Related Searches: Oleic acid, vegetable oleic acid, oleic acid price, acid ester, carboxylic acid, View all

Oleic acid(CAS No. 112-80-1)

Oleic acid C18H34O2 (cas 112-80-1) Molecular Structure

112-80-1 Structure

Identification and Related Records

【Name】
Oleic acid
【CAS Registry number】
112-80-1
【Synonyms】
Metaupon
9-octadecenoic acid
Octadecenoic acid
oleoate
red oil
【EINECS(EC#)】
204-007-1
【Molecular Formula】
C18H34O2 (Products with the same molecular formula)
【Molecular Weight】
282.46
【Inchi】
InChI=1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-
【InChIKey】
ZQPPMHVWECSIRJ-KTKRTIGZSA-N
【Canonical SMILES】
CCCCCCCCC=CCCCCCCCC(=O)O
【Isomers smiles】
CCCCCCCC/C=C\CCCCCCCC(=O)O
【MOL File】
112-80-1.mol

Chemical and Physical Properties

【Appearance】
colourless to light yellow viscous liquid
【Density】
0.89
【Melting Point】
13℃
【Boiling Point】
360℃
【Refractive Index】
1.4585-1.4605
【Flash Point】
189℃
【Water】
negligible
【Solubilities】
negligible
【Color/Form】
Colorless or nearly colorless liq (above 5-7 deg C)
YELLOWISH, OILY LIQUID
WATER-WHITE LIQUID
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents, aluminium.
【Storage temp】
2-8°C
【Spectral properties】
Index of refraction: 1.463 at 18 deg C/D; 1.4585 at 26 deg C/D
MAX ABSORPTION (HEXANE): 185 NM (LOG E= 3.8)
IR: 915 (Sadtler Research Laboratories Prism Collection)
1H NMR: 70 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 480 (Johnson and Jankowski, Carbon-13 NMR Spectra, John Wiley & Sons, New York)
UV: HBCP 185
MASS: 27869 (NIST/EPA/MSDC Mass Spectral database, 1990 version); 2214 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
【Computed Properties】
Molecular Weight:282.46136 [g/mol]
Molecular Formula:C18H34O2
XLogP3:6.5
H-Bond Donor:1
H-Bond Acceptor:2
Rotatable Bond Count:15
Exact Mass:282.25588
MonoIsotopic Mass:282.25588
Topological Polar Surface Area:37.3
Heavy Atom Count:20
Formal Charge:0
Complexity:234
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Anion Count:1
Feature 3D Hydrophobe Count:1
Effective Rotor Count:15
Conformer Sampling RMSD:1.4
CID Conformer Count:89

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Safety】

Hazard Codes:?ToxicT,IrritantXi
Risk Statements:?23/24/25-34-40-43-36/37/38-38
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R34:Causes burns.?
R40:Limited evidence of a carcinogenic effect.?
R43:May cause sensitization by skin contact.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:?36/37-37/39-26-36
S36/37:Wear suitable protective clothing and gloves.?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
RIDADR:?UN 1198 3/PG 3
WGK Germany:?2
F:?10

