857323P
Avanti
16:0 Cyclic LPA
1-palmitoyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder
Synonym(s):
1-hexadecanoyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt); cPA; cLPA
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C19H40NO6P
CAS Number:
Molecular Weight:
409.50
UNSPSC Code:
51191904
NACRES:
NA.25
Recommended Products
Assay
>99% (TLC)
form
powder
packaging
pkg of 1 × 1 mg (857323P-1mg)
manufacturer/tradename
Avanti Research™ - A Croda Brand 857323P
lipid type
cardiolipins
phospholipids
shipped in
dry ice
storage temp.
−20°C
SMILES string
O=P1([O-])O[C@H](COC(CCCCCCCCCCCCCCC)=O)CO1.[NH4+]
General description
Cyclic phosphatidic acid (cPA) is a naturally occurring analog of the growth factor-like phospholipid mediator, lysophosphatidic acid (LPA). The sn-2 hydroxy group of CPA forms a 5-membered ring with the sn-3 phosphate. cPA affects numerous cellular functions, including anti-mitogenic regulation of the cell cycle, induction of stress fiber formation, inhibition of tumor cell invasion and metastasis, and regulation of differentiation and survival of neuronal cells.
Interestingly, many of these cellular responses caused by cPA oppose those of LPA despite the activation of apparently overlapping receptor populations.
Interestingly, many of these cellular responses caused by cPA oppose those of LPA despite the activation of apparently overlapping receptor populations.
Application
16:0 Cyclic LPA may be used for the extraction recovery of cyclic phosphatidic acid (cPA) at different pH conditions using Bligh-Dyer method.
Packaging
5 mL Amber Glass Screw Cap Vial (857323P-1mg)
Legal Information
Avanti Research is a trademark of Avanti Polar Lipids, LLC
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Certificates of Analysis (COA)
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Quantitative determination of cyclic phosphatidic acid in human serum by LC/ESI/MS/MS
Shan L, et al.
Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences, 862(1-2), 161-167 (2008)
Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons.
Fujiwara Y, et al.
Journal of Neurochemistry, 87, 1272-1283 (2003)
Inhibition of cell proliferation by a unique lysophosphatidic acid, PHYLPA, isolated from Physarum polycephalum: signaling events of antiproliferative action by PHYLPA.
Murakami-Murofushi K, et al.
Cell Structure and Function, 18, 363-370 (1993)
D J Fischer et al.
Molecular pharmacology, 54(6), 979-988 (1998-12-18)
Lysophosphatidic acid (LPA), plasmalogen-glycerophosphate (alkenyl-GP) and, cyclic-phosphatidic acid (cyclic-PA) are naturally occurring phospholipid growth factors (PLGFs). PLGFs elicit diverse biological effects via the activation of G protein-coupled receptors in a variety of cell types. In NIH3T3 fibroblasts, LPA and alkenyl-GP
K Murakami-Murofushi et al.
Cell structure and function, 18(5), 363-370 (1993-10-01)
The unique Physarum lysophosphatidic acid, PHYLPA, having a cyclopropane in the fatty acid moiety and a cyclic phosphate at C-2 and C-3 positions of the glycerol, inhibited proliferation of human fibroblast cells, TIG-3 and TIG-7, which were cultured in a
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