The chemistry of fats – part 1
The chemistry of fats – part 1
Understanding the Chemistry of Fats
Clearly something is wrong with the theories we read in the popular press-and used to bolster sales of lowfat concoctions and cholesterol-free foods. The notion that saturated fats per se cause heart disease as well as cancer is not only facile, it is just plain wrong. But it is true that some fats are bad for us. In order to understand which ones, we must know something about the chemistry of fats.
Fats-or lipids-are a class of organic substances that are not soluble in water. In simple terms, fatty acids are chains of carbon atoms with hydrogen atoms filling the available bonds. Most fat in our bodies and in the food we eat is in the form of triglycerides, that is, three fatty-acid chains attached to a glycerol molecule.
Elevated triglycerides in the blood have been positively linked to proneness to heart disease, but these triglycerides do not come directly from dietary fats; they are made in the liver from any excess sugars that have not been used for energy. The source of these excess sugars is any food containing carbohydrates, particularly refined sugar and white flour.
Classification of Fatty Acids by Saturation
Fatty acids are classified in the following way:
- A fatty acid is saturated when all available carbon bonds are occupied by a hydrogen atom.
- They are highly stable, because all the carbon-atom linkages are filled-or saturated-with hydrogen. This means that they do not normally go rancid, even when heated for cooking purposes.
- They are straight in form and hence pack together easily, so that they form a solid or semisolid fat at room temperature.
- Your body makes saturated fatty acids from carbohydrates and they are found in animal fats and tropical oils.
- Monounsaturated fatty acids have one double bond in the form of two carbon atoms double-bonded to each other and, therefore, lack two hydrogen atoms.
- Like saturated fats, they are relatively stable. They do not go rancid easily and hence can be used in cooking.
- Monounsaturated fats have a kink or bend at the position of the double bond so that they do not pack together as easily as saturated fats and, therefore, tend to be liquid at room temperature.
- Your body makes monounsaturated fatty acids from saturated fatty acids and uses them in a number of ways.
- The monounsaturated fatty acid most commonly found in our food is oleic acid, the main component of olive oil as well as the oils from almonds, pecans, cashews, peanuts and avocados.
- Polyunsaturated fatty acids have two or more pairs of double bonds and, therefore, lack four or more hydrogen atoms. In nature, the polyunsaturated fatty acids are usually found in the cis form, which means that both hydrogen atoms at the double bond are on the same side.
- The two polyunsaturated fatty acids found most frequently in our foods are double unsaturated linoleic acid, with two double bonds-also calledomega-6; and triple unsaturated linolenic acid, with three double bonds-also called omega-3. (The omega number indicates the position of the first double bond.)
- The unpaired electrons at the double bonds makes these oils highly reactive. They go rancid easily, particularly omega-3 linolenic acid, and must be treated with care. Polyunsaturated oils should never be heated or used in cooking.
- Your body cannot make these fatty acids and hence they are called “essential.” We must obtain our essential fatty acids or EFA’s from the foods we eat.
- The polyunsaturated fatty acids have kinks or turns at the position of the double bond and hence do not pack together easily. They are liquid, even when refrigerated.
All fats and oils, whether of vegetable or animal origin, are some combination of saturated fatty acids, monounsaturated fatty acids and polyunsaturated linoleic acid and linolenic acid. In general,
- animal fats such as butter, lard and tallow contain about 40-60% saturated fat and are solid at room temperature.
- Vegetable oils from northern climates contain a preponderance of polyunsaturated fatty acids and are liquid at room temperature.
- But vegetable oils from the tropics are highly saturated. Coconut oil, for example, is 92% saturated. These fats are liquid in the tropics but hard as butter in northern climes.
- Vegetable oils are more saturated in hot climates because the increased saturation helps maintain stiffness in plant leaves.
- Olive oil with its preponderance of oleic acid is the product of a temperate climate. It is liquid at warm temperatures but hardens when refrigerated.
Classification of Fatty Acids by Length
Researchers classify fatty acids not only according to their degree of saturation but also by their length.
Short-chain fatty acids:
- have four to six carbon atoms.
- These fats are always saturated.
- Four-carbon butyric acid is found mostly in butterfat from cows, and six-carbon capric acid is found mostly in butterfat from goats.
- These fatty acids have antimicrobial properties-that is, they protect us from viruses, yeasts and pathogenic bacteria in the gut. They contribute to the health of the immune system.
- They do not need to be acted on by the bile salts but are directly absorbed for quick energy. For this reason, they are less likely to cause weight gain than olive oil or commercial vegetable oils.
Medium-chain fatty acids:
- have eight to twelve carbon atoms
- they are found mostly in butterfat and the tropical oils.
- these fats have antimicrobial properties;
- are absorbed directly for quick energy;
- and contribute to the health of the immune system.
Long-chain fatty acids:
- have from 14 to 18 carbon atoms
- they can be either saturated, monounsaturated or polyunsaturated.
