Cis oleic acid. Oleic acid. Receipt and application. Production and chemical properties
General characteristics of oleic acid
Oleic acid is one of the most common unsaturated acids in nature. Found in various vegetable oils and animal fats. It is odorless and appears as a colorless oil, although commercial samples may have a yellowish tint.From a chemical point of view, oleic acid is classified as a monounsaturated omega-9 fatty acid.
The term "oleic" means derived from olive oil, which is predominantly composed of oleic acid.
It is part of such vegetable oils as olive (about 81%), peanut (about 66%), sunflower (about 40%). Also common in animal fats: in beef fat ranging from 41 to 42%, in cod fat from 30%, in pork fat from 37 to 44%).
Synonyms: cis-9-octadecenoic acid
Combines the chemical properties of carboxylic acids and olefins: it forms derivatives at the carboxyl group, adds hydrogen at the double bond. When exposed to strong oxidizing agents (KMnO 4 ; O 3), it forms pelargonic and azelaic acids, which is often used for their industrial production.
Preparation of oleic acid
Oleic acid is obtained on an industrial scale by hydrolysis of oils or fats with fractionation of the resulting mixture of acids and repeated recrystallization from methanol (90%) or acetone (at -40 C).In nature, oleic acid is formed by dehydrogenation of stearic acid (aerobic pathway in animals) or chain elongation of unsaturated fatty acids (anaerobic pathway in microorganisms). The presence of oleic acid in animal fat provides its protection against peroxide oxidation.
Applications of oleic acid
Oleic acid and its esters are actively used for the production of paints and varnishes as plasticizers. It is also used in the production of industrial detergents. Widely used (as lubricating and cooling fluids) when drilling and processing difficult-to-cut stainless steels and alloys. Oleic acid also acts as an emulsifier in the rubber industry.In the form of its sodium salt, oleic acid is the main component of soap as an emulsifying agent. It is also used as an emollient. Small amounts of oleic acid are used as an excipient in pharmaceutical preparations, and oleic acid is used as an emulsifier or solubilizing agent in aerosols.
Oleic acid is often used as an emulsifier-stabilizer for invert emulsions in petroleum-based invert emulsion drilling fluids.
Characteristics of oleic acid
Oleic acid is a major component and has been found in many studies to be closely associated with a reduced risk of cardiovascular disease, obesity and high blood pressure (hypertension). This acid can also improve mood, slow down the aging process and prevent cancer. Below are the many benefits of oleic acid and why large amounts of it may be harmful to your health.
The article is based on the findings of 53 scientific studies
- Laboratory of Molecular and Cellular Biomedicine, Department of Biology, Institute Universitari d’Investigació en Ciències de la Salut, IUNICS, University of the Balearic Islands, Palma de Mallorca, Spain
- Department of Pediatrics, University of Illinois at Chicago, USA
- Institute of Pharmacology, Polish Academy of Sciences, Krakow, Poland
- Department of Neurology, University Medical School, Aachen, Germany
- Department of Physiology, University of Granada, Spain
- and other authors.
To view the research, use the links at the end of the article. (1)
What is oleic acid?
Oleic acid is an essential monounsaturated fatty acid. A large amount of this acid enters the body through food - various oils and fatty fish. Makes up approximately 92% of all cis-isomers of monounsaturated fats in our diet (if the diet is considered healthy). Oleic acid is also synthesized inside our body from saturated fatty acids and partly from carbohydrates.
Oleic acid is included in the class Omega-9 monounsaturated acids, which have only one double bond and are determined by the number of carbon atoms in the side chain. Oleic acid is sometimes abbreviated as C18:1. The most natural and beneficial monounsaturated fats are cis isomers in double bond orientation, while artificial fats are trans isomers and their intake through food is associated with increased health risks.
