ≥ 2.5 mg/mL (19.82 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

Dosage Dosage
mg/kg
Animal Weight (Per Animal) Animal Weight (Per Animal)
g
Dosing Volume (Per Animal) Dosing Volume (Per Animal)
μL
Number of Animals Number of Animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

%
DMSO +

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
%
+
+
%
Tween-80 + +
%
Saline +

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).

Working solution concentration: 0.22 mg/mL

Reinheit & Dokumentation

Select Batch:

Reinheit: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (276 KB)
SDS (557 KB)
- English - EN (557 KB)
- Français - FR (557 KB)
- Deutsch - DE (557 KB)
- Norwegian - NO (557 KB)
- Español - ES (557 KB)
- Swedish - SV (557 KB)
- Italian - IT (557 KB)
- Korean - KR (557 KB)
- Portuguese - PT (557 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

Verweise

[1]. Risa Kamae, et al. Hydroxyhydroquinone, a by-product of coffee bean roasting, increases intracellular Ca²⁺ concentration in rat thymic lymphocytes. Food Chem Toxicol. 2017 Apr;102:39-45. [Content Brief]

[2]. Jung DM, et al. 1,2,4-trihydroxybenzene induces stress granule formation and causes DNA damage in human keratinocytes. Toxicol In Vitro. 2023 Oct;92:105638. [Content Brief]

[3]. Park EJ, et al. 1,2,4-trihydroxybenzene induces non-apoptotic cell death via the structural damage of intracellular organelles. Toxicol Appl Pharmacol. 2024 Nov;492:117096. [Content Brief]

[4]. Inoue S. Effects of 1,3,5-trihydroxybenzene and 2,4,6-trihydroxy-1-propiophenone on the smooth muscle organs. Jpn J Pharmacol. 1969 Jun;19(2):224-33. [Content Brief]

Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

Complete Stock Solution Preparation Table

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	7.9296 mL	39.6479 mL	79.2959 mL	198.2396 mL
	5 mM	1.5859 mL	7.9296 mL	15.8592 mL	39.6479 mL
	10 mM	0.7930 mL	3.9648 mL	7.9296 mL	19.8240 mL
	15 mM	0.5286 mL	2.6432 mL	5.2864 mL	13.2160 mL
	20 mM	0.3965 mL	1.9824 mL	3.9648 mL	9.9120 mL
	25 mM	0.3172 mL	1.5859 mL	3.1718 mL	7.9296 mL
	30 mM	0.2643 mL	1.3216 mL	2.6432 mL	6.6080 mL
	40 mM	0.1982 mL	0.9912 mL	1.9824 mL	4.9560 mL
	50 mM	0.1586 mL	0.7930 mL	1.5859 mL	3.9648 mL
	60 mM	0.1322 mL	0.6608 mL	1.3216 mL	3.3040 mL
	80 mM	0.0991 mL	0.4956 mL	0.9912 mL	2.4780 mL
	100 mM	0.0793 mL	0.3965 mL	0.7930 mL	1.9824 mL

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1,2,4-Trihydroxybenzene

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Biologische Aktivität

Chemical Information

Lösungsmittel & Löslichkeit

Reinheit & Dokumentation

Verweise

Help & FAQs

Complete Stock Solution Preparation Table

1,2,4-Trihydroxybenzene Related Classifications

HY-W010451 Related Classifications