Tag Archives: fatty acids

Chemical composition of olive oil

Chemical composition of olive oil: contents in brief

Olive oil constituents

Olive Oil
Fig. 1 – EVOO

From a chemical point of view, we can identify in the olive oil two fractions, depending on the behavior in the presence of heating and strong alkaline solutions (concentrated solutions of KOH or NaOH):

  • the saponifiable fraction, which represents 98-99% of the total weight, is composed of substances that form soaps in the above conditions;
  • the unsaponifiable fraction, which represents the remaining 1-2% of the total weight, is composed of substances that fail to form soaps in the above conditions.

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Saponifiable fraction of olive oil

It is composed of saturated and unsaturated fatty acids, esterified almost entirely to glycerol to form triglycerides (or triacylglycerols). To a much lesser extent, diglycerides (or diacylglycerols), monoglycerides (monoacylglycerols), and free fatty acids are also found.
Unsaturated fatty acids make up 75 to 85% of the total fatty acids. Oleic (O) and linoleic (L) acids are the most abundant ones; palmitoleic, eptadecenoic, gadoleic and alpha-linolenic (Ln) acids are present in lower/trace amounts.

Oleic Acid
Fig. 2 – IOOC and Fatty Acids

Oleic acid is the major fatty acid in olive oils. According to the rules laid down by the International Olive Oil Council (IOOC), its concentration must range from 55% to 83% of total fatty acids.
Linoleic acid is the most abundant polyunsaturated fatty acid in olive oil; its concentration must vary between 2.5% and 21% (IOOC). Because of its high degree of unsaturation, it is subject to oxidation; this means that an oil high in linoleic acid becomes rancid easily, and thus it may be stored for a shorter time.
In a Mediterranean-type diet, olive oil is the main source of fat: therefore, oleic acid, among monounsaturated fatty acids, and linoleic acid, among polyunsaturated fatty acids, are the most abundant fatty acids.
alpha-Linolenic acid must be present in very low amount, according to the IOOC standards ≤1%. It is an omega-3 polyunsaturated fatty acid, which may have health benefits. However, because of to its high degree of unsaturation (higher than that of linoleic acid), it is very susceptible to oxidation, and therefore it promotes rancidity of the olive oil that contains it.
Saturated fatty acids make up 15 to 25% of the total fatty acids.
Palmitic (P) (7.5-20%) and stearic (S) acids (0.5-5%) are the most abundant saturated fatty acids; myristic, heptadecanoic, arachidic, behenic and lignoceric acids may be present in trace amounts.

The presence of fatty acids that should be absent or present in amounts different than those found is a marker of adulteration with other vegetable oils. On this regard, particular attention is paid to myristic, arachidic, behenic, lignoceric, gadoleic and alpha-linolenic acids, whose limits are set by IOOC.

Fatty acid composition is influenced by several factors.

  • The climate.
  • The latitude.
  • The zone of production.
    Italian, Spanish and Greek olive oils are high in oleic acid and low in palmitic and linoleic acids, while Tunisian olive oils are high in palmitic and linoleic acids but lower in oleic acid. Therefore, oils can be divided into two groups:

one rich in oleic acid and low in palmitic and linoleic acids;
the other high in palmitic and linoleic acids and low in oleic acid.

  • The cultivar.
  • The degree of olive ripeness at the time of oil extraction.
    It should be noted that oleic acid is formed first in the fruit, and data seem to indicate a competitive relationship between oleic acid and palmitic, palmitoleic, and linoleic acids.

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Triglycerides of olive oil

Olive Oil
Fig. 3 – The sn Positions of Triglycerides

As previously said, fatty acids in olive oil are almost entirely present as triglycerides.
In small percentage, they are also present as diglycerides, monoglycerides, and in free form.
During triglyceride biosynthesis, thanks to the presence of specific enzymes, only about 2% of glycerol binds palmitic acid in the sn-2 position (also the percentage of stearic acid in the sn-2 position is very low); for the most part, the sn-2 position is occupied by oleic acid.
On the contrary, if we consider oils that have undergone a nonenzymatic esterification, the percentage of palmitic acid in the sn-2 position increases significantly.
Note: sn = stereospecific numbering

Among triglycerides present in significant proportions in olive oil, there are:

  • OOO: 40-59%;
  • POO: 12-20%;
  • OOL: 12.5-20%;
  • POL:  5.5-7%;
  • SOO: 3- 7%.

