Dioctyl sulfosuccinate sodium salt

Chemical properties

white solid, often supplied as an aqueous solution

Chemical properties

Docusate sodium is a white or almost white, waxlike, bitter tasting, plastic solid with a characteristic octanol-like odor. It is hygroscopic and usually available in the form of pellets, flakes, or rolls of tissuethin material.

The Uses of Dioctyl sulfosuccinate sodium salt

Dioctyl sulfosuccinate sodium salt is a wetting and emulsifying agent that is slowly soluble in water, having a solubility of 1 g in 70 ml of water. It functions as a wetting agent in fumaric acid-containing powdered fruit drinks to help the acid dissolve in water. It is used as a stabilizing agent on gums at not more than 0.5% by weight of the gum. It is used as a flavor potentiator in canned milk where it improves and maintains the flavor of the sterilized milk during storage. It also functions as a processing aid in the manufacture of unrefined sugar. It is also termed sodium dioctylsulfosuccinate.

The Uses of Dioctyl sulfosuccinate sodium salt

Forms reverse micelles in hydrocarbon solvents; Suitable for the solubilization of the major myelin transmembrane proteolipid

The Uses of Dioctyl sulfosuccinate sodium salt

Docusate sodium, the sodium salt of Docusate, is a versatile compound with several applications in medicine and pharmaceutical formulations. Primarily, it is used for the treatment of constipation, where it acts as a laxative or stool softener, helping to relieve symptoms by softening the stool and facilitating its passage.

In addition to its direct medicinal use, Docusate sodium also plays a role in the synthesis of electrospun fibers. These fibers are particularly useful for tailored and controlled antibiotic drug release, offering a method to deliver antibiotics in a sustained and targeted manner.

Furthermore, Docusate sodium has unique properties that allow it to form reverse micelles in hydrocarbon solvents. This capability makes it suitable for the solubilization of certain proteins, including the major myelin transmembrane proteolipid, which is important in the context of neurological research and potential treatments for demyelinating diseases.

In summary, Docusate sodium is a multifaceted compound with applications ranging from relief of constipation to sophisticated drug delivery systems and specialized solubilization techniques in research.

Production Methods

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

Definition

ChEBI: Sodium docusate is an organic sodium salt.

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

Non flammable

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.