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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

Signal Word

Warning

Hazard Statements

H361f

Precautionary Statements

P201 - P308 + P313

Hazard Classifications

Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Jennifer L Allensworth et al.
Molecular cancer therapeutics, 11(7), 1518-1527 (2012-04-18)
We recently identified superoxide dismutase (SOD) overexpression and decreased induction of reactive oxygen species (ROS)-mediated apoptosis in models of inflammatory breast cancer (IBC) cells with acquired therapeutic resistance. This population of cells has high expression of X-linked inhibitor of apoptosis
Jianqin Lu et al.
Biomaterials, 34(5), 1591-1600 (2012-11-28)
Paclitaxel (PTX) is one of the most effective chemotherapeutic agents for a wide spectrum of cancers, but its therapeutic benefit is often limited by severe side effects. We have developed a micelle-based PTX formulation based on a simple conjugate derived
Michael Danquah et al.
Pharmaceutical research, 29(8), 2079-2091 (2012-03-28)
Overexpression of the androgen receptor (AR) and anti-apoptotic genes including X-linked inhibitor of apoptosis protein (XIAP) provide tumors with a proliferative advantage. Therefore, our objective was to determine whether novel antiandrogen (CBDIV17) and XIAP inhibitor based combination therapy can treat
Sekar Mahendran et al.
Chemical & pharmaceutical bulletin, 59(8), 913-919 (2011-08-02)
Antioxidant and related properties of the plant Embelia ribes and embelin are well known. In the present study embelin was condensed with various aromatic substituted primary amines to yield ten new and one reported derivatives along with monomethyl embelin. All
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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