EC / List no.: 207-334-8
CAS no.: 463-40-1
Mol. formula: C18H30O2
Alpha-Linolenic Acid (ALA), (from Greek linon, meaning flax), is an n−3, or omega-3, essential fatty acid.
Alpha-Linolenic Acid is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.
In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.
In physiological literature, it is listed by its lipid number, 18:3, and (n−3).
Alpha-linolenic acid is a carboxylic acid with an 18-carbon chain and three cis double bonds.
The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end.
Thus, Alpha-Linolenic Acid is a polyunsaturated n−3 (omega-3) fatty acid.
Alpha-linolenic acid is an isomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds).
The word linolenic is an irregular derivation from linoleic, which itself is derived from the Greek word linon (flax).
Oleic means "of or relating to oleic acid" because saturating linoleic acid's omega-6 double bond produces oleic acid.
Seed oils are the richest sources of Alpha-Linolenic Acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans.
Alpha-Linolenic Acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).
Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of linolenic acid, that shows up as sharp resonances in high-resolution carbon-13 NMR spectra, invariably.[
Some studies state that Alpha-Linolenic Acid remains stable during processing and cooking.
However, other studies state that Alpha-Linolenic Acid might not be suitable for baking, as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some Alpha-Linolenic Acid may also oxidize at baking temperatures.
Alpha-Linolenic Acid percentages in the table below refer to the oils extracted from each item.
Potential role in nutrition and health
Although the best source of Alpha-Linolenic Acid is seeds, most seeds and seed oils are much richer in an n−6 fatty acid, linoleic acid. Exceptions include flaxseed (must be ground for proper nutrient absorption) and chia seeds.
Linoleic acid is the other essential fatty acid, but it, and the other n−6 fatty acids, compete with n−3s for positions in cell membranes and have very different effects on human health.
There is a complex set of essential fatty acid interactions.
Alpha-Linolenic Acid can only be obtained by humans through their diets because the absence of the required 12- and 15-desaturase enzymes makes de novo synthesis from stearic acid impossible.
Eicosapentaenoic acid (EPA; 20:5, n−3) and docosahexaenoic acid (DHA; 22:6, n−3) are readily available from fish and algae oil and play a vital role in many metabolic processes.
These can also be synthesized by humans from dietary Alpha-Linolenic Acid: ALA → stearidonic acid → eicosatetraeonic acid → eicosapentaenoic acid → docosapentaenoic acid → 9,12,15,18,21-tetracosapentaenoic acid → 6,9,12,15,18,21-yetracosahexaenoic acid → docosahexaenoic acid, but with an efficiency of only a few percent.
Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of Alpha-Linolenic Acid conversion, DHA synthesis from Alpha-Linolenic Acid is even more restricted than that of EPA.
Conversion of Alpha-Linolenic Acid to DHA is higher in women than in men.
Stability and hydrogenation
Alpha-Linolenic Acid is relatively more susceptible to oxidation and will become rancid more quickly than many other oils.
Oxidative instability of Alpha-Linolenic Acid is one reason why producers choose to partially hydrogenate oils containing Alpha-Linolenic Acid, such as soybean oil.
Soybeans are the largest source of edible oils in the U.S., and, as of a 2007 study, 40% of soy oil production was partially hydrogenated.
However, when partially hydrogenated, part of the unsaturated fatty acids become unhealthy trans fats.
Consumers are increasingly avoiding products that contain trans fats, and governments have begun to ban trans fats in food products.
These regulations and market pressures have spurred the development of low-Alpha-Linolenic Acid soybeans.
These new soybean varieties yield a more stable oil that doesn't require hydrogenation for many applications, thus providing trans fat-free products, such as frying oil.
Several consortia are bringing low-Alpha-Linolenic Acid soy to market. DuPont's effort involves silencing the FAD2 gene that codes for Δ6-desaturase, giving a soy oil with very low levels of both Alpha-Linolenic Acid and linoleic acid.
Monsanto Company has introduced to the market Vistive, their brand of low Alpha-Linolenic Acid soybeans, which is less controversial than GMO offerings, as it was created via conventional breeding techniques.
In 1887, linolenic acid was discovered and named by the Austrian chemist Karl Hazura of the Imperial Technical Institute at Vienna (although he didn't separate its optical isomers).
Alpha-Linolenic Acid was first isolated in pure form in 1909 by Ernst Erdmann and F. Bedford of the University of Halle an der Saale, Germany, and by Adolf Rollett of the Universität Berlin, Germany, working independently, as cited in J. W. McCutcheon's synthesis in 1942, and referred to in Green and Hilditch 1930s survey.
