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857231P

Avanti

C18:1 Cyclic LPA

1-O-(9Z-octadecenyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder

Synonym(s):

1-O-octadecenyl-sn-glycero-2,3-cyclic-phosphate (ammonium salt); AGP 18:1

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About This Item

Empirical Formula (Hill Notation):
C21H44NO5P
CAS Number:
Molecular Weight:
421.55
UNSPSC Code:
51191904
NACRES:
NA.25

Assay

>99% (TLC)

form

powder

packaging

pkg of 1 × 1 mg (857231P-1mg)

manufacturer/tradename

Avanti Research - A Croda Brand 857231P

lipid type

cardiolipins
phospholipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

CCCCCCCC/C=C\CCCCCCCCOC[C@@H]1COP(O1)([O-])=O.[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.

Packaging

5 mL Amber Glass Screw Cap Vial (857231P-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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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)
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)
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)
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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