HuagongsheHuagongshe Chemistry Print Report · For research reference only
Oleyl Alcohol
oleyl · Satol · (Z)-Octadec-9-en-1-ol · 9-Octadecen-1-ol, (Z)- · 9-OCTADECEN-1-OL · OLEIC ALCOHOL · (Z)-9-Octadecen-1-ol · Oleyl alcoho
Identifiers & Physical Properties
| CAS No. | 143-28-2 |
|---|---|
| Molecular formula | C18H36O |
| Average molar mass | 268.5 g/mol |
| Monoisotopic mass | 268.27661577 g/mol |
| SMILES | CCCCCCCC/C=C\CCCCCCCCO |
| InChIKey | ALSTYHKOOCGGFT-KTKRTIGZSA-N |
| PubChem CID | 5284499 |
| ChEMBL | CHEMBL2105350 |
| ChEBI | CHEBI:73504 |
| EC No. | 205-597-3 |
| DTXSID | DTXSID0022010 |
Chemical & Physical Properties
| XLogP | 7.4 |
|---|---|
| Topological polar surface area | 20.2 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 15 |
| Heavy atoms | 19 |
| Formal charge | 0 |
| Complexity | 175 |
| Chemical classes | Other Uses -> Emulsifiers/Surfactants |
| Lipids | Fatty Acyls [FA] -> Fatty alcohols [FA05] |
| Cosmetics | Cosmetic ingredients (Oleyl Alcohol) -> CIR (Cosmetic Ingredient Review)EmulsifyingViscosity controllingOpacifyingEmollient |
| SpringerMaterials Properties | Density |
| Fragrances | Fragrance Ingredient ((Z)-Octadec-9-enol) -> IFRA transparency List |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 0.8489 at 20 °C/4 °C0.842-0.854 (20 °C)0.849 g/mL at 25 °C (lit.) |
| Color/Form | Oily liquid, usually pale yellowClear, viscous liquid at room temperature |
| Solubility | Insol in watersol in alcohol, etherSlightly soluble in carbon tetrachlorideInsoluble in watersoluble in non-polar organic solventsSoluble (in ethanol)Soluble in ethanol (95%), and etherpractically insoluble in water.Miscible with alcohol and ether. Slightly miscible with carbon tetrachloride. Immiscible with water. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Boiling point | 195 °C at 8 mm Hg182-184 °C at 1.5 mm Hg (Distilling range at 760 mm Hg: 305-370 °C)BP: 205 to 210 °C at 15 mm Hg207.00 °C. @ 13.00 mm Hg207 °C (13 mm Hg)207 °C/13 mmHg (lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Melting point | 0-5.0 °C (lit.) |
| Vapor pressure | 10.64 hPa (195 °C) |
| FEMA | 4363 | CIS-9-OCTADECENOL |
| Refractive index | n20/D 1.46(lit.) |
| Flash point | >230 °F |
| Storage conditions | -20°C |
| pKa (acidity coefficient) | 15.20±0.10(Predicted) |
| Physical state | Viscous Liquid |
| Color | Clear almost colorless to yellow |
| Odor | fatty animal |
| Odor type | fatty |
| Merck | 14,6831 |
| JECFA Number | 1637 |
| BRN | 1723962 |
| Henry's law constant | 2.1×10-2 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability | Stable. Combustible. Incompatible with strong acids, strong oxidizing agents. |
| Cosmetics Ingredients Functions | EMULSION STABILISINGSKIN CONDITIONING - EMOLLIENTFRAGRANCESOLVENTPERFUMINGVISCOSITY CONTROLLING |
| Cosmetic Ingredient Review (CIR) | Oleyl alcohol (143-28-2) |
| InChI | 1S/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9- |
| InChIKey | ALSTYHKOOCGGFT-KTKRTIGZSA-N |
| SMILES | CCCCCCCC\C=C/CCCCCCCCO |
| LogP (partition coefficient) | 7.07 at 25℃ |
| CAS DataBase Reference | 143-28-2(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | OLEYL ALCOHOL |
| FDA 21 CFR | 176.170176.180176.210177.1210 |
| EWG's Food Scores | 1 |
| FDA UNII | 172F2WN8DV |
| NIST Chemistry Reference | Oleyl Alcohol(143-28-2) |
| EPA Substance Registry System | 9-Octadecen-1-ol, (9Z)- (143-28-2) |
| Cosmetics Info | Oleyl Alcohol |
| UNSPSC Code | 41116107 |
| NACRES | NA.25 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H320 |
| GHS precautionary statements | P280g-P302+P352a-P321-P332+P313-P362+P364-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi |
| Risk statements (R) | 38 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | - |
| RTECS number | RG4120000 |
| TSCA inventory status | TSCA listed |
| Customs code | 29052990 |
| Storage class | 10 - Combustible liquids |