Alpha-linolenic acid was first artificially synthesized in 1995 from C6 homologating agents.
A Wittig reaction of the phosphonium salt of [(Z-Z)-nona-3,6-dien-1-yl]triphenylphosphonium bromide with methyl 9-oxononanoate, followed by saponification, completed the synthesis.
Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15.
Shown to have an antithrombotic effect.
Alpha-linolenic acid is an omega-3 fatty acid and a linolenic acid.
Alpha-linolenic acid is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate.
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The alpha-linolenic acid (ALA 18:3w) an omega-3 (n-3) fatty acid, is an essential fatty acid (EFA) that cannot be synthesized by the body and therefore must be supplied by dietary sources.
Alpha-Linolenic Acid is abundant in certain plant foods including walnuts, rapeseed (canola), several legumes, flaxseed, and green leafy vegetables.
Alpha-Linolenic Acid is the precursor of three important longer-chain n-3 fatty acids, eicosapentaenoic acid, docosapentaenoic acid , and docosahexaenoic acid, which have vital roles in brain development and function, cardiovascular health, and inflammatory response.
Omega-3 fatty acids are incorporated into the membrane lipid bilayer in virtually all body cells and affect membrane composition, eicosanoid biosynthesis, cell signaling cascades, and gene expression.
clear light yellow to yellow liquid
linolenic acid occurs as the glyceride in many seed fats.
Alpha-linolenic acid is an essential fatty acid in the diet.
Linolenic acid has been used to assess the total antioxidative activity of serum and bacteria
Linolenic acid has been used in palleroni chamber assay
Linolenic acid has been used to prepare free fatty acid mixture
An essential fatty acid. Occurs as the glyceride in most drying oils. Nutrient.
Alpha linolenic acid is also known as alpha-linolenic acid; omega-3.
An essential fatty acid found in most drying oils.
Alpha-linolenic acid is slightly irritating to the mucous membranes.
Alpha-linolenic acid may be used in a cosmetic preparation for any of the following broad uses: anti-static, cleansing, emollient, skin-conditioning, and surfactant properties.
A liquid unsaturated carboxylic acid that occurs in LINSEED OIL and other plant oils.
Alpha-linolenic acid contains three double bonds.
linolenic acid: A liquid polyunsaturatedfatty acid with three doublebonds in its structure:CH3CH2CH:CHCH2CH:CHCH2CH:CH-(CH2)7COOH.
Alpha-linolenic acid occurs in certainplant oils, e.g. linseed and soya-beanoil, and in algae.
Alpha-linolenic acid is one of the essentialfatty acids.
ChEBI: A linolenic acid with cis-double bonds at positions 9, 12 and 15.
Shown to have an antithrombotic effect.
Clear colorless liquid.
Alpha-linolenic acid is a type of omega-3 fatty acid found in plants.
Alpha-linolenic acid is found in flaxseed oil, and in canola, soy, perilla, and walnut oils.
Alpha-linolenic acid is similar to the omega-3 fatty acids that are in fish oil, called eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
Your body can change alpha-linolenic acid into EPA and DHA.
However, some researchers suggest that less than 1% of Alpha-Linolenic Acid is converted to physiologically effective levels of EPA and DHA.
Omega-3 fatty acids -- especially EPA and DHA -- have been shown to reduce inflammation and may help prevent chronic diseases, such as heart disease and arthritis.
They may also be important for brain health and development, as well as normal growth and development.
There is good evidence that fish oil containing EPA and DHA may help treat heart disease, prevent heart attack and stroke, and slightly reduce high blood pressure.
Some researchers think the same may be true for alpha-linolenic acid.
There is evidence that this may be so, but the evidence is not as strong as it is for fish oil.
Alpha-linolenic acid is not the same as alpha-lipoic acid, an antioxidant that helps the body turn glucose into energy.
This can be confusing because both alpha-linolenic acid and alpha-lipoic acid are sometimes abbreviated as Alpha-Linolenic Acid.
One of the best ways to help prevent and treat heart disease is to eat a diet that is low in saturated and trans fats, and rich in monounsaturated and polyunsaturated fats, particularly omega-3 fatty acids.
The Mediterranean Diet -- which emphasizes whole grains, root and green vegetables, daily servings of fruit, fish and poultry, olive and canola oils, and alpha-linolenic acid (found in flaxseed oil) -- is an example.
