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Zederone (zedoary epoxy ketone)

Cat No.:V70241 Purity: ≥98%
Zederone is a germacrane-type sesquiterpene with potent cytotoxic effect against human leukocyte cancer cells and human prostate cancer cells.
Zederone (zedoary epoxy ketone)
Zederone (zedoary epoxy ketone) Chemical Structure CAS No.: 7727-79-9
Product category: mTOR
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Zederone is a germacrane-type sesquiterpene with potent cytotoxic effect against human leukocyte cancer cells and human prostate cancer cells. Zederone significantly inhibited SKOV3 cell proliferation/growth and downregulated the protein expression of mTOR and phosphorylated p70 S6 kinase (p-p70s6K).
Zederone (also known as zedoary epoxy ketone) is a natural sesquiterpenoid compound found in the rhizomes of Curcuma species, including Curcuma zedoaria and Curcuma longa. It belongs to the class of sesquiterpenoids and has been extensively studied for its potential therapeutic and industrial applications. Zederone has a molecular formula of C15H18O3, a molecular weight of 246.30 g/mol, and a CAS number of 7727-79-9. The chemical name is (1aR,4E,10aR)-1a,3,6,10a-tetrahydro-1a,5,9-trimethyloxireno[4,5]cyclodeca[1,2-b]furan-10(2H)-one. As a natural product from Curcuma species, zederone may have various biological activities, including anti-inflammatory, antioxidant, and anticancer properties, which are commonly associated with curcuminoids and other sesquiterpenoids from these plants. Zederone is a research tool for studying the pharmacological activities of sesquiterpenoids and their potential therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
mTOR
Zederone is a natural sesquiterpenoid compound from Curcuma species. While specific molecular targets have not been extensively characterized, compounds from Curcuma species are known to modulate various signaling pathways, including NF-κB, MAPK, and PI3K/AKT pathways.
ln Vitro
In vitro, zederone and related compounds from Curcuma species have been shown to exhibit anti-inflammatory, antioxidant, and anticancer activities. These activities are typically mediated through the modulation of signaling pathways such as NF-κB, MAPK, and PI3K/AKT, as well as through the induction of apoptosis and inhibition of cell proliferation.
ln Vivo
In vivo, zederone and related compounds from Curcuma species have been studied for their potential therapeutic applications in various diseases, including cancer, inflammation, and metabolic disorders.
Enzyme Assay
In vitro assays for zederone are performed to evaluate its biological activities. Anti-inflammatory activity is assessed by measuring the inhibition of pro-inflammatory cytokine production or NF-κB activation. Antioxidant activity is assessed by measuring the scavenging of free radicals or the inhibition of lipid peroxidation. Anticancer activity is assessed by measuring the inhibition of cell proliferation and the induction of apoptosis in cancer cell lines.
Cell Assay
In vitro cell-based assays are conducted to evaluate the effects of zederone on cell viability, inflammation, and oxidative stress. Cells are treated with zederone, and cell viability is assessed using standard assays such as MTT or CCK-8. Inflammatory markers such as TNF-α, IL-6, and IL-1β are measured by ELISA. Oxidative stress markers such as ROS and MDA are measured using fluorescent or colorimetric assays.
Animal Protocol
In vivo animal studies with zederone would be conducted in models of inflammation, cancer, or metabolic disorders to evaluate its therapeutic potential. The compound could be administered via oral or intraperitoneal routes. Its effects on disease progression, inflammatory markers, and survival would be assessed.
ADME/Pharmacokinetics
No detailed pharmacokinetic data are publicly available for zederone. As a natural sesquiterpenoid, its oral bioavailability may be limited. Its pharmacokinetic properties would be studied in preclinical models.
Toxicity/Toxicokinetics
No specific toxicity data are publicly available for zederone. As a natural product, it is generally considered to have low toxicity, but comprehensive toxicological studies would be required for therapeutic development.
References

[1]. Zederone, a sesquiterpene from Curcuma elata Roxb, is hepatotoxic in mice. Int J Toxicol. 2013 Nov-Dec;32(6):454-62.

[2]. A study of zederone for the inhibition on ovarian cancer cell proliferation through mTOR/p70s6K signalling pathway. J BUON. 2020 Mar-Apr;25(2):785-791.

Additional Infomation
(3R,5S,8E)-5,9,14-trimethyl-4,12-dioxatricyclo[9.3.0.03,5]tetradec-1(11),8,13-trien-2-one is a sesquiterpene compound. (3R,5S,8E)-5,9,14-trimethyl-4,12-dioxatricyclo[9.3.0.03,5]tetradec-1(11),8,13-trien-2-one has been reported in turmeric (Curcuma ochrorhiza) and turmeric (Curcuma longa), and relevant data are available.
Zederone (zedoary epoxy ketone) is a natural sesquiterpenoid compound found in the rhizomes of Curcuma species, including Curcuma zedoaria and Curcuma longa. It has been studied for its potential therapeutic applications, including anti-inflammatory, antioxidant, and anticancer activities. Zederone is a valuable research tool for studying the pharmacological activities of sesquiterpenoids. The compound is not approved for human therapeutic use and is strictly for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H18O3
Molecular Weight
246.30
Exact Mass
246.125
CAS #
7727-79-9
PubChem CID
71694446
Appearance
Light yellow to yellow solid powder
Density
1.1±0.1 g/cm3
Boiling Point
365.3±42.0 °C at 760 mmHg
Melting Point
153.4-153.9℃ (acetone hexane )
Flash Point
174.7±27.9 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.528
LogP
3.58
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
18
Complexity
401
Defined Atom Stereocenter Count
2
SMILES
C/C/1=C\CC[C@]2([C@@H](O2)C(=O)C3=C(C1)OC=C3C)C
InChi Key
CVIVANCKIBYAOP-WSQYCBKMSA-N
InChi Code
InChI=1S/C15H18O3/c1-9-5-4-6-15(3)14(18-15)13(16)12-10(2)8-17-11(12)7-9/h5,8,14H,4,6-7H2,1-3H3/b9-5+/t14-,15-/m0/s1
Chemical Name
(3R,5S,8E)-5,9,14-trimethyl-4,12-dioxatricyclo[9.3.0.03,5]tetradeca-1(11),8,13-trien-2-one
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)
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 4.0601 mL 20.3004 mL 40.6009 mL
5 mM 0.8120 mL 4.0601 mL 8.1202 mL
10 mM 0.4060 mL 2.0300 mL 4.0601 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • 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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