Cat. No.: HY-Y0315

Hexane-2,5-dione

(Synonyms: 2,5-HD)

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Hexane-2,5-dione (2,5-HD) is an orally active, CNS-penetrant cytotoxic agent. Hexane-2,5-dione reduces BCL-2 and β-catenin/TCF transcriptional activity, increases BAX and active caspase-3 expression, and promotes apoptosis. Hexane-2,5-dione causes an accumulation of neurofilaments within axons in rats. Hexane-2,5-dione can be used for the research of neurodegenerative diseases.

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Pureté: 99.96%
CAS No.: 110-13-4
Formule: C₆H₁₀O₂
Masse moléculaire:114.14

Stockage:

Store at room temperature 3 years.

In solvent -80°C, 2 years , -20°C, 1 year

Hexane-2,5-dione Chemical Structure

CAS No.: 110-13-4

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Activité biologique
- Description
- In Vitro
- In Vivo
Chemical Information
Solvant et solubilité
- In Vitro
- In Vivo
Pureté et documentation
Références
Help & FAQs
Classifications
Bioz

Activité biologique

Description

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In Vitro

Hexane-2,5-dione (16-256 μM; 24 h) induces morphological changes consistent with apoptosis in primary human ovarian granulosa cells^[1].
Hexane-2,5-dione (16-256 μM; 24 h) induces dose-dependent apoptosis in primary human ovarian granulosa cells^[1].
Hexane-2,5-dione (16-256 μM; 24 h) downregulates BCL-2 and upregulates BAX and CASPASE-3 mRNA in a dose-dependent manner in primary human ovarian granulosa cells^[1].
Hexane-2,5-dione (64-256 μM; 24 h) downregulates BCL-2 protein and upregulates BAX and active CASPASE-3 (p17 subunit) protein in a dose-dependent manner in primary human ovarian granulosa cells^[1].
2,5-Hexanedione (100 mM; 16 h) modifies purified bovine brain tubulin to create a pro-assembly component with enhanced nucleating activity, marked by a 19-fold reduction in assembly critical concentration and altered α-tubulin structure^[3].
2,5-Hexanedione (2,5-HD) cross-links microtubules in vitro, which reduces their ability to support kinesin-based transport^[3].
Hexane-2,5-dione (20-60 mM; 24 h) induces G0/G1 phase cell cycle arrest in rat ovarian granulosa cells, accompanied by altered expression of cell cycle-related genes p21, Cdk2, and Ccnd1^[5].
Hexane-2,5-dione (40-60 mM; 24 h) alters apoptosis-related protein expression in rat ovarian granulosa cells, decreasing Bcl-2 and increasing Bax, Caspase3, and Caspase9^[5].
Hexane-2,5-dione (60 mM; 24 h) alters mRNA and miRNA expression profiles in rat ovarian granulosa cells, with differentially expressed genes significantly enriched in cell cycle and Wnt/β-catenin signaling pathways^[5].
Hexane-2,5-dione (20-60 mM; 24 h) dose-dependently inhibits the Wnt/β-catenin signaling pathway in rat ovarian granulosa cells, reducing mRNA expression of key receptors and transcription factors, and altering protein expression of β-catenin, GSK3β, p-β-catenin, and Dvl3^[5].
Hexane-2,5-dione (20-60 mM; 24 h) dose-dependently reduces nuclear localization of β-catenin in rat ovarian granulosa cells^[5].
Hexane-2,5-dione (10 mM; 6-12 h) reduces cell viability in COV434 human ovarian granulosa cells^[5].
Hexane-2,5-dione (10-160 mM; 6-12 h) does not significantly affect viability in rat ovarian granulosa cells^[5].
Hexane-2,5-dione (10-20 mM; 6 h) dose-dependently inhibits β-catenin/TCF transcriptional activity in COV434 human ovarian granulosa cells^[5].
Hexane-2,5-dione (20-60 mM; 24 h) alters expression of Wnt pathway-related miRNAs in rat ovarian granulosa cells, downregulating rno-miR-214-3p, rno-miR-138-5p, rno-miR-199a-3p, rno-miR-145-5p, and rno-miR-143-3p^[5].

