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Chemical Structure| 143-28-2 Chemical Structure| 143-28-2
Chemical Structure| 143-28-2

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Oleyl Alcohol is an unsaturated fatty alcohol, widely used in the manufacture of detergents, wetting agents, defoamers, metal cutting lubricants, plasticizers, and fabric softeners, and as a raw material for organic synthesis and special surfactants.

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Product Citations

Product Citations      Show More

Xuexiang Han ; Mohamad-Gabriel Alameh ; Ningqiang Gong ; Lulu Xue ; Majed Ghattas ; Goutham Bojja , et al.

Abstract: Lipid nanoparticles (LNPs) are widely used for mRNA delivery, with cationic lipids greatly afecting biodistribution, cellular uptake, endosomal escape and transfection efciency. However, the laborious synthesis of cationic lipids limits the discovery of efcacious candidates and slows down scale-up manufacturing. Here we develop a one-pot, tandem multi-component reaction based on the rationally designed amine-thiol-acrylate conjugation, which enables fast (1 h) and facile room-temperature synthesis of amidine-incorporated degradable (AID) lipids. Structure-activity relationship analysis of a combinatorial library of 100 chemically diverse AID-lipids leads to the identifcation of a tail-like amine-ring-alkyl aniline that generally afords efcacious lipids. Experimental and theoretical studies show that the embedded bulky benzene ring can enhance endosomal escape and mRNA delivery by enabling the lipid to adopt a more conical shape. The lead AID-lipid can not only mediate local delivery of mRNA vaccines and systemic delivery of mRNA therapeutics, but can also alter the tropism of liver-tropic LNPs to selectively deliver gene editors to the lung and mRNA vaccines to the spleen.

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Li, Bowen ; Manan, Rajith Singh ; Liang, Shun-Qing ; Gordon, Akiva ; Jiang, Allen ; Varley, Andrew , et al.

Abstract: The expanding applications of nonviral genomic medicines in the lung remain restricted by delivery challenges. Here, leveraging a high-throughput platform, we synthesize and screen a combinatorial library of biodegradable ionizable lipids to build inhalable delivery vehicles for mRNA and CRISPR-Cas9 gene editors. Lead lipid nanoparticles are amenable for repeated intratracheal dosing and could achieve efficient gene editing in lung epithelium, providing avenues for gene therapy of congenital lung diseases.

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Product Details of Oleyl Alcohol

CAS No. :143-28-2
Formula : C18H36O
M.W : 268.48
SMILES Code : CCCCCCCC/C=C\CCCCCCCCO
MDL No. :MFCD00002993
InChI Key :ALSTYHKOOCGGFT-KTKRTIGZSA-N
Pubchem ID :5284499

Safety of Oleyl Alcohol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P305+P351+P338

Application In Synthesis of Oleyl Alcohol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 143-28-2 ]

[ 143-28-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 143-28-2 ]
  • [ 112-05-0 ]
  • [ 3788-56-5 ]
YieldReaction ConditionsOperation in experiment
Oleyl alcohol (100 ml) is dissolved in propanoic acid (200 ml) in a jacketed reactor equipped with a gas sparger and an overhead stirrer. The reaction mixture is cooled to 10C while stirring and an 03/air mixture is sparged through the reactor over the course of 100 minutes until all olefin has been consumed, making sure that the internal temperature does not exceed 15C. The peroxide value of the mixture is tested using iodometric titration and is calculated to be 450 mmol/L. (0192) [00056] This mixture is then pumped through a " OD tube packed with sand mixed with 5% by wt. V2O5 that is kept at 90C. The flow rate is established such that the residence time in the packed tube is less than 15 minutes. After the material has passed through the tube, another peroxide test is performed the peroxide value was calculated to be 40 mmol/L. (0193) [00057] This mixture is then collected, charged with 250 mg of V2O5, and is sparged with oxygen at between 70 and 80C for several hours until lH NMR shows no more aldehyde peak to be present. Finally, the propanoic acid solvent is removed via distillation, resulting in a mixture of nonanoic acid, 9-hydroxynonanoic acid, and corresponding esters. The NMR data for this mixture is provided in Figure 2. The resulting mixture from Example 5 (86 g) is charged with Amberlyst cationic resin beads (~2 g) and is distilled at reduced pressure 0.5-2 mbar and 100C for 4 hours.
 

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