alpha-LINOLENIC ACID

PRODUCT IDENTIFICATION
CAS NO. 463-40-1

alpha-LINOLENIC ACID 

EINECS NO. 207-334-8
FORMULA CH3(CH2CH=CH)3(CH2)7COOH
MOL WT. 278.43

H.S. CODE

  
SMILES

 

TOXICITY

  
SYNONYMS all cis-Delta-9,12,15-octadecatrienoate; Linolensäure; ácido linolénico; Acide linolénique;  
Linolenic acid; All-cis-9,12,15-Octadecatrienoic acid; cis,cis,cis-9,12,15-Octadecatrienoic acid; (Z,Z,Z)-9,12,15-Octadecatrienoic acid; (9E,12E,15E)-9,12,15-Octadecatrienoic acid;

CLASSIFICATION

  

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE clear to yellowish liquid
MELTING POINT -11 C
BOILING POINT 230 C at 1 mmHg
SPECIFIC GRAVITY 0.91 - 0.92
SOLUBILITY IN WATER Insoluble (Soluble in almost common organic solvents)
pH  
VAPOR DENSITY

 

AUTOIGNITION

 

NFPA RATINGS

 Health: 1 Flammability: 0 Reactivity: 0

REFRACTIVE INDEX

 1.479 - 1.481
FLASH POINT

 

STABILITY Stable under ordinary conditions

APPLICATIONS
Linolenic acid is an 18-carbon polyunsaturated fatty acid with three cis- structure double bonds. The omega-3 linolenic acid is called alpha-linolenic acid which has three double bonds at 9,12,15 positions, whereas gamma-linolenic acid, omega-6 linolenic acid, 6,9,12 positions. Chemical designations are all-cis-9,12,15-octadecatrienoic acid and all-cis-6,9,12-octadecatrienoic acid respectively. Linolenic acid is a principal unsaturated fatty acids in plants and an essential fatty acid in mammals, that cannot be synthesized by tissues and must be obtained in the diet. It is used in the formation of prostaglandins, the result of enzymatic oxygenation of polyunsaturated fatty acids. It is a clear liquid; melting point -11 C; boiling point 230 at 1 mm Hg; soluble in many organic solvents; abundant in some fish oils and seed-derived oils. The term linolenate refers to any salt, ester, or anionic form of linolenic acid.
SALES SPECIFICATION
APPEARANCE clear to yellowish liquid
LINOLENIC ACID 80.0% min

FATTY ACID CONTENT

99.0% min
TRANSPORTATION
PACKING
 
HAZARD CLASS Not regulated
UN NO.  
OTHER INFORMATION
Hazard Symbols: n/a, Risk Phrases: n/a, Safety Phrases: 22-24/25

GENERAL DESCRIPTION OF LONG CHAIN UNSATURATED FATTY ACID
Fatty Acids are aliphatic carboxylic acid with varying hydrocarbon lengths at one end of the chain joined to terminal carboxyl (-COOH) group at the other end. The general formula is R-(CH2)n-COOH. Fatty acids are predominantly unbranched and those with even numbers of carbon atoms between 12 and 22 carbons long react with glycerol to form lipids (fat-soluble components of living cells) in plants, animals, and microorganisms. Fatty acids all have common names respectively like lauric (C12), MyrIstic (C14), palmitic (C16), stearic (C18), oleic (C18, unsaturated), and linoleic (C18, polyunsaturated) acids. The saturated fatty acids have no double bonds, while oleic acid is an unsaturated fatty acid has one double bond (also described as olefinic) and polyunsaturated fatty acids like linolenic acid contain two or more double bonds. Lauric acid (also called Dodecanoic acid) is the main acid in coconut oil (45 - 50 percent) and palm kernel oil (45 - 55 percent). Nutmeg butter is rich in myristic acid (also called Tetradecanoic acid ) which constitutes 60-75 percent of the fatty-acid content. Palmitic acid(also called Hexadecylic acid ) constitutes between 20 and 30 percent of most animal fats and is also an important constituent of most vegetable fats (35 - 45 percent of palm oil). Saturated carboxylic acids (C1 – C10) are liquids whereas long chain saturated fatty acids are solids. The long carbon chains form compact pile in a regular pattern with high van der waals attractions resulting in high melting points. If double bonds are present in the fatty acid portion of the molecule, the fat is said to be unsaturated. Monounsaturated contains only one double bond; polyunsaturated contains more than one double bonds (up to an maximum of about six) which are never conjugated and can form geometric cis/trans isomers. Naturally occurring unsaturated fatty acids are liquids as they are in the cis- geometrical configuration which twists molecular structure (the kink of the cis form); can not pack closely, lowers melting points. Unsaturated fatty acids in the kinked, cis- form are much more common in cells than the trans- form continues in the same direction without a pronounced kink. The cis- form of unsaturated fatty acids are more fluid at biological temperatures and are more abundant in living organisms. Fatty acids are named by the number of carbon atoms n and the number of double bonds m as (n:m). The system for naming double bond position is to indicate the first double bond in the carbon backbone counting from the opposite end from the carboxyl group. The terminal carbon atom is called the omega carbon atom. The term "omega-3 or omega-6" signifies that their single double bond is occurred at carbon number 3 or 6 respectively counted from and including the omega carbon. Human bodies are not capable of synthesizing omega-3 and omega-6 fatty acids which are called essential fatty acids must be obtained through the diet. (These fatty acids were designated as "Vitamin F", until it was realized that they must be classified with the fats.) Fatty acids are converted to energy through the process called fatty acid oxidation in liver cells. Fatty acids are used as basic building blocks of biological membranes, for long-term energy storage (the major components of triglycerides) as well as for the precursors of eicosanoid hormones.

