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Home > Encyclopedia > Methyl myristate

Methyl myristate

Methyl myristate structure

Methyl myristate 

structure
  • CAS No:

    124-10-7

  • Formula:

    C15H30O2

  • Chemical Name:

    Methyl myristate

  • Synonyms:

    Tetradecanoic acid,methyl ester;Myristic acid,methyl ester;Metholeneat 2495;Methyl myristate;Methyl tetradecanoate;Uniphat A50;Methyl n-tetradecanoate;Pastell M 14;NSC 5029;Emery 2214

  • Categories:

    Cosmetic Ingredient  >  Skin Conditioning

Description

Liquid


Liquid|colourless, oily liquid or white, waxy solid with a faint onion, honey, orris odour


Methyl tetradecanoate is a fatty acid methyl ester resulting from the formal condensation of the carboxy group of tetradecanoic acid (myristic acid) with methanol. It has a role as a plant metabolite, a flavouring agent and a fragrance. It derives from a tetradecanoic acid.

Methyl myristate Basic Attributes

242.4

242.40

204-680-1

RG9851783C

5029

DTXSID5027019

COLORLESS, OILY LIQ OR WHITE, WAXY SOLID

29322090

Characteristics

26.3

6.41

Clear colorless to yellow Liquid

0.8671 g/cm3 @ Temp: 20 °C

19 °C

295 °C

>230 °F

n20/D 1.436(lit.)

soluble in chloroform and methanol. React with water.

2-8°C

4.9X10-4 mm Hg @ 25 deg C

Honey & orris-like (Iris florentina) odor

HONEY & ORRIS-LIKE FLAVOR AT TRACE LEVELS

Safety Information

NONH for all modes of transport

1

38

23-24/25

Xi

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

H315

SRP: At the time of review, 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.

Methyl myristate is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

Not Classified

SOIL: Methyl myristate was qualitatively detected in soil samples from Southern Alberta, Canada, in strata associated with the Mazama volcano eruption which occurred approximately 7000 years ago(1). SEDIMENT: Methyl myristate was qualitatively detected in a sediment sample from the Calcasieu River, LA, 1979(2).

SOURCE DOMINATED: Methyl myristate was qualitatively detected in samples taken in the Allegheny Mountain Tunnel of the Pennsylvania Turnpike, in 1979(1).

Toxicity

LINEAR ALKANES OF SPECIFIC CHAIN LENGTH ENHANCED DIFFERENTIALLY THE MITOGENIC RESPONSE OF MURINE SPLEEN LYMPHOCYTES TO THE LECTIN PHYTOHEMAGGLUTININ. WITHIN THE HOMOLOGOUS SERIES OF COMPOUNDS HAVING C6-18, A BIPHASIC STRUCTURE-FUNCTION RELATIONSHIP WAS FOUND, WITH MAXIMUM COMITOGENIC ACTIVITY OCCURRING FOR TETRADECANE. THE CONCN OF TETRADECANE HAVING EQUIVALENT COMITOGENIC ACTIVITY WAS SIMILAR TO THAT OF METHYL MYRISTATE.|Linear saturated fatty acid methyl esters were comitogenic with lectins for mouse lymphocytes, the degree of comitogenicity being strongly dependent on the length of the acyl group, and maximal for methyl tetradecanoate. Lesser effects were found for analogs with 10, 12, or 16 acyl carbon atoms, whereas those with fewer than 10 or more than 16 were inactive. /Methyl esters/

REPORTED FOUND IN VIOLET ROOTS.|Methyl myristate has been identified as a component of the rhizome of the decorative perennial iris (Pallida lam)(1). It has also been identified as a component of clams, short neck clams, and corbicula(2).

Methyl myristate's production and use as a synthetic intermediate and flavoring(1) may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,400(SRC), determined from a structure estimation method(2), indicates that methyl myristate is expected to be immobile in soil(SRC). Volatilization of methyl myristate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.005 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl myristate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00049 mm Hg(4). Methyl myristate is expected to rapidly biodegrade in aerobic soils by analogy to structurally similar long-chain fatty acid esters(5-7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5400(SRC), determined from a structure estimation method(2), indicates that methyl myristate is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.005 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Volatilization half-lives for a model river and model lake are 5 hours and 6.2 days, respectively(SRC), using an estimation method(3). 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 estimated to be about 57 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 45 days(5). According to a classification scheme(6), an estimated BCF of 540(SRC) from its log Kow of 6.41(12) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high although it may be lower than that indicated due to the expected rapid metabolism rate for long-chain fatty acid esters(10). Methyl myristate is expected to rapidly biodegrade in aerobic soils by analogy to structurally similar long-chain fatty acid esters(8-10). An estimated base-catalyzed second-order hydrolysis rate constant of 0.030 L/mole-sec(9,SRC) corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectively(11).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl myristate, which has a vapor pressure of 0.00049 mm Hg at 25 °C(2), will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase methyl myristate is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 24 hours(SRC) from its estimated rate constant of 1.6X10-11 cu cm/molecule-sec at 25 °C(3).

