In the realm of advanced pharmaceutical formulations, particularly those involving lipid nanoparticles (LNPs) and liposomes, understanding the specific chemical structure and properties of the lipid components is paramount. 1,2-Dioleoyl-sn-glycero-3-succinate (18:1 DGS) is a synthetic phospholipid that has gained significant traction due to its valuable characteristics. This article will explore its chemical architecture, key physicochemical properties, and the implications for its applications.

Chemical Structure of 18:1 DGS

The nomenclature 1,2-Dioleoyl-sn-glycero-3-succinate provides significant insight into its structure:

  • Glycerol Backbone: At its core is a glycerol molecule, a simple three-carbon alcohol. The 'sn' (stereospecific numbering) designation indicates the precise orientation of substituents on this backbone.
  • Dioleoyl Chains: Esterified at the sn-1 and sn-2 positions of the glycerol backbone are two oleoyl chains. An oleoyl chain is an 18-carbon fatty acid with a single cis double bond at the ninth carbon position (18:1, cis-9-octadecenoic acid). The presence of these unsaturated fatty acids imparts fluidity to the lipid bilayers formed by 18:1 DGS.
  • Succinate Moiety: At the sn-3 position, the glycerol backbone is esterified with succinic acid. This dicarboxylic acid group provides a hydrophilic headgroup. Critically, the succinate moiety can be protonated or deprotonated depending on the pH, making the lipid pH-sensitive. At physiological pH (around 7.4), the succinate group is largely deprotonated, carrying a negative charge, which contributes to its amphipathic character.

The overall molecular formula is C43H76O8, with a molecular weight of approximately 721.06 g/mol. This structure allows 18:1 DGS to self-assemble into various supramolecular structures, most notably unilamellar or multilamellar vesicles, which are the basis of liposomes and LNPs.

Key Physicochemical Properties and Their Significance

Several properties make 18:1 DGS highly desirable for pharmaceutical applications:

  • Amphipathic Nature: The combination of the hydrophobic oleoyl tails and the hydrophilic succinate headgroup drives self-assembly into ordered lipid structures.
  • pH-Sensitivity: The succinate group's ionization state changes with pH. In acidic environments (e.g., endosomes), the succinate group becomes more protonated, which can lead to changes in membrane charge and fluidity, promoting endosomal escape and cargo release. This is crucial for intracellular delivery.
  • High Purity: Manufacturers like us ensure high purity (≥98.0%) for 18:1 DGS. This is critical for reproducible formulation behavior, safety, and efficacy. Impurities can interfere with self-assembly, affect stability, and potentially cause unintended biological effects.
  • Fluidity: The cis double bonds in the oleoyl chains lower the phase transition temperature (Tm) of the lipid bilayers, ensuring that membranes remain fluid and flexible at physiological temperatures. This fluidity is important for membrane fusion and cargo release.

Synthesis and Quality Assurance

The synthesis of 18:1 DGS typically involves controlled esterification reactions. Ensuring the correct regiochemistry and stereochemistry, along with minimizing side products, requires precise manufacturing processes. Quality control measures, including HPLC and mass spectrometry, are employed by reputable suppliers to verify purity and structural integrity. As a dedicated manufacturer and supplier, we adhere to rigorous quality standards, providing you with a reliable and well-characterized product for your critical research and development needs.

For those seeking high-quality 1,2-Dioleoyl-sn-glycero-3-succinate, understanding its chemical intricacies highlights its importance in advanced delivery systems. Contact us to inquire about our product specifications, pricing, and availability.