There's some evidence that eating foods high in alpha-linolenic acid may help, too.
One study suggests that people who eat a diet high in alpha-linolenic acid are less likely to have a fatal heart attack. Another study found that women who ate high levels of alpha-linolenic acid (1.5 g per day) had a 46% lower risk of sudden cardiac death than those who ate the lowest amount of alpha-linolenic acid (about half a gram per day).
Other population studies show that as people eat more foods with alpha-linolenic acid, heart disease deaths go down.
Researchers don't know whether taking alpha-linolenic acid supplements would have the same effect as eating foods rich in alpha-linolenic acid.
People who follow a Mediterranean-style diet tend to have higher HDL ("good") cholesterol levels.
In addition, walnuts -- which are rich in alpha-linolenic acid -- have been shown to lower cholesterol and triglycerides in people with high cholesterol. However, studies with flaxseed oil, which is high in alpha-linolenic acid, have been mixed.
Some studies found that alpha-linolenic acid may help lower cholesterol, while others found it didn't.
Researchers don't know whether alpha-linolenic acid supplements would have the same benefits as foods with alpha-linolenic acid.
High Blood Pressure
Several studies suggest that diets or supplements rich in omega-3 fatty acids lower blood pressure slightly in people with hypertension.
One population study found that eating a diet rich in alpha-linolenic acid reduced the risk of high blood pressure by about 30%.
Preliminary research suggests that omega-3 fatty acid supplements (particularly perilla seed oil, which is rich in alpha-linolenic acid) may decrease inflammation and improve lung function in some people with asthma.
Preliminary studies suggest that higher intakes of Alpha-Linolenic Acid is linked with improvements in dry eye that are comparable to those seen with corticosteroids.
Alpha-Linolenic Acid is also linked with lower inflammatory markers among patients with chronic obstructive pulmonary disease.
Dietary sources of alpha-linolenic acid include:
- Flaxseeds and flaxseed oil
- Canola (rapeseed) oil
- Soybeans and soybean oil
- Pumpkin seeds and pumpkin seed oil
- Perilla seed oil
-Walnuts and walnut oil
Alpha-linolenic oil is available in cooking oils, including canola oil and soybean oil, and in medicinal oils, including flaxseed oil and dietary supplements containing flaxseed oil.
Sometimes the active ingredients in products with alpha-linolenic acid can be destroyed by exposing them to air, heat, or light.
Generally, look for oil bottled in light-resistant containers, refrigerated, and marked with an expiration date.
These oils are not healthful when used for cooking. Instead, use them in salad dressings and dips.
Alpha-linolenic acid (ALA) is an essential omega-3 fatty acid found in nuts such as walnuts.
Alpha-linolenic acid is necessary for normal human growth and development.
Alpha-linolenic acid is thought to decrease the risk of heart disease by helping to maintain normal heart rhythm and pumping.
Alpha-linolenic acid might also reduce blood clots.
Common dietary sources include vegetable oils such as flaxseed and canola oil, as well as red meat and dairy products.
Alpha-linolenic acid is most commonly used for diseases of the heart and blood vessels, such as hardening of the arteries, heart disease, and high blood pressure.
Alpha-linolenic acid is also used for other conditions, but there is no good scientific evidence to support most of these uses.
You have probably heard a lot about other omega-3 fatty acids such as EPA and DHA, which are found in fish oil.
Alpha-linolenic acid may not have the same benefits as EPA or DHA.
Be careful not to confuse alpha-linolenic acid with these other omega-3 fatty acids.
Alpha-linolenic acid is an essential omega-3 fatty acid.
Alpha-linolenic acid is called "essential" because it is needed for normal human growth and development.
Nuts, such as walnuts, are good sources of alpha-linolenic acid.
Alpha-linolenic acid is also found in vegetable oils such as flaxseed (linseed) oil, canola (rapeseed) oil, and soybean oil, as well as in red meat and dairy products.
Alpha-linolenic acid is popular for preventing and treating diseases of the heart and blood vessels.
Alpha-linolenic acid is used to prevent heart attacks, lower high blood pressure, lower cholesterol, and reverse "hardening of the blood vessels" (atherosclerosis).
There is some evidence that alpha-linolenic acid from dietary sources might be effective for all these uses except lowering cholesterol.
Not enough is known yet to be able to rate alpha-linolenic acid's effect on high cholesterol.
Alpha-linolenic acid is used to treat rheumatoid arthritis (RA), multiple sclerosis (MS), lupus, diabetes, renal disease, ulcerative colitis, and Crohn's disease.
