IsofuranodieneCAS# 57566-47-9 |
- Furanodiene
Catalog No.:BCN6454
CAS No.:19912-61-9
Quality Control & MSDS
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| Cas No. | 57566-47-9 | SDF | Download SDF |
| PubChem ID | 5317424 | Appearance | Oil |
| Formula | C15H20O | M.Wt | 216.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (5Z,9Z)-3,6,10-trimethyl-4,7,8,11-tetrahydrocyclodeca[b]furan | ||
| SMILES | CC1=CCC2=C(CC(=CCC1)C)OC=C2C | ||
| Standard InChIKey | VMDXHYHOJPKFEK-ADUATRDFSA-N | ||
| Standard InChI | 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- | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Isofuranodiene has anticancer activity, by inhibiting the proliferation and inducing apoptosis in cancer cells. 2. Isofuranodiene protects GalN/LPS-induced liver injury in SD rats, it may be a potential functional food ingredient for the prevention and treatment of liver diseases. 3. Isofuranodiene can induce apoptosis in colon cancer cells in a time and concentration-dependent manner suggesting a potential role as models for the development of chemopreventive agents. 4. Isofuranodiene at concentrations of 25 and 12.5 lM alone, or in combination with 50 nM nerve growth factor (NGF) , shows a marked stimulation of neuritogenesis,which appears to be a promising neurotrophic and neuroprotective agent. |
| Targets | IL Receptor | NOS |
Isofuranodiene Dilution Calculator
Isofuranodiene Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.6232 mL | 23.116 mL | 46.2321 mL | 92.4642 mL | 115.5802 mL |
| 5 mM | 0.9246 mL | 4.6232 mL | 9.2464 mL | 18.4928 mL | 23.116 mL |
| 10 mM | 0.4623 mL | 2.3116 mL | 4.6232 mL | 9.2464 mL | 11.558 mL |
| 50 mM | 0.0925 mL | 0.4623 mL | 0.9246 mL | 1.8493 mL | 2.3116 mL |
| 100 mM | 0.0462 mL | 0.2312 mL | 0.4623 mL | 0.9246 mL | 1.1558 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Wild celery (Smyrnium olusatrum L.) oil and isofuranodiene induce apoptosis in human colon carcinoma cells.[Pubmed:24924290]
Fitoterapia. 2014 Sep;97:133-41.
Smyrnium olusatrum (Apiaceae), well known as wild celery, is a biennal celery-scented plant used for many centuries as a vegetable, then abandoned after the introduction of celery. In the present work, the essential oil obtained from inflorescences and the amounts of its main constituents Isofuranodiene, curzerene and germacrone were analyzed by GC as well as by HPLC because of their degradation (Cope rearrangement) occurring at high temperatures. The oil and the main constituents were assayed for cytotoxic activity on the human colon cancer cell line (HCT116) by MTT assay. Flower oil and Isofuranodiene showed noteworthy activity on tumor cells with IC50 of 10.71 and 15.06 mug/ml, respectively. Analysis of the cytotoxic activity showed that wild celery oil and Isofuranodiene are able to induce apoptosis in colon cancer cells in a time and concentration-dependent manner suggesting a potential role as models for the development of chemopreventive agents.
A forgotten vegetable (Smyrnium olusatrum L., Apiaceae) as a rich source of isofuranodiene.[Pubmed:22980882]
Food Chem. 2012 Dec 15;135(4):2852-62.
Smyrnium olusatrum, well known as wild celery or Alexanders, is a biennial herb belonging to the Apiaceae and used for many centuries as an edible vegetable because of the aromatic flavour of its parts. Its use on the table has decreased since the Middle Ages when it was replaced by common celery (Apium graveolens). In the present work the composition of the essential oils obtained by hydrodistillation of various plant parts was investigated by gas chromatography (GC-FID and GC-MS), while quantitation of a heat-sensitive compound, Isofuranodiene, known for its anticancer activity, and of its Cope rearrangement product curzerene, was achieved by HPLC-DAD. All essential oils were composed mainly of furanosesquiterpenoids (54.1-76.2%) with Isofuranodiene (19.5-45.8%) as the main constituent. Results showed that GC analysis provides underestimation (up to five times) of Isofuranodiene levels in essential oils and that curzerene could be considered an artifact since it is produced during heating of plant material, occurring during hydrodistillation.
