Myristic acid

228.37

228.37

508624

208-875-2

0I3V7S25AW

5028

DTXSID6021666

C68393

Oily, white, crystalline solid|Crystals from methanol|Leaflets from ethyl ether

29159080

37.3

5.3

White Flakes, Powder, Chunks or Crystalline Mass

0.8622 g/cm³ @ Temp: 54 °C

58.5 °C

326.2 °C

>230 °F

1.451

H2O: <0.1 g/100 mL at 18 ºC

−20°C

<0.01 hPa (20 °C)

LD50 i.v. in mice: 432.6 mg/kg (Or, Wretlind)

Combustible

The odor should be faint with no rancidity.

Henry's Law constant = 4.95X10-7 atm-cu m/mol at 25 °C (est)

pKa = 4.90

159.21 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

Neutralization value: 245.68|Heat of fusion = 44.8 kJ/mol; specific heat = 1.60 J/g (for the solid)|Hydroxyl radical reaction rate constant = 1.68X10-11 cu-cm/molec sec at 25 °C (est)

Insoluble in water.

Acids, Carboxylic

TETRADECANOIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

-8,721.4 kJ/mol

NONH for all modes of transport

-

36/37/38-38

24/25

QH4375000

Xi

Stable. Incompatible with strong oxidizing agents, bases.

P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, P501

H315

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Myristic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.

Cosmetic Ingredient Review; Final Report of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; June 2005.|European Chemicals Bureau; IUCLID Dataset, Myristic acid, pure (CAS #544-63-8) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of January 24, 2008.

This chemical is probably combustible. (NTP, 1992)

|Danger|H315 (31.66%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P310, P321, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 2686 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Combustible

Combustible

Several bar soap formulations with concentrations of Myristic Acid of 10, 22.1, and 91% were tested for skin irritation using 16 human subjects. A 0.2 mL volume of an 8% aqueous preparation was applied to the ventral skin of the forearm under occlusive patches once daily for 5 days using the Frosch-Kligman soap chamber test. The formulations were considered "slightly" to "moderately irritating" and erythema scores were 1.41, 1.73, and 1.95 on a scale of 0 to 5 for the formulations containing 10, 22.1, and 91% myristic acid, respectively.