- Stearic acid is an 18-carbon saturated fatty acid found chiefly in beef and mutton tallows. Oleic acid is an 18-carbon monounsaturated fat which is the chief component of olive oil. Another monounsaturated fatty acid is the 16-carbon palmitoleic acid which has strong antimicrobial properties. It is found almost exclusively in animal fats.
- The two essential fatty acids (omega-3 and omega-6) are also long chain, each 18 carbons in length.
- Another important long-chain fatty acid is gamma-linolenic acid (GLA) which has 18 carbons and three double bonds. It is found in evening primrose, borage and black currant oils. Your body makes GLA out of omega-6 linoleic acid and uses it in the production of substances called prostaglandins, localized tissue hormones that regulate many processes at the cellular level.
Very-long-chain fatty acids:
- have 20 to 24 carbon atoms.
- They tend to be highly unsaturated, with four, five or six double bonds.
- Some people can make these fatty acids from EFA’s, but others, particularly those whose ancestors ate a lot of fish, lack enzymes to produce them. These “obligate carnivores” must obtain them from animal foods such as organ meats, egg yolks, butter and fish oils.
- The most important very-long-chain fatty acids are dihomo-gamma-linolenic acid (DGLA) with 20 carbons and three double bonds; arachidonic acid (AA) with 20 carbons and four double bonds; eicosapentaenoic acid (EPA) with 20 carbons and five double bonds; and docosahexaenoic acid (DHA) with 22 carbons and six double bonds.
- All of these except DHA are used in the production of prostaglandins, localized tissue hormones that direct many processes in the cells.
- In addition, AA and DHA play important roles in the function of the nervous system.
The Dangers of Polyunsaturates
The public has been fed a great deal of misinformation about the relative virtues of saturated fats versus polyunsaturated oils. Politically correct dietary gurus tell us that the polyunsaturated oils are good for us and that the saturated fats cause cancer and heart disease. The result is that fundamental changes have occurred in the Western diet. At the turn of the century, most of the fatty acids in the diet were either saturated or monounsaturated, primarily from butter, lard, tallows, coconut oil and small amounts of olive oil. Today most of the fats in the diet are polyunsaturated from vegetable oils derived mostly from soy, as well as from corn, sunflower and canola.
Modern diets can contain as much as 30% of calories as polyunsaturated oils, but scientific research indicates that this amount is far too high. The best evidence indicates that our intake of polyunsaturates should not be much greater than 4% of the caloric total, in approximate proportions of 1.5% omega-3 linolenic acid and 2.5% omega-6 linoleic acid. EFA consumption in this range is found in native populations in temperate and tropical regions whose intake of polyunsaturated oils comes from the small amounts found in legumes, grains, nuts, green vegetables, fish, olive oil and animal fats but not from commercial vegetable oils.
Excess consumption of polyunsaturated oils has been shown to contribute to a large number of disease conditions including increased cancer and heart disease; immune system dysfunction; damage to the liver, reproductive organs and lungs; digestive disorders; depressed learning ability; impaired growth; and weight gain.
One reason the polyunsaturates cause so many health problems is that they tend to become oxidized or rancid when subjected to heat, oxygen and moisture as in cooking and processing.
Rancid oils are characterized by free radicals-that is, single atoms or clusters with an unpaired electron in an outer orbit. These compounds are extremely reactive chemically. They have been characterized as “marauders” in the body for they attack cell membranes and red blood cells and cause damage in DNA/RNA strands, thus triggering mutations in tissue, blood vessels and skin.
Free radical damage to the skin causes wrinkles and premature aging; free radical damage to the tissues and organs sets the stage for tumors; free radical damage in the blood vessels initiates the buildup of plaque. Is it any wonder that tests and studies have repeatedly shown a high correlation between cancer and heart disease with the consumption of polyunsaturates? New evidence links exposure to free radicals with premature aging, with autoimmune diseases such as arthritis and with Parkinson’s disease, Lou Gehrig’s disease, Alzheimer’s and cataracts.
Too Much Omega-6
Problems associated with an excess of polyunsaturates are exacerbated by the fact that most polyunsaturates in commercial vegetable oils are in the form of double unsaturated omega-6 linoleic acid, with very little of vital triple unsaturated omega-3 linolenic acid. Recent research has revealed that too much omega-6 in the diet creates an imbalance that can interfere with production of important prostaglandins.
This disruption can result in increased tendency to form blood clots, inflammation, high blood pressure, irritation of the digestive tract, depressed immune function, sterility, cell proliferation, cancer and weight gain.
Too Little Omega-3
A number of researchers have argued that along with a surfeit of omega-6 fatty acids the American diet is deficient in the more unsaturated omega-3 linolenic acid. This fatty acid is necessary for cell oxidation, for metabolizing important sulphur-containing amino acids and for maintaining proper balance in prostaglandin production.
Deficiencies have been associated with asthma, heart disease and learning deficiencies.
Most commercial vegetable oils contain very little omega-3 linolenic acid and large amounts of the omega-6 linoleic acid.
In addition, modern agricultural and industrial practices have reduced the amount of omega-3 fatty acids in commercially available vegetables, eggs, fish and meat. For example, organic eggs from hens allowed to feed on insects and green plants can contain omega-6 and omega-3 fatty acids in the beneficial ratio of approximately one-to-one; but commercial supermarket eggs can contain as much as nineteen times more omega-6 than omega-3!
