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A231

Arachidonyl trifluoromethyl ketone

Name: Arachidonyl trifluoromethyl ketone
Brand: SIGMA

oil, ≥97% (NMR)

Synonym(s):

1,1,1-Trifluoromethyl-6,9,12,15-heieicosatetraen-2-one, AACOCF₃, Arach-CF₃

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₃₁F₃O

CAS Number:

149301-79-1

Molecular Weight:

356.47

NACRES:

NA.77

PubChem Substance ID:

24890647

UNSPSC Code:

51111800

MDL number:

MFCD00236427

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Quality Level

100

assay

≥97% (NMR)

form

oil

storage condition

desiccated, protect from light, under inert gas

color

yellow

solubility

DMSO: >5 mg/mL

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)C(F)(F)F

InChI

1S/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-

InChI key

PLWROONZUDKYKG-DOFZRALJSA-N

Gene Information

human ... PLA2G1B(5319)

Application

Arachidonyl trifluoromethyl ketone (AACOCF3) has been used as a anandamide degradation inhibitor to study its effects in primary astrocyte cultures.

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.

Inhibits anandamide hydrolysis in vitro; inhibits phospholipase A₂.

Features and Benefits

This compound is featured on the Phospholipase A2 page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Disclaimer

Hygroscopic, photosensitive, air sensitive

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Arachidonyl trifluoromethyl ketone ameliorates experimental autoimmune encephalomyelitis via blocking peroxynitrite formation in mouse spinal cord white matter.

Adam C Vana et al.

Experimental neurology, 231(1), 45-55 (2011-06-21)

Inhibition of phospholipase A(2) (PLA(2)) has recently been found to attenuate the pathogenesis of experimental autoimmune encephalomyelitis (EAE), a commonly used animal model of multiple sclerosis (MS). However, the protective mechanisms that underlie PLA(2) inhibition are still not well understood.

Altered spinal arachidonic acid turnover after peripheral nerve injury regulates regional glutamate concentration and neuropathic pain behaviors in rats.

Backil Sung et al.

Pain, 131(1-2), 121-131 (2007-02-03)

Spinal glutamate transporters (GT) have been implicated in the mechanisms of neuropathic pain; however, how spinal GT uptake activity is regulated remains unclear. Here we show that alteration of spinal arachidonic acid (AA) turnover after peripheral nerve injury regulated regional

Inhibitors of arachidonoyl ethanolamide hydrolysis.

B Koutek et al.

The Journal of biological chemistry, 269(37), 22937-22940 (1994-09-16)

Arachidonoyl ethanolamide (anandamide) is a naturally occurring brain constituent that binds to a specific brain cannabinoid receptor (CBR1). An amidase activity (anandamide amidase) in membrane fractions of brain and in cultured neuroblastoma cells rapidly degrades anandamide to arachidonic acid (Deutsch

Significance of the nongenomic, inflammatory pathway in mediating the toxic action of TCDD to induce rapid and long-term cellular responses in 3T3-L1 adipocytes.

Wen Li et al.

Biochemistry, 47(52), 13997-14008 (2008-12-10)

TCDD (dioxin) induces a rapid inflammatory response from 3T3-L1 adipocytes as judged by prominent induction of the mRNA expression of prostaglandin-endperoxide synthase 2 (Cox-2) along with other inflammation markers within 1 h. This action of TCDD is clearly antagonized by

Targeting cPLA2 derived lipid hydroperoxides as a potential intervention for sarcopenia.

Gavin Pharaoh et al.

Scientific reports, 10(1), 13968-13968 (2020-08-20)

Defects in neuromuscular innervation contribute significantly to the age-related decline in muscle mass and function (sarcopenia). Our previous studies demonstrated that denervation induces muscle mitochondrial hydroperoxide production (H2O2 and lipid hydroperoxides (LOOHs)). Here we define the relative contribution of mitochondrial

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Global Trade Item Number

SKU	GTIN
A231-5MG	04061832555386

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