Octanoic acid, 8-[(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino]-, 1-octylnonyl ester Chemical Properties

Boiling point:

725.8±50.0 °C(Predicted)

Density 

0.925±0.06 g/cm3(Predicted)

storage temp. 

Storage temp. 2-8°C

solubility 

Soluble in Ethanol, DMSO, DMF

pka

14.67±0.10(Predicted)

form 

Liquid

color 

Colorless to light yellow

InChIKey

BGNVBNJYBVCBJH-UHFFFAOYSA-N

SMILES

C(OC(CCCCCCCC)CCCCCCCC)(=O)CCCCCCCN(CCO)CCCCCC(=O)OCCCCCCCCCCC

Octanoic acid, 8-[(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino]-, 1-octylnonyl ester Usage And Synthesis

Description

SM-102, Heptadecan-9-yl 8-{(2-hydroxyethyl)[6-oxo-6-(undecyloxy)hexyl]amino}octanoate equivalent, is a ionizable cationic lipid used with other lipids to form lipid nanoparticles (LNP) in drug delivery.

Uses

SM-102 is an amino cationic lipid useful in the formation of lipid nanoparticles (LNPs). SM-102 has higher transfection efficiency. SM-102 plays an important role in the effectiveness of lipid nanoparticles (LNPs) in delivering mRNA therapeutics and vaccines[1][2].

References

[1] Staci Sabnis, et al. A Novel Amino Lipid Series for mRNA Delivery: Improved Endosomal Escape and Sustained Pharmacology and Safety in Non-human Primates. Mol Ther. 2018 Jun 6;26(6):1509-1519. DOI:10.1016/j.ymthe.2018.03.010
[2] Escalona-Rayo O, et al. In vitro and in vivo evaluation of clinically-approved ionizable cationic lipids shows divergent results between mRNA transfection and vaccine efficacy. Biomed Pharmacother. 2023 Sep;165:115065. DOI:10.1016/j.biopha.2023.115065
[3] Cho HY, et al. Effective Perturbations on the Amplitude and Hysteresis of Erg-Mediated Potassium Current Caused by 1-Octylnonyl 8-[(2-hydroxyethyl)[6-oxo-6(undecyloxy)hexyl]amino]-octanoate (SM-102), a Cationic Lipid. Biomedicines. 2021 Oct 1;9(10):1367. DOI:10.3390/biomedicines9101367