Isopropyl myristate Property

Melting point:

~3 °C (lit.)

Boiling point:

193 °C/20 mmHg (lit.)

Density 

0.85 g/mL at 25 °C (lit.)

vapor pressure 

<1 hPa (20 °C)

refractive index 

n20/D 1.434(lit.)

FEMA 

3556 | ISOPROPYL MYRISTATE

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

<0.05mg/l

form 

Liquid

Specific Gravity

0.855 (20/4℃)

color 

Clear

Odor

odorless

Water Solubility 

Miscible with alcohol. Immiscible with water and glycerol.

Merck 

14,5215

JECFA Number

311

BRN 

1781127

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

InChIKey

AXISYYRBXTVTFY-UHFFFAOYSA-N

LogP

7.71

CAS DataBase Reference

110-27-0(CAS DataBase Reference)

NIST Chemistry Reference

Isopropyl Myristate(110-27-0)

EPA Substance Registry System

Isopropyl myristate (110-27-0)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

-

RTECS 

XB8600000

Autoignition Temperature

>300 °C

TSCA 

Yes

HS Code 

29159080

Hazardous Substances Data

110-27-0(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 10000 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

Isopropyl myristate Chemical Properties,Usage,Production

Chemical Properties

Isopropyl myristate is a colorless and odorless liquid with a faint odor, and miscible with vegetable oil. It is not easy to be either hydrolyzed or become rancid. The refractive index nD20 is 1.435~1.438, and the relative density (20&deg;C) is 0.85~0.86. it is used in many applications, including pharma, food and personal care product manufacturing.

Content Analysis

Weight 1.5 g sample. Then it is determined by the method ester assay (OT-18). The equivalent factor (e) in the calculation is 135.2. Or it is determined by a non-polar column method of gas chromatography (GT-10-4).

Uses

Isopropyl myristate (IPM) is a fatty acid ester which is used as solvent in water-in-oil emulsion, oils and fatty based ointments. The use of IPM is recommended in the Sterility Test chapter of the European, Japanese and United States Pharmacopoeia (EP, 2.6.13, JP, 4.06 and USP, 71) as diluent for oils and oily solutions, as well as for ointments and creams. Indeed, its solvent properties improve the filterability of these samples.
Isopropyl myristate is known as a penetration enhancer for topical preparations. It is a waterclear, low viscous oily liquid with a very good spreading capacity on the skin. Isopropyl Myristate is mainly used in cosmetics as an oilcomponent for emulsions, bath oils and as a solvent for active substances.

Production Method

It is a product of esterification of myristic acid derived from re-steamed coconut coil with isopropyl alcohol.
(1)  200 kg myristic acid and 450 kg isopropyl alcohol were added into the reaction vessel in turn. After mixing, 360 kg sulfuric acid (98%) was added. The reaction mixture was heated to reflux for 10 hours. Isopropyl alcohol was then recovered, washed with ice water, and neutralized with Na2CO3 aqueous solution (10%). Under normal pressure, isopropyl alcohol and water were distilled. While under reduced pressure, isopropyl myristate was distilled (185°C/1.0kPa~195°C/2.7kPa).
(2) 90 kg isopropyl alcohol was added into the reaction vessel and then sulfuric acid as catalyst, with 5% of the total amount, was added. During mixing, 228 kg myristic acid was added slowly. The mixture was heated to reflux and water was continuously separated. Until no water was separated, the reaction temperature was reduced and probe was obtained to measure the acid value. When the acid value reached 1.5 mg KOH/g, the reaction was completed. Alkali was then added for neutralization. After the removal of water under reduced pressure, the pressure was further reduced for dealcoholization until the acid value was 0.05~1.0 mg KOH/g. The final product is then isopropyl myristate.

Toxicity

ADI is not regulated (FAO/WHO, 2001).

Description

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

Chemical Properties

Pure isopropyl myristate is virtually odorless, very slightly fatty, but not rancid

Chemical Properties

colourless liquid of low viscosity

Chemical Properties

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.

Occurrence

Reported found in kumquat peel oil, papaya, starfruit, plum brandy, coriander seed and loquat

Uses

Isopropyl myristate is an emollient in cosmetic and pharmaceutical bases.

Uses

isopropyl myristate is an emollient, moisturizer, binder, and skin softener that also assists in product penetration. An ester of myristic acid, it is naturally occurring in coconut oil and nutmeg. Although isopropyl myristate is generally considered comedogenic, some ingredient manufacturers clearly specify non-comedogenicity on their data sheets.

Uses

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

Definition

ChEBI: Isopropyl tetradecanoate is a fatty acid ester.

Production Methods

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.

Preparation

By conventional esterification of isopropanol with myristic acid

brand name

Estergel (Merck).

