112-92-5

Stearyl alcohol(112-92-5) occurs as hard, white, waxy pieces, flakes, or granules, which have a slight characteristic odor and a bland taste. It is soluble in alcohol, acetone, and ether, but insoluble in water. Furthermore, it is combustible.

1-Octadecanol is used in the synthesis of O-octadecyl-S-trifluorothiolcarbonate, which is a storable crystalline source of trifluoromethanethiol.
It can be used to improve solution processability of conjugated polymers used in the organic electronic applications.

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.

1-Octadecanol is prepared commercially via Ziegler aluminum alkyl hydrolysis or the catalytic, high-pressure hydrogenation of stearyl acid, followed by filtration and distillation. It may also be derived from natural fats and oils.

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

The Journal of Organic Chemistry, 49, p. 2438, 1984 DOI: 10.1021/jo00187a028
Synthetic Communications, 12, p. 463, 1982 DOI: 10.1080/00397918208065953

Mddl~7 toxic by ingestion. Questionable carcinogen with experimental neoplastigenic data. A skin and eye irritant.

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.

Notclassified

1-Octadecanol(112-92-5) 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.

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

1-Octadecanol is synthesized from Stearic acid, which may be obtained by saponification of Tallow, or hydrogenation of Cottonseed oil, from Castor oil or from other natural oils.

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.

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.]

Incompatible with strong oxidizing agents and strong acids.

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.

Thomas PS, et al. Electrical properties of natural rubber nanocomposites: effect of 1-octadecanol functionalization of carbon nanotubes.J. Mater. Sci.2012,47(7), 3344-49. DOI:10.1007/s10853-011-6174-4
Molecular interactions behind the synergistic effect in mixed monolayers of 1-octadecanol and ethylene glycol monooctadecyl ether. DOI:10.1021/jp401027c
Handbook of pharmaceutical excipients