The study, covering 7 developed countries, is the first to link increased consumption of saturated fat and an increase in total cholesterol, as well as heart disease. Many modern dietary guidelines rely on the findings of this study and recommend paying attention to cholesterol levels as one of the strongest factors in increasing the risk of death from heart disease. (15) A similar finding was found in a study of 180 patients following high- and low-monounsaturated fat diets for 2 years. (16)
The protective effects of oleic acid against cardiovascular disease are largely associated with a decrease in total cholesterol, especially “bad” LDL cholesterol, in the blood. One of the representative studies was an 8-week experiment with 23 patients who had an increased risk of heart disease and were on a diet high in monounsaturated fats throughout the study. The conclusion of this work was to recommend a similar diet to protect heart health by reducing blood clotting and improving circulation.(17)
These findings are not surprising, since oleic acid affects insulin sensitivity, lowers blood pressure, reduces inflammatory markers and improves blood vessel function.
Oleic acid lowers blood pressure
A study of 23 patients with high blood pressure found that a diet high in monounsaturated fat was able to reduce blood pressure in all participants after 6 months. And 8 patients were able to stop taking blood pressure medications while following this diet.(18)
It is worth noting that this was associated with a simultaneous decrease in dietary saturated fat and an increase in nitric oxide levels from polyphenols from olive oil.(19)
Another study involving rats showed encouraging results when animals diagnosed with arterial hypertension were able to reduce their blood pressure to normal levels after 7 days of eating olive oil. This effect was obtained through the influence of 2-hydroxyoleic acid (2-OHOA), a derivative of oleic acid. In this case, the decrease in pressure occurred depending on the dose of olive oil and, accordingly, 2-hydroxyoleic acid. The best effect was shown when taking 2-OHOA at a dose of 600 mg per kilogram of animal weight every 12 hours. (20)
It is known that the integration of oleic acid into cell membranes can change the activity of certain receptors on the membrane (in particular, G-coupled receptors, members of the adrenoreceptor family).(21) An increase in the number of receptors under the influence of olive oil led to a decrease in blood pressure. (22)
Recommended dosage of oleic acid to lower blood pressure:
- 2-4 tablespoons (EVOO) or 10-20 fresh olives per day (23)
- Olive Leaf Extract – 500 mg twice daily (24)
Oleic acid increases insulin sensitivity
When a group of adults (162 healthy people) switched to eating foods high in saturated fat (Western diet) for 3 months, the reduction decreased, but this did not happen in the group of subjects who followed a diet with monounsaturated fats.(27)
In another study, 10 overweight people diagnosed with non-insulin-dependent diabetes mellitus were able to show improvements in their glycemic profile (blood glucose and insulin levels) when following a monounsaturated fat diet for 15 days.(28)
Other research has shown that in obese diabetic mice, when replacing saturated fat with oleic acid in their diet, there were improvements in health indicators (inflammation in the hypothalamus, insulin resistance, and body fat).(29)
Further evidence of the beneficial effects of oleic acid was demonstrated in 11 diabetic patients who followed 3 types of diets. They followed each diet for 28 days. One diet was high in monounsaturated fats, another was high in saturated fat, and the third was high in carbohydrates. Monounsaturated acid foods were most effective in reducing belly fat in these patients.(30)
Oleic acid prevents the development of obesity
According to the World Health Organization, a diet high in monounsaturated fats could be the best way to prevent obesity worldwide. (31) This diet for 28 days is known to reduce central obesity (abdominal and waist size), even in patients with diabetes. (32)
A study in which obese mice were directly injected with oleic acid into the hypothalamus resulted in decreased appetite and improvement in obesity-related symptoms.(33)
ROLE OF OLEIC ACID IN REDUCING INFLAMMATION Oleic acid helps improve immune system function and reduce inflammation
Oleic acid is part of cell membranes and can directly interact with immune cells - neutrophils, which are responsible for the timing and intensity of inflammation of body tissues. (34)
Part of the inflammatory response in the body requires neutrophils to generate reactive oxygen at the site of inflammation. This promotes healing. But in the presence of oleic acid, this reaction is enhanced, which contributes to a faster resolution of inflammation, including more active release cytokines IL-1b. (35, 36)
