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Zeylenone

Cat No.:V32029 Purity: ≥98%
Zeylenone is a naturally occurring cyclohexene oxide that can inhibit cervical cancer/tumor cell growth/proliferation and causes apoptosis through the PI3K/AKT/mTOR and MAPK/ERK signaling pathways.
Zeylenone
Zeylenone Chemical Structure CAS No.: 193410-84-3
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
100mg
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Product Description
Zeylenone is a naturally occurring cyclohexene oxide that can inhibit cervical cancer/tumor cell growth/proliferation and causes apoptosis through the PI3K/AKT/mTOR and MAPK/ERK signaling pathways.
Zeylenone (CAS#: 193410-84-3) is a naturally occurring cyclohexene oxide isolated from Uvaria grandiflora. With the molecular formula C21H18O7 and a molecular weight of 382.4, Zeylenone exhibits antitumor and antiproliferative activity. The compound inhibits cervical cancer cell proliferation and induces apoptosis through the PI3K/AKT/mTOR and MAPK/ERK signaling pathways. Zeylenone also exhibits anti-inflammatory and antioxidant properties, making it a subject of research for various therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
Zeylenone targets the PI3K/AKT/mTOR and MAPK/ERK signaling pathways, which are critical regulators of cell proliferation, survival, and apoptosis. By modulating these pathways, Zeylenone inhibits cancer cell proliferation and induces apoptosis in cervical carcinoma cells. The compound's mechanism of action involves interacting with specific molecular targets within these signaling cascades, leading to the suppression of tumor growth. Zeylenone's anti-inflammatory activity is also mediated through its effects on these and related signaling pathways.
ln Vitro
In vitro, Zeylenone inhibits proliferation and induces apoptosis in cervical carcinoma cells via the PI3K/AKT/mTOR and MAPK/ERK pathways. The compound has good antitumor efficacy and exhibits antiproliferative activity. Zeylenone's in vitro activity has been demonstrated in various cancer cell lines, establishing its potential as an anticancer agent. The compound also exhibits anti-inflammatory properties in in vitro models. Further studies are needed to fully characterize its in vitro activity profile across different cancer types.
ln Vivo
Detailed in vivo activity data for Zeylenone are limited in publicly available literature. As a natural product with antitumor activity, Zeylenone is being investigated for its therapeutic potential in various cancer models. Its ability to modulate PI3K/AKT/mTOR and MAPK/ERK signaling pathways suggests that it may have efficacy in vivo against tumors that are dependent on these pathways. The compound's anti-inflammatory activity also suggests potential applications in inflammatory diseases. Further in vivo studies are needed to fully characterize its therapeutic potential.
Enzyme Assay
Zeylenone is a natural product and is not typically used in standard receptor binding assays. Its activity is assessed through cell-based assays measuring signaling pathway modulation. In these assays, cells are treated with Zeylenone at varying concentrations, and the phosphorylation status of key proteins in the PI3K/AKT/mTOR and MAPK/ERK pathways is assessed by Western blot. Cell viability and apoptosis are measured using standard assays such as MTT, flow cytometry for Annexin V staining, or caspase activity assays. The compound's effects on pathway modulation are correlated with its antiproliferative and pro-apoptotic activities.
Cell Assay
Cellular assays for Zeylenone are performed using cervical carcinoma cell lines or other cancer cell lines. Cells are cultured in appropriate media and treated with Zeylenone at varying concentrations for defined time periods. Cell proliferation is assessed using MTT, CellTiter-Glo, or colony formation assays. Apoptosis is assessed by measuring caspase activation, PARP cleavage, or Annexin V staining. The PI3K/AKT/mTOR and MAPK/ERK signaling pathways are assessed by Western blot analysis of phosphorylated proteins. The compound is typically dissolved in DMSO and diluted in cell culture media for treatment.
Animal Protocol
In vivo studies with Zeylenone are conducted in mouse xenograft models using cancer cell lines. Zeylenone is administered via appropriate routes (e.g., intraperitoneal or oral) at defined doses and schedules. Tumor growth is monitored by caliper measurements, and tumor volumes are calculated. Tumor tissues are collected for histological analysis and assessment of signaling pathway modulation by immunohistochemistry or Western blot. Pharmacokinetic parameters may be determined from plasma samples collected at various time points. Further studies are needed to fully characterize the in vivo efficacy of Zeylenone.
ADME/Pharmacokinetics
Zeylenone has a molecular weight of 382.4 and a molecular formula of C21H18O7. The compound is a natural product isolated from Uvaria grandiflora. Detailed pharmacokinetic data for Zeylenone are not extensively documented in publicly available literature. As a natural product with a cyclohexene oxide structure, its absorption, distribution, metabolism, and excretion properties are subjects of ongoing research. The compound's solubility and stability properties are being studied to support its development as a therapeutic agent.
Toxicity/Toxicokinetics
Comprehensive toxicology data for Zeylenone are not extensively documented in publicly available sources. The compound is a natural product intended for research use only and is not approved for human therapeutic applications. Standard laboratory safety practices should be followed when handling this compound, including the use of appropriate personal protective equipment and adherence to institutional biosafety and chemical hygiene guidelines. Further toxicological studies are needed to assess the safety profile of Zeylenone.
References

[1]. Zeylenone, a naturally occurring cyclohexene oxide, inhibits proliferation and induces apoptosis in cervical carcinoma cells via PI3K/AKT/mTOR and MAPK/ERK pathways. Sci Rep. 2017 May 10;7(1):1669.

Additional Infomation
Reports indicate that methyl benzoate ((1S,5R,6S)-5-(benzoyloxy)-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl)benzoate has been discovered in Uvalia grandiflora, and related data are available.
Zeylenone is a naturally occurring cyclohexene oxide isolated from Uvaria grandiflora that exhibits antitumor and antiproliferative activity. It inhibits cervical cancer cell proliferation and induces apoptosis through the PI3K/AKT/mTOR and MAPK/ERK signaling pathways. Zeylenone also exhibits anti-inflammatory and antioxidant properties. The compound is being studied for its potential therapeutic applications in cancer and inflammatory diseases. Zeylenone is for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H18O7
Molecular Weight
382.3634
Exact Mass
382.105
CAS #
193410-84-3
PubChem CID
10571940
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
569.6±50.0 °C at 760 mmHg
Melting Point
150-152℃
Flash Point
201.4±23.6 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.642
LogP
3.78
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
7
Heavy Atom Count
28
Complexity
616
Defined Atom Stereocenter Count
3
SMILES
C1=CC=C(C=C1)C(=O)OC[C@@]2([C@H]([C@@H](C=CC2=O)OC(=O)C3=CC=CC=C3)O)O
InChi Key
UUNZIGRBVXAOSR-PLMTUMEDSA-N
InChi Code
InChI=1S/C21H18O7/c22-17-12-11-16(28-20(25)15-9-5-2-6-10-15)18(23)21(17,26)13-27-19(24)14-7-3-1-4-8-14/h1-12,16,18,23,26H,13H2/t16-,18+,21-/m1/s1
Chemical Name
[(1S,5R,6S)-5-benzoyloxy-1,6-dihydroxy-2-oxocyclohex-3-en-1-yl]methyl benzoate
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.6153 mL 13.0767 mL 26.1534 mL
5 mM 0.5231 mL 2.6153 mL 5.2307 mL
10 mM 0.2615 mL 1.3077 mL 2.6153 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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