POP, POS, OLnL, OLnO, PLL, PLnO are present in smaller amounts.
Trilinolein (LLL) is a triglyceride that contains three molecules of linoleic acid. Its low content is an indicator of an oil of good quality.
Triglycerides containing three saturated fatty acids or three molecules of alpha-linolenic acid have not been reported.

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Diglycerides and monoglycerides of olive oil

Their presence is due to an incomplete synthesis and/or a partial hydrolysis of triglycerides.
The content of diglycerides in virgin olive oil ranges from 1% to 2.8%. 1,2-Diglycerides prevail in fresh olive oil, representing over 80% of the diglycerides. During oil storage, isomerization occurs with a progressive increase of the more stable 1-3 isomers, which after about 10 months become the major isomers.
Therefore, the ratio 1,2/1,3-diglycerides may be used as an indicator of the age of the oil.
Monoglycerides are present in amounts lower than diglycerides, <0.25%, with 1-monoglycerides far more abundant than 2-monoglycerides.

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Unsaponifiable fractions of olive oil

It is composed of a large number of different molecules, very important from a nutritional point of view, as they contribute significantly to the health effects of olive oil.
Furthermore, they are responsible for the stability and the taste of olive oil, and are also used to detect adulteration with other vegetable oils.
This fraction includes tocopherols, sterols, polyphenols, pigments, hydrocarbons, aromatic and aliphatic alcohol, triterpene acids, waxes, and minor constituents.
Their content is influenced by factors similar to those seen for fatty acid composition, such as:

  • the cultivar;
  • the degree of ripeness of the olive;
  • the zone of production;
  • the crop year and olive harvesting practices;
  • the storage time of olives;
  • the oil extraction process;
  • the storage conditions of the oil.

It should be noted that many of these compounds are not present in refined olive oils, as they are removed during the refining processes.

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They make up 18 to 37% of the unsaponifiable fraction.
They are a very heterogeneous group of molecules with nutritional and organoleptic properties  (for example, oleuropein and hydroxytyrosol give oil its bitter and pungent taste).
For a more extensive discussion, see: ” Polyphenols in olive oil: variability and composition.”

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Olive Oil
Fig. 4 – Squalene

They make up 30 to 50% of the unsaponifiable fraction.
Squalene and beta-carotene are the main molecules.
Squalene, isolated for the first time from shark liver, is the major constituent of the unsaponifiable fraction, and constitutes more than 90% of the hydrocarbons. Its concentration ranges from 200 to 7500 mg/kg of olive oil.
It is an intermediate in the biosynthesis of the four-ring structure of steroids, and it seems to be responsible of several health effects of olive oil.
In the hydrocarbon fraction of virgin olive oil, n-paraffins, diterpene and triterpene hydrocarbons, isoprenoidal polyolefins are also found.
Beta-carotene acts both as antioxidant, protecting oil during storage, and as dye (see below).

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They are important lipids of olive oil, and are:

  • linked to many health benefits for consumers;
  • important to the quality of the oil;
  • widely used for checking its genuineness.
    On this regard, it is to underline that sterols are species-specific molecules; for example, the presence of high concentrations of brassicasterol, a sterol typically found in Brassicaceae (Cruciferae) family, such as rapeseed, indicates adulteration of olive oil with canola oil.

Four classes of sterols are present in olive oil: common sterols, 4-methylsterols, triterpene alcohols, and triterpene dialcohols. Their content ranges from 1000 mg/kg, the minimum value required by the IOOC standard, to 2000 mg/kg. The lowest values are found in refined oils because of the refining processes may cause losses up to 25%.

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Common sterols or 4α-desmethylsterols
Olive Oil
Fig. 5 – beta-Sitosterol

Common sterols are present mainly in the free and esterified form; however they have been also found as lipoproteins and sterylglucosides.
The main molecules are beta-sitosterol, which makes up 75 to 90% of the total sterol, Δ5-avenasterol, 5 to  20%, and campesterol, 4%. Other components found in lower amounts or traces are, for example, stigmasterol, 2%, cholesterol, brassicasterol, and ergosterol.

