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1-オクタデカノール
1-オクタデカノール · ロロール28 · オクタデカン-1-オール · オクタデシルアルコール · ステアロール · ステアリルアルコール · ステラフィン · n-オクタデシルアルコール
識別子と物理属性
| CAS No. | 112-92-5 |
|---|---|
| 分子式 | C18H38O |
| 平均分子量 | 270.5 g/mol |
| 単同位体質量 | 270.29226583 g/mol |
| SMILES | CCCCCCCCCCCCCCCCCCO |
| InChIKey | GLDOVTGHNKAZLK-UHFFFAOYSA-N |
| PubChem CID | 8221 |
| ChEBI | CHEBI:32154 |
| EC No. | 204-017-6 |
| DTXSID | DTXSID8026935 |
| 現地名 | 1-オクタデカノール |
化学・物理的性質
| XLogP | 8.4 |
|---|---|
| 極性表面積 | 20.2 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 1 |
| 回転可能結合数 | 16 |
| 重原子数 | 19 |
| 形式電荷 | 0 |
| 複雑度 | 145 |
| LogP（分配係数） | 8.22 |
| 臭い | Faintwh. unctuous flakes or gran., faint odor, bland taste |
| 味 | Bland |
| 密度 | 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 |
| 溶解度 | 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: noneメタノール：可溶10mg/mL 無色透明不溶性 |
| 引火点 | 200 °C392 °F (200 °C) (Closed cup)170 °C185°C |
| 沸点 | 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. |
| 融点 | 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.) |
| 蒸気圧 | 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. |
| 蒸気密度 | 9.3 (vs air) |
| 屈折率 | 1.4356 (estimate) |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | フレーク |
| pKa（酸解離定数） | 15.20±0.10(Predicted) |
| 比重 | 0.812 |
| 色 | 白い |
| 爆発限界 | ~8% |
| Merck | 14,8805 |
| BRN | 1362907 |
| ヘンリー定数 | 1.2×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 誘電率 | 3.4(58℃) |
| 化粧品成分の機能 | 界面活性剤 - 洗浄界面活性剤 - 乳化剤香料不透明剤脂質補給剤乳化安定剤皮膚コンディショニング剤 - 保湿剤粘度制御界面活性剤 - 泡立ち促進剤 |
| 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（分配係数） | 7.4 |
| CAS データベース | 112-92-5(CAS DataBase Reference) |
| NISTの化学物質情報 | 1-Octadecanol(112-92-5) |
| EPAの化学物質情報 | 1-Octadecanol (112-92-5) |
化学的特性
Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It 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.
安全性と法規制
| GHS 分類 | 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. |
|---|---|
| 規制情報 | 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 |
| その他の安全情報 | IMAP assessments - 1-Octadecanol: Human health tier I assessment |
| 火災危険 | Combustible. |
| 火災の可能性 | Flammable when exposed to heat or flame... |
| 有害性の概要 | 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 要件 | 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. |
| 消火 | In case of fire in the surroundings, use appropriate extinguishing media. |
| 応急処置措置 | First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. |
| 安全保管 | Separated from strong oxidants and strong acids. |
| 消火手順 | To fight fire use foam, carbon dioxide, dry chemical. |
| 清掃方法 | Sweep spilled substance into containers. Carefully collect remainder, then remove to safe place. |
| 処分方法 | 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. |
| 漏出処分 | 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] |
| 環境中動態 | 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). |
| 食品調査値 | 1-Octadecanol has been qualitatively detected as a volatile component of fried bacon(1) and raw beef(2). |
| 有害作用 | 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. |
| 毒性の概要 | 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). |
| 水環境危害等級（WGK） | - |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | RG2010000 |
| 輸送番号（UN） | UN 1986 |
| 毒性 | LD50 orally in Rabbit: > 2000 mg/kg |
| 税関コード | 29051700 |
| 化審法 | (2)-217 |
| 安全措置（S） | 24/25 |
| 自然発火温度 | 842 °F |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 112-92-5(Hazardous Substances Data) |
用途
解説
ステアリルアルコール【stearyl alcohol】化学式CH3(CH2)17OH。マッコウ鯨油の成分である高級脂肪族飽和一価アルコール。ほかに，カモの尾腺，モンタン蠟，綿蠟中にも存在する。無臭，白色の蠟状固体で，純粋なものは薄い板状晶。融点58.0℃，沸点345℃，比重0.8392，比旋光度nD20＝1.4529。水に溶けやすい。おもにマッコウ鯨油の加水分解で製造され，合成洗剤，塩化ビニル可塑剤の原料，また化粧品，医薬品に供されていたが，クジラ資源の減少により工業用原料としての意味は少なくなり，石油化学を主とする合成高級脂肪族アルコールに代替されている。
用途
硫酸エステルとして表面活性剤に使用する。
使用
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.
一般的な説明
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.
製法・合成法
製造方法
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.
調製方法
Historically, stearyl alcohol was prepared from sperm whale oil but is now largely prepared synthetically by reduction of ethyl stearate with lithium aluminum hydride.
純化方法
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.]