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Merck

E1406

Embelin

≥98% (HPLC), powder

Synonym(s):

2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione, Embelic acid, Emberine

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About This Item

Empirical Formula (Hill Notation):
C17H26O4
CAS Number:
550-24-3
Molecular Weight:
294.39
NACRES:
NA.77
PubChem Substance ID:
24724473
UNSPSC Code:
12352200
EC Number:
208-979-8
MDL number:
MFCD00016369
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
200

Key Documents

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InChI key

IRSFLDGTOHBADP-UHFFFAOYSA-N

InChI

1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3

SMILES string

CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O

assay

≥98% (HPLC)

form

powder

solubility

DMSO: >10 mg/mL, H2O: insoluble

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, parasites

mode of action

DNA synthesis | interferes

Quality Level

200

Gene Information

human ... XIAP(331)

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General description

Embelin, a natural benzoquinone-derivative, was initially extracted from Embelia ribes plant. It is structurally similar to ubiquinone.

Application

Embelin has been used:
  • to study its effects on the receptor activator of nuclear factor kappa-B ligand (RANKL)-induced nuclear factor of activated T cells (NFATc1) luciferase activity
  • to study its role in the mechanisms mediating Parkinson′s disease (PD)
  • in treating whole mouse embryos to determine its effects on the X-linked inhibitory apoptosis protein (XIAP) activity

Biochem/physiol Actions

Embelin is an inhibitor of XIAP (X-linked inhibitor-of-apoptosis protein); in vivo antitumor and anti-inflammatory activity.
Embelin elicits anti-oxidant, mitochondrial uncoupling, and anti-fertility properties. It also has anti-diabetic, anti-convulsant, anxiolytic, and anti-microbial activities. Embelin acts as a potent neuroprotective agent and is also beneficial as an adjunct therapy for cerebral stroke.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361f

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000273474
0000273474
0000267261
0000267261
0000150865

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Feng Li et al.
Biomacromolecules, 11(10), 2610-2620 (2010-09-02)
The objective of this study was to design lipopolymers for hydrophobic drug delivery. Poly(ethylene glycol)-block-poly(2-methyl-2-carboxyl-propylene carbonate-graft-dodecanol) (PEG-PCD) lipopolymers were synthesized and characterized by (1)H NMR, FT-IR, GPC, and DSC. The critical micelle concentration (CMC) of PEG-PCD micelles was around 10(-8)
Yixian Huang et al.
Bioconjugate chemistry, 23(7), 1443-1451 (2012-06-12)
Embelin, identified primarily from the Embelia ribes plant, has been shown to be a natural small molecule inhibitor of X-linked inhibitor of apoptosis protein (XIAP). It is also a potent inhibitor of NF-κB activation, which makes it a potentially effective
G Kalyan Kumar et al.
European journal of pharmacology, 662(1-3), 63-69 (2011-05-10)
Tumor necrosis factor-α (TNF-α) is known to play a crucial role in the pathogenesis of psoriasis. The present study was designed to investigate the effects of embelin on lipopolysachharide induced TNF-α production in mice and in human keratinocytes in vitro
Sang-Yoon Park et al.
Journal of pharmacological sciences, 121(3), 192-199 (2013-03-22)
Aggressive tumor growth and diffuse tissue invasion are hallmarks of malignant glioma. Embelin is an active compound identified as a novel XIAP inhibitor from the Embelia ribes that exhibits various medicinal effects including anti-inflammatory and anti-cancer activities. In the present
Boreddy Shivanandappa Thippeswamy et al.
European journal of pharmacology, 654(1), 100-105 (2010-12-28)
The aim of the present study is to evaluate the effect of embelin isolated from Embelia ribes on acetic acid induced colitis in rats. Experimental animals received embelin (25 and 50 mg/kg, p.o.) and sulfasalazine (100mg/kg, p.o.) for five consecutive
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