BUTYL OLEATE

Butyl Oleate = Oleic Acid = Elaidic Acid

CAS Number: 142-77-8
IUPAC Name: butyl (Z)-octadec-9-enoate
Molecular Weight: 338.57 g/mol
EC Number: 205-559-6
Molecular Formula: C18H34O2

Description:
Butyl oleate is a fatty acid that occurs naturally in various animal and vegetable fats and oils. 
Butyl oleate is an odorless, colorless oil, although commercial samples may be yellowish. 
In chemical terms, butyl oleate is classified as a monounsaturated omega-9 fatty acid, abbreviated with a lipid number of 18:1 cis-9. 
Butyl oleate has the formula CH3(CH2)7CH=CH(CH2)7COOH.
The name of butyl oleate derives from the Latin word oleum, which means oil.
Butyl oleate is the most common fatty acid in nature.
The salts and esters of butyl oleate are called oleates.
Butyl oleate is an omega-9 fatty acid. 
Butyl oleate can be made by the body. 
Butyl oleate is also found in foods. 
Butyl oleate is obtained by hydrolysis of olive oil. 
Butyl oleate is insoluble in water and very soluble in alcohol. This acid is used in the elaboration of topic formulations as excipient, e.g., of emulsions.
Due to butyl oleate's capacity to react with alkalis forming soaps with emulgent properties.
Butyl oleate can act as a percutaneous absorption enhancer of several drugs, as it induces the disruption of the lipid structure of the stratum corneum, allowing drug permeation. 
Butyl oleate is able to increase the bioavailability of the corticoids betamethasone 17-benzoate and betamethasone 17-valerate.
Also ketorolac, metronidazole, hydrocortisone, progesterone and estradiol, to cite just a few. 
Butyl oleate is also used in the preparation of the benzyl benzoate lotion for the treatment of scabies. Oleic and linoleic acid can induce the in vitro suppression of the skin pigmentation.
Highest levels of butyl oleate are found in olive oil and other edible oils.
Butyl oleate is most commonly used for preventing heart disease and reducing cholesterol. 
Butyl oleate is also used for preventing cancer and other conditions, but there is no good scientific evidence to support these other uses.
Don't confuse butyl oleate with diets and oils containing butyl oleate, such as the Mediterranean diet, olive oil, and canola oil or sunflower oil made to have higher levels of butyl oleate. 
Butyl oleate, the most widely distributed of all the fatty acids, apparently occurring to some extent in all oils and fats. In oils such as olive, palm, peanut, and sunflower.
Butyl oleate is the principal acid obtained by saponification.
Butyl oleate, CH3(CH2)7CH=CH(CH2)7CO2H, like other fatty acids, does not occur in the free state but is normally found as an ester of glycerol—i.e., as a glyceride or as an ester of a long-chain alcohol.
Butyl oleate is a solid with a low melting point; two crystalline forms (α-form, melting point 13.4 °C [56 °F], and β-form, melting point 16.3 °C [61 °F]) are known. 
Butyl oleate is a long-chain carboxylic acid; its molecule contains one double bond between C9 and C10 with the cis configuration. 
The structure of butyl oleate may be deduced from the following reactions. 
Treatment with selenium or oxides of nitrogen partially transforms butyl oleate into the trans isomer elaidic acid. 
The arrangement of butyl oleate's 18 carbon atoms and the position of the double bond are demonstrated by its catalytic hydrogenation to stearic acid, CH3(CH2)16CO2H.
And butyl oleate's oxidative cleavage to nonanoic (pelargonic) acid, CH3(CH2)7CO2H, and azelaic acid, HO2C(CH2)7CO2H. 
When butyl oleate is heated with alkali, migration of the double bond occurs, giving the α,β-unsaturated acid CH3(CH2)14CH=CHCO2H, and this, on further heating with alkali, gives palmitic acid, CH3(CH2)14CO2H.
Butyl oleate shows the standard reactions of a carboxylic acid and a disubstituted ethylene, including the formation of a dibromide with bromine and a glycol with dilute aqueous potassium permanganate.
Butyl oleate is a naturally occurring, odorless, colorless oil. 
Butyl oleate is found in flaxseed oil, borage (a Mediterranean herb) oil, evening primrose oil, olive oil (less in virgin olive oil), pecan oil, canola oil, peanut oil, macadamia oil, sunflower oil.
Butyl oleate is also found in grape seed oil, sea buckthorn oil and sesame oil.