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

Apoptosis Analysis^[1]

Cell Line:

primary human ovarian granulosa cells
Concentration:

16; 64; 256 μM
Incubation Time:

24 h
Result:

Induced morphological changes consistent with apoptosis in primary human ovarian granulosa cells.
Induced dose-dependent apoptosis.
Showed total apoptotic rates reaching 7.8%, 26.8%, and 56.3%, at 16, 64, 256 μM, respectively.

Real Time qPCR^[1]

Cell Line:

primary human ovarian granulosa cells
Concentration:

16; 64; 256 μM
Incubation Time:

24 h
Result:

Reduced BCL-2 mRNA and increased BAX and CASPASE-3 mRNA in a dose-dependent manner.
Showed no no significant effect on these gene levels at 16 μM.

Western Blot Analysis^[1]

Cell Line:

primary human ovarian granulosa cells
Concentration:

16; 64; 256 μM
Incubation Time:

24 h
Result:

Downregulated BCL-2 protein and upregulated BAX and active CASPASE-3 (p17 subunit) protein in a dose-dependent manner.
Showed no no significant effect on these protein levels at 16 μM.

Cell Viability Assay^[5]

Cell Line:

COV434 human ovarian granulosa cells
Concentration:

10; 20; 40; 80; 160 mM
Incubation Time:

6 h, 12 h
Result:

Reduced cell viability in COV434 cells with 10 mM treatment after 6 h and 12 h.

Cell Cycle Analysis^[5]

Cell Line:

rat ovarian granulosa cells
Concentration:

20; 40; 60 mM
Incubation Time:

24 h
Result:

Induced G0/G1 phase cell cycle arrest.
Increased the proportion of cells in G0/G1
phase.
Decreased the proportion of cells in S
phase.

Real Time qPCR^[5]

Cell Line:

rat ovarian granulosa cells
Concentration:

20; 40; 60 mM
Incubation Time:

24 h
Result:

Altered expression of cell cycle-related genes p21, Cdk2, and Ccnd1.

Western Blot Analysis^[5]

Cell Line:

rat ovarian granulosa cells
Concentration:

20; 40; 60 mM
Incubation Time:

24 h
Result:

Decreasing Bcl-2 and increased Bax, Caspase3, and Caspase9 levels.

In Vivo

Hexane-2,5-dione (2.5-3.5 mmol/kg/day; i.p.; 5 days/week; 17-38 days) induces severe neurotoxicity and testicular damage in adult male rats^[2].
Hexane-2,5-dione (2-6 mmol/kg/day; oral via drinking water; 3-5 weeks) induces irreversible testicular atrophy in rats via disruption of Sertoli cell microtubule function, reduced seminiferous tubule fluid formation, germ cell apoptosis, and altered stem cell factor isoform expression, with severity correlating with dose-rate^[3].
Hexane-2,5-dione (250-500 mg/kg; i.g.; single dose, daily for 15-21 days) causes dose-dependent inhibition of cerebral glucose utilization in LAC Porton rats, and high chronic doses induce overt hexacarbon neuropathy^[4].

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

Animal Model:

Wistar rats (adult male, 400-500 g, with neurotoxicity)^[2]
Dosage:

3.5 mmol/kg/day (17-day treatment); 2.5 mmol/kg/day (38-day treatment)
Administration:

i.p.; 5 days/week; 17 days; 38 days
Result:

