Cas no 111188-59-1 (1-o-hexadecyl-2-o-methyl-rac-glycerol)

1-O-Hexadecyl-2-O-methyl-rac-glycerol is a synthetic glycerol ether derivative characterized by its hydrophobic hexadecyl chain and methyl substitution at the second hydroxyl position. This compound is primarily utilized in lipid research, membrane studies, and surfactant applications due to its amphiphilic properties. The rac-glycerol backbone ensures compatibility with biological systems, while the hexadecyl chain enhances lipid bilayer integration. The methyl group at the 2-position introduces steric and electronic modifications, influencing packing behavior and phase transitions. Its well-defined structure makes it a valuable intermediate for synthesizing more complex lipids or as a reference standard in analytical chemistry. The compound’s stability and predictable behavior under experimental conditions further underscore its utility in controlled studies.
1-o-hexadecyl-2-o-methyl-rac-glycerol structure
111188-59-1 structure
Product Name:1-o-hexadecyl-2-o-methyl-rac-glycerol
CAS No:111188-59-1
MF:C20H42O3
MW:330.545687198639
CID:894413
PubChem ID:1380
Update Time:2025-10-21

1-o-hexadecyl-2-o-methyl-rac-glycerol Chemical and Physical Properties

Names and Identifiers

    • 1-o-hexadecyl-2-o-methyl-rac-glycerol
    • (+/-)1-O-HEXADECYL-2-O-METHYLGLYCEROL
    • 1-O-Palmityl-2-O-methyl-rac-glycerol
    • Inchi: 1S/C20H42O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23-19-20(18-21)22-2/h20-21H,3-19H2,1-2H3
    • InChI Key: XAWCMDFDFNRKGK-UHFFFAOYSA-N
    • SMILES: O(CC(CO)OC)CCCCCCCCCCCCCCCC

Computed Properties

  • Exact Mass: 330.31300
  • Monoisotopic Mass: 330.31339520g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 19
  • Complexity: 209
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 38.7?2
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 7.1

Experimental Properties

  • Color/Form: solid
  • PSA: 38.69000
  • LogP: 5.49160
  • Solubility: Not determined

1-o-hexadecyl-2-o-methyl-rac-glycerol Pricemore >>

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Additional information on 1-o-hexadecyl-2-o-methyl-rac-glycerol

Introduction to 1-o-hexadecyl-2-o-methyl-rac-glycerol (CAS No. 111188-59-1)

1-o-hexadecyl-2-o-methyl-rac-glycerol is a specialized glycerol derivative that has garnered significant attention in the field of pharmaceutical chemistry and biochemistry due to its unique structural properties and potential applications. This compound, identified by the CAS number 111188-59-1, belongs to a class of molecules known for their role in lipid metabolism and membrane interactions. Its molecular structure, featuring a long aliphatic chain and specific functional groups, makes it a candidate for various biochemical studies and therapeutic developments.

The compound’s primary structure consists of a glycerol backbone with an o-hexadecyl substituent at the first carbon position and an o-methyl group at the second carbon position. This configuration imparts distinct physicochemical properties, including solubility characteristics and reactivity profiles, which are critical for its utility in synthetic biology and drug formulation. The presence of a long hydrophobic chain enhances its interaction with lipid bilayers, making it a promising candidate for drug delivery systems targeting membrane-bound receptors or intracellular compartments.

Recent advancements in the field of lipid-based drug delivery have highlighted the importance of glycerol derivatives in enhancing bioavailability and improving pharmacokinetic profiles. Studies have demonstrated that compounds with similar structural motifs can facilitate the translocation of hydrophobic molecules across biological membranes, thereby increasing their therapeutic efficacy. 1-o-hexadecyl-2-o-methyl-rac-glycerol has been explored in preliminary research as a potential component in nanoformulations, such as liposomes or micelles, which are designed to improve the solubility and targeted delivery of poorly soluble drugs.

In addition to its role in drug delivery, this compound has shown promise in biochemical research as a substrate or intermediate in synthetic pathways. The unique reactivity of its glycerol backbone allows for modifications that can be tailored for specific biological applications. For instance, researchers have investigated its use in the synthesis of complex lipid molecules that mimic natural phospholipids, which are essential components of cell membranes. Such modifications could lead to novel therapeutic agents targeting membrane-related diseases or conditions.

The pharmacological potential of 1-o-hexadecyl-2-o-methyl-rac-glycerol has also been examined in the context of metabolic disorders. Preliminary studies suggest that this compound may influence lipid metabolism by interacting with key enzymes or receptors involved in fat storage and utilization. Given the rising prevalence of metabolic syndromes, such as obesity and type 2 diabetes, compounds like this could offer new avenues for therapeutic intervention. Further research is needed to fully elucidate its mechanisms of action and potential side effects.

From a synthetic chemistry perspective, 1-o-hexadecyl-2-o-methyl-rac-glycerol serves as an interesting building block for more complex molecules. Its stability under various reaction conditions makes it suitable for multi-step syntheses without significant degradation. This characteristic is particularly valuable in industrial settings where reproducibility and yield are critical factors. Additionally, its compatibility with green chemistry principles has been noted, as it can be synthesized using relatively benign reagents and conditions compared to some traditional organic transformations.

The compound’s applications extend beyond pharmaceuticals into the realm of materials science. For example, researchers have explored its use as an additive in polymer formulations to improve flexibility or thermal stability. The long hydrophobic chain can interact with polymer backbones, altering their physical properties while maintaining biocompatibility. Such applications could lead to new materials with enhanced performance characteristics suitable for medical devices or biodegradable packaging.

As interest in personalized medicine grows, 1-o-hexadecyl-2-o-methyl-rac-glycerol may find utility in customized drug formulations tailored to individual patient needs. Its ability to enhance drug solubility and targeting could be leveraged to develop treatments that address specific genetic or metabolic variations among patients. This aligns with broader trends in precision healthcare, where compounds like this could play a pivotal role in optimizing therapeutic outcomes.

The regulatory landscape for such compounds is also evolving, with increasing emphasis on safety and efficacy evaluations before clinical translation. Given these considerations, further preclinical studies are warranted to establish dosing guidelines and long-term safety profiles for 1-o-hexadecyl-2-o-methyl-rac-glycerol before it can be considered for human trials. Collaborative efforts between academic researchers and industry partners will be essential to accelerate this process.

In conclusion,1-o-hexadecyl-2-o-methyl-rac-glycerol (CAS No. 111188-59-1) represents a versatile compound with diverse applications across pharmaceuticals, biochemical research, and materials science. Its unique structural features offer opportunities for innovation in drug delivery systems, lipid metabolism studies, and advanced material formulations. While challenges remain regarding regulatory approval and large-scale synthesis, this compound holds significant promise as a tool for addressing complex biological challenges.

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