| Hazardous substances data | 143-28-2(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 92.6% (561 of 606) of all reports.Not ClassifiedAggregated GHS information provided per 606 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatory information | Chemical: 9-Octadecen-1-ol, (Z)-9-Octadecen-1-ol, (9Z)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecen-1-ol, (9Z)- 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: 18-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/131229-Octadecen-1-ol, (9Z)-: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - 9-Octadecen-1-ol, (Z)-: Human health tier I assessment |
| Hazards summary | May cause skin sensitization after prolonged contact, based on human patch test studies[Reference #1] A skin irritant[eChemPortal: ERMA] An irritant[MSDSonline] |
| EPA Safer Chemical | Chemical: cis-Oleyl alcohol |
| FIFRA requirements | Residues of oleyl alcohol are exempted from the requirement of a tolerance when used as a cosolvent (limit: 15%) in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. |
| Hazard Classes and Categories | Not Classified |
| 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. |
| Allowable Tolerances | Residues of oleyl alcohol are exempted from the requirement of a tolerance when used as a cosolvent (limit: 15%) in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. |
| Interactions | Hydrophilic and lipophilic formulations of naproxen were prepared, and the influence of the excipients in the formulations on the ulcerogenic potential of naproxen was investigated in rats. Doses of naproxen suspensions ranging from 3.125-100 mg/kg were administered to fasted rats and excised stomachs were examined macroscopically for the incidence and severity of lesions. Results were expressed as the 50% ulceration dose. Results of the study showed that a lipophilic formulation containing oleyl alcohol provided the greatest gastric protection.Long-chain fatty acids are important nutrients, but obesity is the most common nutritional disorder in humans. In this study /the authors/ investigated the effect of oleyl alcohol on the intestinal long-chain fatty acid absorption in rats. ...[14C]Oleic acid and oleyl alcohol /was administered/ as lipid emulsion intraduodenally in unanesthetized lymph-cannulated rats and measured the lymphatic output of oleic acid. ... Lipid emulsion /was then administered/ with a stomach tube and ... the luminal and mucosal oleic acid residues /were measured/. Furthermore, rats were fed oleyl alcohol as a dietary component for 20 days, and fecal lipid and the weight of adipose tissues were measured. In lymph-cannulated rats, triglyceride and [14C]oleic acid output in the lymph were significantly lower in the presence of oleyl alcohol when compared with the absence of oleyl alcohol in a dose-dependent manner. The radioactivity remaining in the intestinal lumen was more strongly detected in rats that had been orally administered oleyl alcohol than in the controls. The feces of rats fed an oleyl-alcohol-added diet contained much higher amounts of lipids, and the weights of their adipose tissues were significantly lower than in the control group. These results suggest that oleyl alcohol inhibits the rat gastrointestinal absorption of long-chain fatty acids in vivo.Studies of the influence of fatty acids, which were the component of intestinal mucosal lipids, on the permeability of several drugs across bilayer lipid membranes generated from egg phosphatidylcholine and intestinal lipid have been pursued. The permeability coefficients of p-aminobenzoic acid, salicylic acid and p-aminosalicylic acid (anionic-charged drug) increased when fatty acids such as lauric, stearic, oleic, linoleic and linolenic acid were incorporated into the bilayer lipid membranes generated from phosphatidylcholine. In the presence of methyl linoleate and oleyl alcohol, no enhancing effect on p-aminobenzoic acid transfer was obtained. The effect of fatty acids was more marked at pH 6.5 than at pH 4.5. In contrast, upon the addition of fatty acids to intestinal lipid membranes which originally contained fatty acids, the permeability coefficient of p-aminobenzoic acid tended to decrease, though the permeability through intestinal lipid membranes was larger than that of phosphatidylcholine membranes. The permeability of p-aminobenzoic acid across bilayer lipid membranes from intestinal phospholipids was significantly decreased to about equal that of phosphatidylcholine membranes, and reverted to the value of intestinal lipid membranes when fatty acids were added to intestinal phospholipids. It seemed reasonable to assume that free fatty acids in the intestinal neutral lipid fraction could contribute to the increase in the permeability of p-aminobenzoic acid. On the basis of above results, possible mechanisms for good absorbability of weakly acidic drugs from the intestine are discussed. