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1-Tetradecanol
MYRISTYL ALCOHOL · myristic · Tetradecan-1-ol · TETRADECYL ALCOHOL · myristyl · Loxanol V · Lanette 14 · n-Tetradecanol
Identifikatoren & physikalische Daten
| CAS No. | 112-72-1 |
|---|---|
| Summenformel | C14H30O |
| Durchschnittliche Molmasse | 214,39 g/mol |
| Monoisotopische Masse | 214,22966558 g/mol |
| SMILES | CCCCCCCCCCCCCCO |
| InChIKey | HLZKNKRTKFSKGZ-UHFFFAOYSA-N |
| PubChem CID | 8209 |
| ChEMBL | CHEMBL24022 |
| ChEBI | CHEBI:77417 |
| EC No. | 204-000-3 |
| DTXSID | DTXSID9026926 |
Chemische & physikalische Eigenschaften
| XLogP | 6,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 20,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 12 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 102 |
| Stoffklassen | Other Classes -> Other Organic Compounds |
| Lipide | Fatty Acyls [FA] -> Fatty alcohols [FA05] |
| Kosmetika | Cosmetic ingredients (Myristyl Alcohol) -> CIR (Cosmetic Ingredient Review)Viscosity controllingEmulsion stabilizingSkin conditioningEmollientFoam boosting |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (1-Tetradecanol) -> IFRA transparency List |
| Pestizide | AttractantsActive substance -> EU Pesticides database: Approved |
| LogP (Verteilungskoeffizient) | log Kow = 6.036.11 |
| Lebensmittelzusatzstoffe | FORMULATION AID, LUBRICANT OR RELEASE AGENT -> FDA Substance added to food |
| Dichte | 0.824 at 100.4 °F (USCG, 1999) - Less dense than waterwill float0.823 at 40 °CBulk density = 7.0 lb/galspecific gravity: 0.8355 at 20 °C/20 °CDensity: 0.8236 g/cu cm at 38 °C0.823 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | White solidWhite crystalsLeaflets |
| Löslichkeit | In water, 1.91X10-1 mg/L at 25 °CIn water, 0.30 mg/L at 25 °CVery soluble in ethanol, ether, acetone, benzene, chloroformSoluble in ether, slightly soluble in alcoholwater: soluble0.00013g/L at 23°Cinsoluble |
| Schmelzpunkt | 35-39 °C(lit.) |
| Siedepunkt | 289 °C(lit.) |
| Dampfdichte | 7.4 (vs air) |
| Dampfdruck | <1 hPa (20 °C) |
| Brechungsindex | 1.4454 |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Low Melting Solid, Crystalline Powder, Crystals, Flakes, Pellets and/or Chunks |
| pKa (Säurekonstante) | 15.20±0.10(Predicted) |
| Wichte | 0.823 |
| Farbe | White |
| Geruch | fatty |
| Geruchsart | waxy |
| Spezifische Wärmekapazität | Cp(crystal): 1.81 J/(g·K), at 25℃ |
| Merck | 14,6335 |
| BRN | 1742652 |
| Henry-Konstante | 6.2×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 4.4(48℃) |
| Kosmetik-Inhaltsstoffe Funktionen | SURFACTANT - FOAM BOOSTINGEMULSION STABILISINGVISCOSITY CONTROLLINGSKIN CONDITIONING - EMOLLIENTSKIN CONDITIONING |
| InChI | 1S/C14H30O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15/h15H,2-14H2,1H3 |
| InChIKey | HLZKNKRTKFSKGZ-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCCCCO |
| LogP (Verteilungskoeffizient) | 5.5 |
| CAS Datenbank | 112-72-1(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Tetradecanol(112-72-1) |
| EPA chemische Informationen | 1-Tetradecanol (112-72-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 15% (312 of 2077) of reports.WarningH315 (33.1%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2077 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1-TetradecanolCommission Regulation (EC) No 2229/20041-Tetradecanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Tetradecanol 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)2008/127, Reg. (EU) 2017/195, Reg. (EU) 2021/745, Reg. (EU) 2022/1251, Reg. (EU) No 540/2011, Reg. (EU) No 918/2014, Reg. (EU)2020/1160Status: Active Update: 22-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/154221-Tetradecanol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1-Tetradecanol: Human health tier I assessment |
| Brandpotenzial | Combustible when exposed to heat or flame... |
| Gesundheitsgefahren | Low toxicity. Overexposure causes some central nervous system depression. Prolonged skin contact causes skin irritation. (USCG, 1999) |
| Gefahrenübersicht | Low toxicity, but overexposure can cause CNS depression and prolonged skin contact causes irritation[CAMEO] A moderate skin irritantA mild eye irritant[MSDSonline] |
| FDA-Anforderungen | Myristyl alcohol is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Alcohols and Polyols |
| FIFRA-Anforderungen | New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 001510Type of Pesticide: biological - insect pheromoneUse Site: food useYear: 92. |
