Ethyl oleate oil, also known as cis 9-octadecenoic acid ethyl ester or 9-octadecenoic acid ethyl ester, is a colorless oily liquid with a pungent odor. Volatile, flammable, insoluble in water, soluble in organic solvents. It is an ester compound, CAS 112-62-6, with the chemical formula C18H32O. Mainly used for preparing organic chemicals such as lubricants, waterproofing agents, resin toughening agents, surfactants, medicinal excipients, plasticizers, ointment matrices, and fragrances. It is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is a liquid lipid component in nanostructured lipid carriers (NLCs). NLC is an oral carrier of trans ferulic acid (TFA). Shaanxi BLOOM Tech Co., Ltd has ethyl oleate for sale. If you would like to know the price of ethyl oleate, please send us an email.
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Chemical Formula |
C20H38O2 |
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Exact Mass |
310 |
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Molecular Weight |
311 |
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m/z |
310 (100.0%), 311 (21.6%), 312 (2.2%) |
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Elemental Analysis |
C, 77.36; H, 12.34; O, 10.30 |
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Ethyl oleate, as an ester compound generated by esterification reaction between oleic acid and ethanol, has shown wide application value in multiple industrial fields due to its unique chemical structure and physical properties. Its molecular formula is C20H38O2, which is a colorless or light yellow oily liquid at room temperature. It has low polarity, high boiling point (about 360 ℃), and good solubility, making it a key raw material for industries such as chemical, pharmaceutical, food, and daily chemical.
The application depth and breadth in the pharmaceutical industry continue to expand, and its biocompatibility and low toxicity make it an important carrier for drug formulation development.
1. Solvent and Carrier System
As a solvent for steroid hormones (such as testosterone and progesterone) and lipophilic drugs (such as cyclosporine and anticancer drugs), it can significantly enhance the solubility and stability of insoluble drugs. For example, in microemulsion formulations, ethyl oleate oil works synergistically with surfactants to form nanoscale carriers with particle sizes less than 100nm, achieving targeted delivery and sustained release control of drugs.
The oleic acid ethyl ester based microcapsule system developed by a certain research team has successfully increased the bioavailability of cyclosporine to three times that of traditional dosage forms.
2. Injection and implant development
In intramuscular injections, as a concentrated vehicle, it can reduce the injection volume and pain sensation, while prolonging the drug release cycle. For example, a certain long-acting testosterone preparation uses ethyl oleate as the matrix to maintain stable blood drug concentration by administering once a month. In addition, its biodegradability makes it an ideal material for implantable microcapsules.
The oleate ethyl ester polylactic acid copolymer microcapsules developed by a certain biotechnology company have been used for local sustained-release treatment of tumor chemotherapy drugs.
3. Standardized application of medicinal excipients
According to the Chinese Pharmacopoeia and USP-NF standards, medicinal grade ethyl oleate must meet indicators such as monoester content ≥ 60% and peroxide value ≤ 10meq/kg. The ultra pure grade ethyl oleate produced by a certain enterprise through molecular distillation technology has passed FDA certification and is widely used in injections, ophthalmic preparations, and transdermal patches.
Food Industry: The Dual Role of Natural Flavors and Safety Additives
With its GRAS (generally considered safe) certification and natural characteristics, it has become an indispensable essence carrier and functional additive in the food industry.
1. Edible essence base
As the core component of floral and fruity essence, it can simulate the aroma of natural oils and enhance the flavor hierarchy of food. For example, adding 0.1% -0.5% ethyl oleate to baked goods can significantly enhance the butter aroma of bread; In dairy products, its combination with vanillin can form a long-lasting creamy aroma.
2. Food Packaging and Preservation
Its hydrophobicity makes it an ideal material for food packaging coatings. The oleic acid ethyl ester chitosan composite film developed by a research team has a 92% antibacterial rate against Escherichia coli and can extend the shelf life of strawberries to 14 days. In addition, its application as a lubricant in chocolate production can reduce mold demolding resistance and decrease product damage rate.
Daily chemical field: synergistic effect of softener and essence carrier
In cosmetics and personal care products, it has become a key ingredient in high-end formulas through its unique skin feel regulation and essence stabilizing effect.
