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Home > Encyclopedia > Isopropyl palmitate

Isopropyl palmitate

pharmaceutical raw materials
Isopropyl palmitate structure

Isopropyl palmitate 

structure
  • CAS No:

    142-91-6

  • Formula:

    C19H38O2

  • Chemical Name:

    Isopropyl palmitate

  • Synonyms:

    Hexadecanoic acid,1-methylethyl ester;Palmitic acid,isopropyl ester;Deltyl;Deltyl Prime;Emcol IP;Isopal;Isopropyl palmitate;Propal;Sinnoester PIT;Kessco IPP;Wickenol 111;Crodamol IPP;Emerest 2316;Isopalm;Stepan D 70;Isopropyl hexadecanoate;Nikkol IPP;IPP;1-Methylethyl hexadecanoate;Exceparl IPP;Estol 1517;IPP-EX;Palmsurf IPP 98;Lexol IPP;NSC 69169;Versagel MP 1600;Stepan IPP;Neoderm IPP;Nikkol IPP-EX;SR Crodamol IPP-LQ;IPP-R;Radia 7732

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

Liquid


DryPowder|Liquid


Isopropyl palmitate is a fatty acid ester obtained by the formal condensation of carboxy group of palmitic acid with propan-2-ol. Metabolite observed in cancer metabolism. It has a role as a human metabolite. It is a fatty acid ester and an isopropyl ester. It derives from a hexadecanoic acid.

Isopropyl palmitate Basic Attributes

298.5

298.50

1786567

205-571-1

8CRQ2TH63M

69169

DTXSID9027104

Colorless liquid

2915709000

Characteristics

26.3

8.2

DryPowder

0.8404 g/cm3 @ Temp: 38 °C

13.5 °C

160 °C @ Press: 2 Torr

>230 °F

1.443

Not miscible or difficult to mix with water.

2-8°C

5.59X10-5 mm Hg at 25 deg C (extrapolated)

Almost odorless

Henry's Law constant = 4.66X10-2 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.21X10-11 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

-

36/38-36/37/38

26-36

RT4900000

Xi

Stable.

P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362

H315

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.

Incompatible with nitrates. /Esters/

Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: isopropyl palmitate is included in skin protectant drug products.

European Commission, ESIS; IUCLID Dataset,Isopropyl Palmitate (142-91-6) (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/]

Not Classified

Combustible

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Direct contact may cause mild irritation /of the/ eye. Prolonged or repeated contact /with the skin/ may cause mild irritation...|A human skin irritant.

SEDIMENT: Isopropyl palmitate was detected (not quantified) in sediment collected from 3 sites (out of 7) in the German Bight in 1998(1).

Toxicity

... Oxaprozin, nimesulide, gliclazide, and ribavirin ... were selected to assess the enhancing activity of pre-treatment solutions consisting of isopropyl palmitate (IP) in ethanol (5%, 10%, 15%and 20%, w/w, respectively) across excised rat skin using Franz diffusion cells and HPLC detection. All pre-treatment solutions produced a significant increase in the flux and permeation of all four penetrants (p<0.001) and a relationship between penetrant lipophilicity and enhancement effect was observed. The general order of IP effectiveness at concentration was 20%>15%>10%>5% (w/w). The lag-time of drugs did not significantly change except for ribavirin.

LD50 Rabbit dermal > 5000 mg/kg|LD50 Rat oral >64.0 mL/kg|LD50 Mouse ip 100 mg/kg

Isopropyl palmitate's production and use as an emollient and emulsifier in cosmetics and personal care products(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4.0X10+4(SRC), determined from a structure estimation method(2), indicates that isopropyl palmitate is expected to be immobile in soil(SRC). Volatilization of isopropyl palmitate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.66X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Isopropyl palmitate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.59X10-5 mm Hg at 25 °C(4). Biodegradation may be an important environmental fate process for isopropyl palmitate, as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(5-7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 4.0X10+4(SRC), determined from a structure estimation method(2), indicates that isopropyl palmitate 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 4.66X10-2 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 5.1 hours and 6.8 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 11 months when adsorption is considered(6). According to a classification scheme(6), an estimated BCF of 910(SRC), from an estimated log Kow of 8.16(7) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). An estimated base-catalyzed second-order hydrolysis rate constant of 2.14X10-2 L/mole-sec(SRC) corresponds to half-lives of 10 years and 1 year at pH values of 7 and 8, respectively(8). Biodegradation may be an important environmental fate process for isopropyl palmitate, as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(9-11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl palmitate, which has a vapor pressure of 5.59X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase isopropyl palmitate 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 17 hours(SRC), calculated from its rate constant of 2.21X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase isopropyl palmitate may be removed from the air by wet or dry deposition(SRC). Isopropyl palmitate 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).

