Oleic Acid

Base Information

• Chemical Name: Oleic Acid
• CAS No.: 112-80-1
• Deprecated CAS: 17156-84-2,56833-51-3,8046-01-3,949900-16-7,1190712-11-8,1190965-71-9,1380514-02-2,2252262-80-7,1190712-11-8,1190965-71-9,1380514-02-2,56833-51-3,8046-01-3,949900-16-7
• Molecular Formula: C18H34O2
• Molecular Weight: 282.467
• Hs Code.: 29161500
• European Community (EC) Number: 204-007-1,217-977-6,291-731-6,291-733-7
• ICSC Number: 1005
• NSC Number: 9856
• UNII: 2UMI9U37CP
• DSSTox Substance ID: DTXSID1025809
• Nikkaji Number: J2.460K
• Wikipedia: Oleic_acid
• Wikidata: Q207688
• NCI Thesaurus Code: C68405
• RXCUI: 7631
• Pharos Ligand ID: 44KS49R58Z5P
• Metabolomics Workbench ID: 437
• ChEMBL ID: CHEMBL8659
• Mol file: 112-80-1.mol

Synonyms:9 Octadecenoic Acid;9-Octadecenoic Acid;cis 9 Octadecenoic Acid;cis-9-Octadecenoic Acid;Oleate;Oleic Acid

Chemical Property of Oleic Acid

Chemical Property:

• Appearance/Colour: colourless to light yellow viscous liquid
• Vapor Pressure: 52 mm Hg ( 37 °C)
• Melting Point: 13-14 °C(lit.)
• Refractive Index: n20/D 1.377
• Boiling Point: 360 °C at 760 mmHg
• PKA: pKa 5.35(H2O,t =25) (Uncertain)
• Flash Point: 270.1 °C
• PSA: 37.30000
• Density: 0.899 g/cm³
• LogP: 6.10850
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Miscible with ethanol, ether, acetone, chloroform, dimethyl form
• Water Solubility.: negligible
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 15
• Exact Mass: 282.255880323
• Heavy Atom Count: 20
• Complexity: 234

Purity/Quality:

99% ^*data from raw suppliers

Oleic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25-34-40-43-36/37/38-38
• Safety Statements: 36/37-37/39-26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids,Other Classes -> Organic Acids
• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)O
• Recent ClinicalTrials: Effects of Enzymatic Digestion and Probiotic on Oleuropein Bioavailability
• Recent NIPH Clinical Trials: The effects of oleic acid rich peanut product on serum lipid: a double-blind, randomized controlled trial.
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly on spraying.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and skin.
• Uses: GB 2760-96 defines it as a processing aid. It can be used as antifoaming agent, fragrance, binder, and a lubricant. It can be used for the manufacture of soap, lubricants, flotation agents, ointment and oleate, being also an excellent solvent for fatty acids and oil-soluble substances. It can be used for the precise polishing of gold, silver and other precious metals as well as polishing in electroplating industry. It can be used as analysis reagents, solvents, lubricants and flotation agent, but also applied to the sugar processing industry Oleic acid is an organic chemical raw material and can produce epoxidized oleic acid ester after epoxidation. It can be used as plastic plasticizer and for production of azelaic acid by oxidation. It is the raw material of polyamide resin. In addition, oleic acid can also be used as pesticide emulsifier, printing and dyeing auxiliaries, industrial solvents, metal mineral flotation agent, and release agent. Moreover, it can be used as the raw material for manufacture of carbon paper, round bead and typing wax paper. Various kinds of oleate products are also important derivatives of oleic acid. As a chemical reagent, it can be used as a chromatographic comparative sample and for biochemical research, detection of calcium, copper and magnesium, sulfur and other elements. It can be applied to biochemical studies. It can activate the protein kinase C in the liver cells. Oleic Acid is an unsaturated fatty acid that functions as a lubricant, binder, and defoamer. Oleic acid is a monounsaturated omega-9 fatty acid. Oleic Acid is obtained by the hydrolysis of various animal and vegetable fats and oils. Oleic Acid is used as an emulsifying or solubilizing agent i n aerosol products. oleic acid is also known as omega-9. oleic acid can improve the skinpenetration abilities of a preparation’s other components. An essential fatty acid, it is obtained from various animal and vegetable fats and oils, and may be mildly irritating to the skin.
• Production method: Oleic acid and other fatty acids together, are presented in all kinds of animal and vegetable oil fats in the form of glycerides. In animal fats, oleic acid can account for about 40-50% of the fatty acids. Its content in the vegetable oil can vary largely with the content in tea oil being as high as 83%, being 54% in peanut oil while the coconut oil only contains about 5-6%. Oleic acid is the co-product upon the production of stearic acid. The industrial stearic acid and industrial oleic acid actually both contain other fatty acids. There are many oil fats raw materials used for the production of stearic acid and oleic acid. The industry generally take mixed fat formulations, such as 30% melting beef tallow, 10% melting lard, 40% of bone oil and 20% of cottonseed oil. In the mixed fatty acid obtained through refinement and hydrolysis of oil fat, the difference of the melting point between the saturated and unsaturated acid is large. The yield of stearic acid and oleic acid depends mainly on the oil ester formula. Under normal circumstances, cold compressing can give 30-50% oleic acid and 50-70% stearic acid. Put the animal and vegetable oils and emulsions to hydrolysis at 105 ℃; remove the stearic acid after one step of compressing. Separate out the crude oleic acid and conduct dehydration, distillation and freezing; then conduct the second time compressing to remove palmitic acid, and finally obtain the finished product through refinement and dehydration. This method can be applied for co-production of stearic acid. For the same logic, use oleic acid for production of stearic acid will also produce oleic acid. Fixed consumption amount of raw materials: animal and vegetable oils and fats: 1950 kg/t, sulfuric acid (98%) 210kg/t. Use oil fat containing a certain amount of oleic acid as raw materials, for example, tallow, lard, palm oil and hydrolyze out the fatty acids. Use solvent to dissolve fatty acids and cool it to remove solid fatty acids and obtain the crude oleic acid. Then further dissolve it in the solvent, cooling at low temperature to crystallize the oleic acid out.
• Description: Oleic acid is a monounsaturated fatty acid and a major component of membrane phospholipids that has been found in human plasma, cell membranes, and adipose tissue. It contributes approximately 17% of the total fatty acids esterified to phosphatidylcholine, the major phospholipid class in porcine platelets. Oleic acid inhibits collagen-stimulated platelet aggregation by approximately 90% when used at a concentration of 10 μg/ml. It also inhibits fMLF-induced neutrophil aggregation and degranulation by 55 and 68%, respectively, when used at a concentration of 5 μM, similar to arachidonic acid ( | 90010.1 | 10006607). Oleic acid (60 μM) induces release of intracellular calcium in human platelets. In vivo, oleic acid increases TNF-α, IL-8, IL-6, and IL-1β production, neutrophil accumulation, and apoptotic and necrotic cell death in mouse lung and has been used to induce lung injury in a mouse model of acute respiratory distress syndrome (ARDS).