You can also find butyl oleate in animal fat. 
Butyl oleate at appropriate levels has been implicated in cancer prevention in some (but not all studies), and reduces cholesterol levels. 
However, this does not mean that everyone should deliberately consume excessive olive oil. 
Scientists have found that butyl oleate in excess blocks the body from using linoleic acid, another important fatty acid. 
Another major issue is that too much oleic acid can cause lipid accumulation in the liver — or fatty liver. 
In fact, scientists use butyl oleate to create fatty liver simulations in the lab, then test antioxidants with the cells to see which ones can reverse the disease.
Butyl oleate (also called cis-9-octadecenoic acid) is an example of a fatty acid found in animal and vegetable oils. 
Butyl oleate is a mono-unsaturated fatty acid, due to the presence of a single double bond. 
The physical properties of fatty acids like butyl oleate are determined by the number, geometry, and position of the double bonds in the chain, along with the degree of unsaturation. 
In naturally occurring fatty acids, such as those found in vegetable oils, the double bonds are all in the cis configuration (shown in red in the figure), making the molecules bent or curved. 
This also makes the molecules much less flexible than those of fully saturated fatty acids (e.g. stearic acid). 
Their bent shape also hinders crystallisation, and explains why these acids are oils at room temperature.
Oleic acid is also present in the cocoa butter of chocolate as one component of a triglyceride. 
The other two components are often either stearic acid, or the closely related palmitic acid. 
This means that the triglyceride has a much more uniform structure than is normally found in most fats and oils - and this uniformity results in a sharper than normal melting point. 
This allows chocolate to remain stiff almost up to its melting point (34°C). When it does melt, the melting occurs suddenly and endothermically. 
If this occurs in the mouth it gives a feeling of coolness - perhaps one of the reasons for the lasting popularity of chocolate (along with its sweetness due to the added sugar).
Butyl oleate is a liquid oil similar to an omega 9 oil and it is considered the most abundant monounsaturated fatty acid in nature. 
Butyl oleate is a component that can be found in various foods and it usually comes accompanied by saturated and other unsaturated fatty acids.
Butyl oleate answers by the formula C18H34O2, which corresponds to the mono-carboxylic straight-chain acid with 18 carbon atoms and a double “cis” link in 9th position. 
Butyl oleate has a minimum purity of 65%. 
Butyl oleate is a liquid oil that is insoluble in water.
Butyl oleate can be obtained from plant sources, for example olive oil or avocado, or from animal origin, for example in pigs. 
Vegetable butyl oleate is obtained from the hydrolysis of olive-pomace oleins and its subsequent distillation. 
Meanwhile, animal butyl oleate is obtained by the hydrolysis of animal fat (tallow), cold fractionation and its subsequent distillation.
Butyl oleate from plant origin is a yellowish product -at contact with air, it is previously colorless – is solid at room temperature (freezing point about 20-22° C). 
Moreover, the animal butyl oleate is also a yellowish substance -at contact with air, but in this case is liquid at room temperature because of its low freezing point.
The oil is obtained therefore from a distillation process. 
Butyl oleate is a derived substance that is fundamental ingredient for the development of diverse products related to various industries.
Butyl oleate is a type of fatty acid. Oils with butyl oleate are used to replace saturated fats in the diet. 
Butyl oleate might improve heart conditions by lowering cholesterol and reducing inflammation.
Like other omega-9 fatty acids, consuming a moderate, healthy amount of butyl oleate in your daily diet contributes to a multitude of natural health benefits for your body — both internally and externally. 
By changing the cell membrane composition and altering the receptor on the membranes, butyl oleate serves as a building block in both the brain and nervous system. 
Studies show that the following are the tangible health benefits of butyl oleate:
Reduces Cholesterol: An appropriate intake of healthy fats like butyl oleate can help to lower transport protein production and dangerous cholesterol levels.
Improves Heart Health: By decreasing blood cholesterol levels and affecting insulin, blood pressure and blood vessels, butyl oleate can help to prevent heart disease and other related heart conditions.
Lowers Blood Pressure: Consuming butyl oleates in moderation — along with a reduced saturated fat intake — can help increase the body's supply of the receptors that lower blood pressure.
Prevents Obesity: Monounsaturated fats like oleic acid can help to decrease belly fat stores and prevent obesity.