1. Skin softening and barrier repair
As a non-ionic lubricant, it can penetrate into the gaps between the stratum corneum, forming a hydrophobic protective film to prevent water loss. Adding 3% ethyl oleate to a certain brand of skincare cream, clinical tests have shown that after 4 weeks of use, the skin moisture content increases by 28% and the transdermal water loss rate decreases by 15%.
2. Essence stabilization and slow release technology
Its low volatility makes it the preferred wall material for essence microcapsules. A perfume brand uses the composite microcapsule technology of ethyl oleate and gum arabic to extend the release period of essence to 8 hours, while reducing the degradation of aroma components caused by ultraviolet radiation.
Industrial application of lubrication and water-resistant functions in the field of chemical engineering
The lubricity and water resistance of ethyl oleate make it a key additive in industries such as metal processing, textile printing and dyeing.
1. Industrial lubricants
In metal cutting fluid, the friction coefficient can be reduced to below 0.05, while forming a protective film to prevent workpiece oxidation. After a certain automotive parts manufacturer adopted ethyl oleate based lubricant, the tool life was extended by 40%, and the surface roughness of the machined surface was reduced to Ra0.8 μ m.
2. Textile water-resistant finishing agent
By compounding with fluorinated polymers, fabrics can be endowed with superhydrophobic properties. The oleic acid ethyl ester perfluorooctanoic acid copolymer coating developed by a certain outdoor clothing brand achieves a fabric contact angle of 152 ° and a waterproof index exceeding 20000mmH ₂ O.
The chemical stability and selectivity make ethyl oleate oil a key material in gas chromatography (GC) and liquid chromatography (HPLC) analysis.
1. Gas chromatography stationary phase
As a non-polar stationary phase, it is suitable for separating low polarity compounds such as hydrocarbons and esters. A laboratory successfully separated the C ₅ - C ₁ ₂ component in gasoline using a chromatography column coated with ethyl oleate, with a separation degree of over 1.8.
2. High performance liquid chromatography solvent
In reverse phase chromatography, it can be used as a mobile phase additive to improve the retention behavior of polar compounds. A research team achieved baseline separation of flavonoids by adding a methanol water solution containing 0.5% ethyl oleate.
Agricultural field: enhancing pesticide efficacy and regulating plant growth
Its permeability and biological activity make it exhibit dual functions in agriculture.
1. Pesticide adjuvants
As a penetrant, it can destroy the wax layer of insect epidermis and enhance the penetration efficiency of the agent. The oleic acid ethyl ester organic silicon compound additive developed by a certain pesticide enterprise has increased the contact killing effect of pyrethroid insecticides by three times.
2. Plant growth regulation
Low concentrations of ethyl oleate (0.01% -0.1%) can induce the expression of stress resistant genes in plants. A study showed that tomato seedlings treated with ethyl oleate had a 2.3-fold increase in proline content and a 45% increase in survival rate under drought conditions.
With the advancement of materials science, potential value has been demonstrated in the fields of nano synthesis and energy storage.
1. Nano particle synthesis template
Its long-chain alkyl group can control the morphology of metal nanoparticles. A certain team synthesized monodisperse gold nanorods using ethyl oleate as a ligand, with a longitudinal plasmon resonance peak at 820nm, suitable for biological imaging and photothermal therapy.
2. Lithium ion battery electrolyte additive
Ethyl oleate, as a film-forming additive, can form a stable SEI film on the negative electrode surface. A certain battery company has increased the cycle life of lithium-ion batteries to over 2000 times and achieved a capacity retention rate of 92% by adding 1% ethyl oleate.
(1) The optimum reaction conditions for synthesis of Ethyl oleate oil by the combined process of catalytic esterification of p-toluene sulfonic acid supported on active carbon and deacetylation of calcium oxide are: n (ethyl acetate): n (oleic acid)=40:1, the amount of p-toluene sulfonic acid supported on active carbon is 10% of the total mass of oleic acid and ethyl acetate, the reaction temperature is 110C, and the reaction time is 4h. Under this condition, the average conversion rate (transesterification rate) of oleic acid is 8762%.
(2) P-Toluenesulfonic acid supported on activated carbon is a good catalyst for the transesterification of ethyl acetate and oleic acid to synthesize ethyl oleate. The catalyst has high activity, high selectivity, easy removal, decolorization function and high quotient value.
