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TYLOXAPOL

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CAS:25301-02-4
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Products Intro: Product Name:TYLOXAPOL
CAS:25301-02-4

TYLOXAPOL manufacturers

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  • 2024-02-06
  • CAS:25301-02-4
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  • 2023-03-02
  • CAS:25301-02-4
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TYLOXAPOL Basic information
Product Name:TYLOXAPOL
Synonyms:ETHOXYLATED P-TERT-OCTYLPHENOL FORMALDEHYDE POLYMER;4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL POLYMER WITH FORMALDEHYDE AND OXIRANE;TYLOXAPOL;TRITON(R) WR-1339;4-(1,1,3,3-tetramethylbutyl)-phenopolymerwithformaldehydeandoxirane;alevaire;formaldehyde,polymerwithoxiraneand4-(1,1,3,3-tetramethylbutyl)phenol;macrocyclon
CAS:25301-02-4
MF:C17H28O3
MW:280.41
EINECS:
Product Categories:Polymers;Benzene derivatives
Mol File:25301-02-4.mol
TYLOXAPOL Structure
TYLOXAPOL Chemical Properties
density 1.1
Fp 113 °C
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
form Viscous Liquid
color Clear to hazy yellow to amber
Merck 13,9901
InChIInChI=1S/C14H22O.C2H4O.CH2O/c1-13(2,3)10-14(4,5)11-6-8-12(15)9-7-11;1-2-3-1;1-2/h6-9,15H,10H2,1-5H3;1-2H2;1H2
InChIKeyMDYZKJNTKZIUSK-UHFFFAOYSA-N
SMILESC=O.C1OC1.C(C1C=CC(O)=CC=1)(C)(C)CC(C)(C)C
LogP4.930 (est)
CAS DataBase Reference25301-02-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 2
RTECS SM9750000
HS Code 29222990
Toxicitymouse,LD50,intraperitoneal,> 5gm/kg (5000mg/kg),Drugs in Japan Vol. 6, Pg. 467, 1982.
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
TYLOXAPOL Usage And Synthesis
DescriptionTyloxapol is a non-ionic liquid polymer of the alkylaryl polyether alcohol type. It has a wide range of uses as a surfactant (primarily for bronchopulmonary studies and drug delivery systems), an animal model inducer (used for induction of hyperlipidaemia in animals), and a reagent for biological studies (including studies of its mechanism of protection of macrophages against endotoxins and potential cytotoxicity).
Chemical Propertiesclear to hazy yellow to amber viscous liquid
OriginatorSolacen
Usesanthelmintic, hepatotoxic
UsesTyloxapol, is a nonionic liquid polymer of the alkyl aryl polyether alcohol type. It is used as a surfactant to aid liquefaction and removal of mucopurulent (containing mucus and pus) bronchopulmonary secretions. Tyloxapol also blocks plasma lipolytic activity.
DefinitionChEBI: Tyloxapol is a polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions. It has a role as an inhibitor, an excipient, a surfactant and an apoptosis inducer.
Manufacturing ProcessSrep 1: Into a 3-necked flask equipped with thermometer, mechanical agitator, and reflux condenser was charged the following: 412 g of α,α,γ,γ- tetramethylbutylphenol, 162 g of a 37% aqueous solution of formaldehyde, and 27.6 g of water. The mixture was agitated and heated to a temperature of 90°C. At this point, 246 g of oxalic acid and 0.92 g of Twitchell's reagent dissolved in 10 g of water were added. While being agitated, the reaction mixture was refluxed for 6 hours. 200 g of water and 384 g of toluene were added, and refluxing was continued for an hour.
Agitation was stopped and the contents of the flask were removed to a separatory funnel. The aqueous and resinous layers were separated and the solvent was removed from the resinous layer by vacuum distillation. After the removal of the solvent, heating at a reduced pressure of 1.5 to 2.5 mm and at a temperature of 245° to 250°C was continued for 4 1/2 hours. The condensate then had a viscosity of 4.0 poises when measured as a 60% solution in toluene and, on cooling, solidified to a brittle mass.
Step 2: A mixture of 118 parts of the product of Step 1, having hydroxyl number of 260, 2 parts of solid NaH, and 100 parts of toluene was heated to 125° to 150°C in an autoclave. Ethylene oxide was added slowly over a period of 2 1/2 hours until 261 parts of ethylene oxide were absorbed. This corresponds to 11 mols of ethylene oxide per mol of phenol in the product of Step 1. The toluene was then removed by steam distillation and the water by vacuum distillation at 10°C. The product was obtained as a viscous paste having a corrected hydroxyl number of 97. It was readily soluble in water and had marked detergent properties.
Brand nameSuperinone (Sterling Winthrop).
Therapeutic FunctionBronchodilator
General DescriptionTyloxapol is a biocompatible surfactant
Mechanism of actionTyloxapol, when injected IP, blocks plasma lipolytic activity, and thus the breakdown of triglyceride-rich lipoproteins. It has also been shown to be inhibitor of lipoprotein lipase, thus preventing triglyceride uptake.
TYLOXAPOL Preparation Products And Raw materials
Raw materialsFormaldehyde-->ETHYLENE OXIDE
Preparation Products1,2-DIPALMITOYL-SN-GLYCERO-3-PHOSPHOCHOLINE
Tag:TYLOXAPOL(25301-02-4) Related Product Information
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