ミリスチン酸 イソプロピル

Isopropyl Myristate

HCID 8042CAS 110-27-0

基本情報

標準SMILES
CCCCCCCCCCCCCC(=O)OC(C)C
InChIKey
AXISYYRBXTVTFY-UHFFFAOYSA-N
分子式
C17H34O2
平均分子量
270.5 g/mol
単同位体質量
270.25588033

概要

Isopropyl tetradecanoate is a fatty acid ester.

名称と識別子

優先名称
Isopropyl Myristate
IUPAC
propan-2-yl tetradecanoate
現地名
ミリスチン酸 イソプロピル
英語名
Isopropyl myristate
分子式
C17H34O2
分子量
270.45

名称と別名

ISOPROPYL MYRISTATE110-27-0Isopropyl tetradecanoateIsomystEstergelBisomelDeltyl ExtraKesscomirPromyrTetradecanoic acid, 1-methylethyl esterCrodamol IPMpropan-2-yl tetradecanoate
名称をさらに表示
ミリスチン酸 イソプロピルミリスチン酸イソプロピルウィッケノール101テトラデカン酸1-メチルエチルケッスコミルエメレスト2314クロダモールIPMデルチルエクストライソプロピル=ミリスタートエムコールIMイソプロピルミリスタートテトラデカン酸イソプロピルビソメルイソミストステパンD-50N-テトラデカン酸ISO-プロピルミリスチン酸ISO-プロピルミリスチン酸イソプロピルエステルイソプロピル=テトラデカノアートテトラデカン酸イソプロピル, 98%IPMFEMA 35561-Methylethyl tetradecanoateMYRISTIC ACID ISOPROPYL ESTERIPM 100sopropyl myristatePropyl myristateIso Propyl Mystrate
TegesterSinnoester MIPPlymoutm IPMStarfol IPMUnimate IPMKessco IPMEmcol-IMStepan D-50

データベース識別子

CAS
110-27-0
PubChem CID
8042
DTXSID
DTXSID0026838
ChEMBL
CHEMBL207602
ChEBI
CHEBI:90027
UNII
0RE8K4LNJS
EC Number
203-751-4
Nikkaji
J10.110I

物性

構造計算による物性

XLogP
7.2
極性表面積
26.3 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
14
重原子数
19

実験および物理化学的性質

Chemical ClassesOther Uses -> Emulsifiers/Surfactants
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty esters [FA07] -> Short fatty esters [FA0710]
Cosmetics · 3 件

Cosmetic ingredients (Isopropyl Myristate) -> CIR (Cosmetic Ingredient Review)

Binding; Solvent; Skin conditioning; Emollient

Personal care product -> emollient -> wax ester

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Isopropyl myristate) -> IFRA transparency List

物理化学的性質

融点
3 °C · ~3 °C (lit.)
沸点
193 °C/20 · 193 °C/20 mmHg (lit.)
比重(密度)
0.85 g/mL · 0.85 g/mL at 25 °C (lit.)
蒸気圧
1 hPa · <1 hPa (20 °C)
屈折率
20 · n20/D 1.434(lit.)
FEMA
3556 · 3556 | ISOPROPYL MYRISTATE

化学的性質

化学的特性Isopropyl myristate is a clear, colorless, practically odorless liquid of low viscosity that congeals at about 5°C. It consists of esters of propan-2-ol and saturated high molecular weight fatty acids, principally myristic acid.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 84.3% (2565 of 3041) of all reports.

Warning

H315 (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.

危険有害性情報

Regulatory Information · 5 件

Chemical: Tetradecanoic acid, 1-methylethyl ester

Regulation (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/16077

Tetradecanoic acid, 1-methylethyl ester: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Tetradecanoic acid, 1-methylethyl ester: Human health tier I assessment
Hazards SummaryA skin irritant; [SAX] An irritant; [MSDSonline]
Special Reports · 2 件

European Commission, ESIS; IUCLID 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 DLJ; Monograph on fragrance raw materials; Food 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 ChemicalChemical: Isopropyl myristate
FIFRA Requirements · 2 件

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.

安全と保護具

Disposal Methods · 1 件

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 · 2 件

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) · 3 件

81 [mg/m3]

900 [mg/m3]

5400 [mg/m3]

毒性情報

Interactions · 2 件

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.

