(Essential) Fatty Acids (oil) And Lipids In Anti-Aging Cream -
Essential fatty acids (ω-3 and ω-6 fatty acid)
- ω-3 fatty acid
- α-Linolenic acid (an ω-3 fatty acid) [18:3 (n-3)]
- ω-6 fatty acid
- γ-Linolenic acid (an ω-6 fatty acid) [18:3 (n-6)]
- Linoleic Acid (an ω-6 fatty acid) [18:2 (n-6)]
Essential Fatty Acids And Skin Benefits
The fatty acid (as the components of lipid, phospholipids) content of cell membranes is vital. Not only do the essential fats keep cell membranes smooth and soft, but also they help the membranes to do a better job of controlling what goes in and out of the cells. Without enough fats in the skin cell membranes, they are not able to retain water and they lose their plumpness.
As an added benefit, omega 3 fatty acids are anti-inflammatory, which help minimize redness and skin irritation, and inflamed skin or skin disorders such as psoriasis and eczema. There is evidence that omega-3s can improve chronic skin conditions such as eczema (atopic dermatitis), rosacea, acne, and psoriasis, but only preliminary studies have been done. Omega 3s have been shown to aid in wound healing as well.
Introduction
Essential fatty acids, or EFAs, are fatty acids that cannot be constructed within an organism (generally all references are to humans) from other components by any known chemical pathways, and therefore must be obtained from the diet. The term refers to fatty acids involved in biological processes, and not those which may just play a role as fuel. There are two families of EFAs: ω-3 (or omega-3 or n−3) and ω-6 (omega-6, n−6). Fats from each of these families are essential, as the body can convert one omega-3 to another omega-3, for example, but cannot create an omega-3 from omega-6 or saturated fats.
In the body, essential fatty acids serve multiple functions. In each of these, the balance between dietary ω-3 and ω-6 strongly affects function.
- They are modified to make
- the classic eicosanoids (affecting inflammation and many other cellular functions)
- the endocannabinoids (affecting mood, behavior and inflammation)
- the lipoxins from ω-6 EFAs and resolvins from ω-3 (in the presence of aspirin, downregulating inflammation.)
- the isofurans, neurofurans, isoprostanes, hepoxilins, epoxyeicosatrienoic acids (EETs) and Neuroprotectin D
- They form lipid rafts (affecting cellular signaling)
- They act on DNA (activating or inhibiting transcription factors such as NFκB, which is linked to pro-inflammatory cytokine production)
The essential fatty acids start with the short chain polyunsaturated fatty acids (SC-PUFA): ω-3 fatty acids: α-Linolenic acid or ALA (18:3); ω-6 fatty acids: Linoleic acid or LA (18:2)
They form the starting point for the creation of longer and more desaturated fatty acids, which are also referred to as long-chain polyunsaturated fatty acids.
ω-9 fatty acids are not essential in humans, because humans generally possess all the enzymes required for their synthesis. Exceptions do occur in older people or people with a liver problem that do not completely produce a sufficient amount,[citation needed] and hence many supplement companies market Omega 3-6-9 blends.
Fatty Acid Nomenclature
Fatty acids are straight chain hydrocarbons possessing a carboxyl (COOH) group at one end. The carbon next to the carboxylate is known as α, the next carbon β, and so forth. Since biological fatty acids can be of different lengths, the last position is labelled as a “ω”, the last letter in the Greek alphabet. Since the physiological properties of unsaturated fatty acids largely depend on the position of the first unsaturation relative to the end position and not the carboxylate. For example, the term ω-3 signifies that the first double bond exists as the third carbon-carbon bond from the terminal CH3 end (ω) of the carbon chain. The number of carbons and the number of double bonds is also listed. ω-3 18:4 (stearidonic acid) or 18:4 ω-3 or 18:4 n−3 indicates an 18-carbon chain with 4 double bonds, and with the first double bond in the third position from the CH3 end. Double bonds are cis and separated by a single methylene (CH2) group unless otherwise noted.
For saturated fatty acids, for example, palmitic acid (16 carbon saturated fatty acids, is expressed as 18:0, meaning 0 double bonds). Saturated fatty acids and fatty acids salts/ester are commonly used as emollients, surfactants, emulsifier agent. They are not essential fatty acids and are not discussed in this section. Visit our “saturated fatty acids, fatty acids salts, and ester ingredients in topical skin care products” for related information on saturated fatty acids.