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They are intermediates in the biosynthesis of sterols, and are present both in the free and esterified form. They are present in small amounts, much lower than those of common sterols and triterpene alcohols, varying between 50 and 360 mg/kg. The main molecules are obtusifoliol, cycloeucalenol, citrostadienol, and gramisterol.

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Triterpene alcohols or 4,4-dimethylsterols

They are a complex class of sterols, present both in the free and esterified form. They are found in amounts ranging from 350 to 1500 mg/kg.
The main components are beta-amyrin, 24-methylenecycloartanol, cycloartenol, and butyrospermol; other molecules present in lower/trace amounts are, for example, cyclosadol, cyclobranol, germanicol, and dammaradienol.

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Triterpene dialcohols

The main triterpene dialcohols found in olive oil are erythrodiol and uvaol.
Erythrodiol is present both in the free and esterified form; in virgin olive oil, its level varies between 19 and 69 mg/kg, and the free form is generally lower than 50 mg/kg.

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They make up 2 to 3% of the unsaponifiable fraction, and include vitamin E.
Of the eight E-vitamers, alpha-tocopherol represents about 90% of tocopherols in virgin olive oil. It is present in the free form and in very variable amount, but on average higher than 100 mg/kg of olive oil. Thanks to its in vivo antioxidant properties, its presence is a protective factor for health. Alpha-tocopherol concentration seems to be related to the high levels of chlorophylls and to the concomitant requirement for deactivation of singlet oxygen.
Beta-tocopherol, delta-tocopherol, and gamma-tocopherol are usually present in low amounts.

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In this group we find chlorophylls and carotenoids.
In olive oil, chlorophylls are present as phaeophytins, mainly  phaeophytin a (i.e. a chlorophyll from which magnesium has been removed and substituted with two hydrogen ions), and confer the characteristic green color to olive oil. They are photosensitizer molecules that contribute to the photooxidation of olive oil itself.
Beta-carotene and lutein are the main carotenoids in olive oil. Several xanthophylls are also present, such as antheraxanthin, beta-cryptoxanthin, luteoxanthin, mutatoxanthin, neoxanthin, and violaxanthin.
Olive oil’s color is the result of the presence of chlorophylls and carotenoids and of their green and yellow hues. Their presence is closely related.

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Triterpene acids

They are important components of the olive, and are present in trace amounts in the oil.
Oleanolic and maslinic acids are the main triterpene acids in virgin olive oil: they are present in the olive husk, from which they are extracted in small amount during processing.

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Aliphatic and aromatic alcohols

Fatty alcohols and diterpene alcohols are the most important ones.
Aliphatic alcohols have a number of carbon atoms between 20 and 30, and are located mostly inside the olive stones, from where they are partially extracted by milling.

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Fatty alcohols

They are linear saturated alcohols with more than 16 carbon atoms.
They are found in the free and esterified form and are present, in virgin olive oil, in amount not generally higher than 250 mg/kg.
Docosanol (C22), tetracosanol (C24), hexacosanol (C26), and octacosanol (C28) are the main fatty alcohols in olive oil, with tetracosanol and hexacosanol present in larger amounts.
Waxes, which are minor constituents of olive oil, are esters of fatty alcohols with fatty acids, mainly of palmitic acid and oleic acid. They can be used as a criterion to discriminate between different types of oils; for example, they must be present in virgin and extra virgin olive oil at levels <150 mg/kg, according to the IOOC standards.

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Diterpene alcohols

Geranylgeraniol and phytol are two acyclic diterpene alcohols, present in the free and esterified form. Among esters present in the wax fraction of extra virgin olive oil, oleate, eicosenoate , eicosanoate, docosanoate, and tetracosanoate have been found, mainly as phytyl derivatives.

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Volatile compounds

More than 280 volatile compounds have been identified in olive oil, such as hydrocarbons, the most abundant fraction, alcohols, aldehydes, ketones, esters, acids, ethers and many others. However, only about 70 of them are present at levels higher than the perception threshold beyond which they may contribute to the aroma of virgin olive oil.

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Minor components

Phospholipids are found among the minor components of olive oil; the main ones are phosphatidylserine, phosphatidylethanolamine, phosphatidylcholine, phosphatidylinositol.
In the unfiltered oils, trace amounts of proteins may be found.

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Gunstone F.D. Vegetable oils in food technology: composition, properties and uses. 2th Edition. Wiley J. & Sons, Inc., Publication, 2011

Pasqualone A., Sikorska E., Gomes T. Influence of the exposure to light on extra virgin olive oil quality during storage. Eur Food Res Technol 2005;221:92-8. doi:10.1007/s00217-004-1126-8

Servili M., Sordini B., Esposto S., Urbani S., Veneziani G., Di Maio I., Selvaggini R. and Taticchi A. Biological activities of phenolic compounds of extra virgin olive oil. Antioxidants 2014;3:1-23. doi:10.3390/antiox3010001

Examples of foods with trans fats

Foods high in trans fats

Many foods with trans fats are popularly consumed worldwide.
In USA greater part of these trans fats come from partially hydrogenated vegetable oils (about 80%), and the average consumption of trans fats from this source has been constant since the 1960′s.

It should be noted that trans fat values must be interpreted with caution because many fast food establishments, restaurants and industries may have changed the type of fat used for frying and cooking since the analysis were done (e.g. on July 1, 2008 in New York trans fats are banned in its 40.000 restaurants).

Foods with trans fats: margarine

Foods with Trans Fats
Fig. 1 – Margarine

Among foods with trans fats, stick or hard margarine had the highest percentage of them, but levels of these fatty acids have declined as improved technology allowed the production of softer margarines which have become popular. But there are difference in trans fat content of margarine from different country:

  • the greatest contents are found in soft margarine from Iceland, Norway, and the UK (13-16,5% of total fatty acids);
  • less contents are found in Italy, Germany, Finland, and Greece (5.1%, 4.8%, 3.2%, and 2.9% of total fatty acids, respectively);
  • in Portugal, The Netherlands, Belgium, Denmark, France, Spain, and Sweden margarine trans fat contents are less than 2% of the total fatty acids.

USA and Canada lag behind Europe, but with advent of trans fat labeling of foods in USA change is occurring. For this reason, at now, in USA margarine is considered to be only a minor contributor of the total trans fats, whereas the major sources are commercially baked and fast food products like cake, cookies, wafer, snack crackers, chicken nuggets, French fries or microwave-oven popcorn (see below).

Foods with trans fats: shortenings

Trans fat content of shortening ranges from 6% to 50% and varies in different country: in Germany, Austria and New Zealand it is less than France or USA.
However like margarines, trans fat content of shortenings is decreasing; i.e. in German shortenings it decreased from 12% of total fatty acids in 1994 to 6% in 1999, in Denmark is 7% (1996) while in New Zealand is about 6% (1997).

Foods with trans fats: vegetable oils

At now, nonhydrogenated vegetable oils for salad and cooking contain no or only small amounts of trans fats. Processing of these oils can produce minimal level of them ranged from 0.05g/100 g food for extra virgin oil to 2,42 g/100 g food for canola oil. So their contribution to trans fat content to the current food supply is very little.
One exception is represented by Pakistani hydrogenated vegetable oils (vegetable ghee/vanaspati) whose trans fat content range from 14% to 34% of total fatty acids.

Foods with trans fats: prepared soups

Among foods with trans fats, prepared soups contain significant amount of them, ranging from 10% of beef bouillon to 35% of onion cream; so they contribute great amount of trans fats to the diet if frequently consumed.

Foods with trans fats: processed foods

Thanks to their long shelf life as their flavor stability, trans fats are used in many processed foods as cookies, cakes, croissants, pastries and other baked goods.
Baked goods are the greatest source of these fats in North American diet. Of course, their trans fat contents depend on the type of fat used in processing. In USA after 2006, when labeling laws were implemented, many processed foods have been reformulated and contain less than 0,5 g of industrial trans fats per serving; so producers can list their content as 0 on the packaging, but it‘s not 0!

Foods with trans fats: sauces

Mayonnaise, salad dressings and other sauces contribute only small or no-amounts of trans fats to the diet.

Foods with trans fats: human milk and infant foods

Trans fat content of human milk reflects the trans fatty acid content of maternal diet in the previous day. In human milk it comprise 1%-7% of the total fatty acids but decreasing from 7.1 in 1998 to 4.6 in 2005/2006.
Infant formulas have trans fat values on average 0.1%-4.5% with a brand up to 15.7% of the total fatty acids.
Baby foods contain greater than 5% of trans fats.