【Sensitive】
Air Sensitive
【Skin, Eye, and Respiratory Irritations】
/Oleic acid/ ranging formulations ranging from 2.53 to 92.7% were considered "slightly" to "moderately irritating." The erythema scores ranged from 1.41 to 3.21 on a scale of 0 to 5 and were not directly related to oleic acid concentrations in the formulations.
Irritating to skin and eyes.
【Cleanup Methods】
Cover with soda ash or sodium bicarbonate. Mix and add water. Neutralize and drain into a drain with sufficient water.
【Transport】
UN 1198 3/PG 3
【Fire Fighting Procedures】
Use water spray, dry chemical, foam or carbon dioxide. Water or foam may cause frothing. Water spray may be used to flush spills away from exposures.
Water or foam may cause frothing.
【Fire Potential】
Combustible
Combustible when exposed to heat or flame.
【Formulations/Preparations】
GRADE: Variety of technical grades; grade free from chick edema factor; USP; FCC; 99+%. A purified technical oleic acid containing 90% or more oleic, 4% maximum linoleic and 6% maximum saturated acids is available.
Several commercial grades of Oleic Acid are available, distinguished by varying proportions of saturated fatty acids. The commercial grade contains 7-12% saturated acids and some unsaturated acids and is usually derived from edible sources (internally administered Oleic Acid must be derived from edible sources. Oleic Acid derived from tallow contains varying amounts of linolenic and Stearic Acids and small but significant quantities of elaidic (trans-9-octadecenoic) acid, some of which is generated from certain processing operations (e.g., distillation and high-temperature bleaching with clays). /The literature/ reported several technical grades of Oleic Acid: chick edema factor-free grade, U.S. Pharmacopeia (USP) grade, Food Chemicals Codex (FCC) grade, and purified technical grade Oleic Acid. The latter technical grade Oleic Acid contains 90% Oleic Acid and has a 4% maximum linoleic acid.
Commercial products contain 67-80% oleic acid, 6-12& linoleic acid and linolenic acids, and 7-12% saturdated acids.
【Exposure Standards and Regulations】
Oleic acid is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
/Oleic acid derived from tall oil fatty acids/ is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient.
/Oleic acid, sulfated/ is an indirect food additive for use only as a component of adhesives.
Substances migrating to food from paper and paperboard products used in food packaging that are generally recognized as safe for their intended use, within section 409 of the Act. Oleic acid is included on this list.
【Reactivities and Incompatibilities】
The improved preparation of 1,4-octadecanolactone involves heating oleic acid (or other C18 acids) with 70% perchloric acid to 115 deg C. This is considered to be a potentially dangerous method.
Shortly after mixing /aluminum and oleic acid/, an explosion occurred, but this could not be repeated. The acid may have been peroxidized.
Potentially dangerous reaction with perchloric acid and heat.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
【Protective Equipment and Clothing】
Impervious gloves; goggles or face shield; impervious apron.
Wear rubber gloves, face shield, coveralls, full body shields and self-contained breathing apparatuses ... .
【Specification】

? Oleic acid?,?its cas register number is 112-80-1. It also can be called?4-02-00-01641 (Beilstein Handbook Reference) 9-Octadecenoic acid (Z)- ; AI3-01291 ; Acide oleique ; Acide oleique [French] ; BRN 1726542 ; CCRIS 682 ; Caswell No. 619 ; Century cd fatty acid ; EPA Pesticide Chemical Code 031702 ; Elaidoic acid ; Emersol 220 white oleic acid ; Emersol 221 low titer white oleic acid ; Emersol 233LL ; Emersol 6313NF ; Emersol 6321 ; Extra Oleic 80R ; Extra Olein 90R ; Extraolein 90 ; FEMA No. 2815 ; FEMA Number 2815 ; Glycon RO ; Glycon WO ; HSDB 1240?; K 52 ; Lunac O-CA ; Metaupon ; Neo-Fat 92-04 ; Oelsauere ; Oleine 7503 ; Oleinic acid ; Omega-9 Fatty Acids ; Pamolyn ; Tego-oleic 130 ; UNII-2UMI9U37CP ; Vopcolene 27 ; Wecoline OO ; White oleic acid ; Wochem No. 320 ; Z-9-Octadecenoic acid ; cis-Octadec-9-enoic acid ; cis-delta(sup 9)-Octadecenoic acid ; delta9-cis-Oleic acid ; l'Acide oleique . Oleic acid?(CAS NO.112-80-1) is a?colourless to light yellow viscous liquid. And it is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources which? the most abundant fatty acid in human adipose tissue.

