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A231

Sigma-Aldrich

Arachidonyl trifluoromethyl ketone

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
MDL number:
MFCD00236427
UNSPSC Code:
51111800
PubChem Substance ID:
24890647
NACRES:
NA.77

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.

Caution

Hygroscopic, photosensitive, air sensitive

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Arachidonyl trifluoromethyl ketone, a potent inhibitor of 85-kDa phospholipase A2, blocks production of arachidonate and 12-hydroxyeicosatetraenoic acid by calcium ionophore-challenged platelets.
Riendeau D, et al.
The Journal of Biological Chemistry, 269(22), 15619-15624 (1994)
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
Amanda Linkous et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 15(5), 1635-1644 (2009-02-26)
In vascular endothelial cells, low doses of ionizing radiation trigger the immediate activation of cytosolic phospholipase A2 (cPLA2). This event initiates prosurvival signaling that could be responsible for radioresistance of tumor vasculature. Thus, the development of radiosensitizers targeting these survival
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
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.
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