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4-Vinylcyclohexene dioxide

Alias: Vinylcyclohexene diepoxide
Cat No.:V126529 Purity: ≥98%
4-Vinylcyclohexene dioxide is an orally active metabolite of 4-vinylcyclohexene.
4-Vinylcyclohexene dioxide
4-Vinylcyclohexene dioxide Chemical Structure CAS No.: 106-87-6
Product category: PI3K
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
4-Vinylcyclohexene dioxide is the orally active metabolite of 4-vinylcyclohexene. 4-Vinylcyclohexene dioxide can induce apoptosis, increase intracellular reactive oxygen species (ROS) levels, and activate the PI3K/Akt/mTOR signaling pathway. 4-Vinylcyclohexene dioxide selectively damages small ovarian follicles, inhibits granulosa cell function, and disrupts the male reproductive system. 4-Vinylcyclohexene dioxide can be used to study premature ovarian failure, reproductive toxicity, and related fertility disorders.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
4-Vinylcyclohexene dioxide (90 μM-3 mM; 24 h) can induce apoptosis in human ovarian granulosa cell line (SVOG), increase intracellular reactive oxygen species, and inhibit their proliferation [2]. 4-Vinylcyclohexene dioxide (10 nM-10 mM; 6-24 h) can promote the activation of primordial follicles by transiently activating the PI3K/Akt/mTOR pathway [3].
ln Vivo
4-Vinylcyclohexene dioxide (80 mg/kg; intraperitoneal injection; once daily for 1–15 days) can accelerate follicular atresia by activating the caspase cascade in the small preantral follicles of female F344 rats[1]. 4-Vinylcyclohexene dioxide (80 mg/kg; intraperitoneal injection; once daily for 5–10 days) can promote superovulation in middle-aged C57BL/6J mice, increase serum estradiol (E2) and follicle-stimulating hormone (FSH) levels, and enhance follicular development[3]. 4-Vinylcyclohexene dioxide (100–500 mg/kg; oral administration; once daily for 28 days) can disrupt sperm characteristics in male Wistar rats, reduce reproductive hormone levels, and induce oxidative stress and apoptosis in the testes and epididymis[6].
Cell Assay
Apoptosis analysis [2]
Cell Types: Human ovarian granulosa cell line (SVOG)
Tested Concentrations: 0.5 mM, 1 mM
Incubation Duration: 24 hours
Experimental Results: The number of Annexin V positive cells increased, and apoptosis increased. The number of Hoechst 33342 and PI positive cells increased significantly in a dose-dependent manner.
Animal Protocol
Animal/Disease Models:Female F344 rats (28 days old) [1]
Doses: 80 mg/kg
Route of Administration: Intraperitoneal injection, day 1 or day 15
Experimental Results: Cytoplasmic caspase-3 activity increased in small follicles (day 1: 2.86; day 15: 3.25, VCD/control group). Proceaspase-3 protein increased by 212% (day 15). Caspase-8 activity increased (day 15). Caspase-9 activity increased (day 1).
References

[1]. Apoptosis induced in rats by 4-vinylcyclohexene diepoxide is associated with activation of the caspase cascades. Biol Reprod. 2001 Jul;65(1):87-93.

[2]. 4-vinylcyclohexene diepoxide induces apoptosis by excessive reactive oxygen species and DNA damage in human ovarian granulosa cells. Toxicol In Vitro. 2023 Sep;91:105613.

[3]. Hormone-Like Effects of 4-Vinylcyclohexene Diepoxide on Follicular Development. Front Cell Dev Biol. 2020 Jul 31;8:587.

[4]. Effects of 4-vinylcyclohexene diepoxide on the cell cycle, apoptosis, and steroid hormone secretion of goat ovarian granulosa cells. In Vitro Cell Dev Biol Anim. 2022 Mar;58(3):220-231.

[5]. Early effects of ovotoxicity induced by 4-vinylcyclohexene diepoxide in rats and mice. Reprod Toxicol. 1999 Jan-Feb;13(1):67-75.

[6]. 4-Vinylcyclohexene diepoxide disrupts sperm characteristics, endocrine balance and redox status in testes and epididymis of rats. Redox Rep. 2017 Nov;22(6):388-398.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H12O2
Molecular Weight
140.18
CAS #
106-87-6
Related CAS #
4-Vinylcyclohexene dioxide (Standard)
Appearance
Colorless to light yellow liquid (Density: 1.0986 g/cm3)
SMILES
C1(C2CCC3OC3C2)CO1
Synonyms
Vinylcyclohexene diepoxide
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

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 : ~50 mg/mL (~356.68 mM; with sonication)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 5 mg/mL (35.67 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% 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 canAdd 100 μL of DMSO stock solution (50.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of physiological saline: Dissolve 0.9 g of sodium chloride in double-distilled water and dilute to 100 mL to obtain clear physiological saline.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 5 mg/mL (35.67 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 canAdd 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD saline (4°C, store for one week): Dissolve 2 g of SBE-β-CD powder in 10 mL of saline until completely dissolved and clear.
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: ≥ 5 mg/mL (35.67 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 canAdd 100 μL of DMSO stock solution (50.0 mg/mL) to 900 μL of corn oil and mix well.


Solubility in Formulation 4: 25 mg/mL (178.34 mM) in Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution; Need ultrasonic.

Solubility in Formulation 5: 25 mg/mL (178.34 mM) in 15% Cremophor EL + 85% Saline (add these co-solvents sequentially from left to right, and one by one), Suspended solution; Need ultrasonic.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 7.1337 mL 35.6684 mL 71.3369 mL
5 mM 1.4267 mL 7.1337 mL 14.2674 mL
10 mM 0.7134 mL 3.5668 mL 7.1337 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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