| Identification | More | [Name]
LINOLENIC ACID | [CAS]
68424-45-3 | [Synonyms]
9,12,15-OCTADECATRIENIC ACID
9,12,15-OCTADECATRIENOIC ACID
9Z,12Z,15Z-OCTADECATRIENOIC ACID
ALA
ALFA-LINOLENIC ACID
ALL CIS-9,12,15-OCTADECATRIENOIC ACID
ALPHA-LINOLENIC ACID
ALPHA-LNN
C18:3 (ALL CIS-9,12,15) ACID
CIS,CIS,CIS-9,12,15-OCTADECATRIENOIC ACID
DELTA 9 CIS 12 CIS 15 CIS OCTADECATRIENOIC ACID
LINOLENIC ACID
OCTADECA-9Z,12Z,15Z-TRIENOIC ACID
Fatty acids, linseed-oil
LINSEED ACID
Fettsuren, Leinsamenl | [EINECS(EC#)]
207-334-8 | [Molecular Formula]
C18H30O2 | [MDL Number]
MFCD00065720 | [Molecular Weight]
278.43 | [MOL File]
68424-45-3.mol |
| Hazard Information | Back Directory | [Description]
α-Linolenic acid (ALA) is an organic compound found in many common vegetable oils. In terms of its structure, it is named all-cis- 9,12,15-octadecatrienoic acid. In physiological literature, it is given the name 18:3 (n?3).
α-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, α-linolenic acid is a polyunsaturated n?3 (omega-3) fatty acid. It is an isomer of gamma-linolenic acid, a polyunsaturated n?6 (omega-6) fatty acid. | [Occurrence]
Seed oils are the richest sources of α-linolenic acid, notably those of 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). ALA is not suitable for baking, as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA will also oxidize at baking temperatures. | [History]
Alpha-linolenic acid was first isolated by Rollett as cited in J. W. McCutcheon's synthesis in 1942 , and referred to in Green and Hilditch's 1930's survey. It 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. | [Definition]
ChEBI: Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. |
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