HuagongsheHuagongshe Chemistry Print Report · For research reference only
Stearyl Alcohol
STEARYL ALCOHOL · Ceteareth-20 · OCTADECANOL · Octadecan-1-ol · stearyl · Stenol · STEARYLIC ALCOHOL · 1-Hydroxyoctadecane
Identifiers & Physical Properties
| CAS No. | 112-92-5 |
|---|---|
| Molecular formula | C18H38O |
| Average molar mass | 270.5 g/mol |
| Monoisotopic mass | 270.29226583 g/mol |
| SMILES | CCCCCCCCCCCCCCCCCCO |
| InChIKey | GLDOVTGHNKAZLK-UHFFFAOYSA-N |
| PubChem CID | 8221 |
| ChEBI | CHEBI:32154 |
| EC No. | 204-017-6 |
| DTXSID | DTXSID8026935 |
Chemical & Physical Properties
| XLogP | 8.4 |
|---|---|
| Topological polar surface area | 20.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 16 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 145 |
| LogP (partition coefficient) | 8.22 |
| Odor | Faintwh. unctuous flakes or gran., faint odor, bland taste |
| Taste | Bland |
| Density | 0.8124 at 59 °C/4 °CRelative density (water = 1): 0.81 (liquid)0.8124 @ 59°C0.812 g/mL at 25 °C (lit.) |
| Color/Form | Leaflets from ethanolUnctuous white flakes or granules |
| Solubility | Soluble in alcohol, ether, benzene, acetoneSoluble in chloroformslightly soluble in acetone, benzeneIn water, 1.1X10-3 mg/L at 25 °C1.1e-06 mg/mL at 25 °CSolubility in water: nonemethanol: soluble10mg/mL, clear, colorlessinsoluble |
| Flash point | 200 °C392 °F (200 °C) (Closed cup)170 °C185°C |
| Boiling point | 210.5 °C at 15 mm Hg336 °C202 °C @760 [mm Hg]210 °C15 mm Hg |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes. |
| Melting point | 59.5 °CHeat of fusion at melting point = 7.4057X10+7 J/kmol (for the gamma phase, no selection of the alpha phase, crystal I can be made).59.8 °C58 °C56-59 °C (lit.) |
| Vapor pressure | 0.0000027 [mmHg]Vapor pressure = 0.1 mm Hg @ 125 °CVapor pressure, Pa at 150 °C: 1330.0000026 [mm Hg] @25 °C<0.01 mm Hg ( 38 °C) |
| Physical Description | Large CrystalsLiquidOther SolidDry PowderWhite solid[Hawley]COLOURLESS-TO-WHITE SLIGHTLY WAXY FLAKES OR LEAFLETS. |
| Bulk density | 300kg/m3 |
| Vapor density | 9.3 (vs air) |
| Refractive index | 1.4356 (estimate) |
| FLAVIS Number | 02.196 | Octadecan-1-ol |
| Storage conditions | 2-8°C |
| Physical state | Flakes |
| pKa (acidity coefficient) | 15.20±0.10(Predicted) |
| Specific gravity | 0.812 |
| Color | White |
| Explosive limits | ~8% |
| Viscosity | 4.006mm2/s |
| Merck | 14,8805 |
| BRN | 1362907 |
| Henry's law constant | 1.2×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielectric constant | 3.4(58℃) |
| Cosmetics Ingredients Functions | SURFACTANT - CLEANSINGSURFACTANT - EMULSIFYINGFRAGRANCEOPACIFYINGREFATTINGEMULSION STABILISINGSKIN CONDITIONING - EMOLLIENTVISCOSITY CONTROLLINGSURFACTANT - FOAM BOOSTING |
| Cosmetic Ingredient Review (CIR) | 1-Octadecanol (112-92-5) |
| InChI | 1S/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3 |
| InChIKey | GLDOVTGHNKAZLK-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCCCCCCCCO |
| LogP (partition coefficient) | 7.4 |
| CAS DataBase Reference | 112-92-5(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | STEARYL ALCOHOL |
| FDA 21 CFR | 175.300176.180176.200176.210177.1200177.1390178.3480 |
| EWG's Food Scores | 1-3 |
| FDA UNII | 2KR89I4H1Y |
| NIST Chemistry Reference | 1-Octadecanol(112-92-5) |
| EPA Substance Registry System | 1-Octadecanol (112-92-5) |
| Cosmetics Info | Stearyl Alcohol |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P305+P351+P338 |
| Safety statements (S) | 24/25 |
| UN transport number | UN 1986 |
| Water hazard class (WGK) | - |
| RTECS number | RG2010000 |
| Autoignition temperature | 842 °F |
| TSCA inventory status | TSCA listed |
| Customs code | 29051700 |
| Storage class | 11 - Combustible Solids |
| Hazardous substances data | 112-92-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 61.7% (1186 of 1921) of all reports.WarningH319 (23.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H400 (15%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H411 (15.4%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]H412 (15%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]P264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 1921 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1186 of 1921 reports by companies.There are 10 notifications provided by 735 of 1921 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: 1-OctadecanolCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)1-Octadecanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Octadecanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 06-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15937Status: Active Update: 30-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/62451-Octadecanol: Does not have an individual approval but may be used under an appropriate group standardOctadecanol: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 1-Octadecanol: Human health tier I assessment |
