Stearyl Alcohol

HCID 8221CAS 112-92-5

기본 정보

표준 SMILES
CCCCCCCCCCCCCCCCCCO
InChIKey
GLDOVTGHNKAZLK-UHFFFAOYSA-N
분자식
C18H38O
평균 분자량
270.5 g/mol
단동위원소 질량
270.29226583

이름 및 식별자

우선 이름
Stearyl Alcohol
IUPAC
octadecan-1-ol
현지명
스테아릴 알코올
영어명
1-Octadecanol
분자식
C18H38O
분자량
270.49

이름 및 동의어

Stearyl alcohol1-OCTADECANOLOctadecan-1-ol112-92-51-HydroxyoctadecaneOctadecyl alcoholn-OctadecanolStearolStearic alcoholn-Octadecyl alcoholAtalco Sn-1-Octadecanol
이름 더 보기
1-히드록시옥타데칸N-옥타데실알코올N-옥타데칸올옥타데실알코올옥타데칸올1-옥타데칸올스테아릴알코올스테아릴알콜스테아릴알코올1-하이드록시옥타에칸옥사데실 알코올Ceteareth-20OCTADECANOLstearylSTEARYLIC ALCOHOL
SteraffineAlfol 18Sipol SAlcohol stearylicusPolaaxStenolCrodacol-SSiponol S

데이터베이스 식별자

CAS
112-92-5、26762-44-7、68911-61-5
PubChem CID
8221
DTXSID
DTXSID8026935
ChEBI
CHEBI:32154
UNII
2KR89I4H1Y
EC Number
204-017-6
Nikkaji
J10.101J

물성

구조 계산 물성

XLogP
8.4
극성 표면적
20.2 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
1
회전 가능 결합 수
16
무거운 원자 수
19

실험 및 물리화학적 성질

LogP8.22
OdorFaint
TasteBland
Density · 3건

0.8124 at 59 °C/4 °C

Relative density (water = 1): 0.81 (liquid)

0.8124 @ 59°C

Color/Form · 2건

Leaflets from ethanol

Unctuous white flakes or granules

Solubility · 5건

Soluble in alcohol, ether, benzene, acetone

Soluble in chloroform; slightly soluble in acetone, benzene

In water, 1.1X10-3 mg/L at 25 °C

1.1e-06 mg/mL at 25 °C

Solubility in water: none

물리화학적 성질

녹는점
56 · 56-59 °C (lit.)
끓는 점
210 °C15 · 210 °C15 mm Hg
밀도
0.812 g/mL · 0.812 g/mL at 25 °C (lit.)
증기 밀도
9.3 · 9.3 (vs air)
증기압
0.01 mm · <0.01 mm Hg ( 38 °C)
굴절률
1.4356 · 1.4356 (estimate)
화학적 성질 · 1건

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.

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 61.7% (1186 of 1921) of all reports.

Warning

H319 (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.

유해성 정보

Regulatory Information · 6건

Chemical: 1-Octadecanol

Commission 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/15937;Status: Active Update: 30-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/6245

1-Octadecanol: Does not have an individual approval but may be used under an appropriate group standard

Octadecanol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 1-Octadecanol: Human health tier I assessment
Fire HazardsCombustible.
Fire PotentialFlammable when exposed to heat or flame...
Hazards Summary · 1건

Higher alcohols are not highly toxic in the industrial setting; Can 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 exposure; Health effects of exposure to the substance have been investigated extensively but none have been found. [ICSC] An irritant; [MSDSonline]

FDA Requirements · 1건

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.

