1346224-24-5

Basic information

• Product Name: (3R,4R)-1-benzyl-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine
• Synonyms: (3R,4R)-1-benzyl-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine
• CAS NO: 1346224-24-5
• Molecular Weight: 690.15
• Mol File: 1346224-24-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3R,4R)-1-benzyl-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-1-benzyl-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine(1346224-24-5)
• EPA Substance Registry System: (3R,4R)-1-benzyl-3,4-bis((9Z,12Z)-octadec-9,12-dienyloxy)pyrrolidine(1346224-24-5)

Safety Data

• Hazardous Substances Data: 1346224-24-5(Hazardous Substances Data)

Upstream product

• 51154-39-3 (9Z,12Z)-octadeca-9,12-dienyl methanesulfonate 
• 163439-82-5 (3R,4R)-1-benzyl-3,4-pyrrolidinediol 

Relevant articles and documents

Simplifying the Chemical Structure of Cationic Lipids for siRNA-Lipid Nanoparticles

We report a potent cationic lipid, SST-02 ((3-hydroxylpropyl)dilinoleylamine), which possesses a simple chemical structure and is synthesized just in one step. Cationic lipids are key components of siRNA-lipid nanoparticles (LNP), which may serve as potential therapeutic agents for various diseases. For a decade, chemists have given enhanced potency and new functions to cationic lipids along with structural complexity. In this study, we conducted a medicinal chemistry campaign pursuing chemical simplicity and found that even dilinoleylmethylamine (SST-01) and methylpalmitoleylamine could be used for the in vitro and in vivo siRNA delivery. Further optimization revealed that a hydroxyl group boosted potency, and SST-02 showed an ID50 of 0.02 mg/kg in the factor VII (FVII) model. Rats administered with 3 mg/kg of SST-02 LNP did not show changes in body weight, blood chemistry, or hematological parameters, while the AST level decreased at a dose of 5 mg/kg. The use of SST-02 avoids a lengthy synthetic route and may thus decrease the future cost of nucleic acid therapeutics.

CATIONIC LIPID

The present invention provides a cationic lipid, which allow nucleic acids to be easily introduced into cells, represented by formula (I) (wherein: R1 and R2 are, the same or different, alkenyl, etc, andX1 and X2 are hydrogen atoms, or are combined together to form a single bond or alkylene, andX3 is absent or is alkyl, etc,Y is absent or anion,a and b are, the same or different, 0 to 3, andL3 is a single bond, etc,R3 is alkyl, etc,L1 and L2 are —O—, —CO—O— or —O—CO—),a composition comprising the cationic lipid and a nucleic acid, anda method for introducing a nucleic acid into a cell by using the composition comprising the cationic lipid and the nucleic acid, and the like.