| Fire hazards | Combustible. |
| Fire potential | Flammable when exposed to heat or flame... |
| Hazards summary | Higher alcohols are not highly toxic in the industrial settingCan cause liver injury, somnolence, and respiratory depression in experimental animals[HSDB] Causes somnolence in lethal-dose feeding studies of rats[RTECS] No listed effects of short-term or long-term exposureHealth effects of exposure to the substance have been investigated extensively but none have been found. [ICSC] An irritant[MSDSonline] |
| FDA requirements | Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: Stearyl alcohol is included in skin protectant drug products. |
| EPA Safer Chemical | Chemical: 1-OctadecanolGreen circle - The chemical has been verified to be of low concern based on experimental and modeled data. |
| Chemical Dangers | Reacts with strong acids and strong oxidants. |
| NFPA Hazard Classification | 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.0 - Materials that will not burn under typical fire conditions, including intrinsically noncombustible materials such as concrete, stone, and sand.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Eye Irrit. 2A (23.1%)Aquatic Acute 1 (15%)Aquatic Chronic 2 (15.4%)Aquatic Chronic 3 (15%) |
| Explosive Limits and Potential | Explosive limits , vol% in air: 1-8 |
| Hazardous Reactivities and Incompatibilities | Reacts with strong acids and strong oxidants. |
| Fire fighting | In case of fire in the surroundings, use appropriate extinguishing media. |
| First aid measures | First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| Safe storage | Separated from strong oxidants and strong acids. |
| Fire fighting procedures | To fight fire use foam, carbon dioxide, dry chemical. |
| Cleanup methods | Sweep spilled substance into containers. Carefully collect remainder, then remove to safe place. |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Spillage disposal | Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Protective Action Criteria (PAC) | 60 [mg/m3]660 [mg/m3]4000 [mg/m3] |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.8X10+5(SRC), determined from a water solubility of 1.1X10-3 mg/L(2) and a regression-derived equation(3), indicates that 1-octadecanol is expected to be immobile in soil(SRC). Volatilization of 1-octadecanol from moist soil surfaces may be expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.41X10-4 atm-cu m/mole(SRC), derived from a vapor pressure of 2.7X10-6 mm Hg at 25 °C(4), and its water solubility(2). However, adsorption to soil is expected to attenuate volatilization(SRC). 1-Octadecanol is not expected to volatilize from dry soil surfaces(SRC) based upon it's vapor pressure(4). Biodegradation of 1-octadecanol may be an important fate process in soil based on a mixed shake flask culture study(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.8X10+5(SRC), determined from a water solubility of 1.1X10-3 mg/L(2) and a regression-derived equation(3), indicates that 1-octadecanol is expected to adsorb to suspended solids and sediments(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 8.4X10-4 atm-cu m/mole(SRC), calculated from its water solubility(2) and vapor pressure, 2.7X10-6 mm Hg(4), values. Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 2.8 hours and 7 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 140 days if adsorption is considered (5). According to a classification scheme(6), an estimated BCF value of 2.8X10+4(3), from its water solubility(2), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). A percent theoretical oxygen demand value of 0.3 in 24 hrs using a Warburg test(7) suggests that biodegradation may not be an important fate process in water(7).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-octadecanol, which has a vapor pressure of 2.7X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1-octadecanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be about 14 hours(3), calculated from its rate constant of 2.67X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Particulate-phase 1-octadecanol may be removed from the air by wet or dry deposition(SRC). |
| Food survey values | 1-Octadecanol has been qualitatively detected as a volatile component of fried bacon(1) and raw beef(2). |
| Adverse effects | Neurotoxin - Acute solvent syndromeOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Toxicity summary | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org |
| Plant Concentrations | 1-Octadecanol emission rates from green leaf composite samples and dead leaves were 28 ug/g and 30 ug/g, respectively(1). |
