42491
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
UNSPSC Code:
12352211
PubChem Substance ID:
Beilstein/REAXYS Number:
3884561
SMILES string
[Na+].[Na+].CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](COP([O-])([O-])=O)OC(=O)CCCCCCC\C=C/CCCCCCCC
assay
≥98.0% (TLC)
solubility
chloroform: 20 mg/mL, clear, colorless
shipped in
wet ice
storage temp.
−20°C
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
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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
Lipids of Physiologic Significance
Botham, K. M.
Harper′s Illustrated Biochemistry Edition: 28th, 28th, 124-124 (2009)
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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