Pinolenic Acid Ethyl Ester: Properties, Uses & Research

Pinolenic Acid ethyl ester is a polyunsaturated fatty acid ethyl ester derived from pinolenic acid, the characteristic all-cis 5,9,12-octadecatrienoic acid found predominantly in pine nut oil, and is valued in lipid biochemistry research for its unique double-bond geometry and potential physiological activities.

Chemical Name

Ethyl all-cis-5,9,12-octadecatrienoate (ethyl ester of pinolenic acid)

Fatty Acid Class

Polyunsaturated fatty acid (PUFA) ethyl ester; non-methylene-interrupted (NMI) triene

Natural Source

Pine nut oil (Pinus species), where pinolenic acid can constitute up to ~15–20% of total fatty acids

Double Bond Positions

Δ5, Δ9, Δ12 (all cis configuration)

Research Relevance

Used as a reference standard and substrate in lipid metabolism, appetite regulation, and inflammation research

Storage Recommendation

Store under inert atmosphere at low temperature, protected from light and oxygen to prevent oxidation

SKU

P1074224

Chemical Identity and Structure of Pinolenic Acid Ethyl Ester

Pinolenic Acid ethyl ester is the ethyl ester form of pinolenic acid, systematically named ethyl all-cis-5,9,12-octadecatrienoate. Pinolenic acid itself is an 18-carbon polyunsaturated fatty acid (PUFA) featuring three cis double bonds located at the Δ5, Δ9, and Δ12 positions. This double-bond arrangement is classified as non-methylene-interrupted (NMI), distinguishing it structurally from the more common omega-6 linoleic acid (Δ9,12) and omega-3 alpha-linolenic acid (Δ9,12,15).

The NMI triene pattern confers unique conformational and physicochemical properties on the molecule. Conversion to the ethyl ester form improves handling characteristics, enhances solubility in common organic solvents, and provides a stable substrate or reference compound for analytical and biochemical studies. The molecular formula of the ethyl ester is C₂₀H₃₄O₂, with a molecular weight of approximately 306.48 g/mol.

As with all highly unsaturated lipid compounds, Pinolenic Acid ethyl ester is susceptible to autoxidation; therefore, it must be stored under an inert atmosphere (e.g., argon or nitrogen), at low temperature, and protected from light to maintain integrity for research use.

Natural Occurrence and Biosynthetic Context

Pinolenic acid is the signature fatty acid of pine nut oil, extracted from the seeds of various Pinus species, most notably Pinus koraiensis (Korean pine). Within pine nut oil, pinolenic acid can account for a substantial proportion of total fatty acids, reported in the literature to range roughly from 15% to over 20% depending on species and extraction method, making pine nut oil one of the few commercially relevant plant sources of this unusual NMI triene.

Biosynthetically, pinolenic acid is thought to arise via the action of a Δ5 desaturase acting on the common omega-6 fatty acid linoleic acid (18:2 Δ9,12), introducing an additional double bond at the Δ5 position to yield 18:3 Δ5,9,12. This Δ5 desaturation pathway is relatively rare among higher plants, contributing to the restricted natural distribution of pinolenic acid.

Understanding the natural source and biosynthesis is relevant for researchers working on plant lipid metabolism, the nutritional biochemistry of specialty oils, and the development of botanical extracts for functional food or nutraceutical applications.

Biochemical Activities and Research Applications

Pinolenic acid and its derivatives, including the ethyl ester form, have attracted research interest across several biological domains:

• Appetite and satiety regulation: Pinolenic acid has been investigated for its ability to stimulate the release of satiety hormones such as cholecystokinin (CCK) and glucagon-like peptide-1 (GLP-1) from intestinal cells, suggesting a potential role in appetite modulation. The ethyl ester serves as a convenient, chemically defined substrate for in vitro mechanistic studies of these pathways.
• Lipid metabolism and eicosanoid biology: As a Δ5-containing PUFA, pinolenic acid can serve as a substrate or competitive inhibitor within arachidonic acid metabolic pathways, potentially influencing prostaglandin and leukotriene biosynthesis. Researchers use purified ethyl ester standards to probe enzyme specificity (e.g., desaturases, elongases, cyclooxygenases) in controlled assays.
• Anti-inflammatory research: Preliminary studies have examined the anti-inflammatory potential of pinolenic acid-rich preparations, positioning the pure ethyl ester as a useful tool compound for mechanistic in vitro experiments.
• Analytical reference standard: The ethyl ester form is commonly employed in gas chromatography–mass spectrometry (GC-MS) and HPLC-based fatty acid profiling as an authentic reference standard to confirm the identity and quantify pinolenic acid in biological and food matrices.

Researchers should note that direct extrapolation of in vitro findings to in vivo outcomes requires careful experimental design; purified reagent-grade material such as Aladdin's P1074224 ensures consistent, reproducible results.