안전 및 보호

Fire FightingIn case of fire in the surroundings, use appropriate extinguishing media.
First Aid Measures · 2건

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

Safe StorageSeparated from strong oxidants and strong acids.
Fire Fighting ProceduresTo fight fire use foam, carbon dioxide, dry chemical.
Cleanup MethodsSweep spilled substance into containers. Carefully collect remainder, then remove to safe place.
Disposal Methods · 1건

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

독성 정보

Environmental Fate · 3건

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 Values1-Octadecanol has been qualitatively detected as a volatile component of fried bacon(1) and raw beef(2).
Adverse EffectsNeurotoxin - Acute solvent syndrome;Occupational 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 SummarySafe 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 Concentrations1-Octadecanol emission rates from green leaf composite samples and dead leaves were 28 ug/g and 30 ug/g, respectively(1).
Effluent Concentrations · 1건

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).

규제 정보

Regulatory Information · 6건

Chemical: 1-Octadecanol

Commission 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/15937;Status: Active Update: 30-05-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/6245

1-Octadecanol: Does not have an individual approval but may be used under an appropriate group standard

Octadecanol: Does not have an individual approval but may be used under an appropriate group standard

FDA Requirements · 1건

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.

안전 데이터

wgk
-
tsca
TSCA listed
rtecs
RG2010000
ridadr
UN 1986
독성
LD50 orally in Rabbit: > 2000 mg/kg
HS 번호
29051700

화학 및 산업

약리 정보

BionecessityStearyl alcohol is found naturally in various mammalian tissues. It is used in the biosynthesis of lipids and other naturally occurring cellular constituents and enters metabolic pathways for energy production.
Mechanism of Action · 4건

... Ethanol, 1-propanol, 1-butanol, 1-pentanol and 1-octanol had essentially the same effects on the mitochondrial ultrastructure: a mixed population of small and enlarged mitochondria with poorly developed cristae; 1-dodecanol induced ultrastructural changes of mitochondria of two distinct types: a mixed population of small and enlarged mitochondria with poorly developed cristae in some hepatocytes and remarkably enlarged mitochondria with well-developed cristate in others; and 1-octadecanol induced remarkably enlarged mitochondria in all hepatocytes.

... The reactivity of the fatty alcohols with cetrimide decreased with increasing chain length although branching on the tetradecanol and hexadecanol resulted in a higher reactivity. Adding 1-octadecanol to 1-hexadecanol resulted in an increased reactivity rising to a maximum for mixtures containing 20-40% w/w 1-octadecanol.

... Peak inhibition was recorded with saturated primary alcohols (64 microM) varying in chain length from 16 to 19 carbon atoms. The unsaturated alcohols (oleyl, linoleyl, and linolenyl) and the secondary alcohol (pentadecan-2-ol) were considerably less effective growth inhibitors. Stearic and palmitic acids were also ineffective.

After incubation of stationary phase Leishmania donovani with [1-14C]octadecanol, about 70% of the precursor was taken up within 3 hr. Wax esters and acyl moieties of glycerolipids contained most of the 14C-activity from 3 to 6 hr, because octadecanol was partly oxidized to stearate. Ether moieties were only weakly labeled. After 40 hr, 1-0-alkyl and 1-0-alk-1'-enyl diacylglycerols as well as 1-0-alkyl and 1-0-alk-1'-enyl-2-acyl-sn-glycero-3-phosphoethanolamines contained nearly all of the radioactivity. Most of the label in the neutral ether lipids was located in the alkyl ether side chain, whereas, in the phosphatidylethanolamine fraction, most of the label was found in the alkenyl ether side chain.

Metabolism/Metabolites · 2건

Stearyl alcohol ... is used in the biosynthesis of lipids and other naturally occurring cellular constituents and enters metabolic pathways for energy production. This fatty alcohol is readily converted to stearic acid, another common constituent of mammalian tissue.

From the absorbed fraction more than half was metabolized to triglycerides, 6-13% to phospholipids, 2- 8% to cholesterol esters, and 4-10% remained as unchanged octadecanol after 24h period, from dosing.

Absorption, Distribution and Excretion · 2건

Stearyl alcohol is found naturally in various mammalian tissues ... Results from several studies indicate that stearyl alcohol is poorly absorbed from the gastrointestinal tract.