Caused 27% body weight loss.
Exhibited a mean neuropathy score of 5, corresponding to moderate to marked hindlimb paralysis.
Induced numerous neurofilament-packed axonal swellings and scattered axonal degeneration in thoracic and lumbar spinal cord anterior fasciculi.
Caused testicular damage including giant cell formation, spermatogenesis arrest, and pyknotic changes in Sertoli and germinal cell nuclei.
Reached pyrrole adduct concentrations of 7.5 nmol/mg protein in serum, 3.7 nmol/mg protein in brain stem axonal cytoskeletal protein, and 4.7 nmol/mg protein in spinal cord axonal cytoskeletal protein for the 3.5 mmol/kg/day, 17-day group.
Reached pyrrole adduct concentrations of 3.1 nmol/mg protein in serum, 1.7 nmol/mg protein in brain stem axonal cytoskeletal protein, and 2.2 nmol/mg protein in spinal cord axonal cytoskeletal protein for the 2.5 mmol/kg/day, 38-day group.
Showed covalent crosslinking of axonal cytoskeletal protein of 6.4% in brain stem and 12.2% in spinal cord for the 3.5 mmol/kg/day, 17-day group.
Showed covalent crosslinking of axonal cytoskeletal protein of 9.9% in brain stem and 11.6% in spinal cord for the 2.5 mmol/kg/day, 38-day group.

Animal Model:

Sprague-Dawley rats^[3]
Dosage:

2-6 mmol/kg/day
Administration:

oral via drinking water; 3-5 weeks
Result:

Altered assembly of purified testis tubulin starting 2 weeks after exposure.
Decreased seminiferous tubule fluid formation by 3 weeks.
Induced large, basally located Sertoli cell vacuoles in stages I, XII, XIII, and XIV as the first histopathological signs of injury, followed by sloughing and loss of germ cells by 4-5 weeks.
Altered the cycle of the seminiferous epithelium, with decreased prevalence of certain stages and increased prevalence of others.
Rendered seminiferous tubules devoid of differentiating germ cells but containing proliferating spermatogonia by 8-12 weeks after a 3-5 week exposure, with this atrophic state persisting for greater than 70 weeks post-exposure.
Caused progressively more severe histopathological alterations in the testis with higher dose-rates, which positively correlated with the extent of microtubule assembly abnormality in purified testicular tubulin.
Induced germ cell death via apoptosis, with DNA fragmentation ladders most prominent 5 weeks into exposure, and increased germ cell apoptosis detected as early as 2 weeks into treatment.
Altered the ratio of soluble stem cell factor (sSCF) to membrane-bound stem cell factor (mSCF) in the testis, which correlated temporally with the onset of atrophy.
Resulted in only 1% seminiferous tubule repopulation after 23 days of exposure, compared to greater than 90% repopulation in rats given depot GnRH agonist therapy for 10 weeks immediately post-exposure.

Animal Model:

LAC Porton rats (male, 7-9 weeks of age at end of experimental periods)^[4]
Dosage:

250; 500 mg/kg/day
Administration:

i.g.; single dose (acute); daily for 15 days (high chronic); daily for 21 days (low chronic)
Result:

Caused significant region-dependent decreases in cerebral glucose utilization in high-acute-dose group, with cortical regions, inferior colliculus, and hippocampus most affected, and decreased regional unidirectional glucose flux and permeability-surface area product for glucose influx relative to controls, with no significant changes in regional cerebral blood flow.
Caused significant region-dependent decreases in cerebral glucose utilization in high-chronic-dose group, with inferior colliculus most affected, and significant increases in PS_in in thalamus, hypothalamus, and medulla-pons, with significant region-dependent increases in cerebral blood flow in thalamus, postcingulate cortex, and auditory cortex, and increased regional brain glucose contents relative to controls.
Showed no significant changes in cerebral glucose utilization in low-chronic-dose group, but caused significant region-dependent changes in J_in and PS_in in substantia nigra, auditory cortex, superior colliculus, cerebellum, and medulla-pons.

Chemical Information

CAS No. 110-13-4
Appearance Liquid (Density: 1.00910 g/cm³)
Masse moléculaire 114.14
Formule C₆H₁₀O₂
Color Colorless to light yellow
SMILES

O=C(CCC(C)=O)C
Synonyms

2,5-HD
Livraison

Room temperature in continental US; may vary elsewhere.