Neutrophils are also responsible for identifying microorganisms and organizing defenses against them. In the presence of oleic acid, there is a more active presence of phagocytic neutrophils and a more effective destruction of bacteria and microbes.(37)
Oleic acid may help treat rheumatoid arthritis
43 diagnosed patients received a fish oil supplement (high in omega-3) and olive oil (high in oleic acid). They were able to show improvements in joint mobility and pain reduction compared to other patients who took only fish oil or a soybean oil placebo.(39)
Oleic acid may reduce chronic pain
Oleic acid blocks a receptor (TRVP1) involved in pain sensitivity (pungence, heat and itch). This property indicates the natural involvement of oleic acid in the regulation of inflammation.(40)
Injections of oleic acid and albumin into the area of injury in mice were able to reduce pain and involuntary movements associated with paralysis after spinal injury. Albumin and oleic acid also promote the development of new dendritic nerve cells.(41)
Oleic acid is important for brain function
This acid is produced in the body during the repair of neurons (mature axons) and plays a role in the production of myelin.(42) A rare genetic disorder called adrenoleukodystrophy, which leads to the destruction of myelin, can be treated with a mixture of fatty acids, including oleic acid, to slow down course of the disease and reduce brain inflammation.(43)
Oleic acid improves mood
A small 3-week study (14-18 people per test group) showed how a diet high in oleic acid was able to help improve neural response (anger) and increase motivation-related physical activity.(44)
Oleic acid reduces brain dysfunction during aging
Eating foods high in monounsaturated fats was able to reduce brain dysfunction in Italians over 65 years of age in a survey of more than 5,000 people. It is likely that the reduction in brain damage was due to the beneficial effects of oleic acid in maintaining the structural integrity of neurons.(45, 46)
Oleic acid slows down aging
Many studies have demonstrated that mice tended to have higher levels of oleic acid in their cell membranes than mice with shorter lifespans.(47)
Aging is often associated with oxidative stress in cell membranes and the occurrence of DNA damage by free radicals released during energy production. Rats that ate more olive oil and likely had more of this acid in their cell membranes showed less age-related oxidative stress because these acids are less susceptible to free radical damage.(48)
Oleic acid prevents cancer development
Due to the ability of oleic acid to reduce oxidative stress in cells and protect DNA from oxidative damage, the risk of developing cancer is reduced. (49) Two studies surveyed the eating habits of more than 5,000 women without and with cancer. breast cancer. Those women whose diet contained more oleic acid showed a lower risk of developing breast cancer. (50, 51)
In a study on mice, patients lung cancer(adenocarcinoma), it was shown that nutrition with oleic acid led to an increase in survival time and an increase in the duration of the period without relapse. (52) However, when oleic acid alone was given to mice with salivary gland cancer, the tumor progressed dramatically due to the lack of other monounsaturated fats in the diet. (53)
Harmful health effects of oleic acid
High oleic acid levels are bad
Certain concentrations of omega-9 fats in red blood cells were associated with increased risks of death in the next 10 years in an analysis of more than 3,000 patients. This relationship was not linear, but in the form of a U-shaped curve. Which indicated an increased risk of death from cardiovascular disease with both low and high levels of Omega-9 fats. The optimal level was the content of oleic acid in cell membranes within 14% (13% was considered low, 15% was considered high).
Oleic acid may have a negative effect on fertility
In mice, increased intake of omega-9 fatty acids (including oleic acid) led to poor reproductive function, including a reduction in the number of puppies per litter. This is probably due to changes in the synthesis of steroid hormones during pregnancy.
In males, with increased consumption of oleic acid, a decrease in sperm motility was observed.
Oleic acid may not protect skin
Many skin care cosmetics contain oleic acid. But there is little scientific evidence to support the positive (ultraviolet) radiation, free radical scavenging benefits of oleic acid, either in supplement or topical form.
One should be careful when interpreting studies on oleic acid
Many studies on the effects of monounsaturated acids have used olive oil as a source of oleic acid. But this does not differentiate between Omega-9 fatty acids (oleic acid) and other monounsaturated fatty acids (Omega-3 or Omega-6). Other compounds present in olive oil may also have positive health effects. Determining which components contributed most to these positive effects was very difficult, especially when scientists learned about diets when interviewing subjects.