Improves Insulin Sensitivity: By decreasing blood glucose and insulin levels, butyl oleate can be especially beneficial to people with diabetes.
Improves the Immune System: By reaching cell membranes, interacting with immune cells and affecting inflammation responses, healing processes and the body's defenses, butyl oleate can help the immune system.
Assists Brain Function: Crucial to nerve repair, myelin production and inflammation reduction, butyl oleate is essential to healthy brain functions.
Improves Mood: Higher levels of butyl oleate in the blood can lead to a decrease in anger levels and an increase in physical activity, contributing to a healthier mental state and a better mood.
Decreases Effects of Aging: Monounsaturated fats have been shown to reduce the effects of age-related cognitive decline and prevent DNA damage caused by free radicals, causing the cells to be less susceptible to damage and preventing physical signs of aging, as well.
Potentially Fights Cancer: By decreasing oxidative stress in the cells and protecting cells from DNA damage, oleic acid can lead to a lower risk of developing cancer.
Decreases Pain: By inhibiting pain perception receptors and promoting the growth of new nerve cells.
Butyl oleate can alleviate pain and decrease the damage of conditions like chronic nerve pain and rheumatoid arthritis.
To make sure you consume the right amount of butyl oleate from the right sources, try to incorporate the following foods into your daily diet:
-Olives and olive oil
-Peanut oil
-Almond oil
-Canola oil
-Sesame oil
-Sunflower oil
-Avocados and avocado oil
We can find butyl oleate in sack fruits such as peanuts, almonds, hazelnuts, pistachios and walnuts.
The trans isomer of butyl oleate is called elaidic acid or trans-9-octadecenoic acid. 
These isomers have distinct physical properties and biochemical properties. 
Butyl oleate, the most abundant trans fatty acid in diet, appears to have an adverse effect on health.
A reaction that converts butyl oleate to elaidic acid is called elaidinization.
Another naturally occurring isomer of butyl oleate is petroselinic acid.
In chemical analysis, fatty acids are separated by gas chromatography of their methyl ester derivatives. 
Alternatively, separation of unsaturated isomers is possible by argentation thin-layer chromatography.
In ethenolysis, methyl oleate, the methyl ester of the acid, converts to 1-decene and methyl 9-decenoate:
CH3(CH2)7CH=CH(CH2)7CO2Me + CH2=CH2 → CH3(CH2)7CH=CH2 + MeO2C(CH2)7CH=CH2
Butyl oleate is the topmost monounsaturated fat in the human diet.
Monounsaturated fat consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol.
Butyl oleate may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit.
A 2017 review found that diets enriched in butyl oleate are beneficial for regulating body weight.
The FDA has approved a health claim on reduced risk of coronary heart disease for high oleic (> 70% oleic acid) oils.
Some oil plants have cultivars bred to increase the amount of butyl oleate in the oils. 
In addition to providing a health claim, the heat stability and shelf life may also be improved.
But only if the increase in monounsaturated butyl oleate levels correspond to a substantial reduction in polyunsaturated fatty acid (especially α-Linolenic acid) content.
When the saturated fat or trans fat in a fried food is replaced with a stable high oleic oil.
Consumers may be able to avoid certain health risks associated with consuming saturated fat and trans fat.
Butyl oleate is by far the most widely distributed and abundant fatty acid in nature (few fats known to contain less than 10%) where it is mainly found as glycerol ester. 
Butyl oleate is a Δ9 desaturase product of stearic acid.
Butyl oleate is the the precursor of most polyunsaturated fatty acids (or PUFA): 
plants produce both omega-3 polyunsaturated fatty acids and omega-6 polyunsaturated fatty acids from it while animals can elongate and desaturated it to form a variety of omega-9 fatty acids.
The high content is found in olive oil, about 60-70%, but is present also in:
-nut oil and almond (abundant)
-canola oil
-sesame oil
-cocoa butter
-lard
-palm oil
-tallow
-safflower oil
-soybean oil.

Properties and Applications of Butyl Oleate:
Butyl oleate is a substance with multiple properties and applications of great value and importance. 
Depending on the source from which we get the oil we can apply and use it in various areas.
This liquid is applied and used in various sectors and industries that generate multiple products: detergents, textiles, paints, inks, cosmetics, pharmaceuticals, leather, lubricants, etc.
Butyl oleate is highly valued because of the benefits to our health and wellbeing, mainly on the liver and cardiovascular field. 