(3) With the external circulation technology, calcium oxide and acetic acid carried by ethyl acetate are used to generate calcium acetate, which plays a role in separating the cool acid, enabling the reaction of oleic acid and ethyl acetate to generate ethyl oleate through acidolysis and transesterification. This synthesis process is simple and easy, with high transesterification rate, reducing the load in the separation process and low energy consumption in the reaction process.
Describe a method for preparing ethyl oleate by esterification of ethanol with oleic acid.
Synthesis steps
Mix oleic acid and ethanol in a certain proportion, add catalyst concentrated sulfuric acid or p-toluenesulfonic acid, and stir evenly.
01
Heat the mixture to reflux temperature (usually 120-140 ℃) and continue reflux for a period of time (usually 2-4 hours), allowing the oleic acid and ethanol to fully react.
02
Cool the reactant to room temperature, neutralize it with alkaline solution (such as NaOH or KOH) to pH 8-9, and allow the catalyst to react with concentrated sulfuric acid or p-toluenesulfonic acid to generate sodium sulfate or potassium sulfate, while also allowing the unreacted oleic acid to form oleate.
03
Wash off unreacted alcohols and catalysts with water to turn the reactants into aqueous solutions. Filter the aqueous solution to remove solid impurities.
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Distill the filtrate and cut off the ethyl oleate fraction. During the distillation process, ethyl oleate is separated as other low boiling substances evaporate.
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Dry the obtained ethyl oleate fraction with anhydrous calcium chloride to remove moisture and other impurities.
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Perform vacuum distillation on the dried ethyl oleate for further purification. During the process of vacuum distillation, ethyl oleate is separated with the evaporation of other high boiling substances.
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Chemical reaction equation
C18H34O2 + C2H5OH → C18H34O2-COOC2H5 + H2O
In this reaction, a carboxyl group in the oleic acid molecule undergoes esterification with a hydroxyl group in the ethanol molecule, producing Ethyl Oleate Oil and water.
C18H34O2-COOC2H5 + H2SO4 (concentrated) → C18H34O2-COOC2H5 + H2O + SO2 ↑
or
C18H34O2-COOC2H5 + H2SO4 (p-toluenesulfonic acid) → C18H34O2-COOC2H5 + H2O + CH3C6H4SO3H
In this reaction, the catalyst concentrated sulfuric acid or p-toluenesulfonic acid participates in the esterification reaction, generating bisulfate or p-toluenesulfonate and water. These salts are neutralized in subsequent alkaline neutralization steps.
C18H34O2-COOC2H5 + NaOH (or KOH) → C18H34O2-COONa (or KNa) + C2H5OH
In this reaction, the unreacted oleic acid undergoes a neutralization reaction with the alkaline solution, producing sodium oleate or potassium oleate and ethanol. These sodium or potassium salts are washed away in subsequent water washing steps.
C18H34O2-COONa (or KNa) + H2O → C18H34O2-COOH + NaOH (or KOH)
In this reaction, unreacted ethanol undergoes a hydrolysis reaction with water, producing acetaldehyde and water. At the same time, the alkaline solution is also diluted into an aqueous solution of alkali. These hydrolysis reactions are carried out under acidic conditions, thus promoting the hydrolysis of sodium or potassium oleate.
Frequently Asked Questions
What is ethyl oleate oil?
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Ethyl oleate is an ester formed by the condensation of the fatty acid oleic acid and ethanol. In skin care formulas, it serves much the same function as oleic acid – that is, as a skin conditioning, emollient ingredient.
Is ethyl oleate olive oil?
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304 stainless steel meets the international requirements of food grade,316 stainless steel is not only food grade or medical grade. However,the use of this medical grade as a production cup will not bring additional benefits to everyone. Why is it called 304 or 316? This is mainly defined according to the material composition. 316 stainless steel is not similar to mineral materials,after use can release some substances to promote human absorption.1. Ethyl Oleate (EO) What it is: A fatty acid ester derived from ethanol and oleic acid (commonly found in olive oil).
Is ethyl oleate toxic?
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Ethyl oleate is neutral and is a more lipid-soluble form of oleic acid. The compound is one of the fatty acid ethyl esters generated after the breakdown of ethanol in the body. Moreover, ethyl oleate is a toxic mediator of ethanol in the heart, liver, pancreas, and brain.
What is the common name for ethyl oleate?
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Ethyl oleate, also known as ethyl oleic acid or fema 2450, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl oleate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
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