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U0383

Sigma-Aldrich

Umbelliferyl Arachidonate

ethanol solution

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C29H36O4
Numéro CAS:
161180-11-6
Poids moléculaire :
448.59
Numéro CE :
200-578-6
Numéro MDL:
MFCD00797670
Code UNSPSC :
41106300
ID de substance PubChem :
329827591
Nomenclature NACRES :
NA.32

Source biologique

synthetic (organic)

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

ethanol solution

Technique(s)

immunofluorescence: suitable

Solubilité

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

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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-

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Notes préparatoires

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.

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H319

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

57.2 °F - closed cup

Point d'éclair (°C)

14 °C - closed cup

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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
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

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