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Isopropylmyristat
IPM · FEMA 3556 · 1-Methylethyl tetradecanoate · MYRISTIC ACID ISOPROPYL ESTER · IPM 100 · sopropyl myristate · BISOMEL · Propyl myristate
Identifikatoren & physikalische Daten
| CAS No. | 110-27-0 |
|---|---|
| Summenformel | C17H34O2 |
| Durchschnittliche Molmasse | 270,5 g/mol |
| Monoisotopische Masse | 270,25588033 g/mol |
| SMILES | CCCCCCCCCCCCCC(=O)OC(C)C |
| InChIKey | AXISYYRBXTVTFY-UHFFFAOYSA-N |
| PubChem CID | 8042 |
| ChEMBL | CHEMBL207602 |
| ChEBI | CHEBI:90027 |
| EC No. | 203-751-4 |
| DTXSID | DTXSID0026838 |
| Lokaler Name | Isopropylmyristat |
Chemische & physikalische Eigenschaften
| XLogP | 7,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 14 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 199 |
| Stoffklassen | Other Uses -> Emulsifiers/Surfactants |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Fatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710] |
| Kosmetika | Cosmetic ingredients (Isopropyl Myristate) -> CIR (Cosmetic Ingredient Review)BindingSolventSkin conditioningEmollientPersonal care product -> emollient -> wax ester |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (Isopropyl myristate) -> IFRA transparency List |
| Geruch | Practically odorless |
| Lebensmittelzusatzstoffe | Use unspecified -> FDA Substance added to food |
| Dichte | 0.8532 g/cu cm at 20 °C0.847 - 0.8550.8532 @ 20°C0.85 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Liquid of low viscosityColorless oil |
| Löslichkeit | Soluble in castor oil, cottonseed oil, acetone, chloroform, ethyl acetate, ethanol, toluene, and mineral oilpractically insoluble in glycerol, propylene glycolSoluble in ether, very soluble in acetone, benzeneinsoluble in waterinsoluble in water and glycerolsoluble in alcohol(in ethanol)<0.05mg/lMiscible with alcohol. Immiscible with water and glycerol. |
| Schmelzpunkt | ~3 °C (lit.) |
| Siedepunkt | 193 °C/20 mmHg (lit.) |
| Dampfdruck | <1 hPa (20 °C) |
| Brechungsindex | n20/D 1.434(lit.) |
| FEMA | 3556 | ISOPROPYL MYRISTATE |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Wichte | 0.855 (20/4℃) |
| Farbe | Clear |
| Geruch | odorless |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,5215 |
| JECFA Number | 311 |
| BRN | 1781127 |
| Henry-Konstante | 4.2×10-4 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| Kosmetik-Inhaltsstoffe Funktionen | BINDINGFRAGRANCEPERFUMINGSKIN CONDITIONING - EMOLLIENT |
| InChI | 1S/C17H34O2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(18)19-16(2)3/h16H,4-15H2,1-3H3 |
| InChIKey | AXISYYRBXTVTFY-UHFFFAOYSA-N |
| SMILES | CCCCCCCCCCCCCC(=O)OC(C)C |
| LogP (Verteilungskoeffizient) | 7.71 |
| CAS Datenbank | 110-27-0(CAS DataBase Reference) |
| NIST chemische Informationen | Isopropyl Myristate(110-27-0) |
| EPA chemische Informationen | Isopropyl myristate (110-27-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 84.3% (2565 of 3041) of all reports.WarningH315 (15.6%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P280, P302+P352, P321, P332+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 3041 reports by companies from 10 notifications to the ECHA C&L Inventory. |
|---|---|
| Regulatorische Informationen | Chemical: Tetradecanoic acid, 1-methylethyl esterRegulation (EC) No 1831/2003 (amended)Tetradecanoic acid, 1-methylethyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Tetradecanoic acid, 1-methylethyl ester 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/16077Tetradecanoic acid, 1-methylethyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Tetradecanoic acid, 1-methylethyl ester: Human health tier I assessment |
| Gefahrenübersicht | A skin irritant[SAX] An irritant[MSDSonline] |
| Special Reports | European Commission, ESISIUCLID Dataset,Isopropyl Myristate (110-27-0) (2000 CD-ROM edition) contains information on use, toxicology, and environmental effects of this chemical as supplied to the European Union by industry.[Available from, as of May 12, 2010: http://esis.jrc.ec.europa.eu/]Opdyke DLJMonograph on fragrance raw materialsFood Cosmet Toxicol 14 (4): 307-38 (1976). Prepn, cosmetic and perfume uses, legal status of use in food, metab, carcinogenic potential, pharmacology, and toxicology of isopropyl myristate are reviewed. |
| EPA Safer Chemical | Chemical: Isopropyl myristate |
| FIFRA-Anforderungen | Residues of isopropyl myristate are exempted from the requirement of a tolerance when used 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. Use: solvent.Residues of isopropyl myristate are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. Use: solvent. |
| Hazard Classes and Categories | Skin Irrit. 2 (15.6%) |
| Skin, Eye, and Respiratory Irritations | A human skin irritant. |