Foods with trans fats in fast foods and restaurants

Foods with Trans Fats
Fig. 2 – French Fries

Shortenings with high amounts of trans fats are used as frying fats, so fast foods and many restaurant’s foods may contain relatively large amounts of them.
Foods with trans fats are fried pies, French fries, chicken nuggets, hamburgers, fried fish as well as fried chicken.
For French fries and chicken nuggets their  content varies largely from nation to nation, but also within the same fast food chain in the same country because of the cooking oil used. For example oil used in USA and Peru outlets of a famous fast food chain contains 23-24% of trans fats, whereas oil used in many European countries of the same fast food chain contains about 10% trans fats, with some countries as low as 5% and 1% (Denmark).
On 2006, Stender et al. reported that a meal of French fries and chicken nuggets purchased at McDonald ‘s in New York City contained over 10 g of trans fats, while if purchased at Kentucky Fried Chicken in Hungary they are almost 25 g.
Again, from the work of Stender et all. it can see a cross-country comparison of trans fat contents of chicken nuggets and French fries purchased at McDonald ‘s or Kentucky Fried Chicken: trans fat contents vary depending on the country and even the city and often in the same city.

Chicken nuggets and French fries from McDonald’s:

  • less then 1 g in industrial trans fats only if the meals were purchased in Denmark;
  • 1-5 g in Portugal, the Netherlands, Russia, Czech Republic, or Spain;
  • 5-10 g in the United States, Peru, UK, South Africa, Poland, Finland, France, Italy, Norway, Spain, Sweden, Germany, or Hungary.

Chicken and French fries from Kentucky Fried Chicken:

  • less than 2 g in industrial trans fats if the meals were purchased UK (Aberdeen), Denmark, Russia, or Germany (Wiesbaden);
  • 2-5 in Germany (Hamburg), France, UK (London or Glasgow), Spain, or Portugal;
  • 5-10 in the Bahamas, South Africa, or USA;
  • 10-25 g in Hungary, Poland, Peru, or Czech Republic.

Akoh C.C. and Min D.B. “Food lipids: chemistry, nutrition, and biotechnology” 3th ed. 2008

Chow Ching K. “Fatty acids in foods and their health implication” 3th ed. 2008

Eckel R.H., Borra S., Lichtenstein A.H., Yin-Piazza D.Y. Understanding the Complexity of Trans fatty acid reduction in the American diet. American Heart Association trans fat conference 2006 report of the trans fat conference planning group. Circulation 2007;115:2231-46; originally published online Apr 10, 2007 [Abstract]

Mozaffarian D., Jacobson M.F., Greenstein J.S. Food Reformulations to reduce trans fatty acids. N Eng J Med 2010;362:2037-39 [PDF]

Okie S. New York to trans fats: you’re out! N Engl J Med 2007;356:2017-21 [PDF]

Stender S., Astrup A., Dyerberg J. What went in when trans went out?. N Engl J Med 2009;361:314-16 [PDF]

Stender S., Dyerberg J. and Astrup A. Consumer protection through a legislative ban on industrially produced trans fatty acids in foods in Denmark. Scand J Food Nutr 2006;50:155-60 [Abstract]

Stender S., Dyerberg J., Astrup A. High levels of trans fat in popular fast foods. N Engl J Med 2006;354:1650-2 [PDF]

Long chain fatty acid synthesis

Fatty acid synthesis

Fatty Acid Synthesis
Fig. 1 – Long Chain Fatty Acids

When excess calories are consumed from carbohydrates or proteins, such surplus is used to synthesize fatty acids and then triacylglycerols, while it doesn’t occur if the excess come from fats.

De novo fatty acid synthesis in plants and animals

De novo fatty acid synthesis is largely similar among plants and animals.
It occurs in chloroplasts of photosynthetic cells of higher plants, and in cytosol of animal cells by the concerted action of two enzymes: acetyl CoA carboxylase and fatty acid synthase.
Fatty acid synthase is a multienzyme complex that catalyzes a repeating four-step sequence by which the fatty acyl chain is extended by two carbons, at the carboxyl end, every each passage through the cycle; this four-step process is the same in all organisms.
In animals, the primary site for lipid metabolism is liver, not the adipose tissue.  However, adipose tissue is  a major organ system in which fatty acid synthesis occurs, though in humans it is less active than in many other animal species.

