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Merck
CN

857323P

Avanti

16:0 Cyclic LPA

Avanti Research - A Croda Brand

Synonym(s):

1-hexadecanoyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt); cPA; cLPA

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About This Item

Empirical Formula (Hill Notation):
C19H40NO6P
CAS Number:
Molecular Weight:
409.50
UNSPSC Code:
51191904
NACRES:
NA.25
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Product Name

16:0 Cyclic LPA, 1-palmitoyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder

InChI key

NATIUIORRLVXDB-GMUIIQOCSA-N

SMILES string

O=P1([O-])O[C@H](COC(CCCCCCCCCCCCCCC)=O)CO1.[NH4+]

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

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.

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

11 - Combustible Solids

wgk

WGK 3


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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)
Yuko Fujiwara et al.
Journal of neurochemistry, 87(5), 1272-1283 (2003-11-19)
Cyclic phosphatidic acid (cPA; 1-acyl-sn-glycerol-2,3-cyclic phosphate) is an analog of the growth factor-like phospholipid mediator lysophosphatidic acid (LPA). As brain tissue is the richest source of cPA we tested its effects on hippocampal neurons from day 16/17 embryonic rat cultured
M Mukai et al.
International journal of cancer, 81(6), 918-922 (1999-06-11)
Fetal calf serum (FCS) and 1-oleoyl lysophosphatidic acid (LPA) were previously found to be potent inducers of invasion (transcellular migration) in an in vitro system. A novel LPA, composed of cyclic phosphate and cyclopropane-containing hexadecanoic acid (PHYLPA), first isolated from

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