Several studies indicate that /1-octadecanol/ is poorly absorbed from the gastrointestinal tract. The entry of 14C-octadecanol into the thoracic lymph duct of the Sprague-Dawley rat was reported. Lymph flows and blood were monitored for radioactivity in different intervals following dosing. Intestinal radioactivity was determined in the intestinal homogenate which showed the percent absorbed radioactivity in the lymph was 56.6 +/- 14.0. Of this, more than half was found in the triglycerides of the lymph, 6 to 13 % in the phospholipids, 2 to 8% as the cholesterol esters, and 4 to 10% unchanged octadecanol. 90% of octadecanol was found in the lipomicrom fraction of the blood. The absorption of the compound appeared to be a function of its lipid solubility.

Tissue LocationsAdipose Tissue;Bladder;Brain;Epidermis;Eye Lens;Fibroblasts;Intestine;Kidney;Liver;Neuron;Ovary;Pancreas;Placenta;Platelet;Prostate;Skeletal Muscle;Spleen;Testis;Thyroid Gland
Cellular LocationsExtracellular;Membrane

용도 및 제조

Uses · 6건

CIR ingredient: Stearyl Alcohol

Used as a substitute for cetyl alcohol in pharmaceutical dispensing; in cosmetic creams and perfumery; in textile oils and finishes; as an antifoam agent; and in lubricants, resins, and surface active agents; Synthetic stearyl alcohol has been approved as a direct and indirect food additive ingredient and as an ingredient in over-the-counter drugs; [HSDB]

Textiles (Printing, Dyeing, or Finishing) [Category: Industry]

Substitute for cetyl alcohol in pharmaceutical dispensing, in cosmetic creams, for emulsions, textile oils and finishes; as antifoam agent, lubricant, and chemical raw material.

Perfumery, cosmetics, intermediate, surface active agents, lubricants, resins, antifoam agent.

Antifoam agent /for bioprocesses/

U.S. Production · 6건

2023: 70,000,000 - <85,000,000 lb;2022: 70,000,000 - <85,000,000 lb;2021: 70,000,000 - <85,000,000 lb;2020: 70,000,000 - <85,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1986) >10 million-50 million pounds

(1990) >10 million-50 million pounds

(1994) >10 million-50 million pounds

For more U.S. Production (Complete) data for 1-OCTADECANOL (6 total), please visit the HSDB record page.

Consumer UsesCleaning agent;Not Known or Reasonably Ascertainable;Emulsifier;Softener and conditioner;Solvent;Other;Binder;Lubricating agent;Surfactant (surface active agent);Fuel
Industry UsesDefoamer;Intermediate;Emulsifier;Not Known or Reasonably Ascertainable;Stabilizing agent;Sealant (barrier);Cleaning agent;Fuel;Antioxidant;Surfactant (surface active agent);Lubricating agent;Other;Binder;Solvent
Methods of Manufacturing · 2건

Preparation from ethyl stearate. ... Preparation of technical grade from sperm whale oil.

/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.

Formulations/Preparations · 4건

Stearyl alcohol USP...contains not less than 90% of stearyl alcohol, remainder consisting chiefly of cetyl alcohol.

Hydrophilic petrolatum USP /contains/ cholesterol 30 g, stearyl alcohol 30 g, white wax 80 g, & white petrolatum 860 g.

Hydrophilic ointment USP /contains/ methylparaben 0.25 g, propylparaben 0.15 g, sodium lauryl sulfate 10 g, propylene glycol 120 g, stearyl alcohol 250 g, white petrolatum 250 g, purified water 370 g.

Grades: Commercial; technical; USP.

응용 분야 · 2건

용도1-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.

일반 설명Mixed 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.

제조 방법

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.

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

공급사2 곳

HONEST JOY HOLDINGS LIMITED[email protected]
Portail Substances Chimiques[email protected]
추가 설명 · 1건

정의ChEBI: 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.

관련 반응

129건

연결된 노트

불러오는 중…