PRODUCTS

C18:3 LINOLENIC ACID

C18:3 Linolenic Acid (18:3, n-6) is an antitumor agent.
C18:3 Linolenic Acid to have induced reactive oxygen species generation including lipid peroxidation, cell growth inhibition, and heme oxygenase-1 production for antioxidant protection against oxidative stress.

CAS Number: 463-40-1
EC Number: 207-334-0
Chemical formula: C18H30O2
Molecular Weight: 278.43 g/mol

SYNONYMS:
(9Z,12Z,15Z)-Octadeca-9,12,15-trienoic acid, linolenic acid, alpha-Linolenic acid, 463-40-1, linolenate, (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid, a-Linolenic acid, cis,cis,cis-9,12,15-Octadecatrienoic acid, all-cis-9,12,15-Octadecatrienoic acid, (Z,Z,Z)-9,12,15-Octadecatrienoic acid, 9-cis,12-cis,15-cis-Octadecatrienoic acid, alpha-Lnn, alpha-LA, (9,12,15)-linolenic acid, (9Z,12Z,15Z)-Octadecatrienoic acid, 9,12,15-Octadecatrienoic acid, (Z,Z,Z)-, alpha Linolenic Acid, Linolenic acid, crude, CCRIS 656, .alpha.-Linolenic acid, 9Z,12Z,15Z-Octadecatrienoic acid, Industrene 120, UNII-0RBV727H71, cis-delta9,12,15-Octadecatrienoic acid, DTXSID7025506, CHEBI:27432, Prifrac 2942, AI3-23986, cis-Delta(9,12,15)-octadecatrienoic acid, (Z,Z,Z)-Octadeca-9,12,15-trienoic acid, 0RBV727H71, NSC 2042, NSC-2042, EINECS 207-334-8, FA 18:3, CHEMBL8739, 9,12,15-all-cis-Octadecatrienoic acid, DTXCID905506, cis-9,cis-12,cis-15-Octadecatrienoic acid, C18:3, NSC2042, cis-9,12,15-octadecatrienoic acid, 9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-, MFCD00065720, LINOLENIC ACID (18:3 n-3), NCGC00091058-04, Linolenic acid 10 microg/mL in Methanol, FEMA NO. 3380, LINOLENIC ACID-, ALPHA-LINOLENIC ACID (C18:3 N3), C18:3 (N-3), cis-9, cis-12, cis-15-octadecatrienoic acid, Linolenic Acid (~90%), VITAMIN F COMPONENT ALPHA LINOLENIC ACID, 18:3(N-3), LINOLENIC ACID (MART.), LINOLENIC ACID [MART.], C18H30O2, 29857-63-4, CAS-463-40-1, SMR000857336, (9Z,12Z,15Z)-Octadecatrienoate, Linolenic acid (8CI), cis,cis,cis-9,12,15-octadecatrienoate, alpha-Linolenic acid; ALA; cis-alpha-Linolenic acid, Linolensaeure, a-Linolenate, Linolenic acid?, cis,cis-9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid, LNL, alpha-linolenic-acid, Octadeca-9Z,12Z,15Z-trienoic acid, alpha -linolenic acid, Linolenic acid, >=99%, Linolenic acid, tech grade, alpha-Linolenic Acid tech., LINOLENIC ACID [MI], (9Z,12Z,15Z)octadeca-9,12,15-trienoic acid, SCHEMBL15282, 806 - Fish oil supplement, 9,12,15-Octadecatrienoate, BSPBio_001376, MLS001336029, MLS001336030, MLS002454413, LINOLENIC ACID [VANDF], BML3-B05, GTPL1049, Linolenic acid, ~70% (GC), LINOLENIC ACID [WHO-DD], CHEBI:25048, cid_5280934, cis-9,12,15-octadecatrienoate, LINOLENIC ACID AND ISOMERS, FA005, HMS1361E18, HMS1791E18, HMS1989E18, HMS2233C13, HMS3402E18, HMS3649H05, Linolenic acid, analytical standard, CMC_7371, HY-N0728, all-cis-9,15-Octadecatrienoic acid, Tox21_111071, Tox21_201727, Tox21_303322, all-cis-9,12,15-Octadecatrienoate, BDBM50240347, LMFA01030152, AKOS016008598, 1ST1776, DB00132, (Z,Z,Z)-9,12,15-Octadecatrienoate, 9-cis,12-cis,15-cis-octadecatrienoate, Fatty Acid cis, cis, cis 18:3 n-3, IDI1_033846, NCGC00091058-01, NCGC00091058-02, NCGC00091058-05, NCGC00091058-06, NCGC00091058-07, NCGC00091058-08, NCGC00091058-09, NCGC00091058-10, NCGC00257192-01, NCGC00259276-01, (all-Z)-9,12,15-Octadecatrienoic acid, 9,15-Octadecatrienoic acid, (Z,Z,Z)-, AC-33768, AS-57338, 9(Z),12(Z),15(Z)-Octadecatrienoic acid, CS-0009741, L0050, cis,cis,cis-octadeca-9,12,15-trienoic acid, FA(18:3(9Z,12Z,15Z)), Octadecatrienoic acid, 9,12,15-(Z,Z,Z)-, A11389, C06427, Linolenic acid, Vetec(TM) reagent grade, 98%, EN300-6734316, CIS-DELTA-9,12,15-OCTADECATRIENOIC ACID, L000707, Q256502, SR-01000838327, LINOLENIC ACID (CONSTITUENT OF SAW PALMETTO), SR-01000838327-2, 2DCD0473-E5CC-47BB-A0A4-95899AFF6C4B, BRD-K33396764-001-02-0, BRD-K33396764-001-08-7, BRD-K33396764-001-11-1, 9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)- (9CI), alpha-LINOLENIC ACID (CONSTITUENT OF FLAX SEED OIL), LINOLENIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL), LINOLENIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC], alpha-LINOLENIC ACID (C18:3) (CONSTITUENT OF KRILL OIL), alpha-Linolenic acid, 1.0 mg/mL in ethanol, certified reference material, Alpha-linolenic acid, 463-40-1, Linolenate, (9z,12z,15z)-octadeca-9,12,15-trienoic acid, A-linolenic acid, Cis,cis,cis-9,12,15-octadecatrienoic acid, ALA, LNA, Linolenic acid, cis,cis,cis-9,12,15-Octadecatrienoic acid, (9Z,12Z,15Z)-9,12,15-Octadecatrienoic acid, Industrene 120