【Octanol/Water Partition Coefficient】
log Kow = 7.64
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Charge directly or after dissolving in a flammable solvent into the furnace with afterburner.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Hydrolytic splitting of tallow, followed by fractional distillation and solvent crystallization
Obtained by hydrolysis of various animal and vegetable fats and oils. ... Separation from olive oil by double fractionation via urea adducts.
Derived from hydrolysis & distillation of triolein.
Free fatty acid is obtained from the glyceride by hydrolysis, steam distillation & separation by crystallization or solvent extraction. Filtration from press cake results in oleic acid of commerce (red oil) which is purified & bleached for specific uses.
U.S. Exports

(1984) 2.70X10+8 g
U.S. Imports

(1972) 4.2X10+8 GRAMS
(1975) 4.17X10+8 GRAMS
U.S. Production

(1972) 6.4X10+10 GRAMS
(1975) 5.36X10+10 GRAMS
(1984) 2.93X10+8 g
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >100 million - 500 million 1990 >100 million - 500 million 1994 >100 million - 500 million 1998 >100 million - 500 million 2002 >100 million - 500 million
9-Octadecenoic acid (9Z)- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
【Usage】

Adjuvant.

Biomedical Effects and Toxicity

【Pharmacological Action】
Industrial use of compound involves no known hazards. Ingestion causes mild irritation of mouth and stomach. Contact with eyes or skin causes mild irritation.
【Therapeutic Uses】
/EXPTL THER/ Ten Japanese boys with childhood adrenoleukodystrophy (ALD), one adult patient with adrenomyeloneuropathy (AMN), and two presymptomatic ALD boys were treated with dietary erucic acid (C22:1) for more than 12 months; except in a case of childhood ALD patient who died 7 months after beginning erucic acid therapy. During erucic acid therapy, the serum levels of very long-chain fatty acid (VLCFA) (C24:0/C22:0) decreased within 1-2 months in all patients, and these levels in four of the patients decreased to the normal range. Neurological examination and MRI findings in all 10 of the childhood ALD patients showed progression of the disease while they were receiving the dietary therapy. However, the mean interval between the onset of awkward gait and a vegetative state in diet-treated patients was significantly longer than that in the untreated patients. One AMN patient showed slight improvement of spastic gait and lessened pain in the lower limbs due to spasticity. The two presymptomatic ALD boys remained intact on clinical examination and on MRI findings for 38 and 23 months, respectively, after starting the diet. [Asano J et al; Brain Dev 16 (6): 454-8 (1994)]
【Biomedical Effects and Toxicity】
Radioactivity has been traced to the heart, liver, lung, spleen, kidney, muscle, intestine, adrenal, blood, and lymph, and adipose, mucosal, and dental tissues after administration of radioactive oleic, palmitic, and stearic acids.
Simultaneous ingestion of trace amounts of 14C-triolein (10 uCi) and 3H-oleic acid (20 uCi) in 42 g of carrier fat by patients with normal fecal fat excretion resulted in estimated fecal excretion of less than 10% of both substances. Gastrointestinal transit times for 14C-triolein, 3H-oleic acid, and a nonabsorbable marker, CrCl3, did not differ significantly.
Oleic Acid has been reported to penetrate the skin of rats. On histological examination, fluorescence from absorbed oleic acid was found in epidermal cell layers of skin removed from treated rats within 10 min of its application. The path of penetration was suggested to be via the hair follicles. Only minute amounts of oleic acid were visualized in the blood vessels throughout the experiment. Skin permeability was shown to increase with the lipophilic nature of a compound.
METABOLISM OF TRITIATED OLEIC ACID WAS STUDIED IN RATS DURING 600 DAYS. DURING FIRST 4 DAYS, HALF ACTIVITY IS FIXED TO WATER & HALF IS STORED IN ADIPOSE TISSUE WHICH IT LEAVES QUICKLY, THEN MORE SLOWLY WITH T/2 OF ABOUT 200 DAYS.
Fatty acids originating from adipose tissue stores are either bound to serum albumin or remain unesterified in the blood.
Oleic, palmitic, myristic, and stearic acids are primarily transported via the lymphatic system, and lauric acid is transported by the lymphatic and (as a free fatty acid) portal systems.