General Description

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.

Pharmaceutical Applications

Isopropyl myristate is a nongreasy emollient that is absorbed readily by the skin. It is used as a component of semisolid bases and as a solvent for many substances applied topically. Applications in topical pharmaceutical and cosmetic formulations include bath oils; make-up; hair and nail care products; creams; lotions; lip products; shaving products; skin lubricants; deodorants; otic suspensions; and vaginal creams. For example, isopropyl myristate is a self-emulsifying component of a proposed cold cream formula, which is suitable for use as a vehicle for drugs or dermatological actives; it is also used cosmetically in stable mixtures of water and glycerol.
Isopropyl myristate is used as a penetration enhancer for transdermal formulations, and has been used in conjunction with therapeutic ultrasound and iontophoresis.It has been used in a water-oil gel prolonged-release emulsion and in various microemulsions. Such microemulsions may increase bioavailability in topical and transdermal applications. Isopropyl myristate has also been used in microspheres, and significantly increased the release of drug from etoposide-loaded microspheres.
Isopropyl myristate is used in soft adhesives for pressuresensitive adhesive tapes.

Contact allergens

Despite wide use in cosmetics, perfumes, and topical medicaments, isopropyl myristate is a very weak sen- sitizer and a mild irritant.

Biochem/physiol Actions

Isopropyl myristate (myristic acid isopropyl ester) is used to change the physicochemical characteristics of microsheres such as poly(lactic-co-glycolic acid) (PLGA) microspheres. Isopropyl myristate is used as a oil phase component in the formulaton of microemulsion systems.

Pharmacology

Isopropyl myristate is used in pharmaceutical preparations because it improves solubility and increases absorption through the skin. External uses include a non-irritating iodine preparation for disinfecting the skin (Powers & Rieger, 1963) and aerosol bactericidal preparations for feminine hygiene use without irritation of the skin and mucous membranes (Geistlich, 1970; Watson. 1969). Preparations for internal use include oral steroid formulations (Hirata, 1970) and anaesthetic injection solutions (Davis, Pearce & Connor, 1972).
Veterinary medications containing isopropyl myristate include oral or parenteral compositions for lungworm infections (N. V. Philips' Gloielampenfabrieken, 1964) and a spray formulation for bovine udders to treat mastitis, combat infection and improve the general skin condition (Kraus, 1965). Isopropyl myristate has been found to be an effective repository vehicle for im injection of penicillin in rabbits and for sc administration of oestrogens in ovariectomized rats (Platcow & Voss, 1954).
In assays on human forearms, vasoconstrictor activity of ointment preparations containing 0025% betamethasone 17-benzoate in white soft paraffin was increased by the presence of isopropyl myristate (Pepler, Woodford & Morrison, 1971). Donovan, Ohmart & Stoklosa (1954) noted that the good solvent properties of isopropyl myristate might increase the therapeutic activity of formulations by the apparent alteration in particle size of the active ingredients, so that further evaluation and clinical study would be necessary before its use in extemporaneous compounding could be recommended. Studies in which the antifungal activity of paraben esters solubilized by surfactants was decreased by isopropyl myristate (Matsumoto & Aoki, 1962) indicate that the effectiveness of medicinal substances may be influenced by the presence of surfactants and oily ingredients such as isopropyl myristate.

Side effects

Thrapecylate myristate is a medicine used to treat head lice infestations in adults and children 4 years of age and older. Common side effects include skin irritation, rash, and contact dermatitis.

Safety

Isopropyl myristate is widely used in cosmetics and topical pharmaceutical formulations, and is generally regarded as a nontoxic and nonirritant material.
LD50 (mouse, oral): 49.7 g/kg
LD50 (rabbit, skin): 5 g/kg

Synthesis

Isopropyl myristate is synthesized by conventional esterification of iso-Propanol with Myristic acid.

Metabolism

Higher molecular weight aliphatic esters are thought to be readily hydrolysed to the corresponding alcohols and acids which are then metabolized; isopropyl myristate is undoubtedly hydrolysed to normal metabolic products (Fassett, 1963). When myristic acid (as the ethyl ester) was fed to dogs,

storage

Isopropyl myristate is resistant to oxidation and hydrolysis, and does not become rancid. It should be stored in a well-closed container in a cool, dry place and protected from light.

Incompatibilities

When isopropyl myristate comes into contact with rubber, there is a drop in viscosity with concomitant swelling and partial dissolution of the rubber; contact with plastics, e.g. nylon and polyethylene, results in swelling. Isopropyl myristate is incompatible with hard paraffin, producing a granular mixture. It is also incompatible with strong oxidizing agents.

Regulatory Status

Included in the FDA Inactive Ingredients Database (otic, topical, transdermal, and vaginal preparations). Used in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.