Fats and Oils

The technical name for the fats and oils found in our food is Triglycerides. Each molecule of a triglyceride is made by combining three Fatty Acid molecules with one molecule of Glycerin.

Glycerin is a viscous, sweet liquid that consists of a 3-carbon chain, where each carbon has an attached alcohol group (OH). It is non-toxic, and is often used as the carrier for medicines, especially for children.

All fatty acids consist of two parts:

1. Carboxylic Acid Head: This has the chemical formula COOH, and has two important properties: it can react with other things, like alcohols, amines, etc, and it likes to mix with water.
2. Hydrocarbon Chain Tail: This is just a string of carbons tied together, with hydrogen hanging off the sides. There are a number of variations in the chain that determine the properties of the fatty acid (and the resultant triglyceride). These include:
   • Carbon chain length (short, medium, or long)
   • Presence of double bonds (unsaturation)
   • Number of double bonds (saturated, mono-unsaturated, or poly-unsaturated)
   • Configuration of the double bonds (cis or trans)
   • Location of double bonds (Omega-3, Omega-9)
   Each of these variations will be discussed below.

   All fatty acids have the same COOH "head"; the variation in the "tail" is where all the interesting things happen.

   It is important to note that fatty acids are NOT the same thing as mineral gases and oils, which are derived from petroleum, and resemble hydrocarbon tails without a COOH attached.

Depending on the number of carbons in the chain, the properties are different. We can talk about "short chains", "medium chains", and "long chains"

Short chains (without an attached COOH head) are similar to butane (lighter fluid); medium chains are similar to gasoline; and long chains are similar to Vaseline (petroleum jelly).

The hydrocarbon chain tail does not like to mix with water; the COOH head does like to mix with water. In short chain fatty acids, the COOH dominates and the fatty acid is soluble in water but not in mineral oils; In long chain fatty acids, the hydrocarbon chain tail dominates and the fatty acid is insoluble in water but soluble in mineral oils. Medium chain fatty acids have limited solubility in both water and mineral oils.

Short- and medium-chain length fatty acids are liquid at room temperature, and are called Oils, whereas long-chain length fatty acids are solid at room temperature, and are called Fats.

If the hydrocarbon tail length is only one carbon long (attached to the COOH head = total 2 carbons), then we have acetic acid, which when diluted in water is what we call "vinegar". It also gives rise to the very important acetyl group that is important to many biochemical processes in the body. [We don't usually think of vinegar as a fatty acid, but it has the structure of a fatty acid].

Other important short chain fatty acids include:

• Propionic acid (2 carbon tail attached to COOH head = total 3 carbons)
• Butyric acid (3 carbon tail attached to COOH head = total 4 carbons)
• Valeric acid (4 carbon tail attached to COOH head = total 5 carbons)

These all have characteristic unpleasant odors. E.g. butyric acid smells like rancid butter.

Fatty acids with a hydrocarbon tail length of 5 to 11 carbons are called medium chain fatty acids [Jadhav2023  🕮 ]. Important medium chain fatty acids include:

• Caproic acid (5 carbon tail attached to COOH head = total 6 carbons)
• Caprylic acid (7 carbon tail attached to COOH head = total 8 carbons)
• Capric acid (9 carbon tail attached to COOH head = total 10 carbons)
• Lauric acid (11 carbon tail attached to COOH head = total 12 carbons)

Note that all of these important medium chain fatty acids have a even number of total carbons and long chain have more than 12 carbons.

The fatty acids caproic, caprylic, and capric are liquid at room temperature and all have characteristic unpleasant odors similar to goats ("Capricorn"). Lauric acid is solid at room temperature and may have natural anti-viral properties.

Oils formed from medium chain fatty acids are sometimes abbreviated MCT, and have important health benefits [Jadhav2023  🕮 ].

Fatty acids with a hydrocarbon tail length of 12 or more carbons are called long chain fatty acids

If every carbon of the tail has 2 hydrogens attached (except the end carbon, which has 3 hydrogens attached), then we say that the fat is saturated. This is sometimes abbreviated SFA.

Animal fat (and fat made by people) is naturally saturated, but vegetable sources such as coconut oil also contain saturated fat.