Male rats (Wistar strain) were iv injected with a mixture of free (14-(14)C) erucic (22:1) and (9-10 (3)H) oleic (18:1) acid. after 2, 4, 8, 16 and 30 min, radioactivity was examined in blood, liver, heart, kidneys and spleen. At all times studied, the majority of radioactivity was found in the liver, primarily as triglycerides (60% of radioactivity in total lipids) and as phospholipids (20 to 30%). In the other organs tested, radioactivity was found 10 to 15 times lower than in liver. In the heart, (14)C was 3 to 4 times higher than (3)H. More than 80% was recovered as 22:1 in tri-glycerides. In spleen and kidneys, the (14)C:(3)H ratio was particularly high in free fatty acids and monoglycerides. In kidneys, 60% of (14)C was present as nervonic acid (24:1) in monoglycerides and 40% in phospholipids, suggesting that the mononervonin formed was used for phospholipid biosynthesis.
Erucic-14-(14)C acid and oleic-10-(14)C acid were admin orally and iv to female mice, both pregnant and non-pregnant. The radioactivity distribution was studied in the organs by autoradiography of whole body slices. Decreasing quantities of radioactivity were found in the order: liver, myocardium, kidneys and spleen of both pregnant and non-pregnant animals. In fetuses, the amt of radioactivity was lower with erucic acid than with oleic acid. After oral admin, there was no difference in organ radioactivity in the mothers, independent of whether they had received oleic or erucic acid. In contrast, the fetus hearts contained twice the radioactivity after oleic acid as after erucic acid admin. The ratio of concn between mother heart and fetus heart was 2:1 for oleic acid and 4:1 for erucic acid. Erucic acid thus appears to cross the placenta less easily than oleic acid.
THERE WAS AN INCREASE IN OLEIC ACID OF LECITHIN IN ALCOHOLICS, (OBSERVED IN BOTH LECITHIN & TRIGLYCERIDES), AS COMPARED TO NORMALS.
% COMPOSITION OF OLEIC ACID IN LIPID FRAGMENTS DECREASED WITH METHYLMERCURY CHLORIDE (DOSAGE: 1-10 MG/KG) EXCEPT FOR THAT IN PHOSPHOLIPIDS OF KIDNEY OF RATS RECEIVING LOWEST DOSE. [ANDO T ET AL; BULL ENVIRON CONTAM TOXICOL 22 (1-2): 214 (1979)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 340,000 for the free acid(SRC), determined from a log Kow of 7.64(2) and a regression-derived equation(3), indicates that undissociated oleic acid is expected to be immobile in soil(SRC). The pKa of oleic acid is 5.02(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of oleic acid from moist soil is not expected to be an important fate process because the acid is in the anion form and anions do not volatilize(SRC). Oleic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.46X10-7 mm Hg(6). Biodegradation is expected to be an important fate process in soil based on half-lives of 0.2 and 0.66 days in screening tests(7,8).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 340,000 for the free acid(SRC), determined from a log Kow of 7.64(2) and a regression-derived equation(3), indicates that undissociated oleic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 5.02(4) indicates oleic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 10(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 47 and 52 theoretical %BOD for oleic acid measured over a period of 5 days using sewage inoculum(8) and a biodegradation half-life of 0.66 days using activated sludge inocula(9) suggest that biodegradation may be an important environmental fate process in aquatic ecosystems(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), oleic acid, which has a vapor pressure of 5.46X10-7 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase oleic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for cis-oleic acid and trans-oleic acid reactions in air are estimated to be 5.1 and 4.6 hours(SRC), calculated from rate constants of 7.6X10-11 and 8.3X10-11cu cm/molecule-sec at 25 deg C(SRC) that were derived using a structure estimation method(3). Vapor-phase oleic acid is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for cis-oleic acid and trans-oleic acid reactions in air are estimated to be 2.1 and 1.4 hours(SRC), respectively, calculated from rate constants of 1.3X10-16 and 2.0X10-16 cu cm/molecule-sec at 25 deg C(SRC) that were derived using a structure estimation method(3). Particulate-phase oleic acid may be removed from the air by wet or dry deposition(SRC). Oleic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

