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SECTION 1. CHEMICAL IDENTIFICATION

CHEMINFO Record Number: 385
CCOHS Chemical Name: Oleic acid

Synonyms:
cis-Octadec-9-enoic acid
cis-9-Octadecenoic acid
9,10-Octadecenoic acid
9-Octadecenoic acid
(z)-9-Octadecenoic acid
cis-Oleic acid
Elaic acid
Oleinic acid
Red oil
Acide oleique

Trade Name(s):
Century CD fatty acid
Emersol 220 white oleic acid
Emersol 221 low titer white oleic acid
Glycon
Industrene

CAS Registry Number: 112-80-1
RTECS Number(s): RG2275000
EU EINECS/ELINCS Number: 204-007-1
Chemical Family: Unsaturated aliphatic carboxylic acid / unsaturated aliphatic monocarboxylic acid / alkenoic acid
Molecular Formula: C18-H34-O2
Structural Formula: CH3-(CH2)6-CH2-CH=CH-CH2-(CH2)5-CH2-C(=O)-OH

SECTION 2. DESCRIPTION

Appearance and Odour:
Pure oleic acid is a colourless or nearly colourless liquid with a peculiar lard-like odour. If exposed to air, it may develop a yellow to brown colour and a rancid odour as it oxidizes.(22,23)

Odour Threshold:
No information available

Warning Properties:
Information not available for evaluation

Composition/Purity:
Commercial oleic acid usually contains 7-12% saturated acids, such as stearic and palmitic acids, varying amounts of linoleic acid and other unsaturated acids and a small amount of elaidic (trans-9-octadecenoic acid).(2,22) Oleic acid exists in 2 crystalline forms, alpha and beta.(25,26)

Uses and Occurrences:
Oleic acid is used as a soap base; in the manufacture of oleates, ointments, cosmetics, polishing compounds, lubricants and surface coatings; thickening lubricating oils; waterproofing textiles, oiling wool; defoaming agent; ore flotation; solvent for other fatty acids, oils and oil soluble material; and as a food additive.(22,23)


SECTION 3. HAZARDS IDENTIFICATION

EMERGENCY OVERVIEW:
Colourless or nearly colourless liquid with a peculiar lard-like odour. If exposed to air, it may develop a yellow to brown colour and a rancid odour. Can burn if strongly heated, but is difficult to ignite. Practically non-toxic.



POTENTIAL HEALTH EFFECTS

Effects of Short-Term (Acute) Exposure

Inhalation:
There is no animal or human information available about the effects of inhaling oleic acid. Oleic acid has an extremely low tendency to evaporate, so exposure to vapour is unlikely to occur, even at increased temperatures. In general, oleic acid appears to have low toxicity. Exposure to mists is unlikely to cause irritation or injury.

Skin Contact:
Oleic acid is not a skin irritant. In several studies with human volunteers, oleic acid produced no to minimal irritation, even with repeated application.(2) Similar results have been obtained in animal studies. Peroxide formation will increase the irritancy of oleic acid.

Eye Contact:
Oleic acid is probably only a mild eye irritant. Exaggerated use of cosmetic formulations containing 2-3% oleic acid for 3 weeks did not produce eye irritation in volunteers.(2) No to mild irritation has been observed in animal studies. Peroxide formation will increase the irritancy of oleic acid.

Ingestion:
Oleic acid is a normal constituent of many foods and probably does not produce any harmful effects if ingested. Animal evidence has shown that it has very low toxicity by ingestion. Ingestion is not a typical route of occupational exposure.

Effects of Long-Term (Chronic) Exposure

SKIN: There are a few Russian reports of workers developing dermatitis (dry, red, cracked skin) following occupational exposure to several chemicals, including oleic acid.(10,11) No conclusions can be drawn from these report due to the multiple chemical exposures. Animal evidence suggests that oleic acid could cause dermatitis following prolonged, repeated skin contact.

SKIN SENSITIZATION: Sensitization and photosensitization were not observed in clinical trials conducted with cosmetic product formulations containing 2- 6% oleic acid.(2)

Carcinogenicity:

There is no human information available. Animal evidence suggests that oleic acid is not carcinogenic. Animal studies on the co-carcinogenic or tumour promoting ability of oleic acid are inconclusive.

The International Agency for Research on Cancer (IARC) has not evaluated the carcinogenicity of this chemical.

