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Merck
CN

42491

Sigma-Aldrich

1,2-Dioleoyl-sn-glycero-3-phosphoric acid sodium salt

≥98.0% (TLC)

Synonym(s):

3-sn-Phosphatidic acid, 1,2-dioleoyl sodium salt, L-β,γ-Dioleoyl-α-phosphatidic acid sodium salt, DOPA

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About This Item

Empirical Formula (Hill Notation):
C39H71Na2O8P
CAS Number:
Molecular Weight:
744.93
Beilstein:
3884561
UNSPSC Code:
12352211
PubChem Substance ID:
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Assay

≥98.0% (TLC)

solubility

chloroform: 20 mg/mL, clear, colorless

shipped in

wet ice

storage temp.

−20°C

SMILES string

[Na+].[Na+].CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](COP([O-])([O-])=O)OC(=O)CCCCCCC\C=C/CCCCCCCC

Biochem/physiol Actions

1,2-Dioleoyl-sn-glycero-3-phosphoric acid is a phosphatidic acid. Phospholipids, major membrane lipids, are derived from phosphatidic acid .
1,2-Dioleoyl-sn-glycero-3-phosphoric acid regulates phospholipid metabolic genes in yeast by binding to transcriptional factor, Opi1. This binding is regulated by a rapid decrease in pH in response to glucose starvation. 1,2-Dioleoyl-sn-glycero-3-phosphoric acid acts as intracellular pH biosensor, coupling membrane biogenesis to nutrient availability .

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Lipids of Physiologic Significance
Botham, K. M.
Harper′s Illustrated Biochemistry Edition: 28th, 28th, 124-124 (2009)
Barry P Young et al.
Science (New York, N.Y.), 329(5995), 1085-1088 (2010-08-28)
Recognition of lipids by proteins is important for their targeting and activation in many signaling pathways, but the mechanisms that regulate such interactions are largely unknown. Here, we found that binding of proteins to the ubiquitous signaling lipid phosphatidic acid
Fernando J Barreyro et al.
The Journal of biological chemistry, 282(37), 27141-27154 (2007-07-13)
Hepatocyte lipoapoptosis, a critical feature of nonalcoholic steatohepatitis, can be replicated in vitro by incubating hepatocytes with saturated free fatty acids (FFA). These toxic FFA induce Bim expression, which is requisite for their cytotoxicity. Because the FoxO3a transcription factor has

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