C18:3 Linolenic Acid is an essential omega-3 fatty acid with significant health benefits, especially concerning cardiovascular health and inflammation reduction.
Its chemical and physical properties make C18:3 Linolenic Acid a valuable component in both nutritional and industrial applications.

C18:3 Linolenic Acid is an organic compound found in many common vegetable oils.
In terms of its structure, C18:3 Linolenic Acid is named all-cis-9,12,15-octadecatrienoic acid. In physiological literature, it is given the name 18:3 (n−3).

C18:3 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 n end.
Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid.

C18:3 Linolenic Acid is an isomer of γ-linolenic acid, a polyunsaturated n−6 (omega-6) fatty acid
C18:3 Linolenic Acid (18:3, n-6) is an antitumor agent.
C18:3 Linolenic Acid also known as gamma-Linolenic acid, is an unsaturated fatty acid synthesized from linoleic acid (LA) by the enzyme delta-6-desaturase.

Research on hepatocellular cell lines has shown C18:3 Linolenic Acid to have induced reactive oxygen species generation including lipid peroxidation, cell growth inhibition, and heme oxygenase-1 production for antioxidant protection against oxidative stress.
Further experiments have noted that gamma-Linolenic acid inhibits inflammatory responses through inactivation of NFkappaB and activator protein-1 by suppressed oxidative stress.

C18:3 Linolenic Acid is a polyunsaturated omega-3 fatty acid.
C18:3 Linolenic Acid is a component of many common vegetable oils and is important to human nutrition.
C18:3 Linolenic Acid is a clear colorless liquid.

C18:3 Linolenic Acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15.
Shown to have an antithrombotic effect.
C18:3 Linolenic Acid has a role as a micronutrient, a nutraceutical and a mouse metabolite.

C18:3 Linolenic Acid is an omega-3 fatty acid and a linolenic acid.
C18:3 Linolenic Acid is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate.
C18:3 Linolenic Acid is a polyunsaturated omega-3 fatty acid.

C18:3 Linolenic Acid is a component of many common vegetable oils and is important to human nutrition.
C18:3 Linolenic Acid is a metabolite found in or produced by Escherichia coli.
C18:3 Linolenic Acid has been reported in Salvia miltiorrhiza, Calodendrum capense, and other organisms with data available.

C18:3 Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group.
C18:3 Linolenic Acid is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases.

C18:3 Linolenic Acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid.
C18:3 Linolenic Acid is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils.

