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Merck
CN

857231P

Avanti

C18:1 Cyclic LPA

Avanti Research™ - A Croda Brand

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:
799268-69-2
Molecular Weight:
421.55
UNSPSC Code:
51191904
NACRES:
NA.25

Key Documents

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Product Name

C18:1 Cyclic LPA, 1-O-(9Z-octadecenyl)-sn-glycero-2,3-cyclic-phosphate (ammonium salt), powder

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+]

InChI

1S/C21H41O5P.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24-19-21-20-25-27(22,23)26-21;/h9-10,21H,2-8,11-20H2,1H3,(H,22,23);1H3/b10-9-;/t21-;/m1./s1

InChI key

OQYRMQWRTNWOER-WBIWQBECSA-N

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

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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)
Cyclic phosphatidic acid elicits neurotrophin-like actions in embryonic hippocampal neurons.
Fujiwara Y, et al.
Journal of Neurochemistry, 87, 1272-1283 (2003)
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)
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
Yuko Fujiwara
Biochimica et biophysica acta, 1781(9), 519-524 (2008-06-17)
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
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