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.3X10+4(SRC), determined from a structure estimation method(2), indicates that oleyl alcohol is expected to be immobile in soil(SRC). Volatilization of oleyl alcohol from moist soil surfaces may be expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Oleyl alcohol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.3X10-5 mm Hg(SRC), determined from a fragment constant method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Based on one microbial study, oleyl alcohol was found to be utilized as the sole carbon source by bacteria, yeast, and fungi(5). Although this study provides little insight into the rate of biodegradation in soil, it suggests that biodegradation in soil may be important(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.23X10+4(SRC), determined from a structure estimation method(2), indicates that oleyl alcohol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8 hours and 7.4 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 163 days if adsorption is considered(5). Alcohols are generally resistant to hydrolysis(6). According to a classification scheme(7), an estimated BCF of 420(SRC), from an estimated log Kow of 7.5(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Based on one microbial study, oleyl alcohol was found to be utilized as the sole carbon source by bacteria, yeast, and fungi(10). Although this study provides little insight into the rate of biodegradation in water, it suggests that biodegradation in water may be important(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), oleyl alcohol, which has an estimated vapor pressure of 9.3X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase oleyl alcohol 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 4.5 hrs(SRC), calculated from its rate constant of 7.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase oleyl alchol may be removed from the air by wet or dry deposition(SRC). The rate constant for the vapor-phase reaction of oleyl alcohol with ozone has been estimated as 1.3X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). This corresponds to an atmospheric half-life of about 2.1 hrs at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). |
| Food survey values | Oleyl alcohol is found in fish oils(1). |
| Adverse effects | Skin Sensitizer - An agent that can induce an allergic reaction in the skin. |
| 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 |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of oleyl alcohol can be estimated to be 1.3X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that oleyl alcohol is expected to be immobile in soil. |
| Natural Pollution Sources | Oleyl alcohol occurs in fish and marine mammal oils(1). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ ... 34 patients (23.2%), showed a positive patch test to fatty alcohols, 33 of them to oleyl alcohol./SIGNS AND SYMPTOMS/ ... Subjects (51) allergic to wool wax alcohols were tested. ... Lauryl alcohol reacted in 9 cases and oleyl alcohol in 7 cases with reaction grade 2+ and 3+./CASE REPORTS/ ... patch tests using the components of the cutting fluid gave positive reactions to 2-amino-ethanol (141435) and oleyl-alcohol (143282)./CASE REPORTS/ The aim of this study was to investigate the frequency of sensitization to fatty alcohols in a group of patients with suspected cosmetic or medicament contact dermatitis. From May 1992 to September 1995, we patch tested a series of 5 fatty alcohols on 146 patients. These included 108 females and 38 males aged from 13 to 72 years (mean age 42.5). These patients, who had previously been tested with the GIRDCA standard series, were selected because their clinical lesions or histories indicated topical preparations as the possible source of their contact dermatitis. High-grade fatty alcohols (> 99% pure) were used for testing. 