Embelin An anti-nociceptive, anti-inflammatory, and anti-oxidant agent also shown to induce apoptosis

Embelin (CAS 550-24-3)

Embelin | CAS 550-24-3 is rated 5.0 out of 5 by 2.
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Synonym: Embelic acid;2,5-Dihydroxy-3-undecyl-1,4-benzoquinone
Application: An anti-nociceptive, anti-inflammatory, and anti-oxidant agent also shown to induce apoptosis
CAS Number: 550-24-3
Purity: 98%
Molecular Weight: 294.38
Molecular Formula: C17H26O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Embelin, a cell permeable 1,4-Benzoquinone (sc-202873)-derivative originally isolated from Embelia ribes, has been shown to contain antiproliferative characteristics in 3-Methylcholanthrene (sc-216516)-induced fibrosarcoma in albino rats. This compound has also been reported to be an antinociceptive and antiinflammatory agent. Additionally, Embelin has been found to display antibacterial potential against 3 strains of 12 bacteria. Other studies have reported Embelin to have apoptosis induction capabilities through binding of BIR3 domain of XIAP (X-linked inhibitor of apoptosis protein). The antioxidant capabilities of Embelin have also been studied and mechanistic studies suggest that Embelin has a tendency to scavenge DPPH (sc-202591) radicals and inhibit hydