Plant Oils Chemistry & Structure

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This section provides info & links for the chemistry and composition of plant oils – both essential and fixed oils

See resources for the A-Z of plant oils > A, B, C, D, E, F, G, H, I, J, K, L, M, N, O, P, Q, R, S, T, U, V, W, X, Y, Z

Chemistry & Structure of Fixed Oils

Fixed oils from seeds, nuts & vegetables are typically composed of triglyceride molecules (also known as triacylglycerol or triacylglyceride). A triglyceride is a glyceride in which the glycerol is esterified with three fatty acids - a triglyceride is typically composed of a 3-carbon alcohol (glycerol) plus three 18-carbon (or 16-carbon) fatty acids. The 18-carbon fatty acids are Linoleic acid, Stearic acid & Oleic acid.

Glycerol + Three Fatty Acids = A Fat Molecule (Triglyceride)
Linoleic Acid Polyunsaturated: 2 Double Bonds In The Molecule
Stearic Acid Saturated: All Single Bonds Between Atoms Of Carbon
Oleic Acid Monounsaturated: 1 Double Bond between Carbons 9 & 10

The fatty acids may be saturated (with all single bonds), mono-unsaturated (with one double bond) or polyunsaturated (with 2 or more double bonds). Plant fatty acids are usually unsaturated and liquid at room temperature, with one or more double bonds between the carbon atoms (mono-unsaturated and polyunsaturated). A notable exception is the palm fatty acid – palmitin – which is saturated and contains 16 rather than 18 carbon atoms. Since the plant fatty acids are unsaturated, the plant oils it is liquid at room temperature.

Cis & Trans Fatty Acids

Fatty acid isomers containing double bonds may have the cis or trans configuration. In cis fatty acids, all the hygrogen atoms adjacent to the double bonds are on the same side of the longitudinal carbon axis. In trans fatty acids, the hygrogen atoms adjacent to the double bonds occur on alternate sides of the main axis.

The trans configuration is chemically more stable. It is typically produced during partial hydrogenation of polyunsaturated vegetable oils.

Trans fatty acids tend to raise the level of low density lipoproteins (LDLs = bad) and lower the level of high density lipoproteins (HDLs = good). These changes in blood lipids (cholesterol levels) may increase the risk of heart disease (atherosclerosis) in some people. Dieticians generally recommend the use of mono-unsaturated, unhydrogenated oils and the avoidance of trans fatty acids found in french fries, cookies and crackers.

Unsaturated fatty acids found in plant oils and seeds are typically omega-6 fatty acids, in which the first double bond is located on the sixth carbon atom, counting backwards from right to left. Omega-3 fatty acids – in which the first double bond in on carbon #3 - are prevalent in fish oils and flax seeds.

Oil Content of Fixed Oils

Cereals only contain about 2% by weight oil, compared to oilseeds that contain much higher levels. The oil content of oilseeds varies widely from one type to the other. It is about 20% in soybeans and as high as 50% in some new Australian varieties of canola (The oil content of canola seed varies from 35 to 50%, and is usually considered to be averaging 40%). Sunflower has one of the highest oil contents among oilseeds – about 55%. Castor seeds have about 45-50% comprised of oil. Safflower has about 40% of its contents as oil, and cottonseed has about 20% of its weight as oil. Hemp has 30-35% oil content. Copra, the dried coconut meat, has about 60% (sometimes close to 65%) oil content. Peanuts contain approximately 50% oil on a dry weight basis. Palm kernel has about 50% oil. Corn has only 5-10% of its dry weight as oil. The average oil content of mustard is about 40% - yellow mustard have only about 27% while brown mustard have about 36% oil; some oriental mustard have upto 50% oil. Flaxseed has about 45% oil content. For jatropha, the oil content is 35-40% in the seeds and 50-60% in the kernel

Oil content (% of dry weight) – average values

Soy - 20

Canola/rapeseed - 40

Sunflower - 55

Castor - 45

Safflower - 40

Hemp - 30

Copra (Dry Coconut) - 60

Peanuts/Groundnuts - 50

Palm Kernel - 50

Corn - 7

Mustard - 40

Flaxseed - 45

Jatropha seed - 40

Jatropha kernel - 55

Algae (for comparison)- 15-40%

Olive Oil?

Sesame Oil?

Essential oils are a mixture of organic compounds, such as ketones, terpenes, esters, alcohols, aldehydes and hundreds of other molecules.

The constituents of essential oils can be divided into main two groups:

Terpene Hydrocarbons
Oxygenated Compounds

Terpene Hydrocarbons

Monoterpene Hydrocarbons
Sesquiterpenes

Terpenes

Triterpenoids and Saponins

Oxygenated Compounds

Phenols
Alcohols
Sesquiterpene Alcohols
Aldehydes
Ketones
Esters
Lactones
Coumarins
Ethers
Oxides

Phenols - The major classifications within phenolic compounds are:

Anti-oxidants
- Flavonoids
- Flavenols
- Flavanones
- Catechins
- Anthrocyanins
- Isoflavones
- Dihydroflavonols
- Chalcones
- Quercetin

Phenolic Acids
- Ellagic Acid
- Tannic Acid
- Vanillin

Hydroxycinnamic Acid Derivatives
- Caffeic Acid
- Chlorogenic Acid
- Ferulic Acid
- Curcumin
- Courmarins

Lignans

More Links on Phenolic Compounds

Polyphenols - Tannins and Flavonoids

Phytochemistry & Phytochemicals

The term phytochemicals is usually used to refer to compounds found in plants that are not required for normal functioning of the body but that nonetheless have a beneficial effect on health or an active role in the amelioration of disease. Thus, they differ from what are traditionally termed nutrients in that they are not a necessity for normal metabolism, and their absence will not result in a deficiency disease. Phytonutrients have many and various salubrious functions in the body. For instance, they may promote the function of the immune system, act directly against bacteria and viruses, reduce inflammation, and be associated with the treatment and/or prevention of cancer, cardiovascular disease and other maladies.

Many phytochemicals are polyphenol antioxidants that impart bright colors to fruits and vegetables. Lutein makes corn yellow, lycopene makes tomatoes red, carotene makes carrots orange and anthocyanin makes blueberries blue, for example. The bright colors and the antioxidant activities of the phytochemicals are due to alternating single-bonded and double-bonded carbons.

· Glycosides

· Glycosides Information

· Glycoside – from Wikipedia

· Polysaccharides

· Neutral Polysaccharides Info from Dextra Laboratories

· Plant Polysaccharides Research – University of Georgia

· Alkaloids

· Mind-altreing Plant Alkaloids – Wayne’s World

· Plant Alkaloids

· Plant Alkaloids – from Friedli.com

Essential Oils Chemistry Links

The Plant Oil, Vegetable Oils & Essential Oils Database @ PlantOils.in provides directory and web links resources for the plant-based oils, plant extracts, vegetable oils, edible oil, oleoresins, oleoresin extract, biofuels, biodiesel. It is intended to be useful for research and information as well as for buyers, sellers, manufacturers, traders, suppliers, producers, exporters and importers. It will make an effort to provide plant oil, vegetable oil info and link, details on oilseeds, bio-fuel, bio-diesel, bio-fuels, plant oils production and uses, and trade & market resources, data, statistics such as price, prices, demand-supply for buyer, seller, manufacturer, trader, supplier, exporter and producer.

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