Skip to Content
MilliporeSigma
All Photos(1)

Documents

U0383

Sigma-Aldrich

Umbelliferyl Arachidonate

ethanol solution

Synonym(s):

5Z,8Z,11Z,14Z-Eicosatetraenoic acid 2-oxo-2H-1-benzopyran-7-yl ester, 7-Hydroxycoumarinyl Arachidonate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C29H36O4
CAS Number:
161180-11-6
Molecular Weight:
448.59
EC Number:
200-578-6
MDL number:
MFCD00797670
UNSPSC Code:
41106300
PubChem Substance ID:
329827591
NACRES:
NA.32

biological source

synthetic (organic)

Quality Level

200

assay

≥98% (HPLC)

form

ethanol solution

technique(s)

immunofluorescence: suitable

solubility

DMSO: soluble 25 mg/mL
DMF: soluble 50 mg/mL
aqueous buffer: slightly soluble

shipped in

wet ice

storage temp.

−20°C

SMILES string

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)Oc1ccc2C=CC(=O)Oc2c1

InChI

1S/C29H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(30)32-26-22-20-25-21-23-29(31)33-27(25)24-26/h6-7,9-10,12-13,15-16,20-24H,2-5,8,11,14,17-19H2,1H3/b7-6-,10-9-,13-12-,16-15-

InChI key

SFTGFGOBCQCZDY-DOFZRALJSA-N

Application

Umbelliferyl Arachidonate also known as 7-Hydroxycoumarinyl Arachidonate was used as a fluorogenic substrate for developing a fluorescence-based assay to evaluate the inhibitors against human recombinant monoacylglycerol lipase.

Biochem/physiol Actions

Monoacylglycerol lipase (MAGL) protein facilitates the hydrolysis of Umbelliferyl Arachidonate and generates arachidonic acid and the highly fluorescent 7-hydroxyl coumarin (7-HC). Hence, it acts as a marker in a fluorescence-based assay.

Preparation Note

Umbelliferyl Arachidonate can be dissolved in DMSO at 25 mg/ml and in DMF at 50 mg/ml. The product is sparingly soluble in aqueous buffers.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

57.2 °F - closed cup

flash_point_c

14 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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’.

Already Own This Product?

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

Visit the Document Library

Z Huang et al.
Analytical biochemistry, 222(1), 110-115 (1994-10-01)
A sensitive method for continuously monitoring the activity of the human cytosolic phospholipase A2 (cPLA2) is described. Recombinant cPLA2 efficiently hydrolyzes fatty acid esters of 7-hydroxycoumarin, producing the free fatty acid and the highly fluorescent 7-hydroxycoumarin. All of the observed
Angela Holtfrerich et al.
Analytical biochemistry, 399(2), 218-224 (2009-12-18)
A fluorescent assay for the evaluation of inhibitors of monoacylglycerol lipase (MAGL) is described. 1,3-Dihydroxypropan-2-yl 4-pyren-1-ylbutanoate was designed and synthesized as novel fluorogenic substrate. Activity of human recombinant MAGL was determined in the presence of the surfactant Triton X-100 without
Céline Schalk-Hihi et al.
Protein science : a publication of the Protein Society, 20(4), 670-683 (2011-02-11)
A high-resolution structure of a ligand-bound, soluble form of human monoglyceride lipase (MGL) is presented. The structure highlights a novel conformation of the regulatory lid-domain present in the lipase family as well as the binding mode of a pharmaceutically relevant
Yuren Wang et al.
Assay and drug development technologies, 6(3), 387-393 (2008-05-03)
A novel fluorescence-based assay of monoacylglycerol lipase (MAGL) activity that is simple, sensitive, and amenable to the screening of small molecule inhibitors is described. Purified recombinant human MAGL protein and 7-hydroxycoumarinyl-arachidonate (7-HCA), a fluorogenic substrate for MAGL, were employed in
E Turk et al.
The Journal of biological chemistry, 271(4), 1925-1934 (1996-01-26)
The membrane topology of the human Na+/glucose cotransporter SGLT1 has been probed using N-glycosylation scanning mutants and nested truncations. Functional analysis proved essential for establishment of signal-anchor topology. The resultant model diverges significantly from previously held suppositions of structure based

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