Methyl palmitate
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Methyl palmitate
structure -
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CAS No:
112-39-0
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Formula:
C17H34O2
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Chemical Name:
Methyl palmitate
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Synonyms:
Hexadecanoic acid,methyl ester;Palmitic acid,methyl ester;Metholene 2216;Methyl hexadecanoate;Methyl palmitate;Uniphat A60;Methyl n-hexadecanoate;n-Hexadecanoic acid methyl ester;Emery 2216;Pastell M 16;NSC 4197;Edenor ME-C 16-80MY;Edenor ME C16-98;Radia 7120
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CAS No:
Description
Methyl palmitate, an acaricidal compound occurring in green walnut husks, inhibits phagocytic activity and immune response. Methyl palmitate also posseses anti-inflammatory and antifibrotic effects[1][2][3].
Liquid
Methyl palmitate is a fatty acid methyl ester. It has a role as a metabolite.
Methyl palmitate Basic Attributes
270.45
270.45
1780973
203-966-3
DPY8VCM98I
4197
DTXSID4029149
Colorless liq
2915709000
Characteristics
26.3
7.9
Clear colorless Liquid or Low Melting Solid
0.9±0.1 g/cm3
30 °C
417 °C
>230 °F
1.441
H2O: INsoluble
2-8°C
6.04X10-5 @ 25 deg C
Safety Information
NONH for all modes of transport
1
22-24/25
Stable under normal temperatures and pressures.
P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
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.
|Warning|H315 (88.05%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, and P501|Aggregated GHS information provided by 1668 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Methyl palmitate was identified in 1 of 3 New Jersey POTW effluents, date not provided, at an estimated concentration of 1 ppb(1). It was detected in 12 of 13 effluent samples from an olive oil production plant, Spain, at 163-15808 ug/l(2).
SOIL: Methyl palmitate 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 palmitate was qualitatively detected in a sediment sample from the Calcasieu River, LA, 1979(2).
Toxicity
METHYL PALMITATE, AN INHIBITOR OF RETICULOENDOTHELIAL SYSTEM (RES) FUNCTION, INHIBITED BOTH THE RES FUNCTION & SERUM LYSOZYME INCREASES WHEN ADMIN TO GLUCAN TREATED MICE.|GLUCAN-TREATED, ENDOTOXIN-SENSITIVE RATS ADMIN METHYL PALMITATE, A RETICULOENDOTHELIAL DEPRESSANT WHICH RENDERS RATS ENDOTOXIN RESISTANT, FOLLOWED BY SALMONELLA ENTERITIDIS ENDOTOXIN, RESULTED IN ENHANCED ELEVATION OF PLASMA GLUTAMIC OXALACETIC TRANSAMINASE & HYPOGLYCEMIA.|THE VASCULAR REMOVAL & ORGAN UPTAKE OF INCOMPATIBLE SHEEP RED CELLS LABELED WITH CHROMIUM IN MICE WAS DECR DUE TO DECR VASCULAR CLEARANCE CAUSED BY FAILURE IN PHAGOCYTOSIS BY BOTH LIVER & SPLEEN AFTER ADMIN OF METHYL PALMITATE, A RETICULOENDOTHELIAL DEPRESSANT.|THE ADMIN OF METHYL PALMITATE 100 MG/100 G, IV TO RATS CAUSED AN INCR IN SURVIVAL AT ENDOTOXIN DOSES OF 0.75 TO 3.0 MG/100 G. ALTHOUGH A MEAN 38% MORTALITY WAS CAUSED BY SALMONELLA ENTERITIDIS ENTOXIN 0.5 MG/100 G, IV IN NORMAL RATS , A 6-FOLD INCR OF THIS DOSE DID NOT CAUSE MORTALITY IN THE METHYL PALMITATE GROUP. METHYL PALMITATE, WHEN ADMIN TO GLUCAN-TREATED RATS, CAUSED NORMAL PHAGOCYTIC ACTIVITY IN THE PRESENCE OF RETICULOENDOTHELIAL SYSTEM HYPERTROPHY.|For more Interactions (Complete) data for METHYL PALMITATE (8 total), please visit the HSDB record page.
Methyl palmitate is a component of the flowers of the Japanese honeysuckle (Lonicera japonica)(1). Methyl palmitate has been identified as a component of some food including clove essential oil(2), cassava, gari, farine(3), clams, short neck clams, and corbicula(4).
Methyl palmitate's production and use as an synthetic intermediate(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 18,000(SRC), determined from a structure estimation method(2), indicates that methyl palmitate is expected to be immobile in soil(SRC). Volatilization of methyl palmitate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.009 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl palmitate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00006 mm Hg(4). Methyl palmitate is expected to rapidly biodegrade in aerobic soils based on the results of screening studies(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 18,000(SRC), determined from an estimation method(2), indicates that methyl palmitate 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 0.009 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 and 160 hours, 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 60 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 150 days(5). According to a classification scheme(6), an estimated BCF of 620(SRC) from a log Kow of 7.38(10) regression-derived equation(7) suggests the potential for bioconcentration in aquatic organisms is high. Methyl palmitate is expected to rapidly biodegrade in aerobic waters(8). 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(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl palmitate, which has a vapor pressure of 0.00006 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methyl 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 20 hours(SRC) from its estimated rate constant of 1.9X10-11 cu cm/molecule-sec at 25 °C(3). Particulate-phase methyl palmitate may be removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of methyl palmitate with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 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 palmitate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(3).
