1,2-O-Dioctadecyl-Rac-Glycerol

• CAS: 13071-61-9
• Catalog Number: ACM13071619-1
• Category: Main Products
• Molecular Weight: 597.06
• Molecular Formula: C39H80O3
• Canonical SMILES: CCCCCCCCCCCCCCCCCCOCC(CO)OCCCCCCCCCCCCCCCCCC
• Boiling Point: 653.65 °C at 760 mmHg (Predicted)
• Density: 0.87 g/cm3(Predicted)
• Refractive Index: 1.46 (Predicted)

Case Study

1,2-O-Dioctadecyl-Rac-Glycerol for the Construction of Cuboid Vesicles

Dong, Yuanchen, et al. Angewandte Chemie International Edition,2017, 56(6), 1586-1589.

The construction of cuboid and dumbbell-shaped heterovesicles on DNA origami nanostructure scaffolds using a framework-directed assembly (FGA) strategy has been reported. Different types of amphiphilic molecules have been directed to form cuboid and dumbbell-shaped heterovesicles by carefully selecting the primary hydrophobic group (LHG). Among them, the lipid 1,2-O-dioctadecyl-rac-glycerol with double hydrophobic tails as LHG can be used in the FGA process of sodium dodecyl sulfate (SDS).
The FGA process of SDS
· In the FGA process of SDS, lipid 1,2-O-dioctadecyl-rac-glycerol served as the lipid-hydrogel (LHG), while Lip-T was synthesized using a solid-phase conjugation technique. The resulting product underwent purification via C4 reversed-phase high-performance liquid chromatography (HPLC), with acetonitrile (ACN) concentrations ramping up from 50% to 90% over 10 minutes and then held at 90% for an additional 5 minutes.
· The DNA cuboids at a concentration of 4 nM were hybridized with 2 μM Lip-T by incubating at 4 °C for 3 hours in a solution composed of 1 × TAE buffer, 200 mM NaCl, and 1 × SYBR Green I, resulting in a total volume of 10 μL. The formation of green aggregates was observed under UV light at 254 nm, allowing for the direct extraction of a clear supernatant. Subsequently, 10 μL of 5 mM SDS was dissolved in the 1 × TAE buffer with 200 mM NaCl and added to the aggregates. After a gentle shake, the samples were assessed using transmission electron microscopy (TEM) without any additional processing.

1,2-O-Dioctadecyl-Rac-Glycerol for DNA-lipid Assembly

Zhou, Jingsheng, et al. Nanomaterials, 2016, 6(12), 229.

A class of DNA amphiphilic molecules (called DNA-lipids) was successfully synthesized. The study found that DNA-lipids can be further assembled with l-dilauroylphosphatidylcholine (l-DLPC) at the liquid crystal-water interface to form a micrometer-scale mesh structure. This DNA-lipid-modified liquid crystal-water interface has potential applications in biosensing and diagnosis.
Synthesis procedure of DNA-lipids
· 1,2-O-Dioctadecyl-rac-glycerol (0.6 g, 1 mmol) was dissolved in anhydrous tetrahydrofuran (THF) (10 mL). N,N-Diisopropylethylamine (DIPEA, 0.65 g, 5.0 mmol, 0.90 mL) was subsequently added, followed by the gradual addition of 2-cyanoethyl N,N-diisopropylchlorophosphoramidite (0.32 g, 1.35 mmol, 0.30 mL). After allowing the reaction to proceed for 30 minutes, ethyl acetate (50 mL) was used to dilute the mixture. This solution was washed three times with water (50 mL) and once with a saturated aqueous solution of NaCl (50 mL), and then dried over anhydrous Na2SO4 before being concentrated. Following purification via flash column chromatography, compound 1 was obtained as a pale yellow oil.
· The DNA-loaded controlled pore glass (CPG) T1 (4 μmol) was placed into a vial, followed by the addition of compound 1 (0.32 g, 0.4 mmol) and ETT (0.1 g, 0.8 mmol) in succession. After drying under vacuum, 5 mL of anhydrous THF was introduced under a nitrogen atmosphere. The reaction mixture was allowed to sit overnight at room temperature. The CPG was washed twice with anhydrous THF and then treated with iodine and water in THF. After cleavage using a concentrated ammonia solution at 60 °C for 3 hours, the crude product was purified by high-performance liquid chromatography (HPLC).

Custom Q&A

What is the molecular formula of 1,2-O-Dioctadecyl-rac-glycerol?

The molecular formula is C39H80O3.

What are the synonyms for 1,2-O-Dioctadecyl-rac-glycerol?

The synonyms are 2,3-Bis(octadecyloxy)propan-1-ol, 6076-38-6, 13071-61-9, 2,3-dioctadecoxypropan-1-ol.

What is the molecular weight of 1,2-O-Dioctadecyl-rac-glycerol?

The molecular weight is 597.0 g/mol.

What is the IUPAC name of 1,2-O-Dioctadecyl-rac-glycerol?

The IUPAC name is 2,3-dioctadecoxypropan-1-ol.

What is the InChI of 1,2-O-Dioctadecyl-rac-glycerol?

The InChI is InChI=1S/C39H80O3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-41-38-39(37-40)42-36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h39-40H,3-38H2,1-2H3.

What is the InChIKey of 1,2-O-Dioctadecyl-rac-glycerol?

The InChIKey is QEHCYTDFERPPPU-UHFFFAOYSA-N.

What is the canonical SMILES of 1,2-O-Dioctadecyl-rac-glycerol?

The canonical SMILES is CCCCCCCCCCCCCCCCCCOCC(CO)OCCCCCCCCCCCCCCCCCC.

What is the CAS number of 1,2-O-Dioctadecyl-rac-glycerol?

The CAS number is 6076-38-6.

What is the European Community (EC) number of 1,2-O-Dioctadecyl-rac-glycerol?

The European Community (EC) number is 228-012-3.

Is 1,2-O-Dioctadecyl-rac-glycerol a canonicalized compound?

Yes, it is a canonicalized compound.