The American Conference of Governmental Industrial Hygienists (ACGIH) has no listing for this chemical.

The US National Toxicology Program (NTP) has not listed this chemical in its report on carcinogens.

Teratogenicity and Embryotoxicity:
There is no human or animal information available.

Reproductive Toxicity:
There is no human information available. Very limited animal information suggests that oleic acid does not affect fertility.

Mutagenicity:
No human or animal in vivo studies have been reported. Both positive and negative results have been obtained in short-term in vitro tests.

Toxicologically Synergistic Materials:
Animal studies on the co-carcinogenic or tumour promoting ability of oleic acid have been inconclusive.

Potential for Accumulation:
Oleic acid is a normal constituent of the body. It is metabolized and stored in fatty tissues of the body, or broken down and exhaled through the lungs.


SECTION 4. FIRST AID MEASURES

Inhalation:
No health effects expected. If symptoms are experienced, remove source of contamination or move victim to fresh air. Obtain medical advice immediately.

Skin Contact:
If irritation occurs, remove contaminated clothing, shoes and leather goods (e.g. watchbands, belts). Gently blot or brush away excess chemical. Wash gently and thoroughly with water and non-abrasive soap for at least 5 minutes or until the chemical is removed. If irritation persists, obtain medical advice.

Eye Contact:
Gently blot or brush away excess chemical. Immediately flush the contaminated eye(s) with lukewarm, gently flowing water for 5 minutes, while holding the eyelid(s) open. If irritation persists, obtain medical advice.

Ingestion:
If irritation or discomfort occur, obtain medical advice.

First Aid Comments:
All first aid procedures should be periodically reviewed by a doctor familiar with the material and its conditions of use in the workplace.



SECTION 5. FIRE FIGHTING MEASURES

Flash Point:
189 deg C (372 deg F) (closed cup); 184 deg C (364 deg F) (closed cup) (24)

Lower Flammable (Explosive) Limit (LFL/LEL):
Not available

Upper Flammable (Explosive) Limit (UFL/UEL):
Not available

Autoignition (Ignition) Temperature:
363 deg C (685 deg F) (24)

Sensitivity to Mechanical Impact:
Not sensitive. Stable compound

Sensitivity to Static Charge:
Information not available. Probably will not accumulate static discharge. The electrical conductivity of carboxylic acids is high.

Combustion and Thermal Decomposition Products:
Incomplete combustion may also produce irritating fumes and acrid smoke.

Fire Hazard Summary:
Oleic acid can burn if strongly heated, but is difficult to ignite.

Extinguishing Media:
Carbon dioxide, dry chemical powder, alcohol foam, polymer foam, water spray or fog.

Fire Fighting Instructions:
Evacuate area and fight fire from a safe distance or a protected location. Approach fire from upwind to avoid toxic decomposition products.
Water or foam may cause frothing. The frothing may be violent and could endanger personnel close to the fire. However, a water spray or fog that is carefully applied to the surface of the liquid, preferably with a fine spray or fog nozzle, will cause frothing that will blanket and extinguish the fire. In addition, water spray or fog can be used to absorb heat, keep containers cool and protect exposed material. If a leak or spill has not ignited, use water spray to disperse the vapours and protect personnel attempting to stop a leak. Water spray may be used to flush spills away from ignition sources. Solid streams of water may be ineffective and spread material.
Oleic acid is only slightly hazardous to health. Firefighters may enter the area if positive pressure self-contained breathing apparatus (MSHA/NIOSH approved or equivalent) and full Bunker Gear is worn.



NATIONAL FIRE PROTECTION ASSOCIATION (NFPA) HAZARD IDENTIFICATION

NFPA - Health: 1 - Exposure would cause significant irritation, but only minor residual injury.
NFPA - Flammability: 1 - Must be preheated before ignition can occur.
NFPA - Instability: 0 - Normally stable, even under fire conditions, and not reactive with water.