Myristic acid was detected in aqueous industrial effluent extracts collected between Nov 1979-81 in the following industrial categories (concn in one effluent extract): paint and ink (17 ng/uL); printing and publishing (23 ng/uL); textile mills (4 ng/uL); electronics (5513 ng/uL); amusements and athletic goods (470 ng/uL); and publicly owned treatment works at an unknown concn(1). Myristic acid was identified in the effluent of two publicly owned treatment works (POTW) facilities located in an industrial area of NJ and a rural area of NJ at estimated concns of 5 and 69 ppb, respectively(2). Grab samples of the final effluent from the Addison and Decatur, IL POTWs, obtained in April and June 1980, respectively, were found to contain myristic acid at unreported concns(3). A sample of final effluent, 50% grab and 50% 8 hour composite, obtained from the St. Charles, IL POTW in March 1980, was found to contain myristic acid at an unreported concn(3). Myristic acid was detected in the bleaching effluent from straw pulping and in the combined mill effluent from a straw pulp mill in Denmark at unreported concns(4). Myristic acid was detected in Los Angeles County wastewater treatment plant effluent, collected between Nov 1980 and Aug 1981, at a concn of 1200 ug/L(5). Myristic acid was identified in vapor at concns of 100 to 300 ng/cu m and on particles at concns of 8 to 600 ng/g emitted during combustion of coal at the Ames power plant in Iowa(6). Wastewater from two kraft paper mills in Georgia sampled in March 1972 were found to contain approximately 0.010 and 0.020 mg/L myristic acid (identified as the methyl derivative)(7). An effluent-irrigated citrus grove near Glil-Yam, Israel was found to contain 15 ppb myristic acid at a depth of 20 m in the unsaturated soil zone(8). Myristic acid was identified in the acidic fraction of 5 to 7 day sewage and sludge composites from the Iona Island Sewage Treatment Plant, British Columbia at concns ranging from 23 to 150 ug/L(9). Myristic acid was found at a maximum concn of 109 ng/L in groundwater contaminated by industrial wastes near Barcelona, Spain(10). The mean myristic acid concn in discharged effluent waters (24 hour composite samples) from a pulp mill producing 75,000 tons of pulp annually near Kawerau, New Zealand, in Nov to Dec 1991 and Jan to Feb 1992, was 41 ppb(11). Myristic acid was detected in two effluent samples taken from a sewage treatment plant in Prestwich, North West England, at a mean concn of 4.05 ug/L(12). Myristic acid has been identified in leachate samples collected from the interior of a municipal landfill situated in Gryta, Vasteras, Sweden in May 1990, concn unknown(13).|Fine particle aerosol emission rates of myristic acid from heavy-duty diesel trucks, noncatalyst-equipped, and catalyst-equipped automobiles were 45.7, 1.7, and 11.9 ug/km, respectively(1). Myristic acid was detected in road dust particles collected from paved streets in a residential area of Pasadena, CA in May 1988 at a concn of 171.8 ug/g of particle sample; brake lining particles at a concn of 8.1 ug/g of particle sample; and tire wear particles at a concn of 634.5 ug/g of particle sample(2). Myristic acid was emitted from medium duty diesel trucks at 5.3 ug/km(3).|Fine particle emission rates for myristic acid from a natural gas-fired water heater and a natural gas-fired space heater were determined(1). A HEPA-filtered dilution air sample emission rate for myristic acid was determined to be 3.7 pg/kJ; the emission rate for myristic acid through the first filter was determined to be 59.6 pg/kJ; the emission rate for myristic acid through the backup filter was 29.9 pg/kJ(1). Myristic acid was found in candle smoke from paraffin and beeswax at 0.61 and 0.59 mg/g of organic compounds(2). Myristic acid was found in wood smoke from red maple(3), red oak(3), paper birch(3), white pine(3), hemlock(3), balsam fir(3), yellow poplar(4), white ash(4), sweet gum(4), mockernut hickory(4), loblolly pine(4), and slash pine(4). Myristic acid was detected in wood smoke from pine, oak and synthetic logs at 1.74, 4.89 and 2.27 mg/kg of wood burnt(5). Myristic acid was found at 0.764, 1.36 and 1.12 mg/kg of burnt pine, oak and eucalyptus wood, respectively, in the particulate phase and at 0.357 mg/kg of burnt pine in the gas phase(6). Myristic acid was found in extract from a pine wood burning campfire at 170 ng/g(7). Myristic acid was found in the fine aerosols from boilers burning number 2 distillate fuel oil at a rate of 879.8 pg/kJ (burning at 58% capacity with 6.5% excess oxygen in stack gases) and a rate of 283.8 pg/kJ (burning at 54% capacity with 7.1% excess oxygen in stack gases)(8). Myristic acid was found at 894.9 ug/g from heated roofing tar pot fumes(9). Myristic acid was found at 4040 and 17,700 ug/kg in the gas and particulate matter from charbroiling meat(10). Myristic acid was detected in the smoke from charring/burning of chitin biopolymers(11).|IN THE FATS EXTRACTED FROM TANNERY & MUNICIPAL SLUDGE, MYRISTIC ACID WAS ONE OF THE MINOR COMPONENTS IDENTIFIED.|MYRISTIC ACID WAS IDENTIFIED IN THE SLUDGE EXTRACTIONS FROM POINT EDWARD PLANT IN CANADA. THE SLUDGE INHIBITED GROWTH OF ORCHARD GRASS IN LAND DISPOSAL.

SEDIMENT: Myristic acid was detected (as the trimethylsilyl derivative), but not quantitated, in sediment samples collected from Dokai Bay, Japan on Sept 28 1990(1). Myristic acid was identified in sediment samples taken Sept 1995 at the mouth of 3 rivers and in 1 port in Niigata, Japan(2).