Alpha-linolenic acid is also used to prevent pneumonia.
Other uses include treatment of chronic obstructive pulmonary disease (COPD), migraine headache, skin cancer, depression, and allergic and inflammatory conditions such as psoriasis and eczema.
Some people use alpha-linolenic acid to prevent cancer.
Ironically, alpha-linolenic acid may actually raise some men's risk of getting prostate cancer.
You have probably heard a lot about other omega-3 fatty acids such as EPA and DHA, which are found in fish oil.
Be careful. Not all omega-3 fatty acids act the same way in the body.
Alpha-linolenic acid may not have the same benefits as EPA and DHA.
How does it work?
Alpha-linolenic acid is thought to decrease the risk of heart disease by helping to maintain normal heart rhythm and heart pumping.
Alpha-linolenic acid might also reduce blood clots.
Although alpha-linolenic acid seems to benefit the cardiovascular system and might reduce the risk of heart disease, research to date does not show it has a significant effect on cholesterol levels.
Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid.
Alpha-linolenic acid is a component of many common vegetable oils and is important to human nutrition.
Alpha Linolenic Acid (ALA) is an 18-carbon polyunsaturated fatty acid with three double bonds.
Alpha-linolenic acid is also called an omega-3 fatty acid, and is essential for all mammals.
Alpha-linolenic acid (or omega 3 fatty acid) intake can decrease the risk of cardiovascular diseases by
1) preventing arrhythmias that can lead to sudden cardiac death,
2) decreasing the risk of thrombosis (blood clot formation) that can lead to heart attack or stroke,
3) decreasing serum triglyceride levels,
4) slowing the growth of atherosclerotic plaque,
5) improving vascular endothelial function,
6) lowering blood pressure slightly, and
7) decreasing inflammation.
Alpha-Linolenic Acid deficiencies can lead to visual problems and sensory neuropathy.
Scaly and hemorrhagic skin or scalp inflammations may also develop.
Mechanism of action
Alpha Linolenic Acid or ALA is considered an essential fatty acid because it is required for human health, but cannot be synthesized by humans.
Alpha-linolenic acid is in fact a plant-derived fatty acid.
Humans can synthesize other omega-3 fatty acids from Alpha-Linolenic Acid, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).
EPA is a precursor of the series-3 prostaglandins, the series-5 leukotrienes and the series-3 thromboxanes.
These eicosanoids have anti-inflammatory and anti-atherogenic properties.
Alpha-Linolenic Acid metabolites may also inhibit the production of the pro-inflammatory eicosanoids, prostaglandin E2 (PGE2) and leukotriene B4 (LTB4), as well as the pro-inflammatory cytokines, tumor necrosis factor-alpha (TNF-alpha) and interleukin-1 beta (IL-1 beta).
Omega-3 fatty acids like Alpha-Linolenic Acid and its byproducts can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation.
They regulate gene expression through their effects on the activity of transcription factors including NF-kappa B and members of the peroxisome proliferator-activated receptor (PPAR) family.
Incorporation of Alpha-Linolenic Acid and its metabolites in cell membranes can affect membrane fluidity and may play a role in anti-inflammatory activity, inhibition of platelet aggregation and possibly in anti-proliferative actions of Alpha-Linolenic Acid.
Alpha-Linolenic Acid is first metabolized by delta6 desaturease into steridonic acid.
Alpha-linolenic acid (ALA) is the most common omega-3 fatty acid in your diet.
Alpha-Linolenic Acid’s mostly found in plant foods and is an essential precursor of EPA or DHA .
However, this conversion process is inefficient in humans.
Only a small percentage of Alpha-Linolenic Acid is converted into EPA — and even less into DHA.
When Alpha-Linolenic Acid is not converted to EPA or DHA, it is simply stored or used as energy like other fats.
Some observational studies link a diet rich in Alpha-Linolenic Acid to a reduced risk of death from heart disease, while others show an increased risk of prostate cancer.
This increase in prostate cancer risk was not associated with the other main omega-3 types, EPA and DHA, which seem to protect against this cancer.
Alpha-Linolenic Acid is found in many plant foods, including kale, spinach, purslane, soybeans, walnuts, and many seeds, such as chia, flax, and hemp.
Alpha-linolenic acid also occurs in some animal fats.
Some seed oils, such as flaxseed and rapeseed (canola) oil, are also high in Alpha-Linolenic Acid.
