1,2-dioleoyl-sn-glycero-3-phosphate (sodium salt) (18:1 PA) - ≥99% , CAS No.108392-02-5

CAS: 108392-02-5 Cat. No.: D130369 Molecular Weight: 722.95

GRADE & PURITY ≥99%

Synonyms

DOPA-NA | (Z)-(R)-3-(Phosphonooxy)propane-1,2-diyl dioleate sodium salt | L-α-Phosphatidic acid, dioleoyl sodium sal | 1,2-Di(cis-9-octadecenoyl)-sn-glycerol 3-phosphate sodium salt

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Application

Drug Delivery, Surface Modification, PEGylation of Protein, Peptide & Oligo

Overview

Phosphatidic Acid, Dioleoyl has been shown to activate PKC α, ε, or ζ isotypes in the cytosol of COS cells. This compound not only stimulates PKC-ζ-mediated phosphorylation of distinctive substrates, but additionally causes an upward shift in electrophoretic mobility of PKC &zeta. Furthermore, experiments have reported Phosphatidic Acid to be generated by hydrolysis of phosphatidylcholine, via phospholipase D (PLD). Mechanistic studies suggest activation of PLD by insulin and consequential generation of Phosphatidic Acid which then induces Raf-1 translocation to cell membranes. Raf-1 is an essential component to the mitogen-activated protein kinase cascade, and once it has crossed over to the plasma membrane, other factors may activate it through phosphorylation.
An activator of multiple PKC isotypes

Application

18:1 PA (1,2-dioleoyl-sn-glycerol-3-phosphate (sodium salt)):
Can be used as liposomes for liposome leakage assays
Can be used to create liposome templates for the synthesis of calcium phosphate (CaP) nanoshells
Can be used as a liposome/lipid bilayer component
As a neuronal glial culture medium additive to study the role of astrocyte phospholipase D1 (PLD1) on dendritic branching
For chemiluminescent assays of cytochrome c Trp59

Specifications

Synonyms

DOPA-NA | (Z)-(R)-3-(Phosphonooxy)propane-1, 2-diyl dioleate sodium salt | L-α-Phosphatidic acid, dioleoyl sodium sal | 1, 2-Di(cis-9-octadecenoyl)-sn-glycerol 3-phosphate sodium salt

Specifications & Purity

≥99%

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCCCCCCCC=CCCCCCCCC(=O)OCC(COP(=O)(O)O)OC(=O)CCCCCCCC=CCCCCCCCC.[Na]
• InChIKey: KHDHADSEKGCPKW-ZBFGHDQJSA-N
• INCHI: 1S/C39H73O8P.Na/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h17-20,37H,3-16,21-36H2,1-2H3,(H2,42,43,44);/b19-17-,20-18-;/t37-;/m1./s1
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@H](COP(=O)(O)O)OC(=O)CCCCCCC/C=C\CCCCCCCC.[Na]
• WGK Germany: 3
• Alternate CAS: 116004-31-0
• Molecular Weight: 722.95

Chemical and Physical Properties

• Sensitivity: Moisture sensitive; Light sensitive

References

1. Mengqing Xu, Jin Zhang, Yongli Mu, Mohamed Frahat Foda, Heyou Han.  (2022)  Activation of TRPV1 by capsaicin-loaded CaCO3 nanoparticle for tumor-specific therapy.  BIOMATERIALS,      [PMID:35436739] [10.1016/j.biomaterials.2022.121520]

2. Faming Xia, Hongbo Li, Rao Wu, Xuelian He, Xuejiao J. Gao, Junnan Li, Shengliang Zhong.  (2024)  Europium-Based Coordination Polymer-Modified Vanadium Sulfide Nanocomposite with High Photothermal Conversion Efficiency as a Powerful Photothermal and Four-Mode Imaging Technique.  Journal of Physical Chemistry C,      [PMID:] [10.1021/acs.jpcc.4c02519]

3. Xiang-Bo Zeng, Xue-Chen Pei, De-Yang Li, Fa-Wen Yin, Hui-Lin Liu, Meng-Ling Jin, Jiang-Hua Zhang, Da-Yong Zhou.  (2024)  Mechanism of discoloration of Antarctic krill oil upon storage: A study based on model systems.  FOOD CHEMISTRY,      [PMID:39002334] [10.1016/j.foodchem.2024.140376]

4. Huisong Hao, Yunfei Yi, Yanan Fu, Shengjie Sun, Zhangwen Peng, Jia Tang, Yixuan Fang, Shihao Zhuang, Yaqi Ouyang, Tianqi Wang, Meiying Wu.  (2025)  A lipid nanosystem establishes precise NO concentration gradient around tumor vessels via endothelial transcytosis, thereby normalizing tumor vasculature and creating an environment beneficial for antitumor immunotherapy.  Acta Pharmaceutica Sinica B,      [PMID:] [10.1016/j.apsb.2025.11.040]