Supplier Location

Top Suppliers

Diamond member Hubei XinRunde Chemical Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-27-83214668
Diamond member Hangzhou Dayangchem Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-88938639
Diamond member chengdu yancey import& export trade co.,ltd
Country:ChinaChina
Business Type:Trading Company
Telephone:86-153-73023168
Diamond member Hangzhou J&H Chemical Co., Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-87396430
Finetech Industry limited.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-27-87465837
Shenzhen Simeiquan Biotechnology Co.Ltd
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-20-18102838259
Capot Chemical Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-571-85586718
TianJin North JinHeng Chemical Plant
Country:ChinaChina
Business Type:Manufacturer
Telephone:0086-22-59952083
Chengdu Herbpurify CO.,LTD
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-28-85249238
Shanghai Hope Chem Co., Ltd.
Country:ChinaChina
Business Type:Manufacturer
Telephone:86-21-61723543

Quick Search

Cas    Name

Related products

OLEIC ACID-[9,10-3H]

[9,10(N)-3H]OLEIC ACID;OLEIC ACID-[9,10-3H];OLEIC ACID, [9,10-3H(N)];OLEIC ACID, [9,10(N)-3 H]

Oleic acid trimethylsilyl ester

(Z)-9-Octadecenoic acid trimethylsilyl;(Z)-9-Octadecenoic acid trimethylsilyl ester;Oleic acid trimethylsilyl;Oleic acid trimethylsilyl ester

OLEIC ACID BEHENYL ESTER

-;henicosyl (9Z)-octadec-9-enoate

oleic acid, propoxylated, phosphate

oleic acid, propoxylated, phosphate

Oleic acid, compound with triethylamine

9-octadecenoicacid(z)-,compd.withn,n-diethylethanamine(1:1);TRIETHYLAMINE OLEATE;oleic acid, compound with triethylamine

Oleic acid diethanolamide phosphate

Oleic acid diethanolamide phosphate;AC1O5NT3;EINECS 269-042-7;2-[2-hydroxyethyl-[(Z)-octadec-9-enoyl]amino]ethyl dihydrogen phosphate;9-Octadecenamide...

Oleic Acid-d17

Oleic Acid-d17;(9Z)-9-Octadecenoic Acid-d17

OLEIC ACID-1-13C

(Z)-9-OCTADECANOIC ACID;(Z)-9-OCTADECENOIC ACID;OLEIC ACID-WATER SOLUBLE;OLEIC ACID-1-13C;OLEATE;OLEIC-1-13C ACID;M-PEDE;RED OIL

10-Nitro Oleic Acid

10-Nitro Oleic Acid;(9E)-10-Nitro-9-octadecenoic Acid

Oleic acid, sulfated, sodium salt

Octadecanoic acid, 9(or 10)-(sulfooxy)-, sodium salt (1:?);9(or 10)-(Sulfooxy)stearic acid sodium salt;9(Or 10)-(sulphooxy)octadecanoic acid, sodium s...

Oleic acid 3-hydroxypropyl ester

(Z)-9-Octadecenoic acid 3-hydroxypropyl ester;Oleic acid 3-hydroxypropyl ester

Oleic acid 3-pyridylmethyl ester

(9Z)-9-Octadecenoic acid (3-pyridyl)methyl ester;(9Z)-9-Octadecenoic acid 3-pyridylmethyl ester;(Z)-9-Octadecenoic acid (3-pyridyl)methyl ester;Oleic ...