Stockage

Store at room temperature 3 years

In solvent	-80°C	2 years
	-20°C	1 year

Solvant et solubilité

In Vitro:

DMSO : 200 mg/mL (1752.23 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

8.7612 mL

43.8059 mL

87.6117 mL

5 mM

1.7522 mL

8.7612 mL

17.5223 mL

10 mM

0.8761 mL

4.3806 mL

8.7612 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, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Calculateur de molarité

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

Mass Mass

Concentration Concentration

Volume Volume

Molecular Weight Molecular Weight

Calculateur de dilution

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

Concentration _(start) Concentration _(start)

Volume _(start) Volume _(start)

Concentration _(final) Concentration _(final)

Volume _(final) Volume _(final)

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: ≥ 5 mg/mL (43.81 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 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: ≥ 5 mg/mL (43.81 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown).

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil

Solubility: ≥ 5 mg/mL (43.81 mM); Clear solution

This protocol yields a clear solution of ≥ 5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (50.0 mg/mL) to 900 μL Corn oil, 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

Pureté et documentation

Select Batch:

Pureté: 99.98%

Assay: 99.98%

ee.: 99.98%

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Références

[1]. Sun Y, et al. 2,5-Hexanedione induces human ovarian granulosa cell apoptosis through BCL-2, BAX, and CASPASE-3 signaling pathways. Arch Toxicol. 2012 Feb;86(2):205-15. [Content Brief]

[2]. DeCaprio AP, et al. Comparative neurotoxicity and pyrrole-forming potential of 2,5-hexanedione and perdeuterio-2,5-hexanedione in the rat. Toxicol Appl Pharmacol. 1988 Jan;92(1):75-85. [Content Brief]

[3]. Boekelheide K, et al. 2,5-hexanedione-induced testicular injury. Annu Rev Pharmacol Toxicol. 2003;43:125-47. [Content Brief]

[4]. Planas AM, et al. Uncoupling of cerebral glucose supply and utilization after hexane-2,5-dione intoxication in the rat. J Neurochem. 1987 Mar;48(3):816-23. [Content Brief]

[5]. Xu X, et al. The Wnt/β-catenin pathway is involved in 2,5-hexanedione-induced ovarian granulosa cell cycle arrest. Ecotoxicol Environ Saf. 2023 Dec;268:115720. [Content Brief]

[6]. Pereira ME, et al. 2,5-Hexanedione inhibits rat brain acetylcholinesterase activity in vitro. Toxicol Lett. 2004 Feb 2;146(3):269-74. [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, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg
DMSO	1 mM	8.7612 mL	43.8059 mL	87.6117 mL	219.0293 mL
	5 mM	1.7522 mL	8.7612 mL	17.5223 mL	43.8059 mL
	10 mM	0.8761 mL	4.3806 mL	8.7612 mL	21.9029 mL
	15 mM	0.5841 mL	2.9204 mL	5.8408 mL	14.6020 mL
	20 mM	0.4381 mL	2.1903 mL	4.3806 mL	10.9515 mL
	25 mM	0.3504 mL	1.7522 mL	3.5045 mL	8.7612 mL
	30 mM	0.2920 mL	1.4602 mL	2.9204 mL	7.3010 mL
	40 mM	0.2190 mL	1.0951 mL	2.1903 mL	5.4757 mL
	50 mM	0.1752 mL	0.8761 mL	1.7522 mL	4.3806 mL
	60 mM	0.1460 mL	0.7301 mL	1.4602 mL	3.6505 mL
	80 mM	0.1095 mL	0.5476 mL	1.0951 mL	2.7379 mL
	100 mM	0.0876 mL	0.4381 mL	0.8761 mL	2.1903 mL

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Hexane-2,5-dione

Apoptosis Compound Library

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Voir tous les produits spécifiques à Isoform Bcl-2 Family

Voir tous les produits spécifiques à Isoform Caspase

Voir tous les produits spécifiques à Isoform Wnt

Activité biologique

Chemical Information

Solvant et solubilité

Pureté et documentation

Références

Help & FAQs

Complete Stock Solution Preparation Table

Hexane-2,5-dione Related Classifications

HY-Y0315 Related Classifications