Methyl Oleate

log Kow= 7.45

7.45

0.8739 (NTP, 1992) - Less dense than water; will float

0.8739 @ 20 °C

Insoluble (NTP, 1992)

Insol in water; miscible with ethyl alcohol, ether; sol in chloroform

425.3 °F at 20 mmHg (NTP, 1992)

218.5 °C @ 20 mm Hg

Boiling point - 217 °C at 16 torr (decomposes)

This chemical does not meet GHS hazard criteria for 58% (612 of 1055) of all reports.

Warning

H319 (41.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 1055 reports by companies from 4 notifications to the ECHA C&L Inventory.

Chemical: 9-Octadecenoic acid, methyl ester, (Z)-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

9-Octadecenoic acid (9Z)-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 9-Octadecenoic acid (9Z)-, methyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Methyl oleate: Does not have an individual approval but may be used under an appropriate group standard

Esters, such as OLEIC ACID METHYL ESTER, 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

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.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong 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.

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.

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.

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 oleate is expected to be immobile in soil(SRC). Volatilization of methyl oleate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.014 atm-cu m/mole(SRC), using a fragment constant estimation method(3). However, adsorption to soil is expected to attenuate volatilization(SRC). Methyl oleate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.3X10-6 mm Hg(4). Methyl oleate is expected to rapidly biodegrade in aerobic soils as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(5-7).

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 oleate 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 0.014 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 7 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 61 hours ignoring adsorption; when considering maximum adsorption the volatilization half-life increases to 18 months(5). According to a classification scheme(6), an estimated BCF of 490 from its log Kow of 7.45(12) and a regression-derived equation suggests the potential for bioconcentration in aquatic organisms is moderate. Methyl oleate is expected to rapidly biodegrade in aerobic soils as suggested by the rapid biodegradation of structurally similar long-chain fatty acid esters(8-10). An estimated base-catalyzed second-order hydrolysis rate constant of 0.011 L/mole-sec(9,SRC) corresponds to half-lives of 2 years and 70 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 oleate, which has a vapor pressure of 6.3X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase methyl oleate 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 7.5 hours(SRC) from its estimated rate constant of 7.4X10-11 cu cm/molecule-sec at 25 °C(3). Vapor-phase methyl oleate is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 2.1 hours(SRC) from its estimated rate constant of 1.3X10-16 cu cm/molecule-sec at 25 °C(3). Particulate-phase methyl oleate may be removed from the air by wet and dry deposition(SRC).

Methyl oleate was identified in 3 of 3 New Jersey POTW effluents, date not provided, at a estimated concentration of 0.3-18 ppb(1). It was detected in 13 of 13 effluents samples from an olive oil production plant, Spain, at 520-77721 ug/l(2). It was qualitatively detected in the effluent of a pulp and paper mill in Finland(3).

Using a structure estimation method based on molecular connectivity indices(1), the Koc for methyl oleate can be estimated to be about 62,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that methyl oleate is expected to be immobile in soil.

An estimated BCF of 490 was calculated for methyl oleate(SRC) using a log Kow of 7.45(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 moderate.

The Henry's Law constant for methyl oleate is estimated as 0.014 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methyl oleate 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 7 days(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 18 months(3). Methyl oleate's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Methyl oleate is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 6.3X10-6 mm Hg(4).

0.05 ML OF 10% EMULSION OF OLEIC ACID IN NACL SOLN OR 0.05 ML OF 10% SOLN OF SODIUM OLEATE ADJUSTED WITH HCL TO PH 7.2 INJECTED INTO CORNEAS OF RABBITS CAUSED EYES TO BECOME INFLAMED WITHIN FEW HR & TO DEVELOP CORNEAL ABSCESS WITHIN FEW DAYS. ... METHYL OLEATE ALSO PRODUCED NECROSIS & LIPOGENESIS WHEN TESTED IN SAME WAY.

METHYL OLEATE WAS TESTED FOR CARCINOGENICITY BY ORAL & SC ADMIN IN ST/A MICE OF BOTH SEXES, BUT A POSITIVE EFFECT COULD NOT BE ASSESSED.

METHYL OLEATE PROMOTED SKIN TUMOR FORMATION IN MICE. THE RELATION OF MOLECULAR CONFIGURATION & CARCINOGENICITY OF FATTY ACIDS IS DISCUSSED.

GROWTH OF THE CRICKET, CRYLLODES SIGILLATUS, WAS SHOWN TO BE INHIBITED BY FATTY ACIDS & SOME FATTY ACID METHYL ESTERS. THE ROUTE OF ENTRY APPEARED TO BE THROUGH THE CUTICLE OF THE TARSI. METHYL OLEATE SIGNIFICANTLY RETARDED GROWTH, & RESULTED IN LOWER SURVIVAL.

Methyl oleate was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Methyl oleate was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.100, 0.333, 1.000, 3.333, and 10.000 mg/plate. The highest negative dose tested in any S. typhimurium strain was 10.000 mg/plate. Slight clearing of the background bacterial lawn occurred at the high dose in cultures without activation.

The rate constant for the vapor-phase reaction of methyl oleate with photochemically-produced hydroxyl radicals has been estimated as 7.4E-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of methyl oleate with ozone has been estimated as 1.3X10-16 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 0.11 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 2 years and 70 days at pH values of 7 and 8, respectively(3). The predicted near-surface half-life for the photosensitized oxidation of methyl oleate in near suface waters in the Southern US is 1100 hrs(4). Methyl oleate is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(5).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 35,946 workers (1,256 of these are female) are potentially exposed to methyl oleate in the US(1). Occupational exposure to methyl oleate may occur through inhalation and dermal contact with this compound at workplaces where methyl oleate is produced or used(SRC).

Used to make detergents, emulsifiers, wetting agents, stabilizers, textile treatments, plasticizers for duplicating inks, rubbers, waxes, oleonitrile, drying oils, cephalosporin S, alkanolamides, and fatty alcohols and acids; Used as emulsifier and emollient for cosmetics, lubricant for leather, plasticizer for natural and synthetic rubbers, and chromatographic reference standard; [HSDB]

Leather Tanning and Processing [Category: Industry]

Intermediate for detergents, emulsifiers, wetting agents, stabilizers, textiles treatment, plasticizers for duplicating inks, rubbers, waxes, chromatographic reference standard

CHEM INT-EG, FOR ALKANOLAMIDES, FATTY ALCOHOLS & ACIDS

EMULSIFIER/EMOLLIENT FOR COSMETICS

LUBRICANT FOR LEATHER

2023: 10,000,000 - <25,000,000 lb

(1979) PROBABLY GREATER THAN 6.81X10+6 GRAMS

(1981) PROBABLY GREATER THAN 1.14X10+7 GRAMS

Esterification of oleic acid; vacuum fractional distillation; solvent crystallization.

REACTION OF TRIGLYCERIDES, EG, OLIVE OIL, WITH EXCESS METHANOL AND A CATALYST FOLLOWED BY FRACTIONAL DISTILLATION; REACTION OF OLEIC ACID WITH METHANOL IN THE PRESENCE OF SULFURIC ACID

EPA Safer Chemical Functional Use Classes -> Solvents

Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern

Fragrance Ingredients

Cosmetics -> Emollient; Skin conditioning

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

9-Octadecenoic acid (9Z)-, methyl ester: ACTIVE