34 patients (23.2%), 25 female and 9 male aged from 14 to 72 years, showed a positive patch test to fatty alcohols, 33 of them to oleyl alcohol. A total of 39 reactions were detected with 5 patients showing more than 1 positive reaction. Our results show that sensitization to oleyl alcohol is not rare in patients with contact dermatitis due to cosmetics or topical medicaments. |
| Fish/Seafood Concentrations | Oleyl alcohol was qualitatively detected in adult lake trout (Salvelinus namaycush) collected in 1977 from Lake Michigan in Charlevoix, MI and it was qualitatively detected in walleye (Stizostedion v. vitreum) from Lake St. Clair Anchor Bay, MI and Lake Erie Dunkirk, PA(1). |
| Artificial Pollution Sources | Oleyl alcohol's use as a chemical intermediate, automotive lubricant, defoamer, cosolvent and plasticizer for printing ink, and as a cosmetic emollient(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Oleyl alcohol (10 g) was found to be utilized as the sole carbon source by bacteria (Pseudomonas) in 10 days at 30 °C and pH 6.8-7.0. In the same study, 10 g oleyl alcohol was utilized as the sole carbon source by 3 yeasts (Candida, Pichia, and an unknown) in 10 days at 30 °C and pH 6.8-7.0. It was also utilized by 3 fungi (Aspergillus, Penicillium, and an unknown) in 20 days at 20-25 °C and pH 5.5-5.6(1).ANAEROBIC: Oleyl alcohol was reported to achieve 88.6 percent ultimate degradation in 84 days at 35 °C and pH of 6.5 to 7.3 using anaerobic sludge(1). |
| Environmental Bioconcentration | An estimated BCF of 420 was calculated for oleyl alcohol(SRC), using an estimated log Kow of 7.5(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC). |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | - |
| TSCA inventory status | TSCA listed |
| RTECS number | RG4120000 |
| Customs code | 29052990 |
| Toxicity | LD50 orally in Rabbit: > 5000 mg/kg |
| Risk statements (R) | 38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315-H320 |
| REACH registrations | Active |
| GHS precautionary statements | P280g-P302+P352a-P321-P332+P313-P362+P364-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313 |
| Hazardous substances data | 143-28-2(Hazardous Substances Data) |
Applications & Uses
Uses
Oleyl alcohol is used in softening and lubrication of textile fabrics, and in the production of carbon paper, stencil paper, and printing ink. It finds application in cosmetic products viz skin creams and lotions as a thickner, hair conditioners and hair coating shampoos. It is utilized as an antifoaming agent and cutting lubricant, as the precursor for the preparation of its sulfuric ester derivatives, which are used in detergents and wetting agents. It plays a vital role in various formulations for drug delivery.
Uses
Chiefly in the manufacture of its sulfuric esters which are detergents and wetting agents, as an antifoam agent; metal cutting lubricant; in carbon paper, stencil paper, printing ink; as a plasticizer; for softening and lubricating textile fabrics; carrier for medicaments.
Uses
oleyl alcohol is an emollient, solvent, viscosity-increasing agent, and carrier employed in a wide variety of cosmetic formulations including makeup, skin care, and hand and body preparations. oleyl alcohol is an unsaturated fatty alcohol found in fish oils and can also be produced synthetically. According to some sources, it is comedogenic and has a mild irritancy potential.
General Description
Oleyl alcohol has been reported as an effective solvent for oil/water-type tacrolimus (FK506) cream formulation, useful for atopic dermatitis treatment. It was reported as diluting agent for Alamine 336. Palm oil esters derived from oleyl alcohol, have potential applications in the cosmetic and pharmaceutical industries due to the excellent wetting behavior of the esters without the oily feel.