Dilinolein(mixed isomers)

• CAS: 30606-27-0
• Catalog Number: ACM30606270
• Category: Main Products
• Molecular Weight: 616.96
• Molecular Formula: C₃₉H₆₈O₅
• Synonyms: DILINOLEIN (MIXED ISOMERS);(9Z,12Z)-octadeca-9,12-dienoic acid, diester with glycerol;GLYCERYL DILINOLEATE
• IUPAC Name: [3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl](9Z,12Z)-octadeca-9,12-dienoate
• SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCC=CCCCCC
• InChI Key: MQGBAQLIFKSMEM-MAZCIEHSSA-N
• Boiling Point: 669.4ºC at 760 mmHg
• Flash Point: 187.2ºC
• Density: 0.946g/cm³
• EC Number: 250-259-0
• Exact Mass: 616.50700

Case Study

Dilinolein as a Well-Defined Substrate for Electrochemical Lipase Activity Assays

Rogala, Anita, et al. Analytical and Bioanalytical Chemistry 414.17 (2022): 5033-5041.

Dilinolein (1,3-dilinoleoyl-glycerol) was deployed as the defined substrate in a rapid electrochemical lipase-activity assay based on a cobalt(II)-phthalocyanine / MWCNT-modified carbon-paste electrode and differential pulse voltammetry (DPV), providing a sensitive, room-temperature method for measuring lipase activity and inhibitor effects.
Approach: The assay uses dilinolein dissolved in paraffin oil as the standard triglyceride substrate in a 0.1 M borate buffer (pH 9) reaction medium. Hydrolysis by lipase generates electroactive products that are detected by DPV at a Co(II)PC + multi-walled carbon-nanotube modified carbon paste electrode. The method was validated with porcine pancreas, Aspergillus oryzae and Candida rugosa lipases and tested for inhibitor profiling (Orlistat).
Key Results & Impact: Using dilinolein as substrate, the assay showed linear response for porcine lipase between 20-300 U/L, a limit of detection of 7 U/L and a limit of quantification of 20 U/L, with an apparent Km ≈ 0.29 mM - figures that support both routine activity measurement and inhibitor screening. The technique is simple, fast, and avoids ill-defined natural substrates (e.g., olive oil), making dilinolein an attractive, well-characterized substrate for laboratories developing lipase assays, biosensors, or inhibitor screens.

Dilinolein as a Defined Linoleate Donor for PNPLA1-Mediated Acylceramide Biosynthesis

Meyer, Jason M., et al. Journal of Lipid Research 64.6 (2023).

Dilinolein (1,2-/1,3-dilinoleoyl-glycerol) served as a defined linoleate-rich acyl donor in in-vitro assays that demonstrated PNPLA1-catalyzed transfer of linoleate into ω-hydroxy ceramide-supporting PNPLA1's role in epidermal acylceramide biosynthesis and skin-barrier lipid formation.
Approach & Findings: Recombinant, truncated PNPLA1 was assayed with liposomal substrates where dilinolein (and trilinolein) provided acyl groups to ω-hydroxy ceramide acceptors; product analysis by HPLC-UV/LC-MS confirmed PNPLA1-dependent formation of acylceramides and acyl acids. Experiments reported preferential incorporation of linoleate over oleate (≈3:1 selectivity) when comparing dilinolein vs diolein donors, though absolute in-vitro conversion of the supplied substrates was low under the assay conditions (reported ~0.05% conversion).
Practical Impact for Users: As a chemically defined, linoleate-enriched triglyceride, dilinolein is a useful reagent for mechanistic enzyme assays, substrate-selectivity studies, and screening workflows probing acylceramide biosynthesis-especially in research on PNPLA1 function, ichthyosis, or skin-barrier lipidomics. For assay work, use well-characterized liposomal presentations and LC-MS or HPLC-UV endpoints to detect low-abundance transacylation products and include appropriate oleate controls to reveal substrate selectivity.