COMMON NAME

SYSTEMATIC NAME

CAS RN

SYMBOL
Myristolenic Acid

(Z)-9-Tetradecenoic Acid

 544-64-9

14:1 n-5
Palmitoleic Acid (Z)-9-Hexadecenoic Acid 373-49-9

16:1 n-7
Palmitelaidic Acid (E)-9-Hexadecenoic Acid 10030-73-6

16;1 n-7 (trans)
Vaccenic Acid (Z)-11-Octadecenoic Acid 506-17-2 18:1 n-7

Oleic Acid

(Z)-9-Octadecenoic Acid

 112-80-1 18:1 n-9
Elaidic Acid (E)-9-Octadecenoic Acid 112-79-8 18:1 n-9 (trans)
Linoelaidicic Acid (E,E)-9,12-Octadecadienoic Acid 506-21-8

18:2 n-6 (trans)
Linoleic Acid (Z,Z)-9,12-Octadecadienoic Acid 60-33-3

18:2 n-6
Isolinoleic Acid (E,E)-9,11-Octadecadienoic Acid 544-71-8

18:2 n-6 (trans)
Linolenic Acid (Z,Z,Z)-9,12,15-Octadecatrienoic Acid 463-40-1 18:3 n-3
gamma -Linolenic Acid (Z,Z,Z)-6,9,12-Octadecatrienoic Acid 506-26-3 18:3 n-6

Moroctic Acid

(Z,Z,Z,Z)-6,9,12,15-Octadecatetraenoic Acid

20290-75-9

 18:4 n-3
Eicosenoic Acid

(Z)-11-Ecosenoic Acid

 5561-99-9 20:1 n-9
Eicosadienoic Acid

(Z,Z,)-11,14-Ecosadienoic Acid

 2091-39-6 20:2 n-6
Mead Acid

(Z,Z,Z)-5,8,11-Eicosatrienoic Acid

 20590-32-3 20:3 n-9

Eicosatrienoic Acid

(Z,Z,Z)-11,14,17-Eicosatrienoic Acid

17046-59-2

 20:3 n-3
Dihomo-g -Linolenic Acid

(Z,Z,Z)-8,11,14-Eicosatrienoic Acid

 1783-84-2 20:3 n-6
Omega-3 Arachidonic Acid

(Z,Z,Z,Z)-8,11,14,17-Eicosatetraenoic Acid

 24880-40-8 20:4 n-3
Arachidonic Acid

(Z,Z,Z,Z)-5,8,11,14-Eicosatetraenoic Acid

 506-32-1 20:4 n-6
Timnodonic Acid (Z,Z,Z,Z,Z)-5,8,11,14,17-Eicosapentaenoic Acid 10417-94-4 20:5 n-3
Erucic Acid

(Z)-13-Docosenoic Acid

 112-86-7

22:1 n-9
Docosadienoic Acid

(Z,Z)-13,16-Docosadienoic Acid

 17735-98-7

22:2 n-6
Docosatrienoic Acid

(Z,Z,Z)-13,16,19-Docosatrienoic Acid

 28845-86-5

22:3 n-3
Adrenic Acid

(Z,Z,Z,Z)-7,10-13-16-Ocosatetraenoic Acid

 28874-58-0

22:4 n-6
Docosapentaenoic Acid

(Z,Z,Z,Z,Z)-4,7,10,13,16-Docosapentaenoic Acid

 25182-74-5

22:5 n-6
Docosapentaenoic Acid

(Z,Z,Z,Z,Z)-7,10,13,16,19-Docosapentaenoic Acid

 24880-45-3

22:5 n-3
Docosahexaenoic Acid

(Z,Z,Z,Z,Z,Z)-4,7,10,13,16,19-Docosahexaenoic Acid

 6217-54-5

22:6 n-3
Nervonic Acid

(Z)-15-Tetracosaenoic Acid

 506-37-6 24:1 n-9
Tetracosahexaenoic Acid

((Z,Z,Z,Z,Z,Z)-6,9,12,15,18,21-Tetracosahexaenoic Acid

   24:6 n-3