| Effluent Concentrations | 1-Octadecanol has been detected in industrial wastewater from the organics and plastics industry (184 ng/ul extract) and from textile mills (94 ng/ul extract)(1). 1-Octadecanol has been detected in wastewater from a specialty chemicals manufacturing plant at concentrations of 1-4 ppm(2). Emission rates in wood smoke for 1-octadecanol in mg/g of organic carbon were found to be 0.059 for red oak(3), 0.063 for yellow poplar(4), and 0.062 for mockernut hickory(4). 1-Octadecanol emission rates from road dust samples was 4.3 ug/g(5). |
| Soil Adsorption/Mobility | The Koc of 1-octadecanol is estimated as 1.8X10+5(SRC), using a water solubility of 1.1X10-3 mg/L at 25 °C(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-octadecanol is immobile in soil(SRC). |
| Natural Pollution Sources | 1-Octadecanol emission rates from green leaf composite samples and dead leaves were 28 ug/g and 30 ug/g, respectively(1). |
| Atmospheric Concentrations | URBAN/SUBURBAN: 1-Octadecanol was found in California at atmospheric concentrations of 2.5 ng/cu m, and 2.9 ng/cu m in Bakersfield and Fresno, respectively(1).RURAL/REMOTE: 1-Octadecanol was found in California at an atmospheric concentrations of 0.4 ng/cu m in the Kern Wildlife Refuge(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ The results of single-insult clinical patch testing indicate a very low order of skin irritation potential for stearyl alcohol with a sensitization rate of 19 of 3740 (0.51%) individuals./HUMAN EXPOSURE STUDIES/ A 24-hour single insult occlusive patch test with 100% stearyl alcohol produced mild irritation in 1 out of 80 human subjects./HUMAN EXPOSURE STUDIES/ Of 51 patients allergic to wool wax alcohols, 4 reacted to 20% stearyl alcohol in vaseline. Combined scores at 24, 48, and 72 hours showed reactions graded as ++ (erytheme and papeln or infiltrate) or +++ ( erytheme, infiltrate or rather papulovesicle). The authors concluded that free fatty alcohols play a major part in allergic reactions to wool wax. Stearyl alcohol is less allergic than 1-dodecanol or oleyl alcohol./HUMAN EXPOSURE STUDIES/ Patch test with 30% stearyl alcohol in petrolatum was assessed after 48 and 96 hours. The test was conducted during several one-year periods on large numbers of human subjects. In 1975-1976 one-year study out of 172 tested 2 showed allergic reaction (1.2%). In 1976-1977 one-year study out of 446 tested 1 showed allergic reaction (0.22%). In 1978-1979 one year study out of 824 tested 6 showed allergic reaction (0.73%). In 1979-1980 one year study out of 634 tested 6 showed allergic reaction (0.95%). ... According to the authors, the positive results above indicate a very mild sensitization potential./CASE REPORTS/ ... A woman who experienced oozing dermatitis on 2 separate occasions 2 yr apart after contact with green canvas being sewn into tents. Patch testing showed sensitivity to stearyl alcohol. |
| Artificial Pollution Sources | 1-Octadecanol's production and use as a substitute for cetyl alcohol in pharmaceutical dispensing, in cosmetic creams, for emulsions, textile oils and finishes, as an antifoam agent, lubricant, chemical raw material(1), in perfumery, cosmetics, as an intermediate, surface active agent, and in resins(2) may result in its release to the environment through various waste streams. |
| Environmental Biodegradation | AEROBIC: Using the Warburg test which employs activated sludge, 1-octadecanol gave a theoretical oxygen demand of 0.3, 0.5, and 0.3 percent in 6, 12, and 24 hours(1). However, using an acclimated mixed shake flask culture with incremental substrate addition of 1-octadecanol, biomass yield reached 54.5 percent after seven days(2). Given sufficient time in contact with adapted microbial species under conditions otherwise non-limiting, the complete disappearance of 1-octadecanol as identifiable molecular species will occur(2). |
| Water hazard class (WGK) | - |
| TSCA inventory status | TSCA listed |
| RTECS number | RG2010000 |
| UN transport number | UN 1986 |
| Customs code | 29051700 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Safety statements (S) | 24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Active |
| Autoignition temperature | 842 °F |
| GHS precautionary statements | P261-P305+P351+P338 |
| Hazardous substances data | 112-92-5(Hazardous Substances Data) |
Applications & Uses
Uses
1-Octadecanol is used as a surfactant in cosmetics. It effectively moisturizes hands and face with pheohydrane, which is a complex derived from the microalgae Chlorella Vulgaris and hydrolyzed algin found in sea water. 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.
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.
Preparation & Synthesis
Preparation
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.