149301-79-1

Basic information

• Product Name: AACOCF3
• Synonyms: arachidonyltrifluoromethane;ATK;ARACHIDONIC ACID TRIFLUOROMETHYLKETONE;ARACHIDONOYL TRIFLUOROMETHYL KETONE;ARACHIDONYL TRIFLUOROMETHYLKETONE;1,1,1-TRIFLUOROMETHYL-6,9,12,15-HEIEICOSATETRAEN-2-ONE;1,1,1-TRIFLUORO-6,9,12,15-HENEICOSATETRAEN-2-ONE;1,1,1-TRIFLUORO-6Z,9Z,12Z,15Z-HENEICOSATERAEN-2-ONE
• CAS NO: 149301-79-1
• Molecular Formula: C21H31F3O
• Molecular Weight: 356.47
• Product Categories: Lipid signaling
• Mol File: 149301-79-1.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 421.7 °C at 760 mmHg
• Flash Point: 288.7 °C
• Appearance: yellow/liquid
• Density: 0.981 g/cm³
• Vapor Pressure: 2.56E-07mmHg at 25°C
• Refractive Index: 1.463
• Storage Temp.: −20°C
• Solubility: DMSO: >5 mg/mL
• Stability: Light Sensitive
• CAS DataBase Reference: AACOCF3(CAS DataBase Reference)
• NIST Chemistry Reference: AACOCF3(149301-79-1)
• EPA Substance Registry System: AACOCF3(149301-79-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 149301-79-1(Hazardous Substances Data)

Usage

Description

AACOCF3, also known as Arachidonyl trifluoromethyl ketone, is a fatty acid derivative derived from arachidonic acid. In this compound, the hydroxyl group (OH) of the carboxy group is replaced by a trifluoromethyl group. This modification gives AACOCF3 unique properties and potential applications in various fields.

Uses

Used in Pharmaceutical Research:
AACOCF3 is used as an anandamide degradation inhibitor for studying its effects in primary astrocyte cultures. Anandamide is an endogenous cannabinoid that plays a role in various physiological processes, including pain regulation, mood, and appetite. By inhibiting the degradation of anandamide, AACOCF3 can help researchers understand the underlying mechanisms and potential therapeutic applications of this compound.
Used in Neuroscience:
AACOCF3's role as an anandamide degradation inhibitor makes it a valuable tool in neuroscience research. It can be used to investigate the effects of anandamide on neuronal function and signaling pathways, as well as its potential role in neurological disorders and conditions such as chronic pain, anxiety, and depression.
Used in Drug Development:
The unique properties of AACOCF3, as an anandamide degradation inhibitor, make it a promising candidate for the development of new drugs targeting the endocannabinoid system. This system is involved in various physiological processes, and modulating its activity could lead to the development of novel therapeutics for a range of conditions, including pain management, neurodegenerative diseases, and mood disorders.

Biological Activity

Inhibitor of cytosolic (85 kDa) phospholipase A 2 . Also inhibits fatty acid amide hydrolase (FAAH, anandamide amidase) in vitro .

Biochem/physiol Actions

Arachidonyl trifluoromethyl ketone (AACOCF3) plays a role in the inhibition of 12-hydroxyeicosatetraenoic acid (12-HETE) and thromboxane B2 produced by the platelets.

references

[1]. ackermann ej, conde-frieboes k, dennis ea. inhibition of macrophage ca(2+)-independent phospholipase a2 by bromoenol lactone and trifluoromethyl ketones. j biol chem, 1995, 270(1): 445-450.[2]. riendeau d, guay j, weech pk, 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.[3]. malaviya r, ansell j, hall l, et al. targeting cytosolic phospholipase a2 by arachidonyl trifluoromethyl ketone prevents chronic inflammation in mice. eur j pharmacol, 2006, 539(3): 195-204.

InChI:InChI=1/C21H31F3O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(25)21(22,23)24/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-