Men and women react differently to oleic acid
Often studies of large numbers of people do not differentiate between sexes, and many studies have relied on effects in men. But when the results of the experiments were evaluated separately in men and women, the effect of oleic acid on lowering cholesterol levels was less in women than men.
Drug interactions
Oleic acid interacts well with medications for high blood pressure or diabetes. Therefore, when taking these medications, the combination with oleic acid may cause a greater decrease in blood pressure or blood sugar levels.
When a breast cancer drug such as Paclitaxel is used together with oleic acid, the effect of chemotherapy against the tumor is enhanced.
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In the water
Oleic acid (cis-9-octadecenoic acid) CH 3 (CH 2) 7 CH=CH (CH 2) 7 COOH - monounsaturated fatty acid. Belongs to the group of omega-9 unsaturated fatty acids.
Physical properties
Oily liquid, lighter than water, odorless, colorless, insoluble in water, but soluble in organic solvents.
Chemical properties
It is oxidized under harsh conditions with potassium permanganate with cleavage of the double bond, forming a mixture of azelaic and pelargonic acids; under mild conditions, when oxidized with permanganate, a mixture of stereoisomeric dihydroxystearic acids is formed. When exposed to ozone, oleic acid forms ozonide, which hydrolyzes to form pelargonaldehyde and azelaic acid semialdehyde. Hydrogenates to stearic acid.
Alkali metal salts of oleic acid are highly soluble in water and are used in the textile industry (oleic soap). The lead salt of oleic acid, unlike lead salts of saturated fatty acids, is soluble in ether; the method of isolating oleic acid from a mixture of acids obtained by saponification of natural fats is based on this difference in solubility.
The double bond in oleic acid has cis-configuration, isomerization into trance-isomer - elaidic acid - occurs under the influence of various catalysts (nitrogen dioxide, aliphatic nitriles). Isomerization of oleic acid under the influence of nitrous acid into higher melting point (melting point 44 °C) elaidic acid (elaidic test) is used to determine the type of vegetable oils: a mixture of acids obtained from non-drying oils containing predominantly oleic acid esters under the action of an acidic solution of sodium nitrite at room temperature it hardens into a dense mass; the mixture of acids obtained by saponification of non-drying oils containing significant amounts of polyunsaturated acids (linoleic and linolenic) remains liquid under the conditions of the elaidin test.
Being in nature
Contained in many animal fats in the form of esters - glycerides: beef fat (41-42%), pork fat (37-44%), cod fat (30%), and is also found in many vegetable oils: sasanqua oil (85- 89%), hazelnut oil (70-84%), camellia oil (80%), buriti (Mauritia Vinifera) oil (79%), papaya oil (79%), marula oil (70-78%), moringa oil (71%), almond oil (64-82%), olive oil(55.0-83.0%), acai oil (60%), cashew nut oil (60%), avocado oil (59-75%), apricot kernel oil (58-74%), peanut oil (66% ), peach kernel oil (55-75%), pistachio oil (51-54%), macadamia nut oil (50-67%), pecuya pulp oil (54%), andiroba (Carapa guianensis) oil (50.5% ), neem tree oil (50%), puteria oil (50%), argan oil (48%), pecuya kernel oil (46%), oat oil (46%), calodendrum capense oil (45%) , pongamia oil (44.5-71%), pecan oil (43-51%), cupuaçu butter (44%), mango butter (43%), avellan nut oil (42%), shea butter (40-45 %), sunflower oil(14.0-39.4%, high oleic 61.0-69.8%), mustard oil (22-30%), Brazil nut oil (38%), sal tree oil (37-43%), sesame oil (37-42%), pumpkin oil (35-47%), palm oil (35-45%), cocoa butter (34-36%), milk thistle oil (30%), corn oil (24-42%), Kokum oil (Garcinia indica) (30-42%), illip nut oil (Shorea stenoptera) (32-38%), rice oil (32-38%).
Application
Oleic acid and its esters are used to produce paints and varnishes as plasticizers. It is used in soap making, oleic acid and its salts are widely used as emulsifiers, in particular, in the composition of cutting fluids) when processing metals by cutting - honing, drawing, reaming, etc. It is also used as a stabilizer for magnetic fluids based on hydrocarbon carriers of ferromagnetic particles.
