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Furanodiene

Alias: Furanodiene; G0AFT38FJ7; 19912-61-9; DTXSID401319109; (5E,9Z)-3,6,10-Trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan; Germacra-1(10),4,7,11-tetraene, 8,12-epoxy-, (Z,E)-; Cyclodeca(b)furan, 4,7,8,11-tetrahydro-3,6,10-trimethyl-, (5E,9Z)-; (5E,9Z)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca(b)furan;
Cat No.:V21412 Purity: ≥98%
Furanodiene is a natural terpene developed from turmeric.
Furanodiene
Furanodiene Chemical Structure CAS No.: 19912-61-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
100mg
Other Sizes
Official Supplier of:
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Product Description
Furanodiene is a natural terpene developed from turmeric. Furanodiene exerts anti-cancer activities by anti-angiogenesis and inducing ROS production, DNA strand breaks and apoptosis. Furanodiene inhibits the function of the efflux transporter Pgp (P-glycoprotein) and reduces Pgp protein levels.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Human JF 305 pancreatic cancer cells and MCF-7 breast cancer cells xenografted into zebrafish respond well to furadienes (1.4, 4.1, 12.2 uM; 48 hours) [1]. The expression of the Pgp-related gene (MDR1) is unaffected by furandadiene [1].
- Anti-proliferative activity: Furanodiene inhibited the proliferation of lung cancer cells (A549, NCI-H1299, 95-D) in a concentration-dependent manner, with IC50 values ranging from 10 to 30 μM. It also suppressed colony formation in A549 and 95-D cells . - Induction of endoplasmic reticulum (ER) stress: Furanodiene upregulated the mRNA and protein expression levels of binding immunoglobulin protein (BiP) and C/EBP homologous protein (CHOP), indicating ER stress induction. Nuclear accumulation of CHOP further confirmed this effect . - Synergistic effects with paclitaxel: Combined treatment with paclitaxel showed significant synergy in NCI-H1299 and 95-D cells, suggesting potential for combination therapy .
ln Vivo
- Antitumor activity in zebrafish models: Furanodiene reduced tumor growth in zebrafish models, potentially through mechanisms involving cytokine gene stimulation (e.g., upregulation of IL-1α, IL-1β, IL-6, TNF-α, and IFN-γ; downregulation of IL-4, IL-5, IL-10, and TGF-β) . - Toxicity assessment: No significant adverse effects were observed in zebrafish at doses up to 90 μg/g .
Cell Assay
- MTT and apoptosis assays: Furanodiene induced apoptosis in lung cancer cells, as demonstrated by increased caspase-3/7 activity and Annexin V staining . - Western blot and PCR analysis: Upregulation of ER stress markers (BiP, CHOP) and downregulation of anti-apoptotic proteins (Bcl-2) were observed .
Animal Protocol
- Zebrafish model: Furanodiene was administered by immersion in the water at concentrations of 10-90 μg/g. Tumor growth was assessed by visual inspection and histological analysis . - Solubility and formulation: Furanodiene was dissolved in DMSO and diluted in fish water to achieve the desired concentrations .
ADME/Pharmacokinetics
Metabolism: Furandiene is primarily metabolized by cytochrome P450 enzymes (mainly CYP2E1) to produce reactive intermediates, such as cis-2-buten-1,4-dialdehyde (BDA). These metabolites may be associated with its toxicity and anticancer effects. - Tissue Distribution: Rodent studies have shown that furans (a related compound) preferentially accumulate in the liver, kidneys, and heart, with lower concentrations in the lungs and blood.
Toxicity/Toxicokinetics
Metabolism: Furandiene is primarily metabolized by cytochrome P450 enzymes (mainly CYP2E1) to produce reactive intermediates, such as cis-2-buten-1,4-dialdehyde (BDA). These metabolites may be associated with its toxicity and anticancer effects. - Tissue Distribution: Rodent studies have shown that furans (a related compound) preferentially accumulate in the liver, kidneys, and heart, with lower concentrations in the lungs and blood.
References

[1]. Sensitization and synergistic anti-cancer effects of Furanodiene identified in zebrafish models. Sci Rep. 2019 Mar 14;9(1):4541.

Additional Infomation
Furandiene is a sesquiterpene compound. It has been reported in turmeric, Cyperus rotundus, and other organisms with relevant data. See also: Furandiene (note moved here). - Natural Source: Furandiene is a sesquiterpene compound isolated from the traditional Chinese medicine Cuscuta chinensis (turmeric). - Mechanism of Action: In addition to inducing endoplasmic reticulum stress, furandiene may also exert its effects by regulating cytokine signaling and immune responses. - Therapeutic Potential: Furandiene shows potential as an anticancer drug, especially when used in combination with other therapies, but further preclinical and clinical studies are needed to validate its efficacy and safety.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H20O
Molecular Weight
216.3187
Exact Mass
216.151
Elemental Analysis
C, 83.28; H, 9.32; O, 7.40
CAS #
19912-61-9
PubChem CID
636458
Appearance
Off-white to light yellow solid powder
Density
0.945±0.06 g/cm3
Boiling Point
309.6±11.0 °C at 760 mmHg
Melting Point
74-75 °C
Source
Originated from plants: Zingiberaceae Curcuma longa
LogP
4.359
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
0
Heavy Atom Count
16
Complexity
301
Defined Atom Stereocenter Count
0
SMILES
C/C/1=C\CC2=C(C/C(=C/CC1)/C)OC=C2C
InChi Key
VMDXHYHOJPKFEK-IAVOFVOCSA-N
InChi Code
InChI=1S/C15H20O/c1-11-5-4-6-12(2)9-15-14(8-7-11)13(3)10-16-15/h6-7,10H,4-5,8-9H2,1-3H3/b11-7+,12-6+
Chemical Name
(5E,9E)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan
Synonyms
Furanodiene; G0AFT38FJ7; 19912-61-9; DTXSID401319109; (5E,9Z)-3,6,10-Trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan; Germacra-1(10),4,7,11-tetraene, 8,12-epoxy-, (Z,E)-; Cyclodeca(b)furan, 4,7,8,11-tetrahydro-3,6,10-trimethyl-, (5E,9Z)-; (5E,9Z)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca(b)furan;
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: ~100 mg/mL (~462.3 mM; with ultrasonication and warming by heating to 60°C)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.56 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 can add 100 μL of DMSO stock solution (25.0 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 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 (11.56 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 DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.6228 mL 23.1139 mL 46.2278 mL
5 mM 0.9246 mL 4.6228 mL 9.2456 mL
10 mM 0.4623 mL 2.3114 mL 4.6228 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?
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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:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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