| Identification | Back Directory | [Name]
2-chloro Palmitic Acid | [CAS]
19117-92-1 | [Synonyms]
2-chloro Palmitic Acid
2chloro Palmitic Acid,2 chloro Palmitic Acid | [Molecular Formula]
C16H31ClO2 | [MDL Number]
MFCD32695028 | [MOL File]
19117-92-1.mol | [Molecular Weight]
290.87 |
| Chemical Properties | Back Directory | [Melting point ]
52-53 °C | [Boiling point ]
394.6±15.0 °C(Predicted) | [density ]
0.972±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2) (1:3): 0.25 mg/ml | [form ]
A crystalline solid | [pka]
2.97±0.21(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Description]
2-chloro Palmitic acid is a monochlorinated form of palmitic acid . It is produced in a myeloperoxidase (MPO) and time-dependent manner in neutrophils stimulated by phorbol 12-myristate 13-acetate (PMA; ). 2-chloro Palmitic acid (10 μM) induces neutrophil extracellular trap (NET) formation (NETosis) in human neutrophils, increasing DNA release from neutrophils, colocalization of MPO with extracellular DNA (ecDNA), and trapping of E. coli.1 It increases COX-2 protein levels in human coronary artery endothelial cells (HCAECs) when used at a concentration of 50 μM and increases production of P-selectin, von Willebrand factor, and angiopoietin-2 in HCAECs, as well as neutrophil and platelet adherence, when used at a concentration of 10 μM.2,3 2-chloro Palmitic acid (10-50 μM) also induces apoptosis in THP-1 cells and primary human monocytes and increases caspase-3 activity in THP-1 cells.4 | [References]
1. Palladino, E.N.D., Katunga, L.A., Kolar, G.R., et al. 2-Chlorofatty acids: Lipid mediators of neutrophil extracellular trap formation J. Lipid. Res. 59(8),1424-1432(2018).
2. Messner, M.C., Albert, C.J., and Ford, D.A. 2-Chlorohexadecanal and 2-chlorohexadecanoic acid induce COX-2 expression in human coronary artery endothelial cells Lipids 43(7),581-588(2008).
3. Hartman, C.L., Duerr, M.A., Albert, C.J., et al. 2-Chlorofatty acids induce Weibel-Palade body mobilization J. Lipid. Res. 59(1),113-122(2018).
4. Wang, W.Y., Albert, C.J., and Ford, D.A. α-Chlorofatty acid accumulates in activated monocytes and causes apoptosis through reactive oxygen species production and endoplasmic reticulum stress Arterioscler. Thromb. Vasc. Biol. 34(3),526-532(2014). |
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