URBAN/SUBURBAN: The average ambient annual concns of myristic acid in fine particles collected from West Los Angeles, downtown Los Angeles, Pasadena, Rubidoux, and San Nicolas Island, CA in 1982 were 14.4, 19.7, 22.2, 22.8, and 2.73 ng/cu m, respectively(1). Myristic acid was identified in air samples collected along the Niagara River in Sept 1982 at an unreported concn(2). Myristic acid was detected in atmospheric aerosols collected from Tsukuba, Japan in April 1985(3). Myristic acid had an average concentration of 22.1 ng/cu m in 4 urban sites from southern CA from samples taken Sept 8-9, 1993(4). Myristic acid was found in Vienna, Austria at 36 ng/cu m from samples taken June 1997(5). A southern CA atmospheric study gave concns of myristic acid of 6.37, 7.59, 5.59, 6.61 and 8.67 ng/cu m for Long Beach, Mira Loma, Riverside, San Dimas and Upland, respectively(6). Atmospheric concns of myristic acid in Algiers City, Algeria, May 27 to Sept 2, 1998 ranged from 0.2 to 4.7 ng/cu m(7). Atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Fresno, CA had myristic acid concns of 9.42 and 3.71 ng/cu m and samples taken in Bakersfield had 4.01 and 4.03 ng/cu m, respectively(8). Myristic acid was found in atmospheric samples from North Birmingham, AL, Jefferson Street, GA, Gulfport, MS, and Pensacola, FL at concns of 0.50, 0.67, 0.95, and 0.10 ng/cu m, respectively, and was undetected at OLF#8, a suburban site located about 20 km northwest of downtown Pensacola, FL(9).|RURAL/REMOTE: Myristic acid was found on aerosols obtained over the southern North Atlantic Ocean and Chacaltaya, Bolivia at mean concns of 1.8 and 1.6 ng/cu m, respectively(1). Myristic acid was detected at an unreported concn in forest air samples collected in a 45 year old spruce forest in 1988 in Eggegebirge, North-Rhine Westphalia(2). Myristic acid was measured in the gas form at 54.79, 15.59 and 11.99 ng/cu m and in the aerosol form at 10.52, 4.02 and 4.86 ng/cu m at 6am - 12 pm, 12-6 pm and 6 pm-6 am, respectively, in samples taken July 27 to August 8, 1998 in the Pertouli area of the Agrafa Mountains, Greece(3). Myristic acid was found at 4.0 ng/cu m from Sonnblick Observatory, Austria in samples taken May 1997(4). A southern CA atmospheric study gave concns of myristic acid of 2.72, 5.65, 6.69, 3.6, 5.48, 4.41 and 4.9 ng/cu m for Lompoc, Alpine, Atascadero, Lake Arrowhead, Lake Elsinore, Lancaster and Santa Maria, respectively(5). Atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Kern Wildlife Refuge, CA had 2.17 and 4.96 ng/cu m of myristic acid(6). Myristic acid was found at a concn of 1.21 ng/cu m in Centreville, AL, and was not detected in Yorkville, GA and Oak Grove, MS(7).

Settled household dust samples collected from 12 households in three urban areas of central Finland contained myristic acid, concentration not quantified(1). Myristic acid was found in unburned paraffin at 0.60 mg/g of wax and not detected in unburned beeswax(2).|ONE HUNDRED CIGARETTES EACH OF MEXICAN & TURKISH MARIJUANA & STANDARD TOBACCO PREPARED FROM EQUAL WT, WERE SMOKED WITH A STANDARD SMOKING MACHINE & APPROX 35-ML PUFF VCL FOR A DURATION OF 2 SEC @ A FREQUENCY OF 1 MIN. TETRADECANOIC ACID WAS ONE OF THE COMPOUNDS IDENTIFIED BY CAPILLARY GAS CHROMATOGRAPHY--MASS SPECTROMETRY.