Traditional sources of saturated animal fats used in cooking include tallow (beef fat) and lard (pork fat).

Stearic Acid and Palmitic Acid are important SFA made in the human body. They solids at room temperature. Stearic acid contains a total of 18 carbons (17-carbon chain attached to COOH), while palmitic acid contains a total of 16 carbons (15-carbon chain attached to COOH).

Conventional western medicine labels saturated fat as being "bad" [Blackburn1994] [Keys1959] [Keys1994]. However, more recent scientific studies show that saturated fat is not necessarily bad: [Cassiday2015] [Fogelholm2010] [Forsythe2010  🕮 ] [Kratz2013  🕮 ] [Tarino2010  🕮 ] In fact, some saturated fats are contaminated with for example Omega-6 fatty acids (see below) from corn-fed animals.

In addition, saturated fats are the most stable fats for frying foods, because they are naturally resistant to becoming rancid (see below).

If one hydrogen is removed on each of two adjacent carbon atoms in the chain, then we say the fatty acid is unsaturated and has a double bond between the two involved carbons.

There are several types of unsaturated fatty acids discussed below, including: cis, trans, mono-unsaturated, poly-unsaturated, Omega-3, and Omega-6.

Unsaturated fats come mostly from vegetable sources, but are also found in products from animals that eat vegetable sources.

Some are essential for human nutrition, but cannot be made by humans!

Good unsaturated fats include: Mono-unsaturated, Omega-3 (see below).

Bad unsaturated fats include: Trans, too much Omega-6, rancid fats

Fats and oils can react with oxygen (oxidize) to make toxic substances. When this happens we say the fat has become rancid. Rancid fats and oil taste and smell bad. Poly-unsaturated fats (see below) are especially susceptible to becoming rancid, especially when heated; Saturated fats are least susceptible.

When a double bond is formed (as above), there are two different geometric shapes that can result, which we call cis (from Latin, "this side") and trans (from Latin, "across" or "opposite"). These two different shapes are called geometric isomers. The cis form is generally natural, whereas the trans form usually occurs during chemical processing.

The chemical process most responsible for creating trans fats is called Partial Hydrogenation. In this process, a poly-unsaturated oil such as cottonseed oil or soybean oil is mixed together with hydrogen gas in a high-temperature vat containing a catalyst such as nickel.

In general, cis and trans forms have different physical and chemical properties, especially in regards to differences in enzymatic processing in biochemical metabolism in the body.

The food industry likes hydrogenated fats because they are less likely to become rancid, and therefore increase the shelf-life of processed foods

The trans form is generally considered unhealthful and products containing significant amounts, such as Crisco and margarine should be avoided [Mente2009  🕮 ]

An additional down-side to hydrogenated, partially hydrogenated, and other highly processed oils is that the processing destroys the beneficial vitamins and anti-oxidants found in unprocessed oils.

When a fatty acid contains only one double bond, we say that it is mono-unsaturated. This is sometimes abbreviated MUFA.

MUFAs are an important part of the Mediterranean Diet. Important examples of MUFA include olive oil and avocado oil; avocado oil is better for frying because it has a higher "smoke point."

Early-harvest extra-virgin cold-pressed olive oil is the best because it is the least processed and contains the highest amounts of beneficial polyphenols and vitamin E.

See also: [Herting1963  🕮 ].

When a fatty acid contains more than one double bond, we say that it is poly-unsaturated. This is sometimes abbreviated PUFA.

Poly-unsaturated fatty acids are further characterized by specifying how close to the tail-end of the hydrocarbon tail the first double bond occurs. This location is given an "omega" number, such as omega-3 or omega-6.

[Omega is the last letter of the Greek alphabet; alpha is the first].