| Entsorgungsverfahren | SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Allowable Tolerances | Residues of isopropyl myristate are exempted from the requirement of a tolerance when used 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. Use: solvent.Residues of isopropyl myristate are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. Use: solvent. |
| Protective Action Criteria (PAC) | 81 [mg/m3]900 [mg/m3]5400 [mg/m3] |
| Wechselwirkungen | Addn of Polysorbate 80 to alcohols ethanol, butanol or octanol in isopropyl myristate soln reduced their permeability constant when they were initially poorly sol in pure solvent.The permeability constants for percutaneous absorption of propylene glycol & water in human excised skin were 3.2x10-6 cm/hr & 5.5x10-6 cm/hr, respectively. In isopropyl myristate, the permeability constants incr approx 250-fold to 1.1x10-3 cm/hr. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+4(SRC), determined from a structure estimation method(2), indicates that isopropyl myristate is expected to be immobile in soil(SRC). Volatilization of isopropyl myristate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.34X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Isopropyl myristate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.35X10-5 mm Hg at 25 °C(4). Isopropyl myristate, present at 100 mg/L, reached 94% of its chemical oxygen demand in 28 days using a municipal waste water inoculum in the closed bottle test(5), suggesting that biodegradation may be an important environmental fate process(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+4(SRC), determined from a structure estimation method(2), indicates that isopropyl myristate 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 2.34X10-2 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 4.9 hours and 6.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The volatilization half-life from a model pond is about 99 days when adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 2800(SRC), from an estimated log Kow of 7.17(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). A base-catalyzed second-order hydrolysis rate constant of 2.14X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2)this corresponds to half-lives of 10 years and 1 year at pH values of 7 and 8, respectively(8). Isopropyl myristate, present at 100 mg/L, reached 94% of its chemical oxygen demand in 28 days using a municipal waste water inoculum in the closed bottle test(9), suggesting that biodegradation may be an important environmental fate process(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl myristate, which has a vapor pressure of 9.35X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase isopropyl myristate 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 20 hours(SRC), calculated from its rate constant of 1.92X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase isopropyl myristate may be removed from the air by wet or dry deposition(SRC). Isopropyl myristate 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). |
| 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.org |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of isopropyl myristate can be estimated to be 1.2X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that isopropyl myristate is expected to be immobile in soil. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ /In a/ repeated Patch-test 1.28-1.70 g isopropyl myristate was applied for 24 hr every other day for 15 applications to 50 health volunteers. In each case a 48 hr challenge application was given 3 wk later. The study has failed to detect any sensitizing potential./HUMAN EXPOSURE STUDIES/ A bath oil containing 42.9% isopropyl myristate was tested for photo-con tact allergenicity on seven men and 18 women. Applications of 5 uL/sq cm under an occlusive patch for 24 hours, followed by three minimal erythema doses of irradiation from a Xenon Solar Simulator, were repeated twice a week for three weeks. A challenge patch followed by 25-30 mW/sq cm UVA for five minutes from the solar simulator fitted with a Schott WG345 filter was performed 10 days after the last induction exposure. No evidence of photo-contact allergenicity was observed./HUMAN EXPOSURE STUDIES/ A phototoxicity study with a bath oil formulation containing 42.9% isopropyl myristate was conducted on one man and nine women. The material was applied undiluted at 5 uL/sq cm under occlusive patches. Sites were irradiated after 6 and 24 hours with a 150-watt Xenon Solar Simulator fitted with Schott WG345 filter to eliminate UVB radiation, giving a total UVA irradiance of 25-30 mW/sq cm. No evidence of phototoxicity was observed./HUMAN EXPOSURE STUDIES/ Four separate human sensitization studies testing an aerosol antiperspirant concentrate containing 52-58% isopropyl myristate produced no reactions indicative