The Benefits of Saturated Fats
The much-maligned saturated fats-which Americans are trying to avoid-are not the cause of our modern diseases. In fact, they play many important roles in the body chemistry:
- Saturated fatty acids constitute at least 50% of the cell membranes. They are what give our cells necessary stiffness and integrity.
- They play a vital role in the health of our bones. For calcium to be effectively incorporated into the skeletal structure, at least 50% of the dietary fats should be saturated.
- They lower Lp(a), a substance in the blood that indicates proneness to heart disease.
- They protect the liver from alcohol and other toxins, such as Tylenol.
- They enhance the immune system.
- They are needed for the proper utilization of essential fatty acids.
Elongated omega-3 fatty acids are better retained in the tissues when the diet is rich in saturated fats.
- Saturated 18-carbon stearic acid and 16-carbon palmitic acid are the preferred foods for the heart, which is why the fat around the heart muscle is highly saturated. The heart draws on this reserve of fat in times of stress.
- Short- and medium-chain saturated fatty acids have important antimicrobial properties. They protect us against harmful microorganisms in the digestive tract.
The scientific evidence, honestly evaluated, does not support the assertion that “artery-clogging” saturated fats cause heart disease. Actually, evaluation of the fat in artery clogs reveals that only about 26% is saturated. The rest is unsaturated, of which more than half is polyunsaturated.
What about Cholesterol?
And what about cholesterol? Here, too, the public has been misinformed. Our blood vessels can become damaged in a number of ways-through irritations caused by free radicals or viruses, or because they are structurally weak-and when this happens, the body’s natural healing substance steps in to repair the damage. That substance is cholesterol.
Cholesterol is a high-molecular-weight alcohol that is manufactured in the liver and in most human cells. Like saturated fats, the cholesterol we make and consume plays many vital roles:
- Along with saturated fats, cholesterol in the cell membrane gives our cells necessary stiffness and stability. When the diet contains an excess of polyunsaturated fatty acids, these replace saturated fatty acids in the cell membrane, so that the cell walls actually become flabby. When this happens, cholesterol from the blood is “driven” into the tissues to give them structural integrity. This is why serum cholesterol levels may go down temporarily when we replace saturated fats with polyunsaturated oils in the diet.
- Cholesterol acts as a precursor to vital corticosteroids, hormones that help us deal with stress and protect the body against heart disease and cancer; and to the sex hormones like androgen, testosterone, estrogen and progesterone.
- Cholesterol is a precursor to vitamin D, a very important fat-soluble vitamin needed for healthy bones and nervous system, proper growth, mineral metabolism, muscle tone, insulin production, reproduction and immune system function.
- The bile salts are made from cholesterol. Bile is vital for digestion and assimilation of fats in the diet.
- Recent research shows that cholesterol acts as an antioxidant. This is the likely explanation for the fact that cholesterol levels go up with age. As an antioxidant, cholesterol protects us against free radical damage that leads to heart disease and cancer.
- Cholesterol is needed for proper function of serotonin receptors in the brain. Serotonin is the body’s natural “feel-good” chemical. Low cholesterol levels have been linked to aggressive and violent behavior, depression and suicidal tendencies.
- Mother’s milk is especially rich in cholesterol and contains a special enzyme that helps the baby utilize this nutrient. Babies and children need cholesterol-rich foods throughout their growing years to ensure proper development of the brain and nervous system.
- Dietary cholesterol plays an important role in maintaining the health of the intestinal wall. This is why low-cholesterol vegetarian diets can lead to leaky gut syndrome and other intestinal disorders.
Cholesterol is not the cause of heart disease but rather a potent antioxidant weapon against free radicals in the blood, and a repair substance that helps heal arterial damage (although the arterial plaques themselves contain very little cholesterol.) However, like fats, cholesterol may be damaged by exposure to heat and oxygen.
This damaged or oxidized cholesterol seems to promote both injury to the arterial cells as well as a pathological buildup of plaque in the arteries. Damaged cholesterol is found in powdered eggs, in powdered milk (added to reduced-fat milks to give them body) and in meats and fats that have been heated to high temperatures in frying and other high-temperature processes.
High serum cholesterol levels often indicate that the body needs cholesterol to protect itself from high levels of altered, free-radical-containing fats. Just as a large police force is needed in a locality where crime occurs frequently, so cholesterol is needed in a poorly nourished body to protect the individual from a tendency to heart disease and cancer. Blaming coronary heart disease on cholesterol is like blaming the police for murder and theft in a high crime area.
Poor thyroid function (hypothyroidism) will often result in high cholesterol levels. When thyroid function is poor, usually due to a diet high in sugar and low in usable iodine, fat-soluble vitamins and other nutrients, the body floods the blood with cholesterol as an adaptive and protective mechanism, providing a superabundance of materials needed to heal tissues and produce protective steroids. Hypothyroid individuals are particularly susceptible to infections, heart disease and cancer.