[CAS NO. 550-24-3] Embelin

Name: Embelin
Brand: Arctom Scientific
SKU: SLK-S7025

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PRODUCTS SPECIFICATIONS [550-24-3]

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Catalog

SLK-S7025

Brand

Selleck

CAS

550-24-3

DESCRIPTION [550-24-3]

Overview

MDL	MFCD00016369
Molecular Weight	294.39
Molecular Formula	C17H26O4
SMILES	C(CCCCCCCCCC)C=1C(=O)C(O)=CC(=O)C1O

For research use only.

Storage

3 years,-20°C,powder
1 years,-80°C,in solvent

Shipping

Room temperature shipping(Stability testing shows this product can be shipped without any cooling measures.)

Preparing Stock Solutions

Concentration Volume Mass	1 mg	5 mg	10 mg
1 mM	3.3969 mL	16.9843 mL	33.9685 mL
5 mM	0.6794 mL	3.3969 mL	6.7937 mL
10 mM	0.3397 mL	1.6984 mL	3.3969 mL
50 mM	0.0679 mL	0.3397 mL	0.6794 mL

Description

Embelin (Embelic Acid, NSC 91874), a quinone isolated from the Japanese Ardisia herb, is an inhibitor of X-linked inhibitor of apoptosis (XIAP) with of 4.1 μM in a cell-free assay.

Targets

5-LO ^[2] (Cell-free assay)	mPGES-1 ^[2] (Cell-free assay)	XIAP ^[1] (Cell-free assay)
0.06 μM	0.2 μM	4.1 μM

In vitro

Embelin from the Japanese Ardisia herb is a small-molecular inhibitor that binds to the XIAP BIR3 domain with which Smac and caspsase-9 bind. Embelin inhibits cell growth of both PC-3 and LNCap cells in a dose-dependent manner, with IC50 values of 3.7 and 5.7 μM. While, the toxicity of Embelin in normal PrEC and in WI-38 cells is much lower with IC50 values of 20.1 μM and 19.3 μM. Treatment of PC-3 cells with 25 and 50 μM of embelin for 48 h, 30% and 75% of cells undergo apoptosis, representing approximately 3-and 9-fold increase as compared to untreated cells. Embelin also potently suppresses the biosynthesis of eicosanoids by selective inhibition of 5-lipoxygenase (5-LO) and Microsomal prostaglandin E2 synthase-1 (mPGES-1) with IC50 = 0.06 and 0.2 mM, respectively.

References

[1] Nikolovska-Coleska Z, et al. J Med Chem, 2004, 47(10), 2430-2440.
[2] Schaible AM, et al. Biochem Pharmacol, 2013, 86(4), 476-486.

Synonyms

2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl-

p-Benzoquinone, 2,5-dihydroxy-3-undecyl-

Embelin

2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione

Embelic acid

Emberine

NSC 91874

2,5-Dihydroxy-3-undecyl-1,4-benzoquinone

2,5-Dihydroxy-3-undecylcyclohexa-2,5-dien-1,4-dione