SECTION 9. PHYSICAL AND CHEMICAL PROPERTIES

Molecular Weight: 282.45

Conversion Factor:
Not applicable

Physical State: Liquid
Melting Point: 13.6 deg C (56.5 deg F) (alpha form); 16.3 deg C (61.3 deg F) (beta form) (25,26)
Boiling Point: 286 deg C (547 deg F) at 13.3 kPa (100 mm Hg); begins to decompose at 80-100 deg C at atmospheric pressure.(22)
Relative Density (Specific Gravity): 0.89 at 20 deg C (water = 1) (25,26)
Solubility in Water: Practically insoluble (22)
Solubility in Other Liquids: Soluble in all proportions in acetone, ethanol and methanol, benzene, diethyl ether and chloroform; soluble in fixed and volatile oils (2,21,23)
Coefficient of Oil/Water Distribution (Partition Coefficient): Log P(n-heptane) = 5.36 (27)
pH Value: Not applicable (practically insoluble in water)
Vapour Density: Not applicable
Vapour Pressure: Extremely low. 7.28 X 10(-8) kPa (5.46 X 10(-7) mm Hg) at 25 deg C (23)
Saturation Vapour Concentration: Negligible. 0007 ppm at 25 deg C (calculated)
Evaporation Rate: Not available. Probably extremely low.
Critical Temperature: Not available

Other Physical Properties:
ACIDITY: Weak acid. pKa = 5.02 at 25 deg C (23)
VISCOSITY-DYNAMIC: 25.6 mPa.s (25.6 centipoises) at 30 deg C (23)
SURFACE TENSION: 32.8 mN/m (32.8 dynes/cm) at 20 deg C (23)
CRITICAL PRESSURE: 3040 kPa (30 atmospheres) (23)


SECTION 10. STABILITY AND REACTIVITY

Stability:
Moderately stable. Slowly decomposes on exposure to air and light, especially when impure, and at 80-100 deg C at atmospheric pressure.(22,23).

Hazardous Polymerization:
Does not occur.

Incompatibility - Materials to Avoid:

NOTE: Chemical reactions that could result in a hazardous situation (e.g. generation of flammable or toxic chemicals, fire or detonation) are listed here. Many of these reactions can be done safely if specific control measures (e.g. cooling of the reaction) are in place. Although not intended to be complete, an overview of important reactions involving common chemicals is provided to assist in the development of safe work practices.


STRONG OXIDIZING AGENTS (e.g. perchloric acid) - may react violently. Increased risk of fire and explosion.(28)
REACTIVE METALS (e.g. aluminum) - the presence of contaminating peroxides in oleic acid may cause a violent or explosive reaction.(28)
STRONG BASES (e.g. sodium hydroxide) or REDUCING AGENTS - can react vigorously and may generate heat. Increased risk of fire.

Hazardous Decomposition Products:
Peroxides can form during the oxidation of oleic acid in the presence of light and air.(26)

Conditions to Avoid:
Temperatures above 80 deg C, air and light.

Corrosivity to Metals:
Oleic acid is not corrosive to copper and its alloys, nickel and its alloys and stainless steel. Partially corrosive to cast iron and steel.(29)


SECTION 11. TOXICOLOGICAL INFORMATION

LD50 (oral, male rat): greater than 19200 mg/kg (cited as 21.5 mL/kg) (1)

Eye Irritation:

Application of 0.1 mL commercial oleic acid (75% purity) produced mild redness in rabbits with complete clearing in 72 hours.(1) In 2 other studies, commercial oleic acid produced no to very slight irritation in rabbits in Draize tests.(2)

Skin Irritation:

Application of 0.5 mL 10% oleic acid in propylene glycol to rabbit skin for 6 hours under cover produced mild irritation (scored 2.3/8).(13) In another study, application of 0.5 mL oleic acid (75% purity) to the intact or abraded skin of rabbits for 24 hours under cover produced very slight redness (scored 0.5/8).(1) Using the repeated open patch method, application of 0.5 mL oleic acid to rabbit skin caused cumulative irritation increasing from mild redness and no swelling at 24 hours to marked redness and moderate swelling in some rabbits at 72 hours.(2) A single application of 0.3-2 mL oleic acid (which had been aerated for 1 week to facilitate peroxide formation) was rubbed into the skin for 20 seconds. Marked irritation and hair loss was observed in rabbits, guinea pigs and mice.(3) No conclusions can be made from this study.