The rate constant for the vapor-phase reaction of methyl myristate with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 24 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.030 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 7.3 years and 270 days at pH values of 7 and 8, respectively(2). Methyl myristate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(3).

An estimated BCF of 1100 was calculated for methyl myristate(SRC) using a log Kow of 6.41(1) and a regression-derived equation(2). According to a classification scheme(3), the estimated BCF suggests the potential for bioconcentration in aquatic organisms is high. However, bioconcentration studies on compounds which are structurally similar(4,5) suggests that bioconcentration may be lower than that indicated by the regression-derived equation due to the ability of aquatic organisms to readily metabolize this class of compounds(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl myristate can be estimated to be about 5400(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl myristate is expected to be immobile in soil.

The Henry's Law constant for methyl myristate is estimated as 0.0052 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl myristate is expected to volatilize 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 approximately 5 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 approximately 6.2 days(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 57 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 45 days(3). Methyl myristate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur although adsorption is expected to attenuate this process(SRC). Methyl myristate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00049 mm Hg(4).

DRINKING WATER: Methyl myristate has been qualitatively detected in drinking water(1). It was qualitatively detected in treated drinking water supplies in the U.K.(2).|SURFACE WATER: Methyl myristate was detected in 10% of 30 samples taken from the Delaware Basin (Delaware, Schuylkill, and Lehigh Rivers) in February, 1976, at concentrations > 1 ug/l(1). It was detected, but not quantified, in water samples collected from the Delaware River, Summer 1976; it was not detected in samples taken during the Winter(2). In a survey of 14 heavily industrialized river basins in the United States (240 sites), 1975-76, 47 samples were found to contain methyl myristate, detection limit not provided(3). It was detected in 6 of 13 samples taken from the Lake Michigan basin at concentrations ranging from 1-24 ug/l(4). Methyl myristate was also detected in trace quantities in samples from the River Lee, UK(5).

Methyl myristate was identified as a volatile component of clams, short neck clams, and corbicula(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 27,787 workers (4,243 of these are female) are potentially exposed to methyl myristate in the US(1). Occupational exposure to methyl myristate may occur through inhalation and dermal contact with this compound at workplaces where methyl myristate is produced or used(SRC). The general population may be exposed to methyl myristate via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing methyl myristate(SRC). The general population may also be exposed to methyl myristate due to its occurrence in some foods(2,3).

Methyl myristate was detected in thrombogenic coronary plaques in 1 of 2 human aortas samples at 10 ppb(1).

Drug Information

C14-MES

Methyl myristate Use and Manufacturing

Methods of Manufacturing

It is formed by direct esterification of methanol and myristic acid in the presence of gas phase HCl.

Uses

For organic synthesis, gas chromatography and biochemical research.


Fuels and fuel additives


Fuels and related products

Production

50,000,000 - 100,000,000 lb|(1978) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Grades: Technical (93%); Purified (99.8%)

All other chemical product and preparation manufacturing|Tetradecanoic acid, methyl ester: ACTIVE|NON-ALCOHOLIC BEVERAGES 0.25-0.50 PPM; ICE CREAM, ICES, ETC 0.25-0.50 PPM; CANDY 2.4 PPM; BAKED GOODS 0.30-2.0 PPM; GELATINS & PUDDINGS 0.24 PPM.|AN EFFECTIVE INHIBITOR OF TYROPHAGUS PUTRESCENTIAE MITE DEVELOPMENT WHEN INCORPORATED INTO DOG FOOD.|FEMA NUMBER 2722

DETERMINATION OF METHYL MYRISTATE IN FATS & OILS BY GAS CHROMATOGRAPHY.

EPA Safer Chemical Functional Use Classes -> Solvents|Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern|Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]|Cosmetics -> Emollient; Skin conditioning

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:242.40
XLogP3:6.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:13
Exact Mass:242.224580195
Monoisotopic Mass:242.224580195
Topological Polar Surface Area:26.3
Heavy Atom Count:17
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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