CELL GROWTH OF SACCHAROMYCES CEREVISIAE ATCC 12341 WAS INHIBITED BY THE ANTIBIOTIC CERULENIN, A SPECIFIC INHIBITOR OF FATTY ACID & STEROL SYNTHESIS, WAS REVERSED BY MYRISTIC ACID IN A 14:0 RATIO. IT PRODUCED OVER 70% REVERSION OF CELL GROWTH INHIBITION. MYRISTIC ACID TAKEN INTO THE CELLS WAS METABOLIZED & SYNTHESIZED INTO FATTY ACIDS OF A COMPOSITION CLOSELY SIMILAR TO THAT OF THE NATIVE FATTY ACIDS, & THIS WAS CONSIDERED TO BE RESPONSIBLE FOR THE RECOVERY OF CELL GROWTH.|... Reports the results of a 6 week feeding study in rats exposed to a diet that contained 50% fat as caprilic and myristic acids. This resulted in hyperlipidemia but no other effects were reported. ... Describes the results of a 90 day feeding study in rabbits that received 25 mg/kg/day of hydrogenated coconut oil (containing glycerides of lauric, capric, myristic, palmitic, and oleic acids). Rabbits exhibited hypercholesteremia, increased plasma triglycerides and fatty acids, accumulation of cholesterol in the liver and aorta, and alteration of hepatic enzyme activity.|The effect of dietary myristic acid, fed as trimyristin either mixed or interesterified with groundnut oil, on serum cholesterol levels was examined in rats. Incorporation of trimyristin in the oil resulted in marked incr in serum cholesterol levels, compared with rats fed groundnut oil only, although a direct relation between serum cholesterol & the myristic acid content of the dietary fat was not apparent. /Ttrimyristin/|... Associations between serum fatty acid composition as well as fatty acid intakes and prostate cancer risk were examined ... The cohort included 29,133 male smokers aged 50-69 years. During 5-8 years of follow-up, 246 prostate cancer cases were diagnosed. One control was selected and matched by age (1 month) for each case from the cohort subjects alive and free of prostate cancer at the time the case was diagnosed. This study included 198 case-control pairs with baseline serum sample available for both. Fatty acids of serum cholesterol esters were measured as a percentage of total fatty acids, using capillary gas chromatography. Intakes of fatty acids were assessed from a validated self-administered dietary questionnaire ... Twofold risk was found in the highest quartile of serum myristic acid compared with the lowest quartile (odds ratio, 1.93; 95% confidence interval, 1.02-3.64) ...

LD50 Rat oral >10000 mg/kg /C12: 2.7%, C14 95.4%, C16 1.9%/|LD50 Mouse iv 43 mg/kg

/AQUATIC SPECIES/ A non-photosynthetic mutant of /Euglena gracilis (algae)/ strain Z was used /in/ determination of growth /(biomass)/ at ... /5 g/L of myristic acid with/ continuous shaking /at/ 27 °C, pH 3.3. Test substance floated on surface in initial phase of growth, but insol material was consumed during growth. Previous adaptation was required for growth. Stationary phase was reached after 5 days.|/AQUATIC SPECIES/ No mortality /of Hyale plumulosa (gammarus)/ occured at saturation /of myristic acid/ at 25 + / - 2 °C, pH 8.2, salinity 25 ppt for 48 hr in a saltwater test.|/OTHER TERRESTRIAL SPECIES/ Beauveria bassiana (fungus) was incubated in complex medium at 25 °C for 24 hr with 500 mg/L myristic acid (acetone as solvent). After the addition of test substances pH was adjusted to 6.0 with NaOH. Germination of conidia were 75% for myristic acid and 71% for acetone control.|/OTHER TERRESTRIAL SPECIES/ Paecilomyces fumoso-roseus (fungus) was incubated in complex medium at 25 °C for 24 hr with 500 mg/L myristic acid (acetone as solvent). After the addition of test substances pH was adjusted to 6.0 with NaOH. Germination of conidia were 50% for myristic acid and 71% for acetone control.|/OTHER TERRESTRIAL SPECIES/ Myristic acid was included at a final concn of 2.5% (25 g/L) in a diet containing amino acids, vitamins and glucose and fed to /Pseudosarcophaga affinis (not soil dwelling arthropod)/ larvae at 23 °C. There were 1.7% mortality after 24 hr and 3.1% after 7 days. /Potassium salt/

TETRADECANOIC ACID WAS ONE OF 10 FATTY ACIDS ISOLATED FROM THE NATURAL SEX PHEROMONES OF MALE MEDITERRANEAN FRUIT FLY & IDENTIFIED.|MYRISTIC ACID WAS ONE OF 36 CONSTITUENTS DETECTED IN THE VOLATILE OIL FROM DILL SEED.|MYRISTIC ACID WAS ONE OF THE CONSTITUENTS FOUND IN MYRISTICA WOMERSLEYI OIL.|MYRISTIC ACID WAS FOUND TO BE A MINOR COMPONENT OF THE STEAM VOLATILE PART OF THE OIL FROM CRUSHED AIR-DRIED SEEDS OF ELAEOCARPUS GANITRUS.|For more Natural Pollution Sources (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.