Technology Process of Oleic Acid

There total 145 articles about Oleic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 62.0%

methyl-5-thiastearate (114119-34-5) → cis-9-hexadecenoic acid (373-49-9,2091-29-4) + cis-Octadecenoic acid (112-80-1,2027-47-6) + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4)

Guidance literature:

With Saccharomyces cerevisiae NR₂₃₃₅; In ethanol; at 30 ℃; for 48h;

DOI:10.1016/S0040-4039(01)81007-8

Reference yield: 6.0%

methyl-5-thiastearate (114119-34-5) → cis-9-hexadecenoic acid (373-49-9,2091-29-4) + cis-Octadecenoic acid (112-80-1,2027-47-6) + methyl 5-thiaoleate + 1-hexadecylcarboxylic acid (57-10-3) + stearic acid (57-11-4)

Guidance literature:

With Saccharomyces cerevisiae NRC₂₃₃₅; In ethanol; at 30 ℃; for 48h; Product distribution;

DOI:10.1016/S0040-4039(01)81007-8

Reference yield: 5.39%

soybean oil, refined, bleached and deodorized → trans fatty acid; mixture of + cis-Octadecenoic acid (112-80-1,2027-47-6) + linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid (463-40-1,1955-33-5,21661-10-9,21661-09-6,21661-13-2,21661-11-0) + stearic acid (57-11-4)

Guidance literature:

With hydrogen; mineral malachite; at 165 ℃; for 4h; under 3102.97 Torr; Conversion of starting material;

upstream raw materials:

diethyl ether

chloroform

1-chloro-heptadec-8-ene

sodium cyanide

Downstream raw materials:

2-heptadec-8c-enyl-4,5-dihydro-1H-imidazole

(Z)-9-octadecenoyl chloride

cis-9,10-epoxystearic acid

vinyl oleate

Refernces

• 1、 Doulia, Danae,Rigas, Fotis,Gimouhopoulos, Kostantinos. "Chloroacetoxylation of oleic acid - a kinetic study". . p. 239 - 242. Retrieved 2000.
• 2、 Walborsky et al.. "-". . p. 2590,2592. Retrieved 1951.
• 3、 Adkins,Billica. "-". . p. 695,696. Retrieved 1948.
• 4、 Lee, Youngjun,Devaraj, Neal K.. "Lipase mimetic cyclodextrins". . p. 1090 - 1094. Retrieved 2021.
• 5、 Dippe, Martin,Mueller, Mathias Q.,Sinz, Andrea,Ulbrich-Hofmann, Renate. "Phospholipases a1 from armillaria ostoyae provide insight into the substrate recognition of a/b-hydrolase fold enzymes". . p. 1435 - 1448. Retrieved 2012.
• 6、 Reyes-Duarte,Lopez-Cortes,Torres,Comelles,Parra,Pena,Ugidos,Ballesteros,Plou. "Synthesis and properties of ascorbyl esters catalyzed by lipozyme TL im using triglycerides as acyl donors". . p. 57 - 64. Retrieved 2011.
• 7、 Chakraborty, Kajal,Paulraj. "Purification and biochemical characterization of an extracellular lipase from Pseudomonas fluorescens MTCC 2421". . p. 3859 - 3866. Retrieved 2009.
• 8、 Cui, Caixia,Tao, Yifeng,Li, Lingli,Chen, Biqiang,Tan, Tianwei. "Improving the activity and stability of Yarrowia lipolytica lipase Lip2 by immobilization on polyethyleneimine-coated polyurethane foam". . p. 59 - 66. Retrieved 2013.
• 9、 Ayinla, Zainab A.,Ademakinwa, Adedeji N.,Gross, Richard A.,Agboola, Femi K.. "Biochemical and biophysical characterisation of a small purified lipase from Rhizopus oryzae ZAC3". . . Retrieved 2021/02/16.