Fatty Acid Synthesis
Fig. 2 – Palmitic Acid Synthesis

Although myristic, lauric and a trace of stearic acids may also be produced, in animals and plants the main product of these reactions is palmitic acid.
It should be noted that in certain plants, such as palm and coconut, chain termination occurs earlier than palmitic acid release: up to 90% of the fatty acids produced and then present in the oils of these plants are between 8 (caprylic acid) and 14 (myristic acid) carbons long (palmitic acid: 16 carbon atoms).

Synthesis of long chain saturated and unsaturated fatty acids

Fatty Acid Synthesis
Fig. 3 – Palmitic Acid Metabolism

Palmitic acid is the commonest saturated fatty acid in plant and animal lipids, but generally it is not present in very large proportions because it may be undergo into several metabolic pathways.
In fact:

  • it is the precursor of stearic acid;
  • it may be desaturated (insertion of a double bond into fatty acid chain) to palmitoleic acid, the precursor of all fatty acids of omega-7 or n-7 family, in a reaction catalyzed by Δ9-desaturase, an ubiquitous enzyme in both plant and animal kingdoms and the most active lipid enzyme in mammalian tissues, the same enzyme that catalyzes the desaturation of stearic acid to oleic acid (see below).
    Note: Δ9- desaturase inserts double bounds in the 9-10 position of the fatty acid carbon chain, position numbered from the carboxyl end of the molecule, and:

if the substrate is palmitic acid, the double bond will appear between n-7 and n-8 position of the chain (in this case numbered from the methyl end of the molecule), so producing palmitoleic acid, the founder of omega-7 series;

if the substrate is stearic acid, the double bond will appear between n-9 and n-10 position of the chain and oleic acid will be produced.

  • It may be esterified into complex lipids.

Of course, in plants and animals there are fatty acids longer and/or more unsaturated than these just seen thanks to modification systems (again desaturation and elongation) that catalyze reactions of fatty acid synthesis that are organism- tissue- and cell- specific.

Fatty Acid Synthesis
Fig. 4 – Stearic Acid Metabolism

For example, stearic acid may be:

  • elongated to arachidic, behenic and lignoceric acids, all saturated fatty acids, in reactions catalyzed by elongases.
    Again, chain elongation occurs, both in mitochondria and in the smooth endoplasmic reticulum, by the addition of two carbon atom units at a time at the carboxylic end of the fatty acid through the action of fatty acid elongation systems (particularly long and very long saturated fatty acids, from 18 to 24 carbon atoms, are synthesized only on cytosolic face of the smooth endoplasmic reticulum);
  • desaturated, as seen, to oleic acid, an omega-9 or n-9 fatty acid, in a reaction catalyzed by Δ9-desaturase. Several researchers have postulated that the reason for which stearic acid is not hypercholesterolemic is its rapid conversion to oleic acid.
Fatty Acid Synthesis
Fig. 5 – Oleic Acid Metabolism

Oleic acid is the start point for the synthesis of many other unsaturated fatty acids by reactions of elongation and/or desaturation.

In fact:

Omega-3 and omega-6 PUFA synthesis

Fatty Acid Synthesis
Fig. 6 – Omega-3 and Omega-6 Synthesis

Animal tissues can desaturate fatty acids in the 9-10 position of the chain, thanks to the presence of Δ9 desaturase; as previously seen, if the substrate of the reaction is palmitic acid, the double bond will appear between n-7 and n-8 position, with stearic acid between n-9 and n-10 position, so leading to formation respectively of palmitoleic acid and oleic acid.
Animals lack Δ12- and Δ15-desaturases, enzymes able to desaturate carbon carbon bonds beyond the 9-10 position of the chain. For these reason, they can’t produce de novo omega-3 and omega-6 PUFA (which have double bonds also beyond the 9-10 position), that are so essential fatty acids.
Δ12- and Δ15-desaturases are present in plants; though many land plants lack Δ15-desaturase, also called omega-3 desaturase, planktons and aquatic plants in colder water possess it and produce abundant amounts of the omega-3 fatty acids.


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