Skip to Content
Merck
CN

A231

Arachidonyl trifluoromethyl ketone

oil, ≥97% (NMR)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

Arachidonyl trifluoromethyl ketone, oil, ≥97% (NMR)

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-

SMILES string

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

InChI key

PLWROONZUDKYKG-DOFZRALJSA-N

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

Quality Level

100

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.

Disclaimer

Hygroscopic, photosensitive, air sensitive

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.

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
015M4604V
120M4606V
067K4621
064K4612
013K4604

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
The endogenous cannabinoid anandamide potentiates interleukin-6 production by astrocytes infected with Theiler's murine encephalomyelitis virus by a receptor-mediated pathway
Molina H, et al.
Febs Letters, 433(1-2), 139-142 (1998)
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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service