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E1406

Sigma-Aldrich

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
EC Number:
208-979-8
MDL number:
MFCD00016369
UNSPSC Code:
12352200
PubChem Substance ID:
24724473
NACRES:
NA.77

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

SMILES string

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

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

InChI key

IRSFLDGTOHBADP-UHFFFAOYSA-N

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 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.
Embelin is an inhibitor of XIAP (X-linked inhibitor-of-apoptosis protein); in vivo antitumor and anti-inflammatory activity.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361f

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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’.

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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)
Uday P Kundap et al.
Frontiers in pharmacology, 8, 76-76 (2017-03-16)
A Central nervous system (CNS) disease is the one which affects either the spinal cord or brain and causing neurological or psychiatric complications. During the nineteenth century, modern medicines have occupied the therapy for many ailments and are widely used
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
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
Zhonghui Lin et al.
Chemistry & biology, 20(2), 253-261 (2013-02-27)
Plasminogen activator inhibitor-1 (PAI-1), a serpin, is the physiological inhibitor of tissue-type and urokinase-type plasminogen activators and thus also an inhibitor of fibrinolysis and tissue remodeling. It is a potential therapeutic target in many pathological conditions, including thrombosis and cancer.
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