| Fatty Acid Equivalent Names | |||
| Type | Isomer | Systematic Name | Common Name |
| Saturated Fats | 4:0 | butanoic acid | butyric acid |
| 6:0 | hexanoic acid | caproic acid | |
| 8:0 | octanoic acid | caprylic acid | |
| 10:0 | decanoic acid | capric acid | |
| 12:0 | dodecanoic acid | lauric acid | |
| 13:0 | tridecanoic acid | ||
| 14:0 | tetradecanoic acid | myristic acid | |
| 15:0 | pentadecanoic acid | ||
| 16:0 | hexadecanoic acid | palmitic acid | |
| 17:0 | heptadecanoic acid | margaric acid | |
| 18:0 | octadecanoic acid | stearic acid | |
| 19:0 | nonadecanoic acid | ||
| 20:0 | eicosanoic acid | arachidic acid | |
| 22:0 | docosanoic acid | behenic acid | |
| 24:0 | tetracosanoic acid | lignoceric acid | |
| Type | Isomer | Systematic Name | Common Name |
| Monounsaturated Fats | 14:1 | tetradecenoic acid | myristoleic acid |
| 15:1 | pentadecenoic acid | ||
| 16:1undifferentiated | hexadecenoic acid | palmitoleic acid | |
| 16:1 c | |||
| 16:1 t | |||
| 17:1 | heptadecenoic acid | ||
| 18:1undifferentiated | octadecenoic acid | oleic acid | |
| 18:1 c | |||
| 18:1 t | |||
| 20:1 | eicosenoic acid | gadoleic acid | |
| 22:1undifferentiated | docosenoic acid | erucic acid | |
| 22:1 c | |||
| 22:1 t | |||
| 24:1 c | cis-tetracosenoic acid | nervonic acid | |
| Type | Isomer | Systematic Name | Common Name |
| Polyunsaturated Fats | 16:2undifferentiated | hexadecenoic acid | |
| 18:2undifferentiated | octadecadienoic acid | linoleic acid | |
| 18:2 n-6 c,c | |||
| 18:2 c,t | |||
| 18:2 t,c | |||
| 18:2 t,t | |||
| 18:2 i | |||
| 18:2 t not further defined | |||
| 18:3undifferentiated | octadecatrienoic acid | linolenic acid | |
| 18:3 n-3 c,c,c | alpha-linolenic acid | ||
| 18:3 n-6 c,c,c | gamma-linolenic acid | ||
| 18:4undifferentiated | octadecatetraenoic acid | parinaric acid | |
| 20:2 n-6 c,c | eicosadienoic acid | ||
| 20:3undifferentiated | eicosatrienoic acid | ||
| 20:3 n-3 | |||
| 20:3 n-6 | |||
| 20:4undifferentiated | eicosatetraenoic acid | arachidonic acid | |
| 20:4 n-3 | |||
| 20:4 n-6 | |||
| 20:5 n-3 | eicosapentaenoic acid (EPA) | timnodonic acid | |
| 22:2 | docosadienoic acid | brassic acid | |
| 22:5 n-3 | docosapentaenoic acid (DPA) | clupanodonic acid | |
| 22:6 n-3 | docosahexaenoic acid (DHA) | ||
ω−3 fatty acids
ω−3 fatty acids or omega-3 fatty acids are a family of unsaturated fatty acids that have in common a final carbon–carbon double bond in the n−3 position; that is, the third bond from the methyl end of the fatty acid.
Important nutritionally essential n−3 fatty acids are: α-linolenic acid (ALA), eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), all of which are polyunsaturated. The human body cannot synthesize n−3 fatty acids de novo, but it can form 20-carbon unsaturated n−3 fatty acids (like EPA) and 22-carbon unsaturated n−3 fatty acids (like DHA) from the eighteen-carbon n−3 fatty acid α-linolenic acid. These conversions occur competitively with n−6 fatty acids, which are essential closely related chemical analogues that are derived from linoleic acid. Both the n−3 α-linolenic acid and n−6 linoleic acid are essential nutrients which must be obtained from food. Synthesis of the longer n−3 fatty acids from linolenic acid within the body is competitively slowed by the n−6 analogues. Thus accumulation of long-chain n−3 fatty acids in tissues is more effective when they are obtained directly from food or when competing amounts of n−6 analogs do not greatly exceed the amounts of n−3
ω−6 fatty acids
ω−6 fatty acids or omega-6 fatty acids) are a family of unsaturated fatty acids that have in common a final carbon–carbon double bond in the n−6 position, that is, the sixth bond from the end of the fatty acid.
The biological effects of the n−6 fatty acids are largely mediated by their conversion to n-6 eicosanoids that bind to diverse receptors found in every tissue of the body. The conversion of tissue arachidonic acid (20:4n-6) to n-6 prostaglandin and n-6 leukotriene hormones provides many targets for pharmaceutical drug development and treatment to diminish excessive n-6 actions in atherosclerosis, asthma, arthritis, vascular disease, thrombosis, immune-inflammatory processes, and tumor proliferation. Competitive interactions with the n−3 fatty acids affect the relative storage, mobilization, conversion and action of the n-3 and n-6 eicosanoid precursors.
Complete table of ω−3 fatty acids and ω−6 fatty acids
Methylene-Interrupted Polyenes
These fatty acids have 2 or more cis double bonds that are separated from each other by a single methylene group.
The essential fatty acids are all omega-3 and -6 methylene-interrupted polyunsaturated (at least 2 double bonds) fatty acids.