Myristic acid's production and use as an ingredient in soaps and shaving creams, in lubricants, in coatings for anodized aluminum(1), in cosmetics, in the synthesis of esters for flavors and perfumes, and as a component of food-grade additives(2) 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 50,000 for the free acid(SRC), determined from a log Kow of 6.11(2) and a regression-derived equation(3), indicates that undissociated myristic acid is expected to be immobile in soil(SRC). The pKa of myristic acid is 4.90(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of myristic acid from moist soil surfaces is not expected to be an important fate process(SRC) given the pKa(4). Myristic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.4X10-6 mm Hg(6). Myristic acid reached 2% of its theoretical BOD over 5 days in a sewage inoculum(7); a half-life of 20 hours was observed for the sodium salt in Warburg tests using an unacclimated sludge inoculum at 25 °C(8).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 50,000 for the free acid(SRC), determined from a log Kow of 6.11(2) and a regression-derived equation(3), indicates that undissociated myristic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.90(4) indicates myristic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 56(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Myristic acid reached 2% of its theoretical BOD over 5 days in a sewage inoculum(8); a half-life of 20 hours was observed for the sodium salt in Warburg tests using an unacclimated sludge inoculum at 25 °C(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), myristic acid, which has a vapor pressure of 1.4X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase myristic acid 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 23 hours(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase myristic acid may be removed from the air by wet or dry deposition(SRC). Myristic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of myristic acid with photochemically-produced hydroxyl radicals has been estimated as 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 23 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Myristic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Myristic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(2).

An estimated BCF of 56 was calculated in fish for myristic acid(SRC), using a log Kow of 6.11(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate, provided the compound is not metabolized by the organism(SRC).

The Koc of myristic acid is estimated as 50,000 fro the free acid(SRC), using a log Kow of 6.11(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that undissociated myristic acid is expected to be immobile in soil. The pKa of myristic acid is 4.90(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

A pKa of 4.90(1) indicates myristic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces and moist soil is not expected to be an important fate process(2). Myristic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.4X10-6 mm Hg(3).

DRINKING WATER: Myristic acid was detected, but not quantitated, in extracts of British drinking water derived from lowland river water and groundwater(1). Myristic acid was detected in five treated water samples taken from sampling taps in unspecified treatment works at unreported concns(2). Myristic acid was quantitatively detected in drinking water in: Poplarville, MS in March 1979; Cincinnati, OH in Oct 1978 and Jan 1980; Miami, FL in Feb 1976; New Orleans, LA in Jan 1976; Ottumwa, IA in Sept 1976; and Seattle, WA in Nov 1976(3). Myristic acid was identified, but not quantified, in raw and treated water samples from a chlorine dioxide pilot plant in Evansville, IN(4). Myristic acid was identified as an ozone disinfection by-product in drinking water samples from a pilot plant in Jefferson Parish, LA which uses Mississippi River as the raw water source; samples were collected following 4 rounds of ozonation treatment performed in January, 1994, August 1994, May 1995, and September 1996(5).|SURFACE WATER: Water samples taken from the Po and Lambro rivers, Italy, between Sept 1988 and Jan 1990, were found to contain myristic acid at unspecified concns(1). River water samples taken in 1984 from the River Irwell and the River Etherow of North West England contained myristic acid at a mean concn of 8.4 and 9.1 ug/L, respectively; a sample from the River Mersey in North West England contained myristic acid at a concn of 1.8 ug/L(2). Myristic acid was detected at a concn of 0.2 and 0.3 ppb in water samples collected on a flood tide on June 23, 1980 from the Inner Harbor Navigation Canal, Lake Pontchartain, New Orleans, LA collected at depths of 1.5 and 10 m, respectively(3). Myristic acid was detected in water samples taken from Clear Lake, CA on April 5, 1994 at an unreported concn(4). Myristic acid was detected, but not quantified, in unspecified samples taken from the Lower Fox River system, WI between 1976-77(5).|RAIN/SNOW/FOG: Myristic acid was identified at 8 of 10 snow sample sites; 0.83 ug/kg at Neulaniemi (Kuopio, Finland), 0.21 ug/kg at Nellim (Lapland, Finland), 0.17 ug/kg at Muonio (Lapland, Finland), 0.75 ug/kg at Levi (Lapland, Finland), 0.12 ug/kg at Butovo (Moscow, Russia), 0.63 ug/kg at Moscow State University (Moscow, Russia), 2.36 ug/kg at Shuch'e (Volga River, Russia) and 2.36 ug/kg at Baikal'sk (Lake Baikal, Siberia)(1). Myristic acid was detected in surface Antarctic snow in one sample, taken during 1990-91, at a median concn of 3630 ng/L(2).