Environmental Fate · 3 件

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).

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
Soil Adsorption/Mobility · 1 件

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 · 5 件

/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 SourcesIsopropyl 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).

法規制情報

FIFRA Requirements · 2 件

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.

安全データ

wgk
-
tsca
TSCA listed
rtecs
XB8600000
毒性
LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
hs_code
29159080
risk_code
36/37/38

化学と産業

薬理情報

Protein BindingReadily available information regarding the pharmacokinetics of isopropyl myristate is not available.
Pharmacodynamics · 1 件

Isopropyl myristate is an emollient vehicle that is effective at enhancing the penetration of other medical agents that may be incorporated into the vehicle as active agents. In one study, a 50:50 isopropanol-isopropyl myristate binary enhancer synergistically increased the transport of estradiol across a two-layer human epidermis in vitro.

Mechanism of Action · 1 件

As a pediculicide, isopropyl myristate is capable of physically coating the exoskeleton bodies of lice. This physical coating subsequently immobilizes the lice and works to dissolve the wax covering on the insect exoskeleton and blocks the insects' airways, leading to death by dehydration. Although this physical action of isopropyl myristate results in little lice resistance (given the lack of immunologic or chemical activity in this mechanism of action), the substance is also not ovicidal, which means any eggs that may have been laid by lice would not be affected. Moreover, isopropyl myristate is capable of eliciting its pediculicide action in a contact time of only 10 minutes per each necessary administration.

Biological Half-LifeReadily available information regarding the pharmacokinetics of isopropyl myristate is not available.
Metabolism/Metabolites · 3 件

Any isopropyl myristate that is absorbed is likely to be hydrolyzed to its component compounds of isopropylalcohol and myristic acid.

The myristates can be expected to undergo chemical or enzymatic hydrolysis to myristic acid and the corresponding alcohol.

Like other high molecular weight aliphatic esters, the myristates are readily hydrolyzed to the corresponding alcohols and acids which are then further metabolized.

Absorption, Distribution and Excretion · 6 件

Dermal absorption of isopropyl myristate is predicated to be 0.00020 mg/cm2/event, which is considered a very low absorption rate. In a study, topically applied isopropyl myristate was largely retained in the stratum corneum. It was not detected in the receptor fluid of flow-through diffusion cells in in-vitro skin permeation experiments using human epidermis (stratum corneum and viable epidermis) and dermis of varying thickness.

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.

Readily available information regarding the pharmacokinetics of isopropyl myristate is not available.

Four monkeys were exposed for 5 sec to the spray of an aerosol antiperspirant containing 14C-labelled isopropyl myristate. Two animals were sacrificed immediately after exposureand the other two were sacrificed 24 hr later. The distribution of carbon-14 in the exhaled air and in several tissues indicated that only 0.25% of the dose sprayed at the animals was absorbed; about 10% of this reached the lower respiratory tract. Some 85% of the absorbed isopropyl myristate was eliminated in 24 hr, mainly as exhaled carbon dioxide; very little labeled material reached any tissues other than the lungs.

In whole body autoradiography in hairless mice, there was no visible penetration into the skin or organs, whereas microautoradipgraphy with guinea pigs showed local penetration. Isopropyl myristate penetrated to the greatest extent. Percutaneous absorption was examined in Angora rabbits by microautoradiography simultaneously with skin irritation potential by histological method. Isopropyl myristate was distributed into the skin both trans-epidermally and trans-follicularly immediately after 24 hr application. Isopropyl myristate is thought to penetrate into human skin also, though it is known to generate no erythema on the skin. Isopropyl myristate was found to be distributed into almost all organs by means of whole body autoradiography when it was injected sc into mice. The extracts from the liver and kidney were determined to be a fatty acid and a triglyceride. Isopropyl myristate was easily distributed into the organs and metabolized.

