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| | 1-Octadecanol Basic information |
| Product Name: | 1-Octadecanol | | Synonyms: | Octadecanol, 1-;Octadecyl alcohol, Stearyl alcohol;1-Octadecanol,Octadecyl alcohol, Stearyl alcohol;Stearyl alcohol, synthesis grade;Stearyl alcohol, extra pure, Ph Eur, USP;Stearyl Alcohol (125 mg);n-OCTADECYL ALCOHOL, TECH;Ecorol 18/98: Stearyl Alcohol Pastilles | | CAS: | 112-92-5 | | MF: | C18H38O | | MW: | 270.49 | | EINECS: | 204-017-6 | | Product Categories: | Alcohols;Biochemicals and Reagents;Building Blocks;C11 to C30+;Chemical Synthesis;Fatty Acyls;Biochemistry;Higher Fatty Acids & Higher Alcohols;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Fatty Alcohols;Lipids;Organic Building Blocks;Oxygen Compounds;Industrial/Fine Chemicals;1-Alkanols;Saturated Higher Alcohols;bc0001;112-92-5 | | Mol File: | 112-92-5.mol |  |
| | 1-Octadecanol Chemical Properties |
| Melting point | 56-59 °C (lit.) | | Boiling point | 210 °C15 mm Hg | | density | 0.812 g/mL at 25 °C (lit.) | | vapor density | 9.3 (vs air) | | vapor pressure | <0.01 mm Hg ( 38 °C) | | refractive index | 1.4356 (estimate) | | Fp | 185°C | | storage temp. | 2-8°C | | solubility | methanol: soluble10mg/mL, clear, colorless | | pka | 15.20±0.10(Predicted) | | form | Flakes | | Specific Gravity | 0.812 | | color | White | | Odor | wh. unctuous flakes or gran., faint odor, bland taste | | explosive limit | ~8% | | Water Solubility | insoluble | | Merck | 14,8805 | | BRN | 1362907 | | LogP | 7.4 | | CAS DataBase Reference | 112-92-5(CAS DataBase Reference) | | NIST Chemistry Reference | 1-Octadecanol(112-92-5) | | EPA Substance Registry System | 1-Octadecanol (112-92-5) |
| Safety Statements | 24/25 | | RIDADR | UN 1986 | | WGK Germany | - | | RTECS | RG2010000 | | Autoignition Temperature | 842 °F | | TSCA | Yes | | HS Code | 29051700 | | Hazardous Substances Data | 112-92-5(Hazardous Substances Data) | | Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| | 1-Octadecanol Usage And Synthesis |
| Chemical Properties | Stearyl alcohol occurs as hard, white, waxy pieces, flakes, or granules with a slight characteristic odor and bland taste. Soluble in alcohol, acetone, and ether; insoluble in water. Combustible. | | Uses | 1-Octadecanol is used to surfactant in cosmetics. It provides effective hydration to hands and face with pheohydrane which is a complex of the mico algae Chlorella Vulgaris and hydrolysed algin in a sea water base. It is a saturated alcohol of high purity and can substitute for cetyl alcohol in pharmaceutical dispensing, in cosmetic creams, for emulsions, textile oils and finishes, as antifoam agent, lubricant, viscosity agent, builder, and chemical raw material. | | 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. | | 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. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 49, p. 2438, 1984 DOI: 10.1021/jo00187a028
Synthetic Communications, 12, p. 463, 1982 DOI: 10.1080/00397918208065953 | | 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. | | 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. | | References | 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 |
| | 1-Octadecanol Preparation Products And Raw materials |
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