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Germacrone

Alias: Germacron Germacrone
Cat No.:V21560 Purity: ≥98%
Germacrone is found in turmeric and inhibits influenza virus infection.
Germacrone
Germacrone Chemical Structure CAS No.: 6902-91-6
Product category: Influenza Virus
This product is for research use only, not for human use. We do not sell to patients.
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50mg
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Product Description
Germacrone is found in turmeric and inhibits influenza virus infection.
Germacrone (CAS#: 6902-91-6) is a naturally occurring sesquiterpene found in various plants including Curcuma species (turmeric). It is a major bioactive component of essential oils from Curcuma aromatica and other Zingiberaceae plants. Germacrone has been studied for its diverse pharmacological activities including anti-inflammatory, antioxidant, anticancer, antiviral, and neuroprotective effects. The compound's unique structure features a 10-membered ring characteristic of germacrane-type sesquiterpenes.
Biological Activity I Assay Protocols (From Reference)
Targets
Germacrone targets multiple signaling pathways involved in inflammation, cell proliferation, and oxidative stress. The compound inhibits NF-κB activation and downregulates pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6. Germacrone also modulates the Nrf2/ARE antioxidant pathway, enhancing endogenous antioxidant defenses. Its anticancer effects are mediated through induction of apoptosis and cell cycle arrest. The compound's antiviral activity is attributed to its ability to inhibit viral replication.
ln Vitro
In vitro, germacrone exhibits anti-inflammatory, antioxidant, anticancer, and antiviral activities. The compound inhibits the production of pro-inflammatory cytokines in various cell types. Its antioxidant activity has been demonstrated in cell-free and cell-based assays. Germacrone induces apoptosis and inhibits cell proliferation in various cancer cell lines. The compound has shown antiviral activity against influenza virus and other viruses in cell culture models.
ln Vivo
In vivo, germacrone has demonstrated anti-inflammatory, anticancer, and neuroprotective effects in animal models. The compound has been shown to reduce inflammation in models of arthritis and other inflammatory conditions. Its anticancer effects have been evaluated in tumor xenograft models. Germacrone has shown neuroprotective effects in models of neurodegenerative diseases. The compound is typically administered orally or via injection.
Enzyme Assay
In vitro enzyme assays for germacrone involve measuring its effects on enzymes involved in inflammation and oxidative stress. NF-κB activation is assessed using reporter gene assays or electrophoretic mobility shift assays. Antioxidant activity is measured using DPPH, ABTS, or FRAP assays. Enzyme inhibition assays for COX-2, iNOS, and other inflammatory enzymes can be performed using purified enzyme preparations. These assays provide mechanistic insights into the compound's activities.
Cell Assay
In vitro cell-based assays for germacrone involve treating various cell types (immune cells, cancer cells, neuronal cells) with the compound to assess its effects on cell viability, inflammation, and oxidative stress. Cytokine production (TNF-α, IL-6) is measured by ELISA. Cell viability is measured using MTT or similar assays. Apoptosis is quantified by flow cytometry or caspase activity assays. Oxidative stress markers are measured using fluorescent probes. These assays characterize the compound's pharmacological activities.
Animal Protocol
In vivo animal experiments for germacrone have been conducted in models of inflammation, cancer, and neurodegenerative diseases. Animals are treated with germacrone orally or via injection. Anti-inflammatory effects are assessed by measuring inflammatory markers and tissue histology. Anticancer effects are evaluated in tumor xenograft models. Neuroprotective effects are assessed in models of Parkinson's or Alzheimer's disease. Efficacy endpoints include biomarker analysis, histopathology, and behavioral assessments.
ADME/Pharmacokinetics
Germacrone is a sesquiterpene with a molecular weight of 218.34 and a molecular formula of C15H22O. It is a major bioactive component of essential oils from Curcuma species. Germacrone is lipophilic and soluble in organic solvents but has limited aqueous solubility. Following oral administration, germacrone is absorbed and metabolized. Its pharmacokinetic properties include rapid absorption and extensive metabolism. The compound is typically stored under recommended conditions for natural products.
Toxicity/Toxicokinetics
Specific toxicity data for germacrone is not extensively reported. As a natural compound from Curcuma species, which have a long history of use in traditional medicine and as food ingredients, germacrone is generally considered to have a favorable safety profile. However, comprehensive toxicological studies would be required for therapeutic development. Standard safety precautions should be taken when handling the compound in research settings.
References

[1]. Germacrone inhibits early stages of influenza virus infection. Antiviral Res. 2013 Dec;100(3):578-88.

Additional Infomation
(E,E)-Germalone is a sesquiterpene compound with the molecular formula C15H22O. It is a natural product found in traditional medicinal plants of the ginger family (Zingiberaceae). This compound possesses various pharmacological activities, including anti-inflammatory, anticancer, antiviral, anti-androgenic, antioxidant, antibacterial, antifungal, neuroprotective, and insecticidal activities. It can function as a volatile oil component, antiviral agent, insecticide, anti-inflammatory agent, antioxidant, antitumor agent, apoptosis inducer, autophagy inducer, antibacterial agent, androgen antagonist, neuroprotective agent, plant metabolite, antifungal agent, antitussive, antifeedant, and hepatoprotective agent. It is a sesquiterpene compound, belonging to the olefin class of compounds. Germalone has been reported to be found in rhododendron (Rhododendron dauricum), turmeric (Curcuma xanthorrhiza), and other organisms with relevant data.
Germacrone is a naturally occurring sesquiterpene from Curcuma species with diverse pharmacological activities including anti-inflammatory, antioxidant, anticancer, antiviral, and neuroprotective effects. It inhibits NF-κB activation and modulates the Nrf2/ARE antioxidant pathway. Germacrone induces apoptosis in cancer cells and has shown antiviral activity against influenza virus. The compound has potential applications in inflammation, cancer, and neurodegenerative disease research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H22O
Molecular Weight
218.34
Exact Mass
218.167
CAS #
6902-91-6
PubChem CID
6436348
Appearance
White to off-white solid powder
Density
0.9±0.1 g/cm3
Boiling Point
330.3±42.0 °C at 760 mmHg
Melting Point
55-58ºC
Flash Point
148.4±18.7 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.485
LogP
4.76
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Heavy Atom Count
16
Complexity
363
Defined Atom Stereocenter Count
0
SMILES
C/C/1=C\CC(=C(C)C)C(=O)C/C(=C/CC1)/C
InChi Key
CAULGCQHVOVVRN-SWZPTJTJSA-N
InChi Code
InChI=1S/C15H22O/c1-11(2)14-9-8-12(3)6-5-7-13(4)10-15(14)16/h7-8H,5-6,9-10H2,1-4H3/b12-8+,13-7+
Chemical Name
(3E,7E)-3,7-dimethyl-10-propan-2-ylidenecyclodeca-3,7-dien-1-one
Synonyms
Germacron Germacrone
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : 44 ~100 mg/mL (201.52 ~458.02 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.45 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 can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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: ≥ 2.5 mg/mL (11.45 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 can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (11.45 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.5800 mL 22.9001 mL 45.8001 mL
5 mM 0.9160 mL 4.5800 mL 9.1600 mL
10 mM 0.4580 mL 2.2900 mL 4.5800 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

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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)
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  • 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)
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  • 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:
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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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  • 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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