Effects of Short-Term (Acute) Exposure:

Skin Contact:
No deaths were observed following dermal application of 3000 mg/kg commercial oleic acid to guinea pigs.(2)

Ingestion:
Very high oral doses (up to 19200 mg/kg) have produced diarrhea and signs of central nervous system depression with no deaths.(1,2)

Effects of Long-Term (Chronic) Exposure:

Skin Contact:
In several studies, repeated dermal application (from 3 days to 31 weeks) to rabbits, mice and rats has caused inflammation and cellular changes (hyperplasia) at the treatment site, as well as injury to the hair follicles (follicular keratosis).(5,6,7,8,14)

Ingestion:
Long-term oral exposure to very high dietary levels of oleic acid (15%) for 10 weeks prior to mating has produced deficient mammary gland development and impaired lactation in female rats. As a result, high mortality was observed in the offspring.(12) Dietary levels of 1.5 g oleic acid and 100 g corn oil for 2 years caused changes in fat concentration and composition in the liver.(4) It is not possible to interpret these results because of the co- administration of the corn oil.

Skin Sensitization:
Negative results were obtained in the guinea pig maximization test, using Freund's complete adjuvant.(2)

Carcinogenicity:
In 2 studies, oleic acid did not produce an increased incidence of tumours when applied to the skin of mice for up to 440 days.(14,15) In addition, no increase in large intestinal carcinoma was observed in female rats fed a diet containing 25% oleic acid for approximately 24 weeks.(16) In another study, mice administered a diet supplemented with corn oil and oleic acid for 24 months exhibited an increased incidence of colon cancer.(4) It is not possible to draw any conclusions from this study because there was no statistical analysis done and because of the concurrent administration of corn oil. Several studies have investigated oleic acid as a co-carcinogenic or tumour promoter.(8,9,14,15,17,18,20) However, the available information is inconclusive.

Reproductive Toxicity:
Fertility was not impaired in 4 male rats administered very high dietary levels of oleic acid (15%) for 16 weeks prior to mating. In the same study, high mortality was observed in the offspring of female rats administered high dietary levels of oleic acid (15%) for 10 weeks prior to mating. The failure to survive was attributed to deficient mammary gland development and lactation in the mothers.(12)