Butyl oleate is also a substance that balances and makes us maintain a healthy body weight since it influences the regulation of our metabolism. 
Butyl oleate is also used as an intermediate in the chemical synthesis of esters, salts, alkoxides, epoxides and dimer acids.
Butyl oleate is a valuable ingredient to produce different products, primarily pharmaceuticals, textiles, metallurgical and chemicals.
Butyl oleate is a substance of great functionality and usability applied to various industries such to create useful and necessary components generating solutions in different areas and sectors.
The first is that butyl oleate is more stable to oxidation than polyunsaturated fatty acids (omega 6 and omega 3) and that it is more stable at high temperatures than polyunsaturated fatty acids.
According to the Mayo Clinic, these are recommended ranges for the amount of butyl oleate in your blood sample. Amounts are in nanomoles per milliter, a unit of measurement in chemistry and lab science:
-Age <1 year: 250-3,500 nmol/mL
-Age 1-17 years: 350-3,500 nmol/mL
-Age 18 years and up: 650-3,500 nmol/mL
Fatty acids (or their salts) often do not occur as such in biological systems. 
Instead fatty acids such as butyl oleate occur as their esters, commonly triglycerides, which are the greasy materials in many natural oils. 
Butyl oleate is the most common monounsaturated fatty acid in nature. 
Butyl oleate is found in fats (triglycerides), the phospholipids that make membranes, cholesterol esters, and wax esters.
Triglycerides of butyl oleate comprise the majority of olive oil (about 70%). 
Olive oil exceeding 2% free butyl oleate is graded unfit for human consumption.
Butyl oleate also makes up:
-59–75% of pecan oil
-61% of canola oil
-36–67% of peanut oil
-60% of macadamia oil
-20–80% of sunflower oil
-15–20% of grape seed oil
-sea buckthorn oil
-40% of sesame oil
-14% of poppyseed oil
High oleic variants of plant sources such as sunflower (~80%) and canola oil (70%) also have been developed.
Butyl oleate also comprises 22.18% of the fats from the fruit of the durian species, Durio graveolens.
Karuka contains 52.39% butyl oleate.Butyl oleate is abundantly present in many animal fats, constituting 37 to 56% of chicken and turkey fat, and 44 to 47% of lard.
Butyl oleate is the most abundant fatty acid in human adipose tissue, and second in abundance in human tissues overall, following palmitic acid.
The biosynthesis of butyl oleate involves the action of the enzyme stearoyl-CoA 9-desaturase acting on stearoyl-CoA. 
In effect, stearic acid is dehydrogenated to give the monounsaturated derivative, oleic acid.
Butyl oleate undergoes the reactions of carboxylic acids and alkenes. 
Butyl oleate is soluble in aqueous base to give soaps called oleates. 
Iodine adds across the double bond. Hydrogenation of the double bond yields the saturated derivative stearic acid.
Oxidation at the double bond occurs slowly in air, and is known as rancidification in foodstuffs and as drying in coatings. 
Reduction of the carboxylic acid group yields oleyl alcohol. 
Ozonolysis of butyl oleateis an important route to azelaic acid. 
The coproduct is nonanoic acid:
H17C8CH=CHC7H14CO2H + 4"O" → HO2CC7H14CO2H + H17C8CO2H
Esters of azelaic acid find applications in lubrications and plasticizer.

Uses of Butyl Oleate:
Butyl oleate is a mono-unsaturated omega-9 fatty acid found in various animal and vegetable sources. 
Triglyceride esters of butyl oleate comprise the majority of olive oil. 
Butyl oleate is used as an excipient in pharmaceuticals and as an emulsifying or solubilizing agent in aerosol products. 
Butyl oleate may hinder the progression of adrenoleukodystrophy, a fatal disease that affects the brain and adrenal glands, and it may help boost memory. 
Butyl oleate may also be responsible for the hypotensive (or blood pressure reducing) effects of olive oil.
Butyl oleate is used as a component in many foods, in the form of its triglycerides. 
Butyl oleate is a component of the normal human diet, being a part of animal fats and vegetable oils.
Butyl oleate as its sodium salt is a major component of soap as an emulsifying agent. 
Butyl oleate is also used as an emollient.
Small amounts of butyl oleate are used as an excipient in pharmaceuticals, and it is used as an emulsifying or solubilizing agent in aerosol products.
Butyl oleate is used to induce lung damage in certain types of animals for the purpose of testing new drugs and other means to treat lung diseases. 
