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830843C

Avanti

10:0 PA

1,2-didecanoyl-sn-glycero-3-phosphate (sodium salt), chloroform

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Synonym(s):
PA(10:0/10:0)
Empirical Formula (Hill Notation):
C23H44O8PNa
CAS Number:
321883-64-1
Molecular Weight:
502.55
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (830843C-25mg)
pkg of 1 × 20 mL (830843C-500mg)

manufacturer/tradename

Avanti Polar Lipids 830843C

concentration

10 mg/mL (830843C-25mg)
25 mg/mL (830843C-500mg)

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H][C@@](COP([O-])(O)=O)(OC(CCCCCCCCC)=O)COC(CCCCCCCCC)=O.[Na+]

InChI

1S/C23H45O8P.Na/c1-3-5-7-9-11-13-15-17-22(24)29-19-21(20-30-32(26,27)28)31-23(25)18-16-14-12-10-8-6-4-2;/h21H,3-20H2,1-2H3,(H2,26,27,28);/q;+1/p-1/t21-;/m1./s1

InChI key

YVHWEENUNNUSBE-ZMBIFBSDSA-M

General description

Phosphatidic acid (PA) is a diacyl-glycerophospholipid. With the help of ester linkage, two fatty acids and a phosphate group are attached to a glycerol molecule through covalent bonds. PA is rich in soy lecithin. It can be produced through phosphorylation of diacyl glycerol (DAG) with the help of diacylglycerol kinases (DGKs).

Application

10:0 PA has been used for preparation of the ubiquitin specific peptidase 1-mitochondrial distribution and morphology protein 35 (Ups1–Mdm35)– phosphatidic acid (PA) complex.
It may be used:
  • as a component in the lipid bilayer to study how lipid geometry acts in coat protein I (COPI) vesicle fission
  • to study its effects on intracellular Ca2+ concentration ([Ca2+]i) in C6 rat glioma and L2071 mouse fibroblast cells
  • to activate protein kinase C (PKC) in chinese hamster ovary (CHO) cells

Biochem/physiol Actions

Phosphatidic acid (PA) is present in biomembranes. It is the precursor for other phospholipids and acts as a signaling molecule. PA is implicated in nicotinamide adenine dinucleotide phosphate (NADPH) oxidase (NOX) activity. 10:0 PA along with 1-oleoyl-2-acetoyl-sn-glycerol (OAG) and arachidonic acid (AA) can be used as cell-free activators to promote NADPH oxidase activity.

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (830843C-500mg)
5 mL Clear Glass Sealed Ampule (830843C-25mg)

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

Target Organs

Central nervous system, Liver,Kidney

WGK

WGK 3

Regulatory Information

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Eric M Lewis et al.
The Journal of biological chemistry, 285(5), 2959-2967 (2009-12-02)
NADPH oxidase comprises both cytosolic and membrane-bound subunits, which, when assembled and activated, initiate the transfer of electrons from NADPH to molecular oxygen to form superoxide. This activity, known as the respiratory burst, is extremely important in the innate immune
Jordan M Joy et al.
Nutrition & metabolism, 11, 29-29 (2014-06-25)
The lipid messenger phosphatidic acid (PA) plays a critical role in the stimulation of mTOR signaling. However, the mechanism by which PA stimulates mTOR is currently unknown. Therefore, the purpose of this study was to compare the effects of various
Daniel Schlam et al.
The Journal of biological chemistry, 288(32), 23090-23104 (2013-07-03)
It is commonly assumed that all phagosomes have identical molecular composition. This assumption has remained largely unchallenged due to a paucity of methods to distinguish individual phagosomes. We devised an assay that extends the utility of nitro blue tetrazolium for
Eric M Lewis et al.
Clinical immunology (Orlando, Fla.), 129(2), 372-380 (2008-09-09)
Chronic granulomatous disease (CGD) is characterized by defects in the superoxide producing enzyme NADPH oxidase causing phagocytes to improperly clear invading pathogens. Here we report findings of a late presenting 16-year-old female with X-linked CGD. The patient presented with community-acquired
Young-Ja Chang et al.
Prostaglandins & other lipid mediators, 83(4), 268-276 (2007-05-15)
Phosphatidic acid (PA) increased intracellular Ca(2+) concentration ([Ca(2+)](i)) in C6 rat glioma and L2071 mouse fibroblast cells. Dioleoyl PA (PA, 18:1) was the most efficacious, followed by dipalmitoyl PA (16:0 PA) and dimyristoyl PA (14:0 PA). Lysophosphatidic acid (LPA) also
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