The rate constant for the vapor-phase reaction of isopropyl palmitate with photochemically-produced hydroxyl radicals has been estimated as 2.21X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 17 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 palmitate 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).

An estimated BCF of 910 was calculated in fish for isopropyl palmitate(SRC), using an estimated log Kow of 8.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of isopropyl palmitate can be estimated to be 4.0X10+4(SRC). According to a classification scheme(2), this estimated Koc value suggests that isopropyl palmitate is expected to be immobile in soil.

The Henry's Law constant for isopropyl palmitate is estimated as 4.66X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that isopropyl palmitate 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 5.1 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 6.8 days(SRC). Isopropyl palmitate'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 11 months when adsorption is considered(3). Isopropyl palmitate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.59X10-5 mm Hg(4).

According to the 2006 TSCA Inventory Update Report, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of isopropyl palmitate is 100-999; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 200,948 workers (162,709 of these were female) were potentially exposed to isopropyl palmitate in the US(1). Occupational exposure to isopropyl palmitate may occur through dermal contact with this compound at workplaces where isopropyl palmitate is produced or used. Use data indicate that the general population may be exposed to isopropyl palmitate via dermal contact with cosmetics and personal care products containing isopropyl palmitate(SRC).

Drug Information

Several pharmacopoeias recommend the membrane filtration method for the sterility test of ophthalmic ointments. Isopropyl myristate, a fatty acid ester that exhibits high toxicity mainly against Gram-negative microorganisms, is indicated as a solvent for ointments.|... Due to their distinct advantages such as enhanced drug solubility, thermodynamic stability, facile preparation, and low cost, uses and applications of microemulsions have been numerous. Recently, there is a surge in the exploration of microemulsion for transdermal drug delivery for their ability to incorporate both hydrophilic (5-fluorouracil, apomorphine hydrochloride, diphenhydramine hydrochloride, tetracaine hydrochloride, and methotrexate) and lipophilic drugs (estradiol, finasteride, ketoprofen, meloxicam, felodipine, and triptolide) and enhance their permeation.... Besides surfactants, oils can also act as penetration enhancers (oleic acid, linoleic acid, isopropyl myristate, isopropyl palmitate, etc.). ...

Cosmetics continue to be used by acne-prone individuals. ... The data presented were gleaned from the rabbit ear assay, which is not an ideal animal model but is the best we have. If an ingredient is negative in the rabbit ear assay, we feel it is safe on the acne-prone skin. A strong, positive ingredient or cosmetic should be avoided. Ingredient offenders include isopropyl myristate and its analogs, such as isopropyl palmitate, isopropyl isostearate, butyl stearate, isostearyl neopentanoate, myristyl myristate, decyl oleate, octyl stearate, octyl palmitate or isocetyl stearate, and new introductions by the cosmetic industry, such as propylene glycol-2 (PPG-2) myristyl propionate...

Palmitic acid is a component of most animal fats, comprising up to 50% of them. The acid is normally metabolized by beta-oxidation or stored in fat deposits, as are most of the alcohol moieties after they are oxidized to fatty acids. The terminal groups of the iso-alcohols may yield acetone for excretion or for further metabolism. /Palmitic acid/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