Isofuranodiene: A neuritogenic compound isolated from wild celery (Smyrnium olusatrum L., Apiaceae).[Pubmed:26304411]
Food Chem. 2016 Feb 1;192:782-7.
In the search for neuroactive compounds that mimic the nerve growth factor (NGF) activity for the protection against neurodegenerative diseases, the potential medicinal values of foods and plants attracts intense interest. Isofuranodiene is the major constituent of the essential oil of wild celery (Smyrnium olusatrum L., Apiaceae). The cytotoxic effects of Isofuranodiene towards rat neuronal PC-12 pheochromocytoma cells were determined by MTT assay, while the cell differentiation was evaluated with xCELLigence real time cell analysis system (RTCA DP), and the neuritogenic activity was assessed by neurite outgrowth image analysis. Isofuranodiene at concentrations of 25 and 12.5 muM alone, or in combination with 50 nM NGF, showed a marked stimulation of neuritogenesis, but it was more effective at 12.5 muM with or without NGF. The present study reports the first evidence of the neuritogenic effects of Isofuranodiene, which appears to be a promising neurotrophic and neuroprotective agent deserving further investigation.
Isofuranodiene, the main volatile constituent of wild celery (Smyrnium olusatrum L.), protects d-galactosamin/lipopolysacchride-induced liver injury in rats.[Pubmed:25978596]
Nat Prod Res. 2016;30(10):1162-5.
Isofuranodiene is a natural sesquiterpene rich occurring in Smyrnium olusatrum, a forgotten culinary herb which was marginalised after the domestication of the improved form of celery. Our recent data showed that Isofuranodiene inhibited the proliferation and induced apoptosis in cancer cells. In this study, we investigated its protective effect on d-galactosamine/lipopolysacchride (GalN/LPS)-induced liver injury in SD rats. Oral administration of Isofuranodiene (20 and 50 mg/kg) dramatically inhibited GalN/LPS-induced serum elevation of aspartate aminotransferase, alanine aminotransferase and malondialdehyde levels, and significantly ameliorated liver injury as evidenced by the histological improvement in H&E staining. Furthermore, Isofuranodiene treatment significantly inhibited GalN/LPS-induced mRNA expression of IL-1beta, IL-6 and inducible nitric oxide synthase in liver tissues. The results from this study showed that Isofuranodiene protects GalN/LPS-induced liver injury in SD rats and suggested that it may be a potential functional food ingredient for the prevention and treatment of liver diseases.
Antiproliferative evaluation of isofuranodiene on breast and prostate cancer cell lines.[Pubmed:24967427]
ScientificWorldJournal. 2014;2014:264829.
The anticancer activity of Isofuranodiene, extracted from Smyrnium olusatrum, was evaluated in human breast adenocarcinomas MDA-MB 231 and BT 474, and Caucasian prostate adenocarcinoma PC 3 cell lines by MTS assay. MTS assay showed a dose-dependent growth inhibition in the tumor cell lines after Isofuranodiene treatment. The best antiproliferative activity of the Isofuranodiene was found on PC 3 cells with an IC50 value of 29 muM, which was slightly less than the inhibition against the two breast adenocarcinoma cell lines with IC50 values of 59 and 55 muM on MDA-MB 231 and BT 474, respectively. Hoechst 33258 assay was performed in order to study the growth inhibition mechanism in prostate cancer cell line; the results indicate that Isofuranodiene induces apoptosis. Overall, the understudy compound has a good anticancer activity especially towards the PC 3. On the contrary, it is less active on Chinese hamster ovary cells (CHO) and human embryonic kidney (HEK 293) appearing as a good candidate as a potential natural anticancer drug with low side effects.
