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E1406

Sigma-Aldrich

Embelin

≥98% (HPLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C17H26O4
Numéro CAS:
550-24-3
Poids moléculaire :
294.39
Numéro CE :
208-979-8
Numéro MDL:
MFCD00016369
Code UNSPSC :
12352200
ID de substance PubChem :
24724473
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: >10 mg/mL
H2O: insoluble

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria
parasites

Mode d’action

DNA synthesis | interferes

Chaîne SMILES 

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

Clé InChI

IRSFLDGTOHBADP-UHFFFAOYSA-N

Informations sur le gène

human ... XIAP(331)

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Description générale

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

Actions biochimiques/physiologiques

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.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H361f

Conseils de prudence

P201 - P308 + P313

Classification des risques

Repr. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "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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