| Reactivity Profile | TETRADECANOL is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. |
| Air and Water Reactions | Insoluble in water. |
| NFPA Hazard Classification | 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides. |
| Brandbekämpfung | Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing. |
| Erste Hilfe | INGESTION: induce vomiting and call a doctorif necessary, support respiration. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Wear self contained breathing apparatus for fire fighting if necessary.To fight fire use carbon dioxide, dry chemical. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. |
| Reinigungsverfahren | Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.Prevent futher leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist, or gas. Ensure adequate ventilation. Avoid breathing dust. |
| Entsorgungsverfahren | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. |
| Preventive Measures | Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Further processing of solid materials may result in the formation of combustible dusts. The potential for combustible dust formation should be taken into consideration before additional processing occurs. Provide appropriate exhaust ventilation at places where dust is formed. |
| Personal Protective Equipment (PPE) | Goggles or face shield. (USCG, 1999)Safety glasses with side-shields conforming to EN 166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166 (EU).Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection: For nuisance exposures use type P95 (US) or type OP1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/99 (US) or type ABEK-P2 (EU EN 143) respirator cartriges. Use respirator and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. |
| Wechselwirkungen | The objective of this study was to evaluate the skin permeation enhancement effect and skin irritation of saturated fatty alcohols using melatonin as a model compound. A saturated solution of melatonin in a mixture of water and ethanol (40:60) containing 5% w/v of saturated fatty alcohol was used in the skin permeation studies using Franz diffusion cells. For skin irritation studies, 230 uL of fatty alcohol solution was applied on the dorsal surface of the hairless rats using Hill top chamber. The skin irritation was evaluated by visual scoring method and bioengineering methods such as measurement of transepidermal water loss (TEWL) and skin blood flow. The flux of melatonin across hairless rat skin was found to be dependent on the carbon chain length of the fatty alcohols, with decanol showing the maximum permeation of melatonin. All fatty alcohols increased the TEWL and skin blood flow significantly compared with the vehicle. The fatty alcohols (decanol, undecanol and lauryl alcohol), which showed greater permeation of melatonin, also produced greater TEWL, skin blood flow and erythema. Tridecanol and myristyl alcohol showed lower permeation enhancement effect but caused greater skin irritation. Octanol and nonanol may be the most useful enhancers for the transdermal delivery of melatonin considering their lower skin irritation and a reasonably good permeation enhancement effect. ... |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 18,197-26,303 in humic acid(2), indicate that 1-tetradecanol is expected to be immobile in soil(SRC). Volatilization of 1-tetradecanol from moist soil surfaces is expected given a Henry's Law constant of 1.04X10-4 atm-cu m/mole(3). However, adsorption to soil is expected to attenuate volatilization(SRC). 1-Tetradecanol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.1X10-4 mm Hg at 25 °C(4). A biodegradation rate constant of 52.5 1/hr in sludge was reported for 1-tetradecanol(5), indicating that biodegradation may be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 23,320-64,060 in suspended solids(2), indicate that 1-tetradecanol is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.04X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 17 hours and 10 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 20-55 months if adsorption is considered(5). 1-Tetradecanol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(6), an estimated BCF of 190(SRC), from its log Kow of 6.03(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). A biodegradation rate constant of 52.5 1/hr was reported in sludge(9), indicating that biodegradation may be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-tetradecanol, which has a vapor pressure of 1.1X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-tetradecanol 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 18 hours(SRC), calculated from its rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Tetradecanol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | 1-Tetradecanol was identified as a volatile component of aroma of cooked (1) and raw beef(2). 1-Tetradecanol has been detected in wine and spirits(3). |
