LatifolineCAS# 6029-86-3 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 6029-86-3 | SDF | Download SDF |
| PubChem ID | 5281736 | Appearance | Powder |
| Formula | C20H27NO7 | M.Wt | 393.44 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | [(7R,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R,3S,4S)-3-hydroxy-2,4-dimethyl-5-oxooxolane-3-carboxylate | ||
| SMILES | CC=C(C)C(=O)OC1CCN2C1C(=CC2)COC(=O)C3(C(C(=O)OC3C)C)O | ||
| Standard InChIKey | LZKFLVDOCDILCY-CYSCPGKSSA-N | ||
| Standard InChI | InChI=1S/C20H27NO7/c1-5-11(2)17(22)28-15-7-9-21-8-6-14(16(15)21)10-26-19(24)20(25)12(3)18(23)27-13(20)4/h5-6,12-13,15-16,25H,7-10H2,1-4H3/b11-5-/t12-,13-,15-,16-,20+/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. | ||
| In vitro | Structural influences on pyrrolizidine alkaloid-induced cytopathology.[Pubmed: 8378933]Toxicol Appl Pharmacol. 1993 Sep;122(1):61-9.Pyrrolizidine alkaloids (PAs), which are common constituents of hundreds of plant species around the world, have been reported to have cytotoxic, carcinogenic, antineoplastic, and genotoxic activity in vivo and in vitro. The exact mechanism of these biological toxicities is not yet clear.
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| Structure Identification | J Org Chem. 2001 Oct 19;66(21):7025-9.Reactive enols in synthesis 2. Synthesis of (+)-latifolic acid and (+)-latifoline.[Pubmed: 11597224]
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Latifoline Dilution Calculator
Latifoline Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.5417 mL | 12.7084 mL | 25.4168 mL | 50.8337 mL | 63.5421 mL |
| 5 mM | 0.5083 mL | 2.5417 mL | 5.0834 mL | 10.1667 mL | 12.7084 mL |
| 10 mM | 0.2542 mL | 1.2708 mL | 2.5417 mL | 5.0834 mL | 6.3542 mL |
| 50 mM | 0.0508 mL | 0.2542 mL | 0.5083 mL | 1.0167 mL | 1.2708 mL |
| 100 mM | 0.0254 mL | 0.1271 mL | 0.2542 mL | 0.5083 mL | 0.6354 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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Reactive enols in synthesis 2. Synthesis of (+)-latifolic acid and (+)-latifoline.[Pubmed:11597224]
J Org Chem. 2001 Oct 19;66(21):7025-9.
We describe a short, enantioselective synthesis of the naturally occurring pyrrolizidine alkaloid (+)-Latifoline (1) employing a tandem [3,3] sigmatropic rearrangement/[1,2] allyl shift as a key step in constructing (+)-latifolic acid (4).
Structural influences on pyrrolizidine alkaloid-induced cytopathology.[Pubmed:8378933]
Toxicol Appl Pharmacol. 1993 Sep;122(1):61-9.
Pyrrolizidine alkaloids (PAs), which are common constituents of hundreds of plant species around the world, have been reported to have cytotoxic, carcinogenic, antineoplastic, and genotoxic activity in vivo and in vitro. The exact mechanism of these biological toxicities is not yet clear. The ability of eight PA congeners to inhibit mitosis and induce megalocyte formation in cultured bovine kidney epithelial cells was studied to examine possible structural influences on these endpoints. Representatives of the three PA structural groups, the macrocycles (seneciphylline, senecionine, riddelliine, retrorsine, monocrotaline), open diesters (heliosupine, Latifoline), and a necine base (retronecine), were cocultured for 2 hr with a NADPH-generating system and rat liver S9. Macrocyclic PAs with alpha,beta-unsaturation (seneciphylline, senecionine, riddelliine, retrorsine) showed a dose-dependent inhibition of colony formation at 50, 100, and 300 microM and induction of megalocytosis at 500 microM. Colony growth resumed 3 weeks after removal of PAs at 50 and 100 microM, and normal cellular morphology returned 5 or 6 weeks after removal of PAs at 500 microM. The saturated macrocyclic (monocrotaline) and open diesters (heliosupine, Latifoline), elicited only a slight inhibition of colony formation and had no effect on cellular morphology at 500 microM. The necine base (retronecine) had no effect on either colony formation or cell morphology. Pyrrolic PAs (dehydrosenecionine, dehydromonocrotaline, dehydroretronecine) were more active in inhibition of colony formation than their parent compounds and were potent inducers of abnormal cellular morphology at 500 microM. An N-oxide metabolite, indicine N-oxide, was completely inactive. The results support previous studies showing that there are structural influences on PA-induced cytopathological effects.