In terms of its structure, C18:3 Linolenic Acid is named all-cis-9,12,15-octadecatrienoic acid.
In physiological literature, C18:3 Linolenic Acid is listed by its lipid number, 18:3 (n−3).
C18:3 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, C18:3 Linolenic Acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds).

C18:3 Linolenic Acid, is a polyunsaturated omega-3 fatty acid with 18 carbon atoms in the fatty acid chain.
C18:3 Linolenic Acid contains three double bonds, with the first one placed at the third carbon atom from the methyl end.
Other polyunsaturated omega-3 fatty acids are C20:3n-3, C20:4n-3, C20:5n-3, C22:5n-3, and C22:6n-3.

C18:3 Linolenic Acid is found in plant foods such as flaxseeds, chia seeds, walnuts, as well as in fatty fish.
C18:3 Linolenic Acid is a polyunsaturated omega-3 fatty acid found in many supplements.

USES and APPLICATIONS of C18:3 LINOLENIC ACID:
C18:3 Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group.
C18:3 Linolenic Acid is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases.

Research on hepatocellular cell lines has shown gamma-Linolenic Acid to have induced reactive oxygen species generation including lipid peroxidation, cell growth inhibition, and heme oxygenase-1 production for antioxidant protection against oxidative stress.
C18:3 Linolenic Acid (18:3, n-6) is an antitumor agent.

C18:3 Linolenic Acid also known as gamma-Linolenic acid, is an unsaturated fatty acid synthesized from linoleic acid (LA) by the enzyme delta-6-desaturase.
Further experiments have noted that gamma-Linolenic acid inhibits inflammatory responses through inactivation of NFkappaB and activator protein-1 by suppressed oxidative stress.

C18:3 Linolenic Acid is a polyunsaturated omega-3 fatty acid.
C18:3 Linolenic Acid is a component of many common vegetable oils and is important to human nutrition.

USES AND BENEFITS OF C18:3 LINOLENIC ACID:
C18:3 Linolenic Acid is a vital nutrient in human diets, primarily found in seeds and oils such as flaxseed, walnuts, chia, and hemp.
C18:3 Linolenic Acid serves as a precursor for other omega-3 fatty acids, including eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA).

Regular intake of C18:3 Linolenic Acid has been associated with various health benefits, such as reducing the risk of cardiovascular diseases by lowering blood pressure, decreasing serum triglyceride levels, and inhibiting the growth of atherosclerotic plaques.
Additionally, C18:3 Linolenic Acid possesses anti-inflammatory properties and supports overall cellular function.

CHEMICAL CHARACTERISTICS OF C18:3 LINOLENIC ACID:
As a polyunsaturated fatty acid, C18:3 Linolenic Acid contains three cis double bonds located at the 9th, 12th, and 15th carbon atoms from the carboxyl end.
This structure classifies C18:3 Linolenic Acid as an omega-3 fatty acid, with the first double bond at the third carbon from the methyl end.
Due to its multiple double bonds, C18:3 Linolenic Acid is prone to oxidation, which can affect its stability and shelf life.

SAFETY AND HANDLING OF C18:3 LINOLENIC ACID:
While C18:3 Linolenic Acid is generally safe and beneficial when consumed as part of a balanced diet, it is sensitive to heat, light, and air, which can lead to degradation and rancidity.

Proper storage C18:3 Linolenic Acid in cool, dark, and airtight conditions is recommended to maintain its quality.
In industrial applications, handling C18:3 Linolenic Acid requires precautions to prevent oxidation and ensure safety.

PHARMACODYNAMICS OF C18:3 LINOLENIC ACID:
C18:3 Linolenic Acid is an 18-carbon polyunsaturated fatty acid with three double bonds.
C18:3 Linolenic Acid is also called an omega-3 fatty acid, and is essential for all mammals.

HEALTH OF C18:3 LINOLENIC ACID:
C18:3 Linolenic Acid consumption is associated with a lower risk of cardiovascular disease and a reduced risk of fatal coronary heart disease.
Dietary C18:3 Linolenic Acid intake can improve lipid profiles by decreasing triglycerides, total cholesterol, high-density lipoprotein, and low-density lipoprotein.

A 2021 review found that C18:3 Linolenic Acid intake is associated with a reduced risk of mortality from all causes, cardiovascular disease, and coronary heart disease but a slightly higher risk of cancer mortality.

METABOLISM OF C18:3 LINOLENIC ACID:
C18:3 Linolenic Acid can be obtained by humans only through their diets.
Humans lack the desaturase enzymes required for processing stearic acid into C18:3 Linolenic Acid or other unsaturated fatty acids.