Omega-3 fatty acids
| Common name | Lipid name | Chemical name |
|---|---|---|
| 16:3 (n-3) | all-cis 7,10,13-hexadecatrienoic acid | |
| Alpha-linolenic acid (ALA) | 18:3 (n-3) | all-cis-9,12,15-octadecatrienoic acid |
| Stearidonic acid (STD) | 18:4 (n-3) | all-cis-6,9,12,15,-octadecatetraenoic acid |
| Eicosatrienoic acid (ETE) | 20:3 (n-3) | all-cis-11,14,17-eicosatrienoic acid |
| Eicosatetraenoic acid (ETA) | 20:4 (n-3) | all-cis-8,11,14,17-eicosatetraenoic acid |
| Eicosapentaenoic acid (EPA) | 20:5 (n-3) | all-cis-5,8,11,14,17-eicosapentaenoic acid |
| Docosapentaenoic acid (DPA, Clupanodonic acid) | 22:5 (n-3) | all-cis-7,10,13,16,19-docosapentaenoic acid |
| Docosahexaenoic acid (DHA) | 22:6 (n-3) | all-cis-4,7,10,13,16,19-docosahexaenoic acid |
| Tetracosapentaenoic acid | 24:5 (n-3) | all-cis-9,12,15,18,21-tetracosapentaenoic acid |
| Tetracosahexaenoic acid (Nisinic acid) | 24:6 (n-3) | all-cis-6,9,12,15,18,21-tetracosahexaenoic acid |
Omega-6 fatty acids
| Common name | Lipid name | Chemical name |
|---|---|---|
| Linoleic acid | 18:2 (n-6) | all-cis-9,12-octadecadienoic acid |
| Gamma-linolenic acid (GLA) | 18:3 (n-6) | all-cis-6,9,12-octadecatrienoic acid |
| Eicosadienoic acid | 20:2 (n-6) | all-cis-11,14-eicosadienoic acid |
| Dihomo-gamma-linolenic acid (DGLA) | 20:3 (n-6) | all-cis-8,11,14-eicosatrienoic acid |
| Arachidonic acid (AA) | 20:4 (n-6) | all-cis-5,8,11,14-eicosatetraenoic acid |
| Docosadienoic acid | 22:2 (n-6) | all-cis-13,16-docosadienoic acid |
| Adrenic acid | 22:4 (n-6) | all-cis-7,10,13,16-docosatetraenoic acid |
| Docosapentaenoic acid (Osbond acid) | 22:5 (n-6) | all-cis-4,7,10,13,16-docosapentaenoic acid |
Omega-9 fatty acids
| Common name | Lipid name | Chemical name |
|---|---|---|
| Oleic acid† | 18:1 (n-9) | cis-9-octadecenoic acid |
| Eicosenoic acid† | 20:1 (n-9) | cis-11-eicosenoic acid |
| Mead acid | 20:3 (n-9) | all-cis-5,8,11-eicosatrienoic acid |
| Erucic acid† | 22:1 (n-9) | cis-13-docosenoic acid |
| Nervonic acid† | 24:1 (n-9) | cis-15-tetracosenoic acid |
| †Monounsaturated | ||
Conjugated fatty acids
Conjugated fatty acids have two or more conjugated double bonds
| Common name | Lipid name | Chemical name |
|---|---|---|
| Conjugated Linoleic Acids (two conjugated double bonds) | ||
| Rumenic acid | 18:2 (n-7) | 9Z,11E-octadeca-9,11-dienoic acid |
| 18:2 (n-6) | 10E,12Z-octadeca-9,11-dienoic acid | |
| Conjugated Linolenic Acids (three conjugated double bonds) | ||
| α-Calendic acid | 18:3 (n-6) | 8E,10E,12Z-octadecatrienoic acid |
| β-Calendic acid | 18:3 (n-6) | 8E,10E,12E-octadecatrienoic acid |
| Jacaric acid | 18:3 (n-6) | 8E,10Z,12E-octadecatrienoic acid |
| α-Eleostearic acid | 18:3 (n-5) | 9Z,11E,13E-octadeca-9,11,13-trienoic acid |
| β-Eleostearic acid | 18:3 (n-5) | 9E,11E,13E-octadeca-9,11,13-trienoic acid |
| Catalpic acid | 18:3 (n-5) | 9Z,11Z,13E-octadeca-9,11,13-trienoic acid |
| Punicic acid | 18:3 (n-5) | 9Z,11E,13Z-octadeca-9,11,13-trienoic acid |
| Other | ||
| Rumelenic acid | 18:3 (n-3) | 9E,11Z,15E-octadeca-9,11,15-trienoic acid |
| α-Parinaric acid | 18:4 (n-3) | 9E,11Z,13Z,15E-octadeca-9,11,13,15-trienoic acid |
| β-Parinaric acid | 18:4 (n-3) | all trans-octadeca-9,11,13,15-trienoic acid |
| Bosseopentaenoic acid | 20:5 (n-6) | 5Z,8Z,10E,12E,14Z-eicosanoic acid |
Other Polyunsaturate fatty acids
| Common name | Lipid name | Chemical name |
|---|---|---|
| Pinolenic acid | 18:3 (n-6) | (5Z,9Z,12Z)-octadeca-5,9,12-trienoic acid |
| Podocarpic acid | 20:3 (n-6) | (5Z,11Z,14Z)-eicosa-5,11,14-trienoic acid |