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Methyl stearate

Methyl stearate structure

Methyl stearate 

structure
  • CAS No:

    112-61-8

  • Formula:

    C19H38O2

  • Chemical Name:

    Methyl stearate

  • Synonyms:

    Octadecanoic acid,methyl ester;Stearic acid,methyl ester;Methyl octadecanoate;Methyl stearate;Methyl n-octadecanoate;n-Octadecanoic acid methyl ester;Kemester 9718;Pastell M 180;Emery 2218;NSC 9418;Exceparl MS;Esterol A;172226-13-0;172226-14-1;218433-32-0

  • Categories:

    Cosmetic Ingredient  >  Skin Conditioning

Description

Methyl stearate, isolated from Rheum palmatum L. is a compopent of of soybean and rapeseed biodiesels[1].


Methyl stearate appears as white crystals or chunky solid. (NTP, 1992)|Liquid|Solid


Methyl stearate appears as white crystals or chunky solid. (NTP, 1992)|Methyl stearate is a fatty acid methyl ester and an octadecanoate ester. It has a role as a metabolite.

Methyl stearate Basic Attributes

298.5

298.50

1786213

203-990-4

8D4NXF3ZH7

9418

DTXSID2047640

White crystals|Semisolid

2915709000

Characteristics

26.30000

8.68

Off-white to cream or light yellow Paste

0.8498 g/cm3 @ Temp: 40 °C

39.1 °C

443 °C

>230 °F

1.444

soluble in chloroform. Insoluble in water.

−20°C

1.36X10-5 mm Hg @ 25 deg C

CAN REACT WITH OXIDIZING MATERIALS

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

METHYL STEARATE is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Safety Information

NONH for all modes of transport

1

40

22-24/25

WI4460000

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.

... Can react with oxidizing materials.|Incompatible with nitrates. /Esters/

This chemical is combustible. (NTP, 1992)

Not Classified

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 chemical under refrigerated temperatures, and keep it away from oxidizing materials. 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 WHEN EXPOSED TO HEAT OR FLAME ...

TO FIGHT FIRE, USE CARBON DIOXIDE, DRY CHEMICAL.|WATER OR FOAM MAY CAUSE FROTHING.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

SOIL: Methyl stearate 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).

URBAN/SUBURBAN: Methyl stearate was qualitatively detected in ambient air particulate samples collected in Upland CA, Lake Charles, LA, Elizabeth, NJ, and Houston, TX, in 1978(1).

Toxicity

Methyl stearate is a component of raw beef(1) and a flavoring constituent of cassava, gari, farine, and clove(2,3).

Methyl stearate'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 62,000(SRC), determined from a structure estimation method(2), indicates that methyl stearate is expected to be immobile in soil(SRC). Volatilization of methyl stearate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.016 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl stearate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.36X10-5 mm Hg(4). Methyl stearate is expected to rapidly biodegrade in aerobic soils as suggested by biodegradation in an aqueous biodegradation screening test(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 62,000(SRC), determined from a structure estimation method(2), indicates that methyl stearate 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 0.016 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 164 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 61 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 17 months(5). According to a classification scheme(5), a /an estimated BCF of W29(SRC), from a log Kow of 8.35(10) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Methyl stearate is expected to rapidly biodegrade in aerobic waters based on screening study results(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 266 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 stearate, which has a vapor pressure of 1.36X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methyl stearate 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 18 hours(SRC) from its estimated rate constant of 2.1X10-11 cu cm/molecule-sec at 25 °C(3). Particulate-phase methyl stearate may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of methyl stearate with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 18 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 266 days at pH values of 7 and 8, respectively(2). Methyl stearate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(3).

An estimated BCF of 29 was calculated for methyl stearate(SRC) using a log Kow of 8.35(1) and a regression-derived equation(2). According to a classification scheme(3), this 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 stearate can be estimated to be about 62,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl stearate is expected to be immobile in soil.

The Henry's Law constant for methyl stearate is estimated as 0.016 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl stearate 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 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 164 hours(SRC). The volatilization half-life from a model pond 2 m deep is estimated to be about 61 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 17 months(3). Methyl stearate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur although adsorption may attenuate this process(SRC). Methyl stearate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.36X10-5 mm Hg(4).

GROUNDWATER: Methyl stearate was detected but not quantified in 1 of 3 groundwater wells near a heavily industrialized area in Barcelona, Spain, 1984(1).|DRINKING WATER: Methyl stearate has been qualitatively detected in drinking water(1). It was listed as an organic compound identified in drinking water in the US as of 11/25/74(2). It was detected, but not quantified, in tap water samples obtained in Tsukuba, Japan, June 1983(3).|SURFACE WATER: Methyl stearate was detected in 93% 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, 165 samples were found to contain methyl stearate, detection limit not provided(3). It was detected in 10 of 13 samples taken from the Lake Michigan basin at concns ranging from 1-180 ug/l(4). Water samples collected from Spirit Lake shortly after the erruption of Mount Saint Helens, 1980, contained methyl stearate, concentration and detection limit not provided(5). Methyl stearate was qualitatively detected in water samples collected from Lake Pontchartrain, LA, Spring, 1976(6). It was detected but not quantified in samples from the lower Fox River, WI, 1966-7(7). Methyl stearate was also detected in trace quantities in samples from the River Lee, UK(8).

Methyl stearate was identified in raw beef samples, concn not provided(1). It was detected as a flavoring constituent of cassava, gari, and farine(2). Methyl stearate was identified as a volatile flavor componenent of clove essential oil(3).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 50,144 workers (34,965 of these are female) are potentially exposed to methyl stearate in the US(1). Occupational exposure to methyl stearate may occur through inhalation and dermal contact with this compound at workplaces where methyl stearate is produced or used(SRC). The general population may be exposed to methyl stearate via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing methyl stearate. The general population may also be exposed to methyl stearate due to its occurrence in some foods(2,3).

Methyl stearate was detected in thrombogenic coronary plaque in 2 of 2 human aorta samples at 3 and 20 ppb(1).

Drug Information

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic 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)

Methyl stearate Use and Manufacturing

Methods of Manufacturing

Method of purification: vacuum fraction distillation.|Esterification of stearic acid with methanol or stearin with methanol.

Uses

Methyl Stearate is used as a nonionic surfactant in various experiments in helping solubilize a variety of chemical species by dissociating aggregates and unfolding proteins.


Intermediates


Lubricants and greases

Production

1,000,000 - 10,000,000 lb|(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Grades: Distilled; Pressed; Technical; Pure (99.8+%). Most technical methyl stearate is 55% stearate and 45% methyl palmitate.

All other chemical product and preparation manufacturing|Octadecanoic acid, methyl ester: ACTIVE

MASS SPECTROMETRY DETERMINES METHYL STEARATE DOWN TO 5 NG.

Food additives -> Flavoring Agents|Fatty Acyls [FA] -> Fatty esters [FA07] -> Wax monoesters [FA0701]|Cosmetics -> Emollient; Skin conditioning

Flavoring Agents

Computed Properties

Molecular Weight:298.5
XLogP3:9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:17
Exact Mass:298.287180451
Monoisotopic Mass:298.287180451
Topological Polar Surface Area:26.3
Heavy Atom Count:21
Complexity:214
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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