Myristic acid has been identified as a volatile flavor component of mutton and beef(1). Myristic acid was identified as a volatile constituent of blended nectarine skin and pulp(2). Aerosol emission rates of myristic acid from charbroiling hamburger were 17.1 mg/kg of meat cooked for extra lean hamburger (approx. 10.0% fat) and 87.0 mg/kg of meat cooked for regular hamburger (approx. 21% fat); frying hamburger meat led to a myristic acid emission rate of 6.2 mg/kg of meat cooked(3). Myristic acid was found in paprika oleoresin at <0.1 mg/kg(4).

ENVIRONMENTAL: The myristic acid content in milk fat ranges from 15.56 to 22.62% of total acids, with an average myristic acid content of 19.78% of total acids(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 72,432 workers (29,696 of these were female) were potentially exposed to myristic acid in the US(1). Occupational exposure to myristic acid may occur through dermal contact with this compound at workplaces where myristic acid is produced or used. Monitoring data indicate that the general population may be exposed to myristic acid via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound or other products containing myristic acid(SRC).

The myristic acid content in milk fat ranges from 15.56 to 22.62% of total acids, with an average myristic acid content of 19.78% of total acids(1).

/EXPL THER/ The antitumor activity of some fatty acids was studied in vivo using Ehrlich ascites and solid carcinomas implanted into Swiss albino mice of Strain ddY. Suspensions of the fatty acids in Tween 80 and distilled water were admin 24 hr after tumor implantation and were continued for 5 consecutive days. Doses of 8 mg/mouse/day of myristic aicd were effective inhibitors against Ehrlich ascites tumor, more than doubling the survival time of treated versus control mice.|EXPTL THER: MYRISTIC ACID WAS AMONG 11 FATTY ACIDS TESTED AGAINST EHRLICH ASCITES CARCINOMA. EACH AGENT WAS ADMIN TO MICE BY INTRAPERITONEAL INJECTION AT THE DOSE OF 400 MG/KG/DAY 5 TIMES & THE EFFECT WAS EVALUATED WITH TOTAL PACKED CELL VOLUME RATIO ON THE 7TH DAY AFTER THE TUMOR IMPLANTATION. MYRISTIC ACID WAS HIGHLY EFFECTIVE AGAINST THE TUMOR.|/EXP THER/ Liposomes consisting of dicetyl-phosphate, cholesterol, lecithin and stearic or myristic or oleic acid, exert a protective effect for mice against experimental infection by Salmonella typhimurium, and delay both the onset and mortality B16 melanoma in these animals. Liposomes labelled with 3H-myristic acid were used as probes in the spleen and liver. ... the treatment schedule rather than route of administration of liposomes, is important. The results show that in order to induce protection, preventive treatment must start at least three days before. Longer treatments do not increase the degree of protection, and treatments started at the same time as, or following experimental infection or tumor transplantation, have no effect.|/EXPTL THER/ ... The purpose of this study was to examine the effect of moderate intakes of myristic acid (MA) associated with recommended intake of alpha-linolenic acid (ALA) on lecithin-cholesterol acyltransferase (LCAT) activity in humans. Two experimental diets were tested for 3 months each. Diet 1-MA 1.2% of total energy (TE) and ALA 0.9% TE, diet 2-MA 1.8% and ALA 0.9% TE; a control diet (MA 1.2% and ALA 0.4% TE) was given 3 months before diet 1 and diet 2. The endogenous activity of LCAT was determined at completion of each diet. Compared with the control diet (13.2 +/- 3.1 umol CE/(L x h)), LCAT activity increased significantly (P < 0.001) with diet 1 (24.2 +/- 3.6 umol CE/(L x h)) and diet 2 (33.3 +/- 7.4 micromol CE/(L x h)); the increase observed with diet 2 was significantly (P < 0.001) greater than that due to diet 1. These results suggest that ALA (from rapeseed oil, mainly in sn-2 position) and MA (from dairy fat, mainly in sn-2 position) favor LCAT activity, by respective increases of 83 and 38%. When they are supplied together, a complementary effect was observed (average increase of 152%). Moreover, these observations were associated with a decrease of the ratio of total to HDL-cholesterol. In conclusion, /the/results suggest that moderate supply of MA (1.8% TE) associated with the recommended intake of ALA (0.9% TE) contributes to improve LCAT activity.|For more Therapeutic Uses (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.