Some PUFAs are essential - required for human health, but cannot be made by humans. These include some Omega-3 and Omega-6 fatty acids:

• Omega-3: Best source is cold-water seafood; Generally has anti-inflammatory benefits; E.g. EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid). ALA (alpha linolenic acid) is also an Omega-3 fatty acid, which is favored by vegans because it is derived from plant seeds rather than animals; unfortunately, it is not biologically active and must be converted to EPA and DHA through very inefficient enzymatic processes (5% and 0.5% efficient, respectively). DPA (docosapentaenoic acid) is another omega-3 fatty acid; it's claim to fame is that it can be converted in the body to either EPA or DHA, depending on the body's needs.
• Omega-6: Best source is seed oils like corn oil; Generally has pro-inflammatory effects; E.g. AA (arachidonic acid). Our immune system depends on inflammatory processes.

Balance is Essential! Anthropologists believe that primitive humans had a diet with approximately equal parts of Omega-6 to Omega-3 oils (i.e. a 1:1 ratio). Unfortunately modern agricultural processes give a "Standard American Diet" (SAD) that has too much Omega-6 and not enough Omega-3 (typically a ratio of 20:1). This is a Problem! When the ratio of Omega-6 to Omega-3 is too high, the body experiences too much inflammation, which results in:

• Increased pain
• Type 2 Diabetes
• Cardiovascular disease
• Neural degeneration
• Accelerated aging

Problem Solved: Get an Omega-Check blood test from Sonora Quest (or similar test from other providers) and a standard lipid test. If the ratio of AA to (EPA + DHA) is greater than 3 or TG is greater than HDL then follow Dr. Weyrich's "Oil Change Diet".

1. Minimize foods containing seed oils from your diet (corn oil, safflower, canola, grapeseed, sunflower, soybean, etc). READ LABELS!
2. Instead, use foods containing olive oil.
3. Minimize eating animal products that are fed seed oils (listed above). This includes most commercial meats - "You are what your food eats".
4. Instead, eat "grass-fed" animal products and "safe" fish. Generally speaking, fish is a good source of the essential Omega-3 oils EPA and DHA. However, there is concern that sea-food may be contaminated with mercury, pesticides, and other environmental pollutants. To minimize these pollutants and maximize good Omega-3 oils:
   • Avoid farm-raised fish (especially tilapia and catfish)
   • Avoid large fish (like shark)
   • Prefer smaller wild-caught cold-ocean fish (like sardines)
   • Take a high-potency purified fish oil (Dr. Weyrich prefers Zone Labs)
5. Vegans may prefer the non-animal sourced algal oil, made from algae. Do not rely on alpha linolenic acid from flax seeds, etc.
6. Avoid most Fried Foods! Commercial fried foods are fried in seed oils high in Omega-6 and sometimes rancid. (Have you ever felt a bad aftertaste when eating fast-food French fries? - that's rancid).
7. At home use fresh avocado oil to fry with; Do not use olive oil to fry with.
8. How Much Fats and Oils Should I Eat Each Day,and What Kind? This is a question that should be addressed on a individual basis with your physician. But generally: The Zone Diet is a good balanced starting point. Avoid low fat or high fat diets unless required by a diagnosed medical condition. Much of your fat/oil calories should be from Extra Virgin Olive Oil; Remaining fat/oil calories should be from a variety of:
   • Organic grass-fed free-range animal meats, poultry, eggs, and dairy
   • Wild-caught cold water fish (sardines, herring, tuna, salmon, etc.)
   • Fresh unroasted nuts and Extra Virgin Coconut Oil
   • Avocado, cacao, sesame, borage, and other specialty oils
   • Purified high-potency Omega-3 fish or algal oil

The length of the hydrocarbon tail determines the overall solubility of the fatty acid in water versus mineral oil, and the transport mechanism within the body.

Triglycerides can be either liquid or solid, depending on the temperature. As a general rule:

• Fats with higher carbon count solidify at lower temperature.
• Saturated fats solidify at a lower temperature than unsaturated fats with the same carbon count.
• Trans-fats solidify at lower temperature than cis-fats with the same carbon count.

In general, the more double bonds there are in a particular fat, the faster it will "spoil", become "rancid", or (technically) "oxidize."

TBD

Minimally processed vegetable oils (e.g. olive oil) contain other constituents such as polyphenols, tocopherols, and other antioxidants. These oils are labeled as "virgin"; other vegetable oils (e.g. corn oil) are more highly processed and have less of these beneficial constituents.