| Toxizitätsübersicht | 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.orgIDENTIFICATION AND USE: 1-Tetradecanol is a white solid or crystal used in organic synthesis, plasticizers, antifoaming agent, intermediate, perfume fixative for soaps and cosmetics, wetting agents and detergents, ointments and suppositories, shampoos, toothpaste, cold creams, and specialty cleaning preparations. 1-tetradecanol and 1-dodecanol are also used in combination with the (E, E) -8, 10-dodecadiene-1-ol, (Z)-11-tetradecene-1-yl acetate, and (Z)-9-tetradecene-1-yl acetate as a pheromone confusion mixture for controlling pests on plants, e.g., codling moths and leaf wrappers. In Denmark, the product is used for insect control in apples and pears. It is registered for pesticide use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. 1-Tetradecanol has been tested as experimental medication in controlling the progression of chronic periodontal disease. HUMAN EXPOSURE AND TOXICITY: Thirty-one patients allergic to Hirudoid cream were patch tested with the ingredients. 29 were allergic to the cream base and 16 to one or more components. The most common allergens were for 1-tetradecanol, cetostearyl alcohol, and parabens. It has been stated that 1-tetradecanol should not be patch tested at 10% in petrolatum, but at a lesser concentration, due to irritant properties. ANIMAL STUDIES: It has been reported that 1-tetradecanol causes no skin irritation and slight eye irritation. |
| Plant Concentrations | 1-Tetradecanol emission rates from green leaf composite samples and dead leaves were 51 ug/g and 25 ug/g, respectively(1). Essential oil from the herbal part of Cymocarpum erythracum was 73.1% 1-tetradecanolplants were collected in Erzincan, Turkey(2). 1-Tetradecanol was detected at a range of 0-432 ppm in the shoots of Mitracarpus scaber (Rubiaceae)(3). |
| Ongoing Test Status | EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assaysClick on the "Chemical Explorer" button on the tool bar to see the data./[USEPAICSS Dashboard ApplicationAvailable from, as of April 22, 2015: http://actor.epa.gov/dashboard/] |
| Effluent Concentrations | 1-Tetradecanol was detected in an advanced waste treatment concentrate from a plant in Dallas, TX, in 1974(1). 1-Tetradecanol was detected in wastewater effluent at unreported concentrations from printing and publishing industries, textile mills, and publically-owned treatment works(one occurrence reported for each industry type)(2). 1-Tetradecanol emission from road dust samples was 3.6 ug/g(3). 1-Tetradecanol was emitted to the air at a rate of 6 ug/sq m hour from one of 10 cushion poly vinyl floorings installed for 3 days, the emission rate increased to 7 ug/sq m hour 28 days after installation(3). |
| Soil Adsorption/Mobility | Koc values of 18,197-26,303 were reported for 1-tetradecanol in humic acid(1). According to a classification scheme(2), this Koc range suggests that 1-dodecanol is expected to be immobile in soil. Koc values of 5248-12,882, 19,953-32,256, 23,320-64,060 and 44,136-70,202 were reported for 1-tetradecanol in activated sludge, sediment, suspended solids and suspended solids with activated sludge, respectively(1). |
| Natural Pollution Sources | 1-Tetradecanol emission rates from green leaf composite samples and dead leaves were 51 ug/g and 25 ug/g, respectively(1). Essential oil from the herbal part of Cymocarpum erythracum was 73.1% 1-tetradecanolplants were collected in Erzincan, Turkey(2). |
