PahutoxinCAS# 27742-14-9 |
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 27742-14-9 | SDF | Download SDF |
| PubChem ID | 119452 | Appearance | Powder |
| Formula | C23H46NO4 | M.Wt | 400.6 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 2-[(3S)-3-acetyloxyhexadecanoyl]oxyethyl-trimethylazanium;chloride | ||
| SMILES | CCCCCCCCCCCCCC(CC(=O)OCC[N+](C)(C)C)OC(=O)C.[Cl-] | ||
| Standard InChIKey | NJEOXMPQOCEVAI-FTBISJDPSA-M | ||
| Standard InChI | InChI=1S/C23H46NO4.ClH/c1-6-7-8-9-10-11-12-13-14-15-16-17-22(28-21(2)25)20-23(26)27-19-18-24(3,4)5;/h22H,6-20H2,1-5H3;1H/q+1;/p-1/t22-;/m0./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. Pahutoxin is a natural fish-killing (ichthyotoxic) agent derived from the defensive secretions of trunkfish. 2. Pahutoxin is a haemolytic agent. |
Pahutoxin Dilution Calculator
Pahutoxin Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.4963 mL | 12.4813 mL | 24.9626 mL | 49.9251 mL | 62.4064 mL |
| 5 mM | 0.4993 mL | 2.4963 mL | 4.9925 mL | 9.985 mL | 12.4813 mL |
| 10 mM | 0.2496 mL | 1.2481 mL | 2.4963 mL | 4.9925 mL | 6.2406 mL |
| 50 mM | 0.0499 mL | 0.2496 mL | 0.4993 mL | 0.9985 mL | 1.2481 mL |
| 100 mM | 0.025 mL | 0.1248 mL | 0.2496 mL | 0.4993 mL | 0.6241 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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Receptor-mediated toxicity of pahutoxin, a marine trunkfish surfactant.[Pubmed:12893062]
Toxicon. 2003 Jul;42(1):63-71.
Pahutoxin (PHN, choline chloride ester of 3-acetoxypalmitic acid) is a natural fish-killing (ichthyotoxic) agent derived from the defensive secretions of trunkfish. In spite of its obvious structural resemblance to synthetic cationic long-chain quaternary ammonium detergents, we show that PHN's action does not rely on its surfactant properties and is in fact, receptor-mediated. The above conclusion is supported by the following data: 1. Ichthyotoxicity is not related to its detergency or surfactivity, as indicated by the fact that the lethal concentration is about 1.5 orders of magnitude below its critical micelle concentration value (69 microM) and its liposomal/seawater partition coefficient is low (62-85); 2. The trunkfish is tolerant to its own Pahutoxin; 3. Ichthyotoxicity occurs only upon application to the surrounding water, suggesting the existence of externally located receptors; 4. The receptor hypothesis was supported by the aid of equilibrium saturation binding assays revealing the presence of specific binding sites to PHN on the fish gill membranes; 5. The PHN tolerant trunkfish was shown to be devoid of PHN-binding sites. Some chemo-ecological, and environmental implications are discussed.
Occurrence of pahutoxin and homopahutoxin in the mucus secretion of the Japanese boxfish.[Pubmed:3617085]
Toxicon. 1987;25(4):459-61.
The mucus secreted by the Japanese boxfish O. immaculatus was extracted with n-butanol. The extract was fractionated by silica gel open column chromatography and reversed phase high performance liquid chromatography to give two hemolytic components. The major hemolysin was identical with Pahutoxin which was previously isolated from the Hawaiian boxfish O. lentiginosus, while the other hemolysin was a new choline chloride ester, named homoPahutoxin.
Endogenous regulation of the functional duality of pahutoxin, a marine trunkfish surfactant.[Pubmed:15530977]
Toxicon. 2004 Dec 15;44(8):939-42.
Pahutoxin (PHN) is a long chain detergent-like quaternary ammonium cationic substance derived from defensive skin secretions of trunkfish. A recent study has revealed that PHN's ichthyotoxicity and its phospholipid membrane disruption effect are produced by two separate mechanisms, which presumably represent two separate physicochemical domains in the PHN molecule [Kalmanzon, E., Rahamim, Y., Barenholz, Y., Carmeli, S., Zlotkin, E., 2003. Receptor-mediated toxicity of Pahutoxin, a marine trunkfish surfactant. Toxicon 42, 63-71]. Here we report on the occurrence of a natural endogenous mechanism, which regulates the above PHN's functional duality. The regulation is performed by the aid of two separates constituents of the trunkfish secretion, which either selectively amplify PHN's ichthyotoxicity (factor I) or suppress its phospholipids permeabilization effect (factor II). The ecological significance of such endogenous regulation is discussed.
