| Identification | More | [Name]
TYLOXAPOL | [CAS]
25301-02-4 | [Synonyms]
4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOL POLYMER WITH FORMALDEHYDE AND OXIRANE
ETHOXYLATED P-TERT-OCTYLPHENOL FORMALDEHYDE POLYMER
TRITON(R) WR-1339
TYLOXAPOL
4-(1,1,3,3-tetramethylbutyl)-phenopolymerwithformaldehydeandoxirane
alevaire
formaldehyde,polymerwithoxiraneand4-(1,1,3,3-tetramethylbutyl)phenol
macrocyclon
oxyethylatedtertiaryoctyl-phenol-formaldehydepolymer
p-(1,1,3,3-tetramethylbutyl)phenolpolymerwithethyleneoxideandformaldehy
p-(1,1,3,3-tetramethylbutyl)-phenopolymerwithethyleneoxideandformalde
p-isooctylpolyoxyethylenephenolformaldehydepolymer
superinone
superiuone
tritona-20
tritonwr1339
tyloxypal
TYLOXAPOL SIGMAULTRA
TYLOXAPOL REAGENT GRADE
4-(1,1,3,3,-Tetramethyl buthyl)phenol (Tloxapol) etc... | [Molecular Formula]
C8H11NO | [MDL Number]
MFCD00149002 | [Molecular Weight]
137.179 | [MOL File]
25301-02-4.mol |
| Chemical Properties | Back Directory | [Appearance]
clear to hazy yellow to amber viscous liquid | [density ]
1.1
| [Fp ]
113 °C
| [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Viscous Liquid | [color ]
Clear to hazy yellow to amber | [Merck ]
13,9901 | [InChI]
InChI=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 | [InChIKey]
MDYZKJNTKZIUSK-UHFFFAOYSA-N | [SMILES]
C=O.C1OC1.C(C1C=CC(O)=CC=1)(C)(C)CC(C)(C)C | [LogP]
4.930 (est) | [CAS DataBase Reference]
25301-02-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
SM9750000
| [HS Code ]
29222990 | [Toxicity]
mouse,LD50,intraperitoneal,> 5gm/kg (5000mg/kg),Drugs in Japan Vol. 6, Pg. 467, 1982. |
| Hazard Information | Back Directory | [Description]
Tyloxapol 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 Properties]
clear to hazy yellow to amber viscous liquid | [Originator]
Solacen | [Uses]
anthelmintic, hepatotoxic | [Definition]
ChEBI: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 Process]
Srep 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 name]
Superinone (Sterling Winthrop). | [Therapeutic Function]
Bronchodilator | [General Description]
Tyloxapol is a biocompatible surfactant | [Mechanism of action]
Tyloxapol, 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. | [storage]
Store at -20°C,protect from light |
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