110-27-0 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 110-27-0 differently. You can refer to the following data:
1. 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°C) is 0.85~0.86. it is used in many applications, including pharma, food and personal care product manufacturing.
2. Pure isopropyl myristate is virtually odorless, very slightly fatty, but not rancid
3. colourless liquid of low viscosity
4. 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.
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
Different sources of media describe the Uses of 110-27-0 differently. You can refer to the following data:
1. 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.
2. Isopropyl myristate is an emollient in cosmetic and pharmaceutical bases.
3. In cosmetic and topical medicinal Preparations where good absorption through the skin is desired. A jellied isopropyl myristate was marketed as Estergel (Merck & Co.) .
4. 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.
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.
Occurrence
Reported found in kumquat peel oil, papaya, starfruit, plum brandy, coriander seed and loquat
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.
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 110-27-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 110-27:
(5*1)+(4*1)+(3*0)+(2*2)+(1*7)=20
20 % 10 = 0
So 110-27-0 is a valid CAS Registry Number.
InChI:InChI=1/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
110-27-0Relevant articles and documents
Efficient, stable, and reusable Lewis acid-surfactant-combined catalyst: One-pot Biginelli and solvent-free esterification reactions
Qiu, Yunfeng,Sun, Hongnan,Ma, Zhuo,Xia, Wujiong
, p. 76 - 82 (2014)
Cerium(III) trislaurylsulfonate (Ce(LS)3), a Lewis acid and surfactant combined catalyst, was prepared and characterized by SEM, SEM-EDX, XRD, NMR, FT-IR, TG, and elemental analysis. Ce(LS)3 was found to be stable and efficient to catalyze one-pot Biginelli and solvent-free esterification reactions. Furthermore, Ce(LS)3 is easy to recycle after reaction by pouring into cold water and filtration. Present work will shed deep insight into the understanding of the catalytic nature of LASCs, and extend its application in important organic transformations.
Kinetics and mechanism of myristic acid and isopropyl alcohol esterification reaction with homogeneous and heterogeneous catalysts
Yalcinyuva, Tuncer,Deligoez, Hueseyin,Boz, Ismail,Guerkaynak, Mehmet Ali
, p. 136 - 144 (2008)
The reaction of myristic acid (MA) and isopropyl alcohol (IPA) was carried out by using both homogeneous and heterogeneous catalysts. For a homogeneously catalyzed system, the experimental data have been interpreted with a second order, using the power-law kinetic model, and a good agreement between the experimental data and the model has been obtained. In this approach, it was assumed that a protonated carboxylic acid is a possible reaction intermediate. After a mathematical model was proposed, reaction rate constants were computed by the Polymath program. For a heterogeneously catalyzed system, interestingly, no pore diffusion limitation was detected. The influences of initial molar ratios, catalyst loading and type, temperature, and water amount in the feed have been examined, as well as the effects of catalyst size for heterogeneous catalyst systems. Among used catalysts, p-toluene sulfonic acid (p-TSA) gave highest reaction rates. Kinetic parameters such as activation energy and frequency factor were determined from model fitting. Experimental K values were found to be 0.54 and 1.49 at 60°C and 80°C, respectively. Furthermore, activation energy and frequency factor at forward were calculated as 54.2 kJ mol-1 and 1828 L mol-1 s-1, respectively.
Use of Lecitase-Ultra immobilized on styrene-divinylbenzene beads as catalyst of esterification reactions: Effects of ultrasounds
Alves, Joana S.,Garcia-Galan, Cristina,Danelli, Daiane,Paludo, Natália,Barbosa, Oveimar,Rodrigues, Rafael C.,Fernandez-Lafuente, Roberto
, p. 27 - 32 (2015/08/06)
Abstract In this work it was evaluated for the first time, the ester synthesis catalyzed by the phospholipase Lecitase-Ultra immobilized styrene-divinylbenzene beads (MCI-Lecitase), comparing the mechanical stirring and the ultrasonic energy. It was studied the specificity of the enzyme using carboxylic acids from C4 to C18, as well as the effects of alcohol chain, organic solvents, biocatalyst content, reaction temperature and substrate concentration. Caprylic and myristic acids were those with the highest reaction rates and yields, using ethanol as substrate. The shorter the alcohol chain, the higher the enzyme activity. Regarding the secondary alcohols, while MCI-Lecitase had no activity versus isopropanol, using 2-pentanol the activity was similar to that with 1-pentanol. Comparing the agitation systems, MCI-Lecitase presented an initial reaction rate more than 2-times higher in the ultrasound-assisted reaction than under traditional mechanical stirring. Moreover, under ultrasonic energy the maximum rate was achieved using 0.5 M of substrates, while under mechanical stirring the maximum enzyme activity was reached at 0.3 M of substrates. Concerning the operational stability, MCI-Lecitase was quite unstable, losing its activity after 6 reaction cycles. By adding molecular sieves in the reaction medium, MCI-Lecitase retained 30% of its initial activity after 6 cycles.
Composition and method of preparing a tomato-based topical formulation for enhanced healing of burns, ultraviolet and radiation erythema
-
, (2013/03/26)
The present invention is a topical treatment. which can be in the form of cream, ointment, spray or other topically administered composition, which is used to enhance healing of burns, ultraviolet and radiation erythema. The treatment not only reduces pain and inflammation, prevents blistering, and maintains flexibility of the skin, but also accelerates the normal healing process.