Specifically in sheep, intravenous administration of butyl oleate causes acute lung injury with corresponding pulmonary edema.
Butyl oleate is used as a soldering flux in stained glass work for joining lead came.
Butyl oleate is widely used in the solution phase synthesis of nanoparticles, functioning as a kinetic knob to control the size and morphology of nanoparticles.
Butyl oleate uses and applications include: Plasticizer for PVC, PVB, PVAc, PS, cellulosics, surface coatings; solvent; lubricant in rolling oils; water-resisting agent; coatings; polishes.
Butyl oleate uses and applications also include waterproofing compds.; emulsifier, bodying agent, emollient for cosmetics, toiletries; textile surfactant finisher, softener, thread lubricant and antistat.
Butyl oleate uses and applications also include:
-lubricant in textile spin finishes, coning oils, cording, and dye baths; plasticizer, softener for NR, SR; flexibilizer; heat stabilizer,
-retards CR cures; plasticizer in food-contact rubber articles for repeated use; defoamer in food-contact paperpaperboard; food-contact textiles.

Chemical and Physical Properties:
MDL number: MFCD00053819
PubChem Substance ID: 24897934    
XLogP3-AA: 8.8    
Hydrogen Bond Donor Count: 0    
Hydrogen Bond Acceptor Count: 2    
Rotatable Bond Count:19    
Exact Mass: 338.318480578    
Monoisotopic Mass: 338.318480578    
Topological Polar Surface Area: 26.3 Ų    
Heavy Atom Count: 24    
Formal Charge: 0    
Complexity: 284    
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    
Compound Is Canonicalized    : Yes    
Appearance: pale yellow clear liquid (est)
Assay: 75.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: -26.50 °C. @ 760.00 mm Hg
Boiling Point: 414.00 to 415.00 °C. @ 760.00 mm Hg (est)
Boiling Point: 228.00 °C. @ 15.00 mm Hg
Vapor Pressure: 0.000002 mmHg @ 25.00 °C. (est)
Flash Point: > 200.00 °F. TCC ( > 93.33 °C. )
logP (o/w): 9.754 (est)
Shelf Life: 12.00 month(s) or longer if stored properly.

Synonyms:
Butyl oleate
142-77-8
n-Butyl oleate
Kesscoflex BO
Advaplast 42
Butyl cis-9-octadecenoate
butyloleate
OLEIC ACID, BUTYL ESTER
Wilmar Butyl Oleate
Witcizer 100
Witcizer 101
Butyl 9-octadecenoate
Kessco 554
1-Butyl oleate
Hallco C-503 Plasticizer
butyl (Z)-octadec-9-enoate
9-Octadecenoic acid (9Z)-, butyl ester
9-Octadecenoic acid (Z)-, butyl ester
UNII-487I65419Q
butyl (9Z)-octadec-9-enoate
CHEBI:82946
(Z)-octadec-9-enoic acid butyl ester
Bytyl oleate
487I65419Q
Uniflex BYO
Vinicizer 30
Plasthall 503
Plasthall 914
9-Octadecenoic acid, butyl ester
Hallco C 503
Advaplast 42 (VAN)
HSDB 5483
NSC 6700
EINECS 205-559-6
9-Octadecenoic acid, butyl ester (Z)-
BRN 1728057
9-Octadecenoic acid, butyl ester (cis)
AI3-00660
(E)-9-Octadecenoic acid butyl ester
Butyl oleic acid
Oleic acid butyl
N-Butyl oleic acid
Oleate, butyl ester
1-Butyl oleic acid
Butyl 9-octadecenoic acid
Elaidic acid, butyl ester
DSSTox_CID_7099
Oleic acid n-butyl ester;
DSSTox_RID_78310
DSSTox_GSID_27099
SCHEMBL79292
butyl (9Z)octadec-9-enoate
4-02-00-01653 (Beilstein Handbook Reference)
CHEMBL3183174
DTXSID7027099
Oleic acid, butyl ester (8CI)
NSC6700
Butyl 9-octadecenoate or 9-18:1
NSC-6700
Tox21_202744
LMFA07010975
MFCD00053819
ZINC85480590
(Z)-9-Octadecenoic acid butyl ester
AKOS024386323
NCGC00260292-01
AS-13009
CAS-142-77-8
CIS-9-OCTADECENOIC ACID BUTYL ESTER
ST51037381
J-007695
Q27156481