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857225P

Avanti

C16 Cyclic LPA

1-O-hexadecyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder

Synonym(s):

1-hexadecyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt)

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About This Item

Empirical Formula (Hill Notation):
C19H42NO5P
CAS Number:
Molecular Weight:
395.51
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857225P-1mg)

manufacturer/tradename

Avanti Research - A Croda Brand 857225P

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=P1([O-])O[C@H](COCCCCCCCCCCCCCCCC)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.

Application

C16 Cyclic LPA or 1-O-hexadecyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt) has been used as an internal standard for the quantification of lysophosphatidic acid (LPA) in proton samples using reversed-phase ultra-performance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS).

Biochem/physiol Actions

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.

Packaging

5 mL Amber Glass Screw Cap Vial (857225P-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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Standardization and Quantification of Lysophosphatidic Acid Compounds by Normal-Phase and Reversed-Phase Chromatography-Tandem Mass Spectrometry
Moore JD, et al.
Lysophospholipid Receptors: Signaling and Biochemistry, 137-137 (2013)
Standardization and Quantification of Lysophosphatidic Acid Compounds by Normal-Phase and Reversed-Phase Chromatography-Tandem Mass Spectrometry
Moore JD, et al.
Lysophospholipid Receptors: Signaling and Biochemistry, 137-137 (2013)
Standardization and Quantification of Lysophosphatidic Acid Compounds by Normal-Phase and Reversed-Phase Chromatography-Tandem Mass Spectrometry
Moore JD, et al.
Lysophospholipid Receptors: Signaling and Biochemistry, 137-137 (2013)
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
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

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