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
Alpha-linolenic acid (ALA) is an essential omega-3 fatty acid.
Alpha-linolenic acid is necessary for our health, but our bodies can’t produce it. We need to take it through food (and supplements).
Alpha-Linolenic Acid is found in flaxseed oil, chia seeds, sage, some vegetables, and nut oils.
Alpha-linolenic acid is converted in the body into the unsaturated fatty acids, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), which reduce inflammation.
These fatty acids promote eye health, as well as brain and nervous system development.
They also reduce blood pressure, cholesterol, and incidence of stroke and cancer, improve memory, slow aging, and probably prevent heart disease.
The omega-3 index is the percentage of EPA and DHA total fatty acids in the blood.
An omega-3 index greater than 8% is associated with a 90% lower rate of heart disease-related death.
Alpha-Linolenic Acid Deficiency
Alpha-linolenic acid is considered essential in the diet because it is an omega-3 building block of the fatty acids EPA and DHA.
Alpha-Linolenic Acid deficiency can cause:
nability to walk
Pain in the legs
Blurry vision (in monkeys)
Scaliness of skin
Excessive cholesterol and inflammation
To prevent deficiency, your diet should contain between 0.2 to 0.3% of total calories from Alpha-Linolenic Acid.
Health Benefits of Alpha-Linolenic Acid
Omega-3 fatty acids are considered essential nutrients, and most of our dietary omega-3s tend to be in the form of Alpha-Linolenic Acid.
That said, regulations set manufacturing standards for Alpha-Linolenic Acid supplements but don’t guarantee that they’re safe or effective. Speak with your doctor before supplementing.
Possibly Effective For:
- Alpha-Linolenic Acid, like other fatty acids in the diet, is usually attached to two or three glycerols; they are classified as diglyceride or triglyceride depending on the number of glycerols they have.
2) Cancer Prevention
- Prostate Cancer
3) Stroke Prevention
4) Heart Health
- Blood Pressure
6) Pneumonia & Respiratory Infections
7) Multiple Sclerosis Symptoms
9) Skin Health
11) Inflammatory Bowel Disease
12) Kidney Function
14) Eye Health
15) Constipation and Diarrhea
17) Stomach Ulcers
18) Rheumatoid Arthritis
9,12,15-Octadecatrienoic acid, (Z,Z,Z)-
Linolenic acid (8CI)
LINOLENIC ACID (18:3 n-3)
cis-9, cis-12, cis-15-octadecatrienoic acid
9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-, dimer
Linolenic acid, crude
Linolenic acid, >=99%
alpha-Linolenic Acid tech.
Linolenic acid, ~70% (GC)
Linolenic acid, analytical standard
Linolenic acid 10 microg/mL in Methanol
9,15-Octadecatrienoic acid, (Z,Z,Z)-
Octadecatrienoic acid, 9,12,15-(Z,Z,Z)-
Linolenic acid, Vetec(TM) reagent grade, 98%
9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- (9CI)
UNII-0JXR8F0V1Q component DTOSIQBPPRVQHS-PDBXOOCHSA-N
UNII-5U9XZ261ER component DTOSIQBPPRVQHS-PDBXOOCHSA-N
UNII-71M78END5S component DTOSIQBPPRVQHS-PDBXOOCHSA-N
UNII-96GS7P39SN component DTOSIQBPPRVQHS-PDBXOOCHSA-N
UNII-F85N2YHE4E component DTOSIQBPPRVQHS-PDBXOOCHSA-N
UNII-HBA528N3PW component DTOSIQBPPRVQHS-PDBXOOCHSA-N
alpha-Linolenic acid, 1.0 mg/mL in ethanol, certified reference material
ALL CIS-9,12,15-OCTADECATRIENOIC ACID
DELTA 9 CIS 12 CIS 15 CIS OCTADECATRIENOIC ACID
C18:3 (ALL CIS-9,12,15) ACID
LINOLENIC ACID, STANDARD FOR GC
Linolenic acid, tech., remainder linoleic acid, 90%
9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-
LINOLENIC ACID WITH GC
α-Lnn, cis,cis,cis-9,12,15-Octadecatrienoic acid
Linolenic acid, 90%, remainder linoleic acid, tech.
Linolenic acid, 98.5%
Linolenic acid,α-Lnn, cis,cis,cis-9,12,15-Octadecatrienoic acid
Linolenic acid,70%, remainder isomers
Linolenic acid,90%,tech., remainder linoleicacid
α-linolenic acid (ALA)
Linolenic acid, 99% 1GR