CarabroneCAS# 1748-81-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1748-81-8 | SDF | Download SDF |
| PubChem ID | 164879 | Appearance | Cryst. |
| Formula | C15H20O3 | M.Wt | 248.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3aR,4aS,5S,5aR,6aR)-5a-methyl-3-methylidene-5-(3-oxobutyl)-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-2-one | ||
| SMILES | CC(=O)CCC1C2C1(CC3C(C2)C(=C)C(=O)O3)C | ||
| Standard InChIKey | AGIQIKMGJVLKMA-NLRWUALESA-N | ||
| Standard InChI | InChI=1S/C15H20O3/c1-8(16)4-5-11-12-6-10-9(2)14(17)18-13(10)7-15(11,12)3/h10-13H,2,4-7H2,1,3H3/t10-,11+,12+,13-,15-/m1/s1 | ||
| 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. Some of carabrone derivatives exhibit antifungal activities in vitro or in vivo, the compounds with a pyridinyl residue can either efficiently inhibit spore germination or efficiently inhibit hyphal growth of B. cinerea. |
| Targets | Antifection |
Carabrone Dilution Calculator
Carabrone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 4.0274 mL | 20.1369 mL | 40.2739 mL | 80.5477 mL | 100.6847 mL |
| 5 mM | 0.8055 mL | 4.0274 mL | 8.0548 mL | 16.1095 mL | 20.1369 mL |
| 10 mM | 0.4027 mL | 2.0137 mL | 4.0274 mL | 8.0548 mL | 10.0685 mL |
| 50 mM | 0.0805 mL | 0.4027 mL | 0.8055 mL | 1.611 mL | 2.0137 mL |
| 100 mM | 0.0403 mL | 0.2014 mL | 0.4027 mL | 0.8055 mL | 1.0068 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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Synthesis and antifungal activity of carabrone derivatives.[Pubmed:20877238]
Molecules. 2010 Sep 16;15(9):6485-92.
Nine derivatives 6-14 of Carabrone (1) were synthesized and tested in vitro against Colletotrichum lagenarium Ell et Halst using the spore germination method. Among all of the derivatives, compounds 6-8 and 12 showed more potent antifungal activity than 1. Structure-activity relationships (SAR) demonstrated that the gamma-lactone was necessary for the antifungal activity of 1, and the substituents on the C-4 position of 1 could significantly affect the antifungal activity.
Semisynthesis and antifungal activity of novel oxime ester derivatives of carabrone modified at C(4) against Botrytis cinerea.[Pubmed:24934674]
Chem Biodivers. 2014 Jun;11(6):886-903.
To continuously improve the potential utility of the natural lead compound of Carabrone in agrochemistry, Carabrone oxime and 36 novel oxime ester derivatives of Carabrone modified at C(4) were synthesized, and evaluated for their antifungal activities against Botrytis cinerea in vitro and in vivo. Of these 36 oxime ester derivatives, some compounds exhibited antifungal activities in vitro or in vivo. It was found that compounds with a pyridinyl residue can either efficiently inhibit spore germination or efficiently inhibit hyphal growth of B. cinerea, and compound 9 exhibited the highest activity in vitro and in vivo with IC50 and EC50 values of 1.17 and 12.9 mug/ml, respectively. Further, the structure-activity relationships are also discussed.
Sesquiterpene lactones from Inula hupehensis inhibit nitric oxide production in RAW264.7 macrophages.[Pubmed:22648378]
Planta Med. 2012 Jun;78(10):1002-9.
Phytochemical investigation of the aerial parts of Inula hupehensis Ling. led to the isolation and identification of 27 sesquiterpene lactones (1-27), including three new eudesmanolides (3-5), three new germacranolides (9-11), one new xanthanolide (16), two new Carabrone derivatives (25-26), and 18 known sesquiterpene lactones. The structures were elucidated by extensive spectroscopic methods and comparison to previously reported spectroscopic data. All compounds were evaluated for their inhibitory effects against LPS-induced nitric oxide production in RAW264.7 macrophages, and compound 5 showed the strongest activity with the IC(5)(0) value of 3.2 +/- 0.4 microM.
Synthesis, antifungal activities and qualitative structure activity relationship of carabrone hydrazone derivatives as potential antifungal agents.[Pubmed:24619221]
Int J Mol Sci. 2014 Mar 11;15(3):4257-72.
Aimed at developing novel fungicides for relieving the ever-increasing pressure of agricultural production caused by phytopathogenic fungi, 28 new hydrazone derivatives of Carabrone, a natural bioactive sesquisterpene, in three types were designed, synthesized and their antifungal activities against Botrytis cinerea and Colletotrichum lagenarium were evaluated. The result revealed that all the derivatives synthesized exhibited considerable antifungal activities in vitro and in vivo, which led to the improved activities for Carabrone and its analogues and further confirmed their potential as antifungal agents.