SECTION 16. OTHER INFORMATION

Selected Bibliography:
(1) Briggs, G.B., et al. Safety studies on a series of fatty acids. American Industrial Hygiene Association Journal. (April, 1976). p. 251-253
(2) Final report on the safety assessment of oleic acid, lauric acid, palmitic acid, myristic acid, and stearic acid. Journal of the American College of Toxicology. Vol. no. 3 (1987). p. 321-401
(3) Flesch, P. Hair loss from sebum. A.M.A. Archives of Dermatology and Syphilology. Vol. 67, no. 1 (January, 1953). p. 1-9
(4) El-Khatib, S.M., et al. Role of high-fat diet in tumorigenesis in C57BL/1 mice. Journal of the National Cancer Institute. Vol. 66, no. 2 (February, 1981). p. 297-301
(5) Butcher, E.O. The effects of applications of various substances on the epidermis of the rat. Journal of Investigative Dermatology. Vol. 16 (1952). p. 85-90
(6) Kanaar, P. Follicular-keratogenic properties of fatty acids in the external ear canal of the rabbit. Dermatologica. Vol. 142 (1971). p. 14-22
(7) Puhvel, S.M., et al. Decreased induction of aryl hydrocarbon hydroxylase activity in hyperproliferative hairless mouse epidermis. British Journal of Dermatology. Vol. 110, no. 1 (1984). p. 29-35
(8) Setala, K., et al. Mechanism of experimental tumorigenesis. I. Epidermal hyperplasia in mouse caused by locally applied tumor initiator and dipole-type tumor promoter. Journal of the National Cancer Institute. Vol. 23, no. 5 (November, 1959). p. 925-951
(9) Shubik, P., et al. Studies on the promoting phase in the stages of carcinogenesis in mice, rats, rabbits, and guinea pigs. Cancer Research. Vol. 10 (1950). p. 13-17
(10) Yampol'skaya, Y.B., et al. Some changes in the skin of workers in a plastic products plant. Gigiena Truda Professional 'nya Zabolevaniya. Vol. 17, no. 9 (1973). p. 53-55 (English translation: NIOSHTIC Control Number: 00104485).
(11) Elizarov, G.P. Occupational skin diseases caused by some cooling emulsions. Vestnik Dermatologii Venerologiya. Vol. 42 (1968). p. 52-56 (English translation: NIOSHTIC Control Number: 00103880).
(12) Carroll, K.K., et al. Influence of a dietary supplement of erucic acid and other fatty acids on fertility in the rat: sterility caused by erucic acid. Canadian Journal of Biochemistry and Physiology. Vol. 35 (1957). p. 1093-1105
(13) Aungst, B.J. Structure/effect studies of fatty acid isomers as skin penetration enhancers and skin irritants. Pharmaceutical Research. Vol. 6, no. 3 (1989). p. 244-247
(14) Holsti, P. Tumour promoting effects of some long chain fatty acids in experimental skin carcinogenesis in the mouse. Acta Pathologica et Microbiologica Scandinavica. Vol. 46 (1959). p. 51-58
(15) Van Duuren, B.L., et al. Cocarcinogenic and tumor-promoting agents in tobacco carcinogenesis. Journal of the National Cancer Institute. Vol. 56, no. 6 (June, 1976). p. 1237-1242
(16) Hogan, M.L., et al. Large intestinal carcinogenesis. I. Promotional effect of dietary fatty acid isomers in the rat model. Journal of the National Cancer Institute. Vol. 73, no. 6 (December, 1981). p. 1293-1296
(17) Twort, C.C., et al. Further experiments on the carcinogenicity of synthetic tars and their fractions. Journal of Pathology and Bacteriology. Vol. 33 (1931). p. 119-143
(18) Twort, J.M., et al. Comparative activity of some carcinogenic hydrocarbons. American Journal of Cancer. Vol. 35 (1939). p. 80-85
(19) Kinsella, A.R. Elimination of metabolic co-operation and the induction of sister chromatid exchanges are not properties common to all promoting or co-carcinogenic agents. Carcinogenesis. Vol. 3, no. 5 (1982). p. 499-503
(20) Parry, J.M., et al. Tumour promoters induce mitotic aneuploidy in yeast. Nature. Vol. 294 (19 November, 1981). p. 263-265
(21) Katz, G.V. and Guest, D. Aliphatic carboxylic acids. In: Patty's Industrial Hygiene and Toxicology. Edited by G.D. Clayton et al. 4th edition. Volume II. Toxicology. Part E. John Wiley and Sons, 1994. p. 3523-3524, 3594-3599, 3626-3630
(22) The Merck index: an encyclopedia of chemicals, drugs, and biologicals. 11th edition. Merck and Co., Inc., 1989. p. 1079-1080
(23) HSDB record for oleic acid. Date of last update: 9504
(24) Fire protection guide to hazardous materials. 13th ed. Edited by A.B. Spencer, et al. National Fire Protection Association, 2002. NFPA 325
(25) Bagby, M.O. Carboxylic acids: survey. In: Kirk-Othmer encyclopedia of chemical technology. 4th edition. Volume 5. John Wiley and Sons, 1993. p. 147-168
(26) Brockmann, R., et al. Fatty acids. Ullmann's encyclopedia of industrial chemistry. 5th completely revised edition. Vol. A 10. VCH Verlagsgesellschaft, 1987. p. 245-276
(27) Leo, A., et al. Partition coefficients and their uses. Chemical Reviews. Vol. 71, no. 6 (December, 1971). p. 607
(28) Bretherick, L. Bretherick's handbook of reactive chemical hazards. 5th edition. Volume 5. Butterworths, 1995. p. 31, 1174, 1256
(29) Corrosion data survey. Metals section. 6th edition. National Association of Corrosion Engineers, 1985. p. 92-93
(30) Forsberg, K., et al. Quick selection guide to chemical protective clothing. 4th ed. Van Nostrand Reinhold, 2002

Information on chemicals reviewed in the CHEMINFO database is drawn from a number of publicly available sources. A list of general references used to compile CHEMINFO records is available in the database Help.


Review/Preparation Date: 1996-05-17

Revision Indicators:
Engineering controls 1996-12-01
Resistance of material 1998-05-01
Bibliography 1998-05-01
Bibliography 2003-04-16
NFPA (health) 2003-04-16
Resistance of materials for PPE 2004-04-03
Long-term oral exposure to very high dietary levels of oleic acid (15%) for 10 weeks prior to mating has produced deficient mammary gland development and impaired lactation in female rats. As a result, high mortality was observed in the offspring.(12) Dietary levels of 1.5 g oleic acid and 100 g corn oil for 2 years caused changes in fat concentration and composition in the liver.(4) It is not possible to interpret these results because of the co- administration of the corn oil. 2005-12-29



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