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P8727

Sigma-Aldrich

Palmityl trifluoromethyl ketone

phosholipase A2 inhibitor

Synonym(s):

PACOCF3, Pentadecyl trifluoromethyl ketone

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About This Item

Empirical Formula (Hill Notation):
C17H31F3O
CAS Number:
141022-99-3
Molecular Weight:
308.42
MDL number:
MFCD00797669
UNSPSC Code:
12352202
PubChem Substance ID:
329820334
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (TLC)

form

liquid

concentration

10 mg/mL in ethanol

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCCC(=O)C(F)(F)F

InChI

1S/C17H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(21)17(18,19)20/h2-15H2,1H3

InChI key

MAHYXYTYTLCTQD-UHFFFAOYSA-N

Biochem/physiol Actions

Reversible inhibitor of calcium-dependent phospholipase A2 (IC50 = 3.8 μM). Unlike other PLA2 inhibitors studied, PACOCF3 at 50 μM induced an increase in intracellular [Ca2+], and at 10 μM, enhanced calcium-ion influx induced by ATP and bradykinin.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

57.2 °F - closed cup

flash_point_c

14.0 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Dual action of palmitoyl trifluoromethyl ketone (PACOCF3) on Ca2+ signaling: activation of extracellular Ca2+ influx and alteration of ATP- and bradykinin-induced Ca2+ responses in Madin Darby canine kidney cells
Jan, C.R., et al.
Toxicology, 74, 447-451 (2000)
Oscar Yanes et al.
Nature chemical biology, 6(6), 411-417 (2010-05-04)
Metabolites offer an important unexplored complementary approach to understanding the pluripotency of stem cells. Using MS-based metabolomics, we show that embryonic stem cells are characterized by abundant metabolites with highly unsaturated structures whose levels decrease upon differentiation. By monitoring the
Y C Lio et al.
Biochimica et biophysica acta, 1302(1), 55-60 (1996-07-12)
Methyl arachidonyl fluorophosphonate (MAFP) has been recently reported to be a selective, active-site directed, irreversible inhibitor of the Group IV 85 kDa cytosolic phospholipase A2 (cPLA2). We have now shown that this compound also potently inhibits the Ca(2+)-independent cytosolic phospholipase
Susann Liebscher et al.
PLoS pathogens, 14(4), e1007029-e1007029 (2018-05-01)
Positive-sense RNA virus intracellular replication is intimately associated with membrane platforms that are derived from host organelles and comprised of distinct lipid composition. For flaviviruses, such as West Nile virus strain Kunjin virus (WNVKUN) we have observed that these membrane
E J Ackermann et al.
The Journal of biological chemistry, 270(1), 445-450 (1995-01-06)
A novel Ca(2+)-independent phospholipase A2 (PLA2) has recently been purified from the murine macrophage-like cell line P388D1 (Ackermann, E. J., Kempner, E. S., and Dennis, E. A. (1994) J. Biol. Chem. 269, 9227-9233). This enzyme is now shown to be

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