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MilliporeSigma

840875C

Avanti

18:1 PA

Avanti Research™ - A Croda Brand

Synonym(s):

1,2-di-(9Z-octadecenoyl)-sn-glycero-3-phosphate (sodium salt); DOPA; PA(18:1(9Z)/18:1(9Z))

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About This Item

Empirical Formula (Hill Notation):
C39H72O8PNa
CAS Number:
108392-02-5
Molecular Weight:
722.95
MDL number:
MFCD00674303
UNSPSC Code:
51191904
NACRES:
NA.25
This product is not available through MilliporeSigma in United States. Please go to avantilipids.com to order directly.

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description

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

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 2.5 mL (840875C-25mg)
pkg of 2 × 20 mL (840875C-1g)
pkg of 2 × 4 mL (840875C-200mg)
pkg of 5 × 4 mL (840875C-500mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand

concentration

10 mg/mL (840875C-25mg)
25 mg/mL (840875C-1g)
25 mg/mL (840875C-200mg)
25 mg/mL (840875C-500mg)

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

[Na].[P](=O)(OC[C@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC)(O)O

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

InChI key

KHDHADSEKGCPKW-ZBFGHDQJSA-N

General description

18:1 PA (1,2-dioleoyl-sn-glycero-3-phosphate (sodium salt)) is a sodium salt of modified lipid which has phosphatidic acid group as the backbone.

Application

18:1 PA (1,2-dioleoyl-sn-glycero-3-phosphate (sodium salt)) has been used:
  • as a synthetic standard to identify the position of PA after iodine staining in phosphatidic acid assay by thin-layer chromatography (TLC)[1]
  • as a lipid standard in the optimization of the liquid chromatography−mass spectrometry (LC-MS) method conditions[2]
  • as a lipid standard in radiolabeling analysis of phospholipids[3]

Biochem/physiol Actions

Phosphatidic acid (PA) serves as a lipid messenger. It plays a key role in mammalian target of rapamycin (mTOR) signaling.[4]

Packaging

30 mL Amber Narrow Mouth Glass Bottle with Screw Cap (840875C-1g)
5 mL Clear Glass Sealed Ampule (840875C-200mg)
5 mL Clear Glass Sealed Ampule (840875C-25mg)
5 mL Clear Glass Sealed Ampule (840875C-500mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

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

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk_germany

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

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Shutao Guo et al.
Journal of controlled release : official journal of the Controlled Release Society, 174, 137-142 (2013-11-28)
The poor solubility of cisplatin (CDDP) often presents a major obstacle in the formulation of CDDP in nanoparticles (NPs) by traditional methods. We have developed a novel method for synthesizing CDDP NPs taking advantage of its poor solubility. By mixing
Shireesha Sankella et al.
The Journal of biological chemistry, 289(8), 4762-4777 (2014-01-16)
In this study we examined the role of phosphatidic acid (PA) in hepatic glucose production (HGP) and development of hepatic insulin resistance in mice that lack 1-acylglycerol-3-phosphate O-acyltransferase 2 (AGPAT2). Liver lysophosphatidic acid and PA levels were increased ∼2- and
Xinhui Sun et al.
Cell cycle (Georgetown, Tex.), 14(5), 721-731 (2015-01-16)
It had been known for decades that primordial follicles in mammalian ovaries are assembled with definite numbers and represent the ovarian reserve throughout the reproductive life. Intra-oocyte PI3K/mTOR pathways have been indicated to play a central role on the activation
Zhenping Cao et al.
Nature communications, 10(1), 5783-5783 (2019-12-21)
The gut microbiota represents a huge community of microorganisms that play essential roles in immune modulation and homeostasis maintenance. Microbiota transplantation is an important approach to prevent and treat disease as it can inhibit pathogen colonization and positively modulate bacterial
Kathleen Frondorf et al.
The Journal of biological chemistry, 285(21), 15837-15847 (2010-03-23)
Phosphatidic acid (PA) is a pleiotropic lipid second messenger in mammalian cells. We report here that extracellular PA acts as a leukocyte chemoattractant, as membrane-soluble dioleoyl-PA (DOPA) elicits actin polymerization and chemotaxis of human neutrophils and differentiated proleukemic HL-60 cells.
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