112-92-5

Production Methods

Historically, stearyl alcohol was prepared from sperm whale oil but is now largely prepared synthetically by reduction of ethyl stearate with lithium aluminum hydride.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2438, 1984 DOI: 10.1021/jo00187a028Synthetic Communications, 12, p. 463, 1982 DOI: 10.1080/00397918208065953

Health Hazard

Mildly toxic by ingestion. Questionable carcinogen with experimental neoplastigenic data. A skin and eye irritant.

Fire Hazard

Flammable when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Flammability and Explosibility

Notclassified

Pharmaceutical Applications

1-Octadecanol is used in cosmetics and topical pharmaceutical creams and ointments as a stiffening agent. By increasing the viscosity of an emulsion, stearyl alcohol increases its stability. 1-Octadecanol also has some emollient and weak emulsifying properties, and is used to increase the water-holding capacity of ointments, e.g. petrolatum. In addition, 1-Octadecanol has been used in controlled-release tablets, suppositories, and microspheres.It has also been investigated for use as a transdermal penetration enhancer.

Safety

Stearyl alcohol is generally considered to be an innocuous, nontoxic material. However, adverse reactions to stearyl alcohol present in topical preparations have been reported. These include contact urticaria and hypersensitivity reactions, which are possibly due to impurities contained in stearyl alcohol rather than stearyl alcohol itself. The probable lethal oral human dose is greater than 15 g/kg. LD50 (rat, oral): 20 g/kg

storage

Stearyl alcohol is stable to acids and alkalis and does not usually become rancid. It should be stored in a well-closed container in a cool, dry place.

Purification Methods

Crystallise octadecanol from MeOH, or dry Et2O and *C6H6, then fractionally distil it in vacuo. Also purify it by column chromatography. Free it from cetyl alcohol by zone refining. [Beilstein 1 IV 1888.]

Incompatibilities

Incompatible with strong oxidizing agents and strong acids.

Regulatory Status

Included in the FDA Inactive Ingredients Database (oral tablets, rectal topical, and vaginal preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

Definition

ChEBI: Octadecan-1-ol is a long-chain primary fatty alcohol consisting of a hydroxy function at C-1 of an unbranched saturated chain of 18 carbon atoms. It has a role as a plant metabolite, a human metabolite and an algal metabolite. It is a long-chain primary fatty alcohol, a fatty alcohol 18:0 and a primary alcohol. It derives from a hydride of an octadecane.

Application

1-Octadecanol is a long chain primary alcohol that is used in the production of emulsions, textile oils, antifoam agents, and lubricants. Other large scale applications include the manufacture of alkyl amines, tertiary amines, ethoxylates, halides/mercaptans, and polymerization stabilizers. It generally occurs as a mixture of solid alcohols whose primary constituent is 1-octadecanol. It occurs naturally in sperm whale oil and has been isolated from the hyperthermophilic bacterium Pyrococcus furiosus.1-Octadecanol has been used to model the plant epicuticular wax layer for an investigation by differential scanning calorimetry and Fourier transform infrared spectroscopy.The use of 1-octadecanol to prepare microsphere formulations for such compounds as paclitaxel and indomethacin has been described.

General Description

Mixed monolayers of 1-octadecanol and ethylene glycol monooctadecyl ether were studied to investigate their evaporation suppressing performance. The rate dependence of the collapse pressure for an octadecanolmonolayer using axisymmetric drop shape analysis has been investigated.