In the production of lubricants (for chemical fibers), flotation reagents, synthetic rubber, defoamers, wetting agents for dyeing with disperse dyes, plasticizers. Included in cosmetic products. Part of olein.
Researchers
- Albitsky, Alexey Andreevich “On some transformations of oleic and other related acids”, Kazan, 1898;
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Notes
Literature
- "Chemical Encyclopedic Dictionary" ed. Knunyants I. L., M.: Soviet Encyclopedia, 1983 p. 407
- Rabinovich V. A., Khavin Z. Ya. “A short chemical reference book” L.: Chemistry, 1977 p. 170
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Excerpt characterizing Oleic acid
The north was very quiet and sad. Apparently, having observed human weakness and cruelty for so many centuries, and seeing how the strongest perished, his heart was poisoned with bitterness and disbelief in the imminent victory of Knowledge and Light... And I so wanted to shout to him that I still believe that people will wake up soon !.. Despite the anger and pain, despite the betrayal and weakness, I believe that the Earth will finally not be able to withstand what is being done to its children. And he would wake up... But I understood that I could not convince him, since I myself would soon have to die, fighting for this same awakening.But I didn’t regret... My life was just a grain of sand in an endless sea of suffering. And I just had to fight to the end, no matter how terrible it was. Since even drops of water, falling constantly, are capable of someday breaking through the strongest stone. So is EVIL: if people crushed it even grain by grain, it would someday collapse, even if not during this lifetime. But they would return again to their Earth and see - it was THEY who helped her survive!.. It was THEY who helped her become Light and Faithful. I know that the North would say that man does not yet know how to live for the future... And I know that so far this has been true. But this is precisely what, in my understanding, stopped many from making their own decisions. Because people are too accustomed to thinking and acting “like everyone else,” without standing out or interfering, just to live in peace.
“I’m sorry I put you through so much pain, my friend.” – The voice of the North interrupted my thoughts. “But I think it will help you meet your destiny easier.” Will help you survive...
I didn’t want to think about it... At least a little more!.. After all, I still had plenty of time left for my sad fate. Therefore, in order to change the painful topic, I started asking questions again.
– Tell me, Sever, why did I see the sign of the royal “lily” on Magdalene and Radomir, and on many Magi? Does this mean that they were all Franks? Can you explain it to me?
“Let’s start with the fact that this is a misunderstanding of the sign itself,” Sever answered, smiling. “It was not a lily when it was brought to Frankia Meravingli.”
Trefoil - the battle sign of the Slavic-Aryans
– ?!.
“Didn’t you know that it was they who brought the “Threfoil” sign to Europe at that time?..,” Sever was sincerely surprised.
- No, I've never heard of it. And you surprised me again!
– The three-leaf clover once, a long time ago, was the battle sign of the Slavic-Aryans, Isidora. It was a magical herb that helped wonderfully in battle - it gave warriors incredible strength, it healed wounds and made it easier for those leaving for another life. This wonderful herb grew far in the North, and only magicians and sorcerers could get it. It was always given to warriors who went to defend their homeland. Going into battle, each warrior uttered the usual spell: “For Honor! For Conscience! For Faith! While also making a magical movement, he touched the left and right shoulders with two fingers and the middle of the forehead with the last. This is what the Three Leaf Tree truly meant.
And so the Meravingli brought it with them. Well, and then, after the death of the Meravingley dynasty, the new kings appropriated it, like everything else, declaring it a symbol of the royal house of France. And the ritual of movement (or baptism) was “borrowed” by the same Christian church, adding to it a fourth, lower part... the part of the devil. Unfortunately, history repeats itself, Isidora...
Yes, history really repeated itself... And it made me feel bitter and sad. Was anything real from all that we knew?.. Suddenly I felt as if hundreds of people I didn’t know were looking at me demandingly. I understood - these were those who KNEW... Those who died defending the truth... It was as if they bequeathed to me to convey the TRUTH to those who do not know. But I couldn't. I left... Just as they themselves once left.
