Introduction：Basic information about FLAVOXATE CAS 15301-69-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
FLAVOXATE Basic information
| Product Name: | FLAVOXATE |
| Synonyms: | FLAVOXATE;2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate;2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate;4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-(1-piperidinyl)ethyl ester;3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-piperidinoethyl ester;Piperidinoethyl 3-methyl-2-phenyl-4-oxo-4H-1-benzopyran-8-carboxylate;2-(Piperidin-1-yl)ethyl 3-Methyl-4-oxo-2-phenyl-4H-chroMene-8-carboxylate;Flavoxate-d5 |
| CAS: | 15301-69-6 |
| MF: | C24H25NO4 |
| MW: | 391.46 |
| EINECS: | 239-337-5 |
| Product Categories: | |
| Mol File: | 15301-69-6.mol |
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FLAVOXATE Chemical Properties
| Melting point | 87-88 °C |
| Boiling point | 564.1±50.0 °C(Predicted) |
| density | 1.203±0.06 g/cm3(Predicted) |
| form | Off-white solid. |
| pka | 7.3(at 25℃) |
| InChI | InChI=1S/C24H25NO4/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25/h2,4-5,8-12H,3,6-7,13-16H2,1H3 |
| InChIKey | SPIUTQOUKAMGCX-UHFFFAOYSA-N |
| SMILES | C1(C2=CC=CC=C2)OC2=C(C(OCCN3CCCCC3)=O)C=CC=C2C(=O)C=1C |
| CAS DataBase Reference | 15301-69-6(CAS DataBase Reference) |
Safety Information
| Toxicity | LD50 in rats (mg/kg): 1110 orally; 20.8 i.v. (Setnikar, 1975) |
FLAVOXATE Usage And Synthesis
| Chemical Properties | Flavoxate is also known as urology. Crystallized from ethanol/ether. Its hydrochloride is a white or creamy white crystalline powder. Crystallized from ethanol/ether. Melting point 232～234℃. Soluble in water, methanol, ethanol, chloroform, insoluble in acetone, ether. |
| Originator | Urispas,SKF,US,1971 |
| Uses | Flavoxate is a pharmaceutical active-containing film delivery device for oral transmucosal administration. |
| Uses | Relaxant (smooth muscle). |
| Definition | ChEBI: A carboxylic ester resulting from the formal condensation of 3-methylflavone-8-carboxylic acid with 2-(1-piperidinyl)ethanol. |
| Manufacturing Process | A mixture of 13.3 grams of anhydrous aluminum chloride and 100 ml ofcarbon disulfide is added to 19.4 grams of 2-propionyloxybenzoic acid(prepared from the reaction of propionyl chloride and 2-hydroxybenzoic acid).After an initial evolution of hydrogen chloride, the solvent is removed bydistillation and the mixture is heated at 150° to 160°C for 4 hours. The cooledreaction mixture is treated with ice and hydrochloric acid and the product, 2-hydroxy-3-carboxypropiophenone, is obtained from the oily residue bydistillation in vacuo.
A mixture of 1.9 grams of 2-hydroxy-3-carboxypropiophenone, 5.0 grams ofsodium benzoate and 20.0 grams of benzoic anhydride is heated at 180° to190°C for 6 hours. A solution of 15.0 grams of potassium hydroxide in 50 mlof ethanol and 20 ml of water is added and refluxed for 1 hour. The mixture isevaporated and the residue after addition of water yields 3-methylflavone-8-carboxylic acid.
To a suspension of 12.0 grams of 3-methylflavone-8-carboxylic acid in 200 mlof anhydrous benzene is added 10.0 grams of thionyl chloride. The mixture isrefluxed for 2 hours during which the suspended solid goes into solution. Thesolvent is completely removed by distillation, the residue extracted withbenzene and the extract evaporated to dryness. The product, 3-methylflavone-8-carboxylic acid chloride, is recrystallized from ligroin to givecrystals melting at 155° to 156°C.
To 11.0 grams of 3-methylflavone-8-carboxylic acid chloride dissolved in 150ml of anhydrous benzene is added at room temperature 4.8 grams ofpiperidinoethanol and the mixture refluxed for 2 to 3 hours. The separatedsolid is filtered, washed with benzene and dried. The product, piperidinoethyl3-methylflavone-8-carboxylate hydrochloride is obtained as a colorlesscrystalline solid, MP 232° to 234°C, (from US Patent 2,921,070). |
| Brand name | Urispas (Ortho-McNeil). |
| Therapeutic Function | Spasmolytic |
FLAVOXATE Preparation Products And Raw materials
| Raw materials | 2-Piperidinoethanol-->Propionyl chloride-->Benzoic anhydride-->Thionyl chloride-->Aluminum chloride-->Salicylic acid-->Methyl salicylate |
