Methyl laurate
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Methyl laurate
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CAS No:
111-82-0
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Formula:
C13H26O2
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Chemical Name:
Methyl laurate
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Synonyms:
Dodecanoic acid,methyl ester;Lauric acid,methyl ester;Metholene 2296;Methyl dodecanoate;Methyl laurate;Methyl laurinate;Uniphat A 40;Methyl dodecylate;Methyl n-dodecanoate;Stepan C 40;CE 1295;Pastell M 12;Emery 2296;Texaprint SDM 100;CE 1290;Edenor ME-C 1298-100;NSC 5027;Agnique ME 1270U;Agnique ME 1290;Agnique ME 1298;Exceparl ML 85;Radia 7118;409108-19-6
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CAS No:
Description
Liquid
Liquid|colourless to pale yellow liquid with a fatty, floral, winey odour
Methyl laurate is a fatty acid methyl ester of lauric acid. It has a role as a metabolite. It is a fatty acid methyl ester and a dodecanoate ester.
Methyl laurate Basic Attributes
214.34
214.34
1767780
203-911-3
8IPS6BI6KW
5027
DTXSID5026889
COLORLESS LIQUID|Water-white liquid
Characteristics
26.3
5.8
Clear colorless to slightly yellow Liquid
0.8702 g/cm3 @ Temp: 20 °C
5.2 °C
267 °C
>230 °F
1.433
Not miscible in water. soluble in alcohol, dipropylene glycol.
2-8°C
4.11X10-3 mm Hg @ 25 deg C
FATTY, FLORAL ODOR REMINISCENT OF WINE
FATTY TASTE
Safety Information
Ⅲ
UN 3082 9 / PGIII
1
50
24/25-61
OF0670000
N
P273
H410
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 laurate 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.
|Warning|H400 (82.55%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 389 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501
SOIL: Methyl dodecanoate 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).
Toxicity
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 ORRIS ABSOLUTE.
Methyl dodecanoate's production and use as a synthetic intermediate and flavoring(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 1,600(SRC), determined from a structure estimation method(2), indicates that methyl dodecanoate is expected to be immobile in soil(SRC). Volatilization of methyl dodecanoate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.003 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl dodecanoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.004 mm Hg(4). Methyl dodecanoate 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 1,600(SRC), determined from a structure estimation method(2), indicates that methyl dodecanoate 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 0.003 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 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 56 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 14 days(5). According to a classification scheme(6), an estimated BCF of 290(SRC) from its log Kow of 5.41(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 this compound(9). Methyl dodecanoate 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 dodecanoate, which has a vapor pressure of 0.0041 mm Hg at 25 °C(2), will exist in solely as a vapor in the ambient atmosphere. Vapor-phase methyl dodecanoate 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 29 hours(SRC) from its estimated rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(3).
The rate constant for the vapor-phase reaction of methyl dodecanoate with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 29 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 dodecanoate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(3).
An estimated BCF of 290 was calculated for methyl dodecanoate(SRC) using a log Kow of 5.41(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 dodecanoate can be estimated to be about 1600(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl dodecanoate is expected to have low mobility in soil.
The Henry's Law constant for methyl dodecanoate is estimated as 0.003 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl dodecanoate 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 days(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 56 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 14 days(3). Methyl dodecanoate'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 dodecanoate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0041 mm Hg(4).
SURFACE WATER: In a survey of 14 heavily industrialized river basins in the United States (240 sites), 1975-76, 7 samples were found to contain methyl dodecanoate, detection limit not provided(1). Water samples collected from Spirit Lake shortly after the erruption of Mount Saint Helens, 1980, contained methyl dodecanoate, concentration and detection limit not provided(2). Methyl dodecanoate was also detected in trace quantities in samples from the River Lee, UK(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 34,133 workers (75 of these are female) are potentially exposed to methyl dodecanoate in the US(1). Occupational exposure to methyl dodecanoate may occur through inhalation and dermal contact with this compound at workplaces where methyl dodecanoate is produced or used(SRC). The general population may be exposed to methyl dodecanoate via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other consumer products containing methyl dodecanoate(SRC). The general population may also be exposed to methyl dodecanoate due to its use as a flavoring(2).
Drug Information
EXPTL USE: METHYL LAURATE (5 MG) GIVEN DAILY FOR 5 DAYS TO MICE IMPLANTED IP WITH 106 EHRLICH ASCITES TUMOR CELLS PROLONGED SURVIVAL.
lauric acid methyl ester
Methyl laurate Use and Manufacturing
Derived from the esterification of lauric acid and methanol. The mixture of lauric acid, anhydrous methanol and concentrated sulfuric acid was heated to reflux for 18 hours, the reaction was poured into water, and the ester layer was separated. Wash with water, saturated sodium bicarbonate solution and water successively. After drying, it is distilled to collect the fraction at 261-263°C, which is methyl dodecanoate with a yield of 81%.
Gas chromatography analysis standard. Organic Synthesis.
Functional fluids (closed systems)
Metal products not covered elsewhere
100,000,000 - 250,000,000 lb
Grades: 69%, 74%, 90%, 96%, 99.8%
All other basic organic chemical manufacturing|Dodecanoic acid, methyl ester: ACTIVE|Method of purification: vacuum fractional distillation.|NON-ALCOHOLIC BEVERAGES 0.50-5.0 PPM; ICE CREAM, ICES, ETC 0.50-5.0 PPM; CANDY 0.02-0.50 PPM; BAKED GOODS 1.0 PPM.|USEFUL IN FATTY FLAVORS, COCONUT, NUT.
DETERMINATION OF FATTY ACIDS IN FATS AND OILS BY GAS CHROMATOGRAPHY.
EPA Safer Chemical Functional Use Classes -> Emollients;Skin Conditioning Agents;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:214.34
XLogP3:5.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:11
Exact Mass:214.193280068
Monoisotopic Mass:214.193280068
Topological Polar Surface Area:26.3
Heavy Atom Count:15
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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