Suddenly the door swung open with a noise and a smiling, joyful Anna burst into the room like a hurricane. My heart jumped high and then sank into the abyss... I couldn’t believe that I was seeing my sweet girl!.. And she, as if nothing had happened, smiled widely, as if everything was great with her, and as if she wasn’t hanging over ours. lives are a terrible disaster. - Mommy, honey, I almost found you! Oh, North!.. Have you come to help us?.. Tell me, you will help us, right? – Looking into his eyes, Anna asked confidently.
North just smiled at her tenderly and very sadly...
* * *
Explanation
After a painstaking and thorough thirteen-year (1964-1976) excavation of Montsegur and its surroundings, the French Group of Archaeological Research of Montsegur and the Environment (GRAME), announced in 1981 its final conclusion: No trace of ruins from the First Montsegur, abandoned by its owners in the 12th century, has been found. . Just as the ruins of the Second Fortress of Montsegur, built by its then owner, Raymond de Pereil, in 1210, have not been found.
(See: Groupe de Recherches Archeologiques de Montsegur et Environs (GRAME), Montsegur: 13 ans de rechreche archeologique, Lavelanet: 1981. pg. 76.: "Il ne reste aucune trace dan les ruines actuelles ni du premier chateau que etait a l" abandon au debut du XII siecle (Montsegur I), ni de celui que construisit Raimon de Pereilles vers 1210 (Montsegur II)...")
According to the testimony given to the Holy Inquisition on March 30, 1244 by the co-owner of Montsegur, arrested by Lord Raymond de Pereil, the fortified castle of Montsegur was “restored” in 1204 at the request of the Perfects - Raymond de Miropois and Raymond Blasco.
(According to a deposition given to the Inquisition on March 30, 1244 by the captured co-seigneur of Montsegur, Raymond de Pereille (b.1190-1244?), the fortress was "restored" in 1204 at the request of Cather perfecti Raymond de Mirepoix and Raymond Blasco.)
However, something still remains to remind us of the tragedy that unfolded on this small piece of mountain soaked through with human blood... Still firmly clinging to the foundation of Montsegur, the foundations of the disappeared village literally “hang” over the cliffs...
Anna looked at Sever enthusiastically, as if he was able to give us salvation... But little by little her gaze began to fade, because from the sad expression on his face she understood: no matter how much he wanted it, for some reason there would be no help.
“You want to help us, don’t you?” Well, tell me, you want to help, Sever?..
Anna took turns peering carefully into our eyes, as if wanting to make sure that we understood her correctly. Her pure and honest soul could not understand that someone could, but did not want to save us from a terrifying death...
“Forgive me, Anna... I can’t help you,” Sever said sadly.
- But why?!! Don’t you regret that we will die?.. Why, North?!..
- Because I DO NOT KNOW how to help you... I don’t know how to destroy Karaffa. I don't have the right "weapons" to get rid of him.
OLEIC ACID- cis-9-octadecenoic (cis-octadecene-9-oic) acid, a higher monounsaturated fatty acid that is part of the lipids involved in the construction of biological membranes and largely determines the properties of these lipids. The formula of O. c. is CH 3 (CH 2) 7 CH = CH (CH 2) 7 COOH. Replacing O. to. in lipids of biol, membranes with another fatty to - that sharply changes such a property of biol, membranes as their permeability. The presence of large quantities of O.c. in the fat of human fat depots it ensures the stability of deposited lipids to peroxidation at a moderate concentration of biol, antioxidants (see Antioxidants). O.K. - replaceable fatty acid; it is synthesized, in particular, in the cytoplasm of human liver cells from malonyl-CoA; however, O. co. is one of the most common fatty acids included in dietary fats and plays an important role in human nutrition. Lipids with a high content of oxygen are characterized by increased digestibility. In medicine, a drug containing O. to. is used - linetol (see).
In industry, ointment is used as a basis for the production of varnishes, coatings, enamels, drying oils, and paints; its esters are used as plasticizers in the perfume industry, and its salts are used as detergents.
The importance of oleic acid in human nutrition
In animal fats (see Fat products), O.'s share accounts for approx. 35-45% of all fatty acids, and in most vegetable oils - from 20 to 40%. Very rich O.K. olive oil (64-85%) and peanut oil (37-47%).