of sensitization in a total of 320 subjects.For more Human Toxicity Excerpts (Complete) data for Isopropyl myristate (10 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Isopropyl myristate's production and use in cosmetic and topical medicinal preparations(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Long chain fatty acid esters, structurally similar to isopropyl myristate, were rapidly degraded by mixed sewage sludge(1,2,3). Isopropyl myristate, present at 100 mg/L, reached 94% of its chemical oxygen demand in 28 days using a municipal waste water inoculum in the closed bottle test(4). These data suggest that biodegradation may be an important environmental fate process(SRC).PURE CULTURE: Pure cultures of bacteria (Bacillus and Pseudomonas), yeast (Candida, and Pichia) and Fungi (Asperigillus, Penicillium, and Cladosporian) were found to degrade isopropyl myristate(1). |
| Sediment/Soil Concentrations | SEDIMENT: Isopropyl myristate was detected, not quantified, in sediment collected from 6 sites (out of 7) in the German Bight in 1998(1). |
| Environmental Bioconcentration | An estimated BCF of 2800 was calculated in fish for isopropyl myristate(SRC), using an estimated log Kow of 7.17(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not metabolized by the organism(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for isopropyl myristate is estimated as 2.34X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that isopropyl myristate is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4.9 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 6.5 days(SRC). Isopropyl myristate's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 99 days when adsorption is considered(3). Isopropyl myristate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.35X10-5 mm Hg(4). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Isopropyl myristate (diluted and undiluted material) /produced a/ slightly irritating /reaction/ when the substance was applied on intact and abraded rabbit skin under occlusive conditions for 24 hr./LABORATORY ANIMALS: Acute Exposure/ A volume of 0.3 mL of isopropyl myristate was injected intracutaneously into two areas of abdominal skin in each of five adult albino rabbits. Using injected trypan blue as a diagnostic aid, the investigators found no indication of parenteral irritation./LABORATORY ANIMALS: Acute Exposure/ An aerosol antiperspirant containing 4.7% isopropyl myristate was tested on six rats. The animals were exposed to a nominal concentration of 9.7 mg/L of isopropyl myristate for four 15 minute periods, each separated by a 5-minute fresh air periodsix other rats served as control. There were no significant adverse effect during exposure, no deaths, and no finding at necropsy which distinguished treated from control animals./LABORATORY ANIMALS: Acute Exposure/ Two product formulations containing isopropyl myristate were tested for acute inhalation toxicity in rats. One aerosol antiperspirant containing 16-20% isopropyl myristate was dispensed from its commercial container for 6.5 sec/min for 1 hr. The normal concentration of isopropyl myristate was 33-41mg/L. The 20 exposed animals were lethargic and had slight muzzle and eye discharge during exposure, but they exhibited normal appearance and behavior throughout the 14-day post-exposure observation period. No deaths occurred, and no evidence of systemic toxicity was found at necropsy.For more Non-Human Toxicity Excerpts (Complete) data for Isopropyl myristate (31 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of isopropyl myristate with photochemically-produced hydroxyl radicals has been estimated as 1.92X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 2.14X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(2)this corresponds to half-lives of 10 years and 1 year at pH values of 7 and 8, respectively(2). Isopropyl myristate does not contain chromophores that absorb at wavelengths >290 nm(3), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC). |
| Wassergefährdungsklasse (WGK) | - |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29159080 |
| RTECS-Nr. | XB8600000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 110-27-0(Hazardous Substances Data) |
| Selbstentzündungstemperatur | >300 °C |
Anwendungen & Verwendung
Beschreibung
Isopropyl myristate is odorless when pure. May be synthesized by conventional esterification of isopropanol with myristic acid.
Occurrence
Reported found in kumquat peel oil, papaya, starfruit, plum brandy, coriander seed and loquat
Verwenden
In cosmetic and topical medicinal Preparations where good absorption through the skin is desired. A jellied isopropyl myristate was marketed as Estergel (Merck & Co.) .
Herstellung & Synthese
synthetische
By conventional esterification of isopropanol with myristic acid