25088-57-7

Basic information

• Product Name: (Z,Z)-di-9-octadecenyl phosphonate
• Synonyms: Dioleyl hydrogen phosphite; Dioleyl phosphite; Dioleyl phosphonate; HSDB 2602; Phosphonic acid, di-9-octadecenyl ester (Z,Z)-; (Z,Z)-Di-9-octadecenyl phosphonate; di-(9Z)-octadec-9-en-1-yl hydrogen phosphite
• CAS NO: 25088-57-7
• Molecular Formula: C₃₆H₇₁O₃P
• Molecular Weight: 582.9209
• EINECS: 246-608-1
• Mol File: 25088-57-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 652.6°C at 760 mmHg
• Flash Point: 348.5°C
• Vapor Pressure: 1.03E-18mmHg at 25°C
• CAS DataBase Reference: (Z,Z)-di-9-octadecenyl phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,Z)-di-9-octadecenyl phosphonate(25088-57-7)
• EPA Substance Registry System: (Z,Z)-di-9-octadecenyl phosphonate(25088-57-7)

Safety Data

• Hazardous Substances Data: 25088-57-7(Hazardous Substances Data)

Usage

General Description

(Z,Z)-di-9-octadecenyl phosphonate is a chemical compound belonging to the class of phosphonates. It is a lipid-based molecule with two long hydrophobic chains that are derived from oleic acid, a common unsaturated fatty acid. (Z,Z)-di-9-octadecenyl phosphonate is commonly used as a surfactant and emulsifying agent in various industrial applications. It is known for its ability to stabilize and disperse insoluble substances in aqueous solutions. Additionally, (Z,Z)-di-9-octadecenyl phosphonate has been studied for its potential applications in drug delivery systems and as a component in biomedical materials due to its ability to interact with cell membranes and improve the solubility of hydrophobic drugs. Overall, (Z,Z)-di-9-octadecenyl phosphonate has versatile properties that make it a valuable ingredient in various fields of science and industry.

Upstream product

• 143-28-2 oleoyl alcohol 
• 4712-55-4 diphenyl hydrogen phosphite 

Downstream Products

• 14450-07-8 dioleyl phosphate 

Relevant articles and documents

Key determinants of siRNA delivery mediated by unique pH-responsive lipid-based liposomes

Lipid-based nanoparticles, a potential nonviral vector due to their good biocompatibility and biodegradability, have been extensively developed for the delivery of small interfering RNA (siRNA). We designed a unique pH-responsive lipid derivative, a dioleylphosphate-diethylenetriamine conjugate (DOP-DETA). DOP-DETA consists of a pH-responsive triamine and unsaturated fatty acids that accelerate membrane fusion. Our results showed that DOP-DETA-based liposomes (DL) efficiently delivered siRNA into the cytoplasm and induced RNA interference even at a low siRNA concentration. The knockdown efficiency of DL depended on the molar ratio of total DL lipids to siRNA. When siRNA was formulated with a sufficient amount of DL, it was efficiently taken up by cells and induced effective gene silencing. Time-lapse imaging showed that siRNA transfected with DL was rapidly internalized into the cells and uniformly dispersed in the cytoplasm within a few minites. The results also showed that DL induced sufficient change in surface charge to allow it to interact with the cell membrane and to allow for rapid endosomal escape. Uptake pathway and time-lapse imaging studies revealed that siRNA was delivered by DL into the cytoplasm, possibly through both macropinocytosis and membrane fusion. The present results emphasize that the modulation of surface charge on nanoparticles is crucial for each siRNA delivery process. Our results also suggest that DL is a potentially useful vector for inducing gene silencing with low-doses of siRNA.

NANOPARTICLE PEG MODIFICATION WITH H-PHOSPHONATES

The present invention provides phosphonate conjugates and methods of preparing the phosphonate conjugates so as to allow, for example, improved methods and compounds for modifying the surface of a nanoparticle to increase in vivo circulation times and targeted delivery performance.