149301-79-1

149301-79-1 structure

Name: Arachidonyl trifluoromethyl ketone
Chemical Name: aacocf3
CAS Number: 149301-79-1
Molecular Formula: C₂₁H₃₁F₃O
Molecular Weight: 356.465
Catalog: Signaling Pathways Metabolic Enzyme/Protease Phospholipase
Create Date: 2018-07-22 17:01:41
Modify Date: 2024-01-10 12:21:08
AACOCF3 (Arachidonyl trifluoromethyl ketone) is a cell-permeant trifluoromethyl ketone analog of arachidonic acid. AACOCF3 is a potent and selective slow binding inhibitor of the 85-kDa cytosolic phospholipase A2 (cPLA2). AACOCF3 blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. AACOCF3 inhibits glucose-induced insulin secretion from isolated rat islets. AACOCF3 has the potential for the research of cardiovascular disease[1][2][3].

Name	aacocf3
Synonyms	Arachidonic acid trifluoromethyl ketone AACOCF3 Arachidonyl trifluoromethyl ketone UNII:00XIW1CR0F Arachidonic acid trifluoromethylketone MFCD00236427 6,9,12,15-Heneicosatetraen-2-one, 1,1,1-trifluoro-, (6Z,9Z,12Z,15Z)- (6Z,9Z,12Z,15Z)-1,1,1-Trifluoro-6,9,12,15-henicosatetraen-2-one Arach-CF3 Arachidonyltrifluoromethane (6Z,9Z,12Z,15Z)-1,1,1-Trifluorohenicosa-6,9,12,15-tetraen-2-one

Description	AACOCF3 (Arachidonyl trifluoromethyl ketone) is a cell-permeant trifluoromethyl ketone analog of arachidonic acid. AACOCF3 is a potent and selective slow binding inhibitor of the 85-kDa cytosolic phospholipase A2 (cPLA2). AACOCF3 blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. AACOCF3 inhibits glucose-induced insulin secretion from isolated rat islets. AACOCF3 has the potential for the research of cardiovascular disease[1][2][3].
Related Catalog	Research Areas >> Cardiovascular Disease Signaling Pathways >> Metabolic Enzyme/Protease >> Phospholipase
In Vitro	AACOCF3 inhibits the release of arachidonic acid from calcium ionophore-challenged U937 cells (IC50= 8 μM, 2 x 106 cells ml-1) and from platelets (IC50= 2 μM, 4 x 107 cells ml-1)[1]. AACOCF3 (10 μM) suppresses phosphate-induced calcification and osteogenic/chondrogenic signaling in HAoSMCs. AACOCF3 significantly inhibits both basal and Pi-induced release of arachidonic acid, the product of PLA2 activity[2].
In Vivo	AACOCF3 (10 mg/kg; gavage; 5 days a week; ApoE–/– mice (6-week-old males) were fed a high-cholesterol diet) significantly reduces type III collagen plaque expression but had no significant influence on total collagen accumulation[3].
References	[1]. Riendeau D, et al. Arachidonyl trifluoromethyl ketone, a potent inhibitor of 85-kDa phospholipase A2, blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets. J Biol Chem. 1994;269(22):15619-15624. [2]. Schanstra JP, et al. Systems biology identifies cytosolic PLA2 as a target in vascular calcification treatment. JCI Insight. 2019;4(10):e125638. Published 2019 May 16. [3]. Loweth AC, et al. A specific inhibitor of cytosolic phospholipase A2 activity, AACOCF3, inhibits glucose-induced insulin secretion from isolated rat islets. Biochem Biophys Res Commun. 1996;218(2):423-427.

Density	1.0±0.1 g/cm3
Boiling Point	421.7±45.0 °C at 760 mmHg
Molecular Formula	C₂₁H₃₁F₃O
Molecular Weight	356.465
Flash Point	288.7±20.2 °C
Exact Mass	356.232697
PSA	17.07000
LogP	7.78
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.463

Personal Protective Equipment	Eyeshields;Gloves;half-mask respirator (US);multi-purpose combination respirator cartridge (US)
Hazard Codes	Xi
RIDADR	NONH for all modes of transport

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