Handling, Storage, and Quality Considerations

Due to its three conjugation-prone cis double bonds, Pinolenic Acid ethyl ester is inherently susceptible to oxidative degradation. The following best practices are recommended for researchers:

• Storage conditions: Store at −20 °C or below under an inert gas blanket (nitrogen or argon). Avoid repeated freeze-thaw cycles by aliquoting stock solutions upon first thaw.
• Solvent selection: The compound is soluble in common organic solvents including ethanol, DMSO, chloroform, and hexane. Prepare working solutions fresh and use promptly to minimize oxidative exposure.
• Quality verification: Prior to critical experiments, verify compound integrity by GC-MS or NMR. Check for absence of oxidation products (hydroperoxides, aldehydes) using peroxide value assays or conjugated diene analysis if long-term storage is involved.
• Safety: Handle in a well-ventilated fume hood; consult the Safety Data Sheet (SDS) for Aladdin product P1074224 for full hazard information before use.
• Regulatory and purity: For quantitative assays, confirm lot-specific purity certification provided with the reagent. Aladdin Scientific supplies Pinolenic Acid ethyl ester (SKU P1074224) with documented purity specifications to support reproducible research.

Selecting Pinolenic Acid Ethyl Ester for Your Research

When sourcing Pinolenic Acid ethyl ester for laboratory use, researchers and procurement professionals should consider the following selection criteria:

• Purity grade: For mechanistic enzyme studies or quantitative analytical work, select the highest available purity grade to minimize interference from related fatty acid impurities. Confirm lot purity via the Certificate of Analysis (CoA).
• Quantity and packaging: Lipid reagents are best purchased in quantities that can be consumed within a reasonable timeframe to maintain freshness. Aladdin Scientific offers flexible pack sizes to match experimental throughput.
• Documentation: Ensure the supplier provides a CoA, SDS, and structural confirmation data (e.g., GC purity, NMR). These documents support regulatory compliance and reproducibility reporting in publications.
• Application fit: Whether the application is GC-MS reference standard work, cell-based satiety hormone assays, enzyme kinetics, or lipidomics, confirm that the reagent's purity and formulation (neat liquid or solution) are appropriate for the intended use.

Aladdin Scientific's Pinolenic Acid ethyl ester (SKU: P1074224) is available for order through the Aladdin platform, with technical support available for application-specific guidance.

Frequently asked questions

What is Pinolenic Acid ethyl ester and how does it differ from pinolenic acid?

Pinolenic Acid ethyl ester is the ethyl ester derivative of pinolenic acid (all-cis-5,9,12-octadecatrienoic acid). Compared to the free acid, the ethyl ester form offers improved chemical stability, enhanced solubility in organic solvents, and easier handling in laboratory settings, making it particularly useful as an analytical reference standard and biochemical substrate.

What are the primary research applications of Pinolenic Acid ethyl ester?

Key applications include its use as a GC-MS or HPLC reference standard for fatty acid profiling, as a substrate in enzyme activity assays targeting desaturases and elongases, and as a tool compound in cell-based studies investigating appetite hormone release (CCK, GLP-1) and anti-inflammatory mechanisms. Its defined chemical structure makes it suitable for controlled, reproducible experiments.

How should Pinolenic Acid ethyl ester be stored to prevent degradation?

Store Pinolenic Acid ethyl ester at −20 °C or below under an inert atmosphere (nitrogen or argon), protected from light and moisture. Aliquot the compound upon first opening to avoid repeated freeze-thaw cycles. Working solutions should be prepared fresh immediately before use, and compound integrity should be verified by GC-MS or peroxide value testing if stored for extended periods.

What distinguishes pinolenic acid from common omega-3 and omega-6 fatty acids?

Pinolenic acid is classified as a non-methylene-interrupted (NMI) polyunsaturated fatty acid due to its unique Δ5,9,12 double bond pattern, in which the double bonds are not separated by single methylene groups as in typical omega-3 or omega-6 fatty acids. This structural distinction results in different enzyme interactions and potential biological effects compared to linoleic acid (Δ9,12) or alpha-linolenic acid (Δ9,12,15).

Is Pinolenic Acid ethyl ester suitable for cell culture experiments?

Yes, the ethyl ester form is commonly used in cell-based assays. It is typically dissolved first in a small volume of ethanol or DMSO and then diluted into aqueous cell culture media, often in the presence of albumin (BSA) as a carrier to aid delivery. Researchers should verify solvent vehicle controls and concentration ranges appropriate for the cell type used, and consult the relevant literature for specific protocols.

References

1. Drusch S, Groß N, Schwarz K. 'Pine nut oil' — a review on its composition, quality, and potential applications. European Journal of Lipid Science and Technology. (General reference for pine nut oil fatty acid composition including pinolenic acid content.)
2. Paik HD, et al. Biological activities of pinolenic acid from pine nut (Pinus koraiensis) in relation to appetite regulation and anti-inflammatory effects. (Representative literature area; specific citation details require verification.)
3. Grienke U, et al. Pinolenic acid and non-methylene-interrupted fatty acids: structural diversity and biological significance. (General biochemistry reference; specific journal and volume details require verification.)
4. Christie WW. Fatty Acids and Lipids: Structures, Metabolism, and Functions. AOCS Press. (Textbook reference for PUFA classification and NMI fatty acid biochemistry.)

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