用途と製造

Uses · 6 件

CIR ingredient: Isopropyl Myristate

Used as emollient and emulsifier in cosmetics and topical medicines, parenteral solvent (intravenous solutions), and reagent in tests for sterility; [HSDB]

For isopropyl myristate (USEPA/OPP Pesticide Code: 000207) there are 0 labels match. /SRP: Not registered for current 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./

Isopropyl myristate is an effective agent for solubilizing lanolin; mixtures of up to about 50% lanolin in isopropyl myristate remain stable, free-flowing liquid at room temperature. Therefore, isopropyl myristate is used as a solubilizing, spreading, and penetrating agent in anhydrous skin lubricating lotions with high lanolin content. Isopropyl myristate leaves the skin soft and smooth without an oily surface film. It is used in bath oils, perfumes, creams lotions, lipsticks, hair preparations, shaving lotions, aerosol toiletries, and pharmaceutical ointments.

In cosmetic and topical medicinal preparations

EMOLLIENT & EMULSIFIER IN COSMETIC OILS, CREAMS & LOTIONS, MAKEUP, LIPSTICK, SKIN LUBRICANTS, DEODORANTS, SUN SCREENS, HAIR PREPARATIONS, NAIL LACQUER REMOVER; PARENTERAL SOLVENT IN MEDICINE; REAGENT IN MEDICAL TEST FOR STERILITY

Impurities · 2 件

The commercial product may contain small amounts of esters of palmitic and other saturated fatty acids.

Myristic acid and other free fatty acids are present at a maximum concentration of 1.0%, and unsponifiable material is present at a maximum concentration of 0.2%. There are no known dilutents, solvents, or adhesives present.

U.S. Production · 6 件

2023: 10,000,000 - <25,000,000 lb

(1972) 2.2X10+9 GRAMS

(1975) 1.1X10+9 GRAMS

Tetradecanoic acid, 1-methylethyl ester is listed as a High Production Volume (HPV) chemical (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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1744]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Tetradecanoic acid, 1-methylethyl ester. Aggregated National Production Volume: 1 to < 10 million lbs.

Consumer UsesSurface modifier
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 3 件

Isopropyl myristate is commercially produced by distillation, which is preceded by the esterification of myristic acid and isopropanol, alkali refined to neutralize the catalyst, and the product is then distilled to obtain isopropyl myristate.

By reacting myristoyl chloride with 2-propanol with the aid of a suitable dehydrochlorinating agent.

Esterification of isopropyl alcohol with myristic acid

応用分野 · 6 件

解説1-methylethyl tetradecanoate.C17H34O2(270.44).CH3(CH2)12COOCH(CH3)2.ミリスチン酸 イソプロピルは,ミリスチン酸と2-プロパノールとを反応させ,エステル化すると得られる.無色の透明液体.融点8~9 ℃,沸点140 ℃(0.3 kPa).d2020 0.855.n20D 1.435.208 ℃ で分解する.アセトン,エタノール,トルエン,植物油および鉱物油に可溶.化粧品用油性原料,外用医薬品基剤用原料,プラスチックや繊維の滑剤,塗料および印刷インキの添加剤,金属加工用潤滑油などに用いられる.森北出版「化学辞典(第2版)

用途化粧品原料。

説明Isopropyl myristate is odorless when pure. May be synthesized by conventional esterification of isopropanol with myristic acid.

天然物の起源Reported found in kumquat peel oil, papaya, starfruit, plum brandy, coriander seed and loquat

使用In cosmetic and topical medicinal Preparations where good absorption through the skin is desired. A jellied isopropyl myristate was marketed as Estergel (Merck & Co.) .

一般的な説明Isopropyl myristate is an ester of isopropyl alcohol myristic acid. It is mainly used as a solubilizer, emulsifier and emollient in cosmetic and topical medicines. It also finds applications as a flavoring agent in the food industry.Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

調製方法 · 2 件

製造方法By conventional esterification of isopropanol with myristic acid

Isopropyl myristate may be prepared either by the esterification of myristic acid with propan-2-ol or by the reaction of myristoyl chloride and propan-2-ol with the aid of a suitable dehydrochlorinating agent. A high-purity material is also commercially available, produced by enzymatic esterification at low temperature.

上流・下流製品情報

サプライヤー50 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

補足説明

定義本品は、ミリスチン酸(*)とイソプロパノール(*)のエステルであり、次の化学式で表される。参照表示名称:ミリスチン酸, イソプロパノール

関連反応

30 件

関連ノート

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