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857324P

Avanti

17:0 Cyclic LPA

Avanti Research™ - A Croda Brand 857324P, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H42NO6P
CAS Number:
2260669-82-5
Molecular Weight:
423.52
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857324P-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 857324P

lipid type

phospholipids
cardiolipins

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

Application

17:0 Cyclic LPA or 1-heptadecanoyl-glycero-2,3-cyclic-phosphate (ammonium salt) has been used as an internal standard for the quantification of cyclic lysophosphatidic acid (LPA) esters 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 (857324P-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

Flash Point(F)

No data available

Flash Point(C)

No data available

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)
Naturally occurring analogs of lysophosphatidic acid elicit different cellular responses through selective activation of multiple receptor subtypes.
Fischer DL, et al.
Molecular Pharmacology, 54, 979-988 (1998)
Inhibition of tumor invasion and metastasis by a novel lysophosphatidic acid (cyclic LPA).
Mukai M, et al.
International Journal of Cancer. Journal International Du Cancer, 81, 918-922 (1999)
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)
Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons.
Fujiwara Y, et al.
Journal of Neurochemistry, 87, 1272-1283 (2003)
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