Linolenic acid

Synonyms: α-Linolenic acid, ALA, (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid, cis,cis,cis-9,12,15-octadecatrienoic acid, linolenic acid (alpha)

Linolenic acid, specifically α-linolenic acid (ALA), is an 18-carbon polyunsaturated fatty acid (PUFA) characterized by three cis double bonds at positions 9, 12, and 15 along the hydrocarbon chain. This ω-3 fatty acid is a fundamental building block in human nutrition and a precursor to longer-chain ω-3 fatty acids such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). Its unique structure, with a methylene-interrupted triene system, underpins its distinct chemical reactivity and biological roles.

α-Linolenic acid is widely distributed in plant oils, with flaxseed (linseed), chia, perilla, and walnut oils being particularly rich sources. It is obtained through fractional distillation or low-temperature crystallization of these oils, yielding high-purity fractions suitable for research, pharmaceutical, and nutraceutical applications. LyvBio supplies linolenic acid in various purities, from technical grade to ≥99% GC, to meet the rigorous demands of our global clientele.

In the pharmaceutical and nutraceutical industries, linolenic acid serves as an active ingredient in cardiovascular health supplements, anti-inflammatory formulations, and parenteral nutrition. Its role extends to cosmetic formulations for its emollient and barrier-repair properties, and to biochemical research as a reference standard and substrate in enzymatic studies. The growing body of evidence linking ω-3 fatty acids to metabolic and cognitive health continues to drive demand for high-purity ALA.

Chemical Structure & Properties

Linolenic acid consists of a straight 18-carbon chain terminating in a carboxylic acid group, with three cis double bonds at carbons 9, 12, and 15 (counting from the carboxyl carbon). This configuration imparts a pronounced kink in the molecule, preventing tight packing and resulting in a low melting point (approximately –11 °C) and high fluidity. The conjugated double bonds are prone to oxidation, making the compound sensitive to light, heat, and oxygen; thus, it is typically stabilized with antioxidants such as tocopherols and stored under inert gas. Its iodine value (270–280) reflects the high degree of unsaturation, while its refractive index and density are characteristic of long-chain PUFAs.

Mechanism of Action

• Precursor to EPA and DHA: ALA undergoes desaturation and elongation in the body to form EPA and DHA, which are incorporated into cell membranes and modulate eicosanoid synthesis.
• Membrane fluidity modulation: As a component of phospholipids, ALA influences membrane fluidity and the function of membrane-bound enzymes and receptors.
• Anti-inflammatory pathways: Through conversion to EPA, ALA can shift eicosanoid production toward less inflammatory mediators, affecting prostaglandins and leukotrienes.
• Gene expression regulation: ALA and its metabolites act as ligands for peroxisome proliferator-activated receptors (PPARs), influencing lipid metabolism and glucose homeostasis.
• Antioxidant defense: Although susceptible to oxidation itself, ALA can modulate endogenous antioxidant systems when incorporated into cellular membranes.

Quality Specifications

Supply & Documentation

• Capacity: 50 metric tons per year
• Lieferzeit: 3–5 Werktage (Lagerware)
• Dokumentation: COA, MSDS, TDS available upon request
• Verpackung: 1 kg, 5 kg, 25 kg HDPE drums; custom packaging options

Angebotsanfrage

• LyvBio GmbH. — E-Mail: info@lyvbio.com