577-11-7

Chemical Properties

white solid, often supplied as an aqueous solution

Uses

dioctyl sodium sulfosuccinate is a mild surfactant used as a cleans ing agent.

Production Methods

Maleic anhydride is treated with 2-ethylhexanol to produce dioctyl maleate, which is then reacted with sodium bisulfite.

Brand name

Colace (Roberts Pharmaceutical); Correctol Stool Softener Laxative (Schering-Plough HealthCare); Dialose (Johnson & Johnson-Merck Consumer); Doxinate (Hoechst-Roussel); D-S-S (Parke-Davis); Modane Soft (Savage); Molofac (Bristol-Myers Squibb).

General Description

Odorless colorless to white waxy solid. Sinks and mixes slowly with water.

Air & Water Reactions

Mixes slowly with water.

Reactivity Profile

Docusate sodium causes foaming and spreading of water. Assists in putting out fires by water. [USCG, 1999].

Health Hazard

Liquid is strong irritant to eye and may irritate skin by removing natural oils. Ingestion causes diarrhea and intestinal bloating.

Fire Hazard

Behavior in Fire: Causes foaming and spreading of water. Assists in putting out fires by water.

Flammability and Explosibility

Nonflammable

Pharmaceutical Applications

Docusate sodium and docusate salts are widely used as anionic surfactants in pharmaceutical formulations. Docusate sodium is mainly used in capsule and direct-compression tablet formulations to assist in wetting and dissolution.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. A skin and severe eye irritant. See also ESTERS. When heated to decomposition it emits toxic fumes of SOx and Na2O.

Safety

Docusate salts are used in oral formulations as therapeutic agents for their fecal softening and laxative properties. As a laxative in adults, up to 500mg of docusate sodium is administered daily in divided doses; in children over 6 months old, up to 75 mg in divided doses is used. The quantity of docusate sodium used as an excipient in oral formulations should therefore be controlled to avoid unintended laxative effects. Adverse effects associated with docusate sodium include diarrhea, nausea, vomiting, abdominal cramps, and skin rashes. As with the chronic use of laxatives, the excessive use of docusate sodium may produce hypomagnesemia. Docusate salts are absorbed from the gastrointestinal tract and excreted in bile; they may cause alteration of the gastrointestinal epithelium. The gastrointestinal or hepatic absorption of other drugs may also be affected by docusate salts, enhancing activity and possibly toxicity. Docusate sodium should not be administered with mineral oil as it may increase the absorption of the oil. LD50 (mouse, IV): 0.06 g/kg LD50 (mouse, oral): 2.64 g/kg LD50 (rat, IP): 0.59 g/kg LD50 (rat, oral): 1.9 g/kg

Solubility in organics

Dioctyl sodium sulfosuccinate (DSS) is the dioctyl ester of sodium sulfosuccinate (bis-2-ethyl-hexyl sodium sulfosuccinate). It dissolves slowly in water; at 25°C to the extent of 1.5 gm/100cc; at 70°C, 5.5 gm/100cc. It dissolves in oils, hydrocarbons, fats and waxs by heating above 75°C and remains in solution when cooled to room temperature. At room temperature, it is readily soluble in most organic solvents, both polar and non-polar. soluble in carbon tetrachloride, petroleum ether, naphtha, xylene, dibutyl phthalate, liquid petroleum, acetone, alcohol, vegetable oils.

storage

Docusate sodium is stable in the solid state when stored at room temperature. Dilute aqueous solutions of docusate sodium between pH 1–10 are stable at room temperature. However, at very low pH (<1) and very high pH (>10) docusate sodium solutions are subject to hydrolysis. The solid material is hygroscopic and should be stored in an airtight container in a cool, dry place.

Purification Methods

Dissolve it in MeOH and the inorganic salts which precipitate are filtered off. Water is added and the solution is extracted several times with hexane. The residue is evaporated to one-fifth its original volume, *benzene is added and azeotropic distillation is continued until no water remains. The solvent is evaporated. The white residual solid is crushed and dried in vacuo over P2O5 for 48hours [El Seoud & Fendler J Chem Soc, Faraday Trans 1 71 452 1975]. [Beilstein 4 IV 114.] It solubilises major myelin trans membrane proteolipids, and forms reverse micelles in hydrocarbon solvents.

Incompatibilities

Electrolytes, e.g. 3% sodium chloride, added to aqueous solutions of docusate sodium can cause turbidity. However, docusate sodium possesses greater tolerance to calcium, magnesium, and other polyvalent ions than do some other surfactants. Docusate sodium is incompatible with acids at pH < 1 and with alkalis at pH > 10.

Regulatory Status

GRAS listed. Included in the FDA Inactive Ingredients Database (IM injections; oral capsules, suspensions, and tablets; also topical formulations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Who Evaluation

Evaluation year: 1995