Dietary C18:3 Linolenic Acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).

Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of C18:3 Linolenic Acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.
Conversion of C18:3 Linolenic Acid to DHA is higher in women than in men.

ETYMOLOGY OF C18:3 LINOLENIC ACID:
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 an omega-6 double bond of linoleic acid produces oleic acid.
Similarly saturating one of linolenic acid's double bonds produces linoleic acid.

DIETARY SOURCES OF C18:3 LINOLENIC ACID:
Vegetable oil § Composition of fats
Seed oils are the richest sources of C18:3 Linolenic Acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans.

C18:3 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 C18:3 Linolenic Acid, evident as sharp resonances in high-resolution carbon-13 NMR spectra.
Some studies state that C18:3 Linolenic Acid remains stable during processing and cooking.

However, other studies state that C18:3 Linolenic Acid might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts.
Some C18:3 Linolenic Acid may also oxidize at baking temperatures.
C18:3 Linolenic Acid percentages in the table below refer to the oils extracted from each item.

HISTORY OF C18:3 LINOLENIC ACID:
In 1887, linolenic acid was discovered and named by the Austrian chemist Karl Hazura of the Imperial Technical Institute at Vienna (although he did not separate its isomers).

C18:3 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's 1930s survey.

C18:3 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.

STABILITY AND HYDROGENATION OF C18:3 LINOLENIC ACID:
Compared to many other oils, C18:3 Linolenic Acid is more susceptible to oxidation.
C18:3 Linolenic Acid becomes rancid more quickly in air.

Oxidative instability of C18:3 Linolenic Acid is one reason why producers choose to partially hydrogenate oils containing α-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.

Hydrogenation of C18:3 Linolenic Acid-containing fats can introduce trans fats.
Consumers are increasingly avoiding products that contain trans fats, and governments have begun to ban trans fats in food products, including the US government as of May 2018.

These regulations and market pressures have spurred the development of soybeans low in C18:3 Linolenic Acid.
These new soybean varieties yield a more stable oil that often do not require hydrogenation for many applications.

PHYSICAL and CHEMICAL PROPERTIES of C18:3 LINOLENIC ACID:
Chemical Formula: C₁₈H₃₀O₂
Molar Mass: 278.436 g·mol−1
Density: 0.9164 g/cm³
Melting Point: −11 °C (12 °F; 262 K)[2]
Boiling Point: 232 °C (450 °F; 505 K) at 17.0 mmHg
Molecular Weight: 278.4 g/mol
XLogP3: 5.9
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 13
Exact Mass: 278.224580195 Da

Monoisotopic Mass: 278.224580195 Da
Topological Polar Surface Area: 37.3 Å²
Heavy Atom Count: 20
Formal Charge: 0
Complexity: 301
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 3
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1

Compound Is Canonicalized: Yes
SMILES: CC/C=CC/C=CC/C=CCCCCCCCC(=O)O
InChI Code: InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10H,2,5,8,11-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-
InChI Key: DTOSIQBPPRVQHS-PDBXOOCHSA-N
Side Chain Carbon Sum: 18:3
Chemical Properties:
Chemical Formula: C₁₈H₃₀O₂
Molecular Weight: 278.43 g/mol
IUPAC Name: (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
CAS Number: 463-40-1
EC Number: 207-334-0

Appearance: Colorless to pale yellow clear oily liquid
Density: 0.9140 g/cm³
Melting Point: −11°C
Boiling Point: 230-232°C at 16 mm Hg
Solubility: Insoluble in water; soluble in organic solvents
Appearance: Oil
Physical State: Liquid
Solubility: Soluble in ethanol, DMSO, and DMF (PBS pH7.2).
Insoluble in water.
Storage: Store at -20°C
Refractive Index: n20D 1.48
Ki Data: [3H]-LTB4 binding to porcine neutrophil membranes: Ki = 1 µM
pK Values: pKa: 4.72

FIRST AID MEASURES of C18:3 LINOLENIC ACID:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available

ACCIDENTAL RELEASE MEASURES of C18:3 LINOLENIC ACID:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.

FIRE FIGHTING MEASURES of C18:3 LINOLENIC ACID:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

EXPOSURE CONTROLS/PERSONAL PROTECTION of C18:3 LINOLENIC ACID:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.

HANDLING and STORAGE of C18:3 LINOLENIC ACID:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.

STABILITY and REACTIVITY of C18:3 LINOLENIC ACID:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature) .
-Possibility of hazardous reactions:
No data available