An estimated BCF of 2 was calculated for methyl palmitate (SRC) using a log Kow of 7.38(1) and a regression-derived equation developed for hydrophobic chemicals(2). According to a classification scheme(3), the estimated BCF suggests the potential for bioconcentration in aquatic organisms is low.
Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl palmitate can be estimated to be about 18,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl palmitate is expected to be immobile in soil.
The Henry's Law constant for methyl palmitate is estimated as 0.009 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl palmitate 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 6.5 days(SRC). Methyl palmitate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 60 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 150 days(3). Methyl palmitate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00006 mm Hg(4).
GROUNDWATER: Methyl palmitate was detected but not quantified in 1 of 3 groundwater wells near a heavily industrialized area in Barcelona, Spain, in 1984(1). It was qualitatively detected in composite well water samples from Waterloo, IA, 1972(2).|DRINKING WATER: Methyl palmitate has been qualitatively detected in drinking water(1).|SURFACE WATER: Methyl palmitate was detected in 100% of 30 samples taken from the Delaware Basin (Delaware, Schuylkill, and Lehigh Rivers) in February, 1976, at concentrations > 1 ug/l(1). In a survey of 14 heavily industrialized river basins in the United States (240 sites), 1975-76, 183 samples were found to contain methyl palmitate, detection limit not provided(2). It was detected in 11 of 13 samples taken from the Lake Michigan basin at concns ranging from 1-117 ug/l(3). Water samples collected from Spirit Lake shortly after the erruption of Mount Saint Helens, 1980, contained methyl palmitate, concentration and detection limit not provided(4). Methyl palmitate was qualitatively detected in water samples collected from Lake Pontchartrain, LA, Spring, 1976(5). It was detected but not quantified in samples from the lower Fox River, WI, 1966-7(6). Methyl palmitate was also detected in trace quantities in samples from the River Lee, UK(7).
Methyl palmitate was detected as a volatile flavor component of clove essential oil(1). It was identified as a constituent of cassava, gari, farine(2), clams, short neck clams, and corbicula(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 1932 workers (293 of these are female) are potentially exposed to methyl palmitate in the US(1). Occupational exposure to methyl palmitate may occur through inhalation and dermal contact with this compound at workplaces where methyl palmitate is produced or used(SRC). The general population may be exposed to methyl palmitate via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing methyl palmitate. The general population may also be exposed to methyl palmitate due to is occurrence in some foods(2-4).
Methyl palmitate was detected in thrombogenic coronary plaques in 2 of 2 human aortas samples at 9 and 120 ppb(1).
Drug Information
RETENTION & DISTRIBUTION OF (14)-CARBON ACTIVITY IN TISSUE LIPIDS AND FATTY ACIDS WERE DETERMINED 2 DAYS AFTER ADMIN OF (14)C-LABELED PALMITATE METHYL ESTER BY STOMACH TUBE. RETENTION WAS LOW IN YOUNG RATS WITHOUT ADIPOSE TISSUE. RETENTION IN THE BRAIN WAS FOUND AFTER 17 DAYS. THE HIGHEST LEVEL OF ACTIVITY WAS FOUND IN THE CARCASS.
THE UTILIZATION OF (14)C-LABELED PALMITIC ACID BY RATS WAS DETERMINED BY THE LEVEL OF (14)-CARBON IN EXPIRED AIR AFTER ADMIN OF PALMITATE METHYL ESTER BY STOMACH TUBE. TWO SUCCESSIVE PEAKS IN THE OUTPUT OF LABELED CO2 OCCURRED, AT 3 & 18 HR. PALMITIC ACID ADMIN WAS ONLY HALF THE SIZE OF THE 1ST PEAK. THE 2 SUCCESSIVE PEAKS INDICATED A RECIRCULATION OF FATTY ACIDS IN THE RAT. T/2 OF THE LABELED PALMITIC ACID WAS 3 HR.
methyl palmitate
Methyl palmitate Use and Manufacturing
Esterification of palmitic acid with methanol or alcoholysis of palm oil plus vacuum distillation.
Methyl Palmitate is a fatty acid ester essential oil that naturally occurs in many plant species. Methyl Palmitate concentration in cells are known to be modulated by methanol. In experimental studies with isolated Kupffer cells, Methyl palmitate exhibited inhibitory activity towards phagocytosis and decreases cell viability.
Intermediates
Agricultural products (non-pesticidal)
10,000,000 - 50,000,000 lb
All other basic organic chemical manufacturing|Hexadecanoic acid, methyl ester: ACTIVE
FATTY ACID DETERMINATION IN FATS BY GAS CHROMATOGRAPHY.|SEPARATION OF PARTIALLY DEUTERATED METHYL PALMITATE FROM NONDEUTERATED METHYL PALMITATE BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY.
Food additives -> Flavoring Agents|Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]|Cosmetics -> Emollient; Skin conditioning
Flavoring Agents
Computed Properties
Molecular Weight:270.5
XLogP3:7.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:15
Exact Mass:270.255880323
Monoisotopic Mass:270.255880323
Topological Polar Surface Area:26.3
Heavy Atom Count:19
Complexity:190
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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