Although O. to. is not a standardized component of the diet (it is replaceable fatty acid), in the human diet the most favorable content of O. to. is considered to be close to its content in human reserve fat. This prevents the need for a significant restructuring of the fatty acid composition of lipids supplied with food, which is associated with the consumption of the body's metabolic funds (primarily hydrogen ions) and energy. Optimal intake of O*, K from food is ensured by following the balanced nutrition formula, according to which in the diet of a healthy person, 1/3 of fats should be of vegetable origin, and 2/3 of animal origin; in this case, the diet will contain approx. 40% O.c. During heat treatment of oils rich in O.K., they are significantly less susceptible to deterioration as a result of oxidation than other oils. This serves as the basis for their use when frying certain products made from potatoes, corn, etc. etc., as well as for filling canned food (olive oil, special fractions of cottonseed oil, etc.). When vegetable oils are hydrogenated to obtain the fatty base of margarines, trans-oleic acid is formed. This isomer is absorbed by the human body just as well as O.K., but is included in fat depots to a lesser extent. In the formulations of modern margarines (see), along with the natural cas-form of O., a sufficient content of trans-oleic acid is provided.
Bibliography: Levachev M. M. New aspects of the biological qualities of food fats, Zhurn. All-Union, chem. about-va them. D. I. Mendeleev, vol. 23, no. 4, p. 443, 1978, bibliogr.; Leninger A. Biochemistry, trans. from English, M., 1976; Pokrovsky A.A., Levachev M.M. and Gapparov M.M. On the issue of the importance of balancing the fatty acid formula of diets, in the book: Lipids in the body of animals and humans, ed. S. E. Severina, p. 86, M., 1974, bibliogr.; T yu t yu ii n and to about in B. N. Chemistry of fats, M., 1966; The role of fats in human nutrition, ed. by A. J. Vergroesen, L., 1975.
N. V. Prokazova; M. M. Levachev (pit.).
Oleic acid has the chemical properties of carboxylic acids and olefins. It forms derivatives at the carboxyl group, and when saturated with hydrogen it turns into. According to its chemical properties, it belongs to the group of monounsaturated -9 fatty acids.
Under the influence of strong oxidizing agents, such as ozone or potassium permanganate, a mixture of pelargonic and azelaic acids is formed. This chemical property is used for their industrial production. Cis and trans occur in the presence of various catalysts, such as aliphatic nitriles, oxides of sulfur and nitrogen. These processes are reversible, and the equilibrium mixture contains about 75-80% elaidic acid. Esters of oleic acid and its salts are called oleates. Oleic acid is soluble in benzene, chloroform and ethanol.
Oleic acid in nature
In the human body and animals, oleic acid is formed during dehydrogenation, and in microorganisms - during chain elongation of unsaturated fatty acids. Its presence in animal fat prevents its peroxidation. It is part of vegetable oils and animal fats; sunflower oil contains about 40% oleic acid, olive oil - up to 81%, almond oil - up to 85%, peanut oil - 66%, pork fat - up to 45%, and beef - up to 42%.
Receipt
In industry, oleic acid is obtained by hydrolysis of fats and vegetable oils. First, the resulting mixture of fatty acids is fractionated, then multiple crystallization from acetone or methanol is started at a temperature of -40°C.
Technical oleic acid is called olein; it is an almost transparent paste or liquid product that hardens at temperatures from +10 to +34°C. Its color varies from light yellow to brown. As a rule, olein contains impurities of saturated and unsaturated fatty acids. Some varieties may contain up to 15% naphthenic acid.
Application
Oleic acid and its esters are added in the production of paints and varnishes as a plasticizer. Its salts are an emulsifying agent and one of the main components of soap, and it is also widely used as an emollient. Small amounts of the substance may be present in pharmaceutical preparations. Oleic acid is used as an emulsifier and stabilizer of invert emulsions in petroleum-based drilling fluids, in the processing of stainless steels and alloys, and also as a solubilizing agent and emulsifier in aerosols.