/HUMAN EXPOSURE STUDIES/ Twenty-five adult subjects of unspecified age, sex, and race participated in a photo-contact allergenicity study of a bath oil containing 45.6% isopropyl palmitate. Applications of 5 uL/sq cm of the undiluted test material were repeated twice a week for a total of six applications. The test site remained occluded for 24 hours after each application, and the area was irradiated with a Xenon Solar Simulator (25-30 mW/sq cm) following the removal of each patch. A challenge application with irradiation was made 10 days after the last induction exposure. No instances of photocontact allergenicity were reported, and it was concluded that this formulation is "unlikely to present a risk of photo-contact allergenicity under conditions of normal use."|/HUMAN EXPOSURE STUDIES/ A phototoxicity study of a bath oil formulation containing 45.6% isopropyl palmitate was conducted on 10 normal adult subjects of unreported age, sex, and color. Applications of 5 uL/sq cm of the undiluted test material were made under occlusive patches, and the application sites were irradiated with a Xenon Solar Simulator (25-30 mW/sq cm) after six and 24 hours of contact. No instances of phototoxicity were reported. It was concluded that this formulation is "unlikely to present a risk of phototoxicity under conditions of normal intended use."|/HUMAN EXPOSURE STUDIES/ Kligman's modified maximization procedure was used on 25 subjects to test an undiluted sample of a bath oil formulation containing 45.6% isopropyl palmitate. All patch tests were negative, and it was concluded that, 'based on the maximization scale, the material would be considered the lowest grade, weak potential sensitizer and would be unlikely to present a risk of contact sensitization under conditions of normal intended use."|/HUMAN EXPOSURE STUDIES/ One hundred two men and women of unspecified race participated in a modified Draize-Shelanski repeated insult patch test which was use to ascertain the irritation and sensitization potential of isopropyl palmitate. Approximately 0.1 mL of undiluted isopropyl Palmitate was dispersed onto an absorbent non-woven cotton swatch, 20 x 20 mm, which was then applied to the upper back under an adhesive bandage. The patches were applied three time a week for three weeks and were left in place for 24 hours at each application. Reactions were scored on a 0-4 irritancy scale 24 hours after patch removal. Seventeen days after the last induction patch was removed, a 24-hour challenge application of the test material was made; 24 an 48 hours following the removal of these applications, the challenge reactions were graded. Barely perceptible erythema was noted in three subjects after the second induction insult. All other scores in the induction and challenge periods were 0.0, and it was concluded that isopropyl palmitate did not demonstrate potential for inducing allergic sensitization.|For more Human Toxicity Excerpts (Complete) data for Isopropyl palmitate (8 total), please visit the HSDB record page.

isopropyl palmitate

Isopropyl palmitate Use and Manufacturing

Methods of Manufacturing

Add 1 mol of hexadecanoic acid to the reaction kettle, add 1.5 mol of isopropanol, stir to dissolve, add a catalyst amount of sulfuric acid and reflux for 10 h under stirring, distill out excess isopropanol and water. After cooling, add 5% Na2CO3 aqueous solution to neutralize, separate the water layer, and then decompress and dehydrate to obtain the product.

Uses

Widely used in pharmaceutical industry and cosmetic industry


Solvents (which become part of product formulation or mixture)


Personal care products

Production

1,000,000 - 10,000,000 lb|(1972) 2.93X10+9 GRAMS|(1975) 7.67X10+8 GRAMS|(1984) 2.47X10+9 g/PALMITIC ACID ESTERS/|Hexadecanoic 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).|For more U.S. Production (Complete) data for Isopropyl palmitate (6 total), please visit the HSDB record page.

BELIEVED TO BE USED ALMOST EXCLUSIVELY AS AN EMOLLIENT & EMULSIFIER (1976)

Soap, cleaning compound, and toilet preparation manufacturing|Hexadecanoic acid, 1-methylethyl ester: ACTIVE|... A large number of oils and surfactants are available, which can be used as components of microemulsion systems for transdermal delivery but their toxicity, irritation potential, and unclear mechanism of action limit their use. Besides surfactants, oils can also act as penetration enhancers (oleic acid, linoleic acid, isopropyl myristate, isopropyl palmitate, etc.). ...|Isopropyl palmitate may be used in cosmetics and personal care products marketed in Europe ... provided the fatty acids and fatty alcohols are not of animal origin.

EPA Safer Chemical Functional Use Classes -> Emollients|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives -> Flavoring Agents|Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]|Cosmetics -> Antistatic; Binding; Emollient; Skin conditioning; Solvent

Flavoring Agents

Computed Properties

Molecular Weight:298.5
XLogP3:8.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:16
Exact Mass:298.287180451
Monoisotopic Mass:298.287180451
Topological Polar Surface Area:26.3
Heavy Atom Count:21
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Emollient and solvent; may have comedogenic potential in sensitive individuals

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • IOI ACIDCHEM SDN BHD

    United States United States
    Active
  • Zhongnuo Kailin Pharmaceutical Development (Suzhou) Co., Ltd.

    China China
    Inactive
  • Jinsheng Dagong Pharmaceutical (Qidong) Co., Ltd.

    China China
    Inactive

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