IN NORMAL RATS, HIGHER RADIOACTIVITY WAS FOUND IN HEART, LIVER, SPLEEN & ADRENALS 2 HR AFTER ADMIN OF PALMITIC ACID THAN AFTER ADMIN OF MYRISTIC ACID. IN GRANULOMA POUCH-BEARING RATS, RADIOACTIVITY SHOWED HIGHER DISTRIBUTION IN ADRENALS & POUCH EXUDATE 2 HR AFTER PALMITIC ACID ADMIN, COMPARED TO THOSE GIVEN MYRISTIC ACID. RADIOACTIVITY IN THE POUCH WALL WAS GREATER IN RATS GIVEN MYRISTIC ACID.|Fatty acids originating from adipose tissue stores are either bound to serum albumin or remain unesterified in the blood.|Oleic, Palmitic, Myristic, and Stearic Acids are primarily transported via the lymphatic system, and Lauric Acid is transported by the lymphatic and (as a free fatty acid) portal systems.

IN RATS FED COCONUT OIL, MYRISTIC ACID WAS ONE OF THE PRINCIPAL FATTY ACIDS PRESENT IN HEPATIC AND ADIPOSE TISSUE TRIGLYCERIDES. ETHANOL INCR THE PROPORTIONS OF MYRISTIC ACID.|IN ADDITION TO METABOLISM BY BETA-OXIDATION, MYRISTIC ACID HAS BEEN SHOWN TO UNDERGO CHAIN ELONGATION TO PALMITIC & STEARIC ACIDS, DESATURATION TO MYRISTOLEIC ACID & INCORPORATION INTO HEPATIC NEUTRAL LIPIDS (& TO A LESSER EXTENT, PHOSPHOLIPIDS).|THE CONVERSION OF SATURATED FATTY ACIDS TO MONOUNSATURATED FATTY ACIDS BY THE 9000 X G SUPERNATANT RAT LIVER HOMOGENATE WAS LESS FOR MYRISTIC ACID THAN FOR PALMITIC ACID. THESE FATTY ACIDS PRODUCED ONLY DELTA9-MONOENOIC ACIDS OF THE SAME CHAIN LENGTH.|MYRISTATE INCORPORATED FROM (14)C-LABELED ACETATE WAS PREFERENTIALLY ESTERIFIED INTO TRIGLYCERIDE, WHEREAS THE LABELED STEARATE WAS CONVERTED INTO PHOSPHOLIPIDS IN THE ISOLATED RAT ADIPOSE CELLS.|For more Metabolism/Metabolites (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.|Tetradecanoic acid has known human metabolites that include 13-Hydroxytetradecanoic acid.

