CatalpalactoneCAS# 1585-68-8 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 1585-68-8 | SDF | Download SDF |
| PubChem ID | 3014018 | Appearance | Powder |
| Formula | C15H14O4 | M.Wt | 258.3 |
| Type of Compound | Sesquiterpenoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 3-(2,2-dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-one | ||
| SMILES | CC1(CC=C(C(=O)O1)C2C3=CC=CC=C3C(=O)O2)C | ||
| Standard InChIKey | GFYSRANGENPXDF-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C15H14O4/c1-15(2)8-7-11(14(17)19-15)12-9-5-3-4-6-10(9)13(16)18-12/h3-7,12H,8H2,1-2H3 | ||
| 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. Catalpalactone can inhibit dopamine biosynthesis by reducing tyrosine hydroxylase (TH) and aromatic-l-amino acid decarboxylase (AADC) activities and enhance L-DOPA- induced cytotoxiciy in PC12 cells. 2. Catalpalactone displays good cytotoxicity activities against two human tumor cell lines(MCF-7,BxPC3). 3. Catalpalactone exhibits significant inhibitory activity against 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells. 4. Catapalactone exhibits potent inhibitory effects on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells , with IC50 values of 9.80 microM. 5. Catalpalactone exhibits high antitermitic activity. |
| Targets | cAMP | NO |
Catalpalactone Dilution Calculator
Catalpalactone Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.8715 mL | 19.3573 mL | 38.7147 mL | 77.4293 mL | 96.7867 mL |
| 5 mM | 0.7743 mL | 3.8715 mL | 7.7429 mL | 15.4859 mL | 19.3573 mL |
| 10 mM | 0.3871 mL | 1.9357 mL | 3.8715 mL | 7.7429 mL | 9.6787 mL |
| 50 mM | 0.0774 mL | 0.3871 mL | 0.7743 mL | 1.5486 mL | 1.9357 mL |
| 100 mM | 0.0387 mL | 0.1936 mL | 0.3871 mL | 0.7743 mL | 0.9679 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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Antitumor-promoting naphthoquinones from Catalpa ovata.[Pubmed:9599262]
J Nat Prod. 1998 May;61(5):629-32.
Bioassay-directed fractionation of an extract of the stem-bark of Catalpa ovata led to the isolation of three new naphthoquinones: 8-methoxydehydroiso-alpha-lapachone (1), 9-methoxy-4-oxo-alpha-lapachone (2), and (4S,4aR,10R,10aR)-4, 10-dihydroxy-2,2-dimethyl-2,3,4,4alpha,10, 10alpha-hexahydrobenzo[g]chromen-5-one (3), which is a 1,4-reductive form of 6. The known compounds 3-hydroxydehydroiso-alpha-lapachone (4), 4,9-dihydroxy-alpha-lapachone (5), 4-hydroxy-alpha-lapachone (6), and 9-methoxy-alpha-lapachone (7), and Catalpalactone (8) were also isolated. Their structures were elucidated by spectral methods. These compounds all exhibited significant inhibitory activity against 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells.
Major antitermitic components of the heartwood of southern catalpa.[Pubmed:24254942]
J Chem Ecol. 1992 Mar;18(3):359-69.
The heartwood of southern catalpa,Catalpa bignonioides Walt., is resistant to attack by the eastern subterranean termiteReticulitermes flavipes (Kollar), but extraction with a ternary solvent mixture of acetone-hexanewater (54ratio44ratio2) by volume removed the antitermitic characteristics from the heartwood. Four compounds comprised approximately 98% of the antitermitic fraction of the extract: the sesquiterpene alcohol, catalponol (67%); its epimer, epicatalponol (5%); a structurally related ketone, catalponone (1%); and the phthalide, Catalpalactone (25%). Pure compounds were isolated by semipreparative scale reversed-phase HPLC and identified by GC-MS and UV spectroscopy. The structure of catalponol was further confirmed by the formation of derivatives. Bioassays indicated that catalponol had the greatest toxicity in cellulose pad tests, but in tests using vacuum impregnation of these compounds into termite-susceptible wood blocks at levels approximating those found in catalpa heartwood, Catalpalactone exhibited the highest antitermitic activity.
Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide.[Pubmed:20361302]
Arch Pharm Res. 2010 Mar;33(3):381-5.
Bioassay-guided fractionation of a CH2Cl2-soluble fraction of the stems of Catalpa ovata led to isolation of a new naphthoquinone, 4-hydroxy-2-(2-methoxy-3-hydroxy-3-methyl-but-1-enyl)-4-hydro-1H-naphthalen-1-one (10), together with nine known compounds, catalponol (1), catalponone (2), Catalpalactone (3), alpha-lapachone (4), 9-hydroxy-alpha-lapachone (5), 4,9-dihydroxy-alpha-lapachone (6), 9-methoxy-alpha-lapachone (7), 4-oxo-alpha-lapachone (8), and 9-methoxy-4-oxo-alpha-lapachone (9). The structures were elucidated on the basis of spectroscopic analyses. The inhibitory effects of these isolates on lipopolysaccharide-induced NO synthesis in RAW 264.7 cells were evaluated. Among them, catapalactone (3), 9-hydroxy-alpha-lapachone (5) and 4,9-dihydroxy-alpha-lapachone (6) exhibited potent inhibitory effects, with IC(50) values of 9.80, 4.64 and 2.73 microM, respectively.
Effects of catalpalactone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells.[Pubmed:21783893]
Environ Toxicol Pharmacol. 2008 Jul;26(1):86-91.
The effects of Catalpalactone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells were investigated. Catalpalactone at 5-30muM decreased intracellular dopamine content with the IC(50) value of 22.1muM. Catalpalactone at 5-20muM, but not 30muM, did not alter cell viability. Catalpalactone at 20muM inhibited tyrosine hydroxylase (TH) and aromatic-l-amino acid decarboxylase (AADC) activities. Catalpalactone also decreased cyclic AMP levels and inhibited TH phosphorylation. In addition, Catalpalactone at 20muM reduced the increases in dopamine levels induced by L-DOPA (20-50muM). Catalpalactone (5-30muM) associated with L-DOPA (50-100muM) enhanced L-DOPA-induced cytotoxicity at 48h, which was prevented by N-acetyl-l-cysteine. These results suggest that Catalpalactone inhibited dopamine biosynthesis by reducing TH and AADC activities and enhanced L-DOPA-induced cytotoxiciy in PC12 cells.
