Linolenic acid-13C18

Catalog Number	ACM287111288-2
CAS	287111-28-8
Molecular Weight	296.42
Molecular Formula	13CH313(CH213CH13CH)313(CH2)713COOH
Application	A labeled essential fatty acid. Used in making quick-drying oils. Also used as a surfactant. Increased use in cosmetics for it's anti-inflammatory, acne reductive, and moisture retentive properties. May promote overeating and damaging the arcuate nucleus in the hypothalamus.
Storage	Keep container closed when no tin use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances
C No. Chain	C18:3
Double Bonds	9 cis, 12 cis, 15 cis
Isotopic Enrichment	>98%13C
Type	Unsaturated Fatty Acids 13C & 2H

Case Study

Tracing Defense Signaling Pathways with Linolenic acid-13C18

Yaguchi, Takaomi, et al. Bioscience, Biotechnology, and Biochemistry 81.11 (2017): 2071-2078.

Understanding the metabolic origins of azelaic acid (AzA) and jasmonate derivatives was critical for elucidating how yeast cell wall extract (YCWE) induces plant disease resistance. Stable isotope-labeled precursors, including Linolenic acid-13C18, were employed to enable precise metabolic flux analysis. Researchers supplemented rice cell suspension cultures with 13C-uniform-labeled oleic, linoleic, and linolenic acids. Ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was then used to track the incorporation of the 13C label into downstream metabolites, specifically targeting AzA and the jasmonoyl-isoleucine conjugate (12OHJA-Ile).
Application & Findings:
Utilizing Linolenic acid-13C18 revealed distinct metabolic partitioning:
· All three 13C-labeled C18 fatty acids (oleic, linoleic, linolenic) were converted into 13C-uniform-labeled AzA, confirming their role as AzA precursors.
· YCWE treatment significantly increased endogenous 13C-AzA levels derived from 13C-oleic and 13C-linoleic acids.
· Crucially, Linolenic acid-13C18 demonstrated preferential utilization for jasmonate pathway activation. UPLC-MS/MS analysis showed significantly higher accumulation of 13C-uniform-labeled 12OHJA-Ile derived from Linolenic acid-13C18 compared to the other labeled fatty acids upon YCWE treatment. This indicated channeling of linolenic acid towards JA-Ile biosynthesis rather than AzA production.

Quantifying Human Fatty Acid Metabolism with Linolenic Acid-13C18

Hussein, Nahed, et al. Journal of lipid research 46.2 (2005): 269-280.

Understanding the metabolic conversion efficiency of dietary α-linolenic acid (ALA) and linoleic acid (LA) into long-chain polyunsaturated fatty acids (LC-PUFAs) in humans is critical for nutritional science. To directly track and quantify ALA metabolism, researchers employed Linolenic acid-13C18 ([U-13C]ALA) as a metabolic tracer. In a controlled dietary intervention study with moderately hyperlipidemic men, participants consumed diets enriched with either flaxseed oil (high ALA, FXO diet) or sunflower oil (high LA, SO diet).
Key Findings:
· The FXO diet resulted in significant increases in the phospholipid levels of ALA (over threefold), eicosapentaenoic acid (EPA, more than double), and docosapentaenoic acid (DPA, 50% increase), with no observed changes in docosahexaenoic acid (DHA), LA, or arachidonic acid (AA). The increases in EPA and DPA on the FXO diet paralleled those seen in participants on the SO diet who received an additional 3 g of EPA plus DHA from fish oil (n = 19). The SO diet led to a slight increase in LA but did not alter AA levels.
· Long-chain conversions of [U-13C]ALA and [U-13C]LA, estimated from peak plasma 13C concentrations through basic modeling for tracer dilution in subsets from the FXO (n = 6) and SO (n = 5) groups, were similarly low for both tracers (AA, 0.2%; EPA, 0.3%; and DPA, 0.02%). These conversions were directly related to precursor concentrations and inversely related to the levels of fatty acids from the alternative series.

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Linolenic acid-13C18 (287111-28-8)

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