... The specific hypothesis tested was that free fatty acid association with CD36, a class B scavenger receptor, induces the activation of endothelial nitric-oxide synthase (eNOS). A human microvascular endothelial cell line and a transfected Chinese hamster ovary cell system were used to determine which free fatty acids stimulate eNOS. Surprisingly, only myristic acid, and to a lesser extent palmitic acid, stimulated eNOS. The stimulation of eNOS was dose- and time-dependent. Competition experiments with other free fatty acids and with a CD36-blocking antibody demonstrated that the effects of myristic acid on eNOS required association with CD36. Further mechanistic studies demonstrated that the effects of myristic acid on eNOS function were not dependent on PI 3-kinase, Akt kinase, or calcium. Pharmacological studies and dominant negative constructs were used to demonstrate that myristic acid/CD36 stimulation of eNOS activity was dependent on the activation of AMP kinase. These data demonstrate an unexpected link among myristic acid, CD36, AMP kinase, and eNOS activity.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes. ACUTE/CHRONIC HAZARDS: This compound may cause irritation of the skin and eyes. When heated to decomposition it emits acrid smoke and fumes. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Organic acids and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. 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 ... . 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. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|/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. Early intubation, at the first sign of upper airway obstruction, may be necessary. 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 (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/HUMAN EXPOSURE STUDIES/ In an SIOPT (single insult occlusive patch test), commercial grade myristic acid produced no irritation in 17, mild erythema in 2, and moderate erythema in 1 of 20 panelists. The primary irritation index was 0.2, and myristic acid was considered "practically nonirritating."|/HUMAN EXPOSURE STUDIES/ In a soap chamber test, 0.2 mL of a 50% solution of myristic acid in mineral oil was applied to the ventral skin of the forearm of 16 human subjects once daily for 5 days. The erythema score was 0.48 on a scale of 0 to 5. Myristic acid was considered "non-irritating under conditions of this test".|/HUMAN EXPOSURE STUDIES/ Several bar soap formulations with concentrations of Myristic Acid of 10, 22.1, and 91% were tested for skin irritation using 16 human subjects. A 0.2 mL volume of an 8% aqueous preparation was applied to the ventral skin of the forearm under occlusive patches once daily for 5 days using the Frosch-Kligman soap chamber test. The formulations were considered "slightly" to "moderately irritating" and erythema scores were 1.41, 1.73, and 1.95 on a scale of 0 to 5 for the formulations containing 10, 22.1, and 91% myristic acid, respectively.|/HUMAN EXPOSURE STUDIES/ A white cleanser lotion formulation containing 5% myristic acid was tested for cumulative irritation on the skin of 12 human subjects using a 21-day consecutive closed-patch test. The total irritation score for all subjects for all 21 applications of the formulation was 609 of a maximal possible score of 756. The formulation was considered "highly irritating".|For more Human Toxicity Excerpts (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.

Acid, Myristic

GRADES: Technical; 99.8%; FCC

All other basic organic chemical manufacturing|Tetradecanoic acid: ACTIVE|Potassium salts of fatty acids are used as insecticides, acaricides, herbicides and algaecides. They are used to control a variety of insects and mosses, algae, lichens, liverworts and other weeds, in or on many food and feed crops, ornamental flower beds, house plants, trees, shrubs, walks and driveways, and on dogs, puppies and cats. /Fatty acid salts/|Commercial products contain 91 to 93% C14 or 96 to 99% C14.

A MAJOR COMPONENT (MYRISTIC ACID) OF THE CHROMATOGRAPHIC PROFILE DECREASED IN ABUNDANCE WITH TIME WHILE METHYL MYRISTATE INCREASED. IDENTIFICATION WAS BY GAS CHROMATOGRAPHY-MASS SPECTROMETRY.|PROCEDURE IS DESCRIBED FOR THE RAPID PREPN OF PHENACYL AND NAPHTHACYL DERIVATIVES OF FATTY ACIDS (WHICH INCLUDED TETRADECANOIC ACID). ANALYSIS BY HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY. ANALYSES OF PHENACYL & NAPHTHACYL DERIVATIVES OF FATTY ACIDS FROM SEVERAL SEED OILS COMPARED WELL WITH VALUES OBTAINED BY GAS-LIQUID CHROMATOGRAPHY.|CONSTITUENTS OF NUTMEG WERE DETERMINED BY TANDEM MASS SPECTROMETRY.|Analyte: myristic acid; matrix: chemical purity; procedure: gas chromatography with flame ionization detection and comparison to standards|For more Analytic Laboratory Methods (Complete) data for MYRISTIC ACID (10 total), please visit the HSDB record page.

Analyte: myristic acid; matrix: blood (serum); procedure: high-performance liquid chromatography with ultraviolet detection at 280 nm|Analyte: myristic acid; matrix: blood (plasma); procedure: high-performance liquid chromatography with fluorescence detection at 365 nm (excitation) and 460 nm (emission); limit of quantitation: 5 pmole|Analyte: myristic acid; matrix: blood (serum); procedure: high-performance liquid chromatography with fluorescence detection at 350 nm (excitation) and 530 nm (emission)|Analyte: myristic acid; matrix: blood (plasma); procedure: high-performance liquid chromatography with fluorescence detection at 360 nm (excitation) and 420 nm (emission): limit of detection: 50 ng|For more Clinical Laboratory Methods (Complete) data for MYRISTIC ACID (16 total), please visit the HSDB record page.

EPA Safer Chemical Functional Use Classes -> Surfactants|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]|Cosmetics -> Cleansing; Emulsifying

Flavoring Agents