| Atmospheric Concentrations | URBAN/SUBURBAN: 1-Tetradecanol was detected, not quantified, in air samples collected along the Niagara River from Buffalo, NY to Niagara-on-the-Lake, Ontario in 1982-1983(1). 1-Tetradecanol was detected in atmospheric samples at 1.4 ng/cu m and 1.1 ng/cu m in Bakersfield and Fresno, CA, respectively(2).RURAL/REMOTE: 1-Tetradecanol was detected at 0.6 ng/cu m in air samples from Kern Wildlife Refuge, CA(1). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ During a two-year period contact allergy to topically applied medicaments in the urban population of Malmo was investigated prospectively by patch testing patients with suspected products and their ingredients as well as with standard allergens. Contact dermatitis to specified medicaments was diagnosed in 40 of 408 patients with a positive patch test, and to standard allergens of medicament nature in a further 123 patients. Medicament contact allergy therefore constituted 40% of all allergies observed. This is equivalent to an annual incidence of 43/100,000. Among responsible products the leading antigens were ethylenediamine, phenylbutazone, myristyl alcohol, chlorocresol and cincocaine. In comparison with patients having other contact allergies the present material of medicament contact allergy was characterized by a rather high mean age (57 years), a higher percentage of males, a higher percentage of lower leg and anogenital dermatitis, and a lower percentage of hand dermatitis. A secondary spread occurred in half the cases of lower leg and anogenital dermatitis./HUMAN EXPOSURE STUDIES/ BACKGROUND: Although many allergens in metalworking fluids (MWF) are identified, there are still some MWF components, which are not sufficiently investigated concerning their sensitizing properties. OBJECTIVES: To investigate sensitization to 10 frequently used MWF components, which are not part of the established MWF test series, in metalworkers with suspected occupational dermatitis due to MWF. PATIENTS/METHODS: Oleyl alcohol, myristyl alcohol, dimethylolurea, 4,4'-methylenebis morpholine, imazalil, 1-amino-2-propanol (monoisopropanolamineMIPA), 2-amino-2-ethyl-1,3-propanediol (AEPD), 2,5-bis(n-octyldithio)-1,3,4-thiadiazole, zinc alkyl dithiophosphate and dibenzyl disulfide have been patch tested in 144 patients. RESULTS: 7 patients reacted positively to the formaldehyde releaser 4,4'-methylenebis morpholine, and 6 of these patients also reacted to formaldehyde and/or other formaldehyde releasers. 4 patients reacted positively to myristyl alcohol tested at 10% petrolatum (pet.). Additionally, 20 doubtful or irritant reactions occurred. 1 patient each reacted positively to oleyl alcohol, MIPA, and AEPD. None of the other test substances mentioned above elicited any clear-cut positive reaction. Patch testing with well-known MWF allergens showed proportions of positive reactions, which were comparable to those from other studies, e.g. 11% to monoethanolamine, 8% to colophonium and 3%-5% to various preservatives. CONCLUSIONS: 4,4'-methylenebis morpholine may be an important MWF allergen, although clinical relevance could not be stated definitely in every case. Myristyl alcohol should not be patch tested at 10% pet., but at a lesser concentration, due to irritant properties./CASE REPORTS/ 31 patients allergic to Hirudoid cream were patch tested with the ingredients. 29 were allergic to the cream base and 16 to one or more components. The most common allergens were myristyl alcohol, cetostearyl alcohol and parabens. 14 patients reacted only to the base. |
| Fish/Seafood Concentrations | 1-Tetradecanol was detected in lake trout (Salvelinus namaycush) and walleye (Stizostedion v. vitreum) sampled in the fall of 1977 from Lake Michigan at Saugatuck and Charlevoix, Lake Huron at Rockport, Lake St. Clair, and Lake Erie at Port Clinton and Dunkirk at unreported concentrations(1). |
| F | 9 |
| Wassergefährdungsklasse (WGK) | - |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3077 9 / PGIII |
| Zollcode | 2905 19 00 |
| RTECS-Nr. | XB8655000 |
| R-Sätze (R) | 38-36 |
| Toxizität | LD50 orally in Rabbit: > 2000 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 24/25-26 |
| Gefahrenklasse | 9Aquatic Chronic 1Eye Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 112-72-1(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 489 °F |
Anwendungen & Verwendung
Verwenden
1-Tetradecanol is used as an ingredient in cosmetics such as cold creams. It is an active intermediate in the chemical synthesis of sulfated alcohol. It is also employed in the fabrication of temperature-regulated drug release system based on phase-change materials. It plays a vital role in filling the hollow interiors of gold nanocages in the fabrication of new theranostic system, which has unique feature of photoacoustic imaging.
Herstellung & Synthese
synthetische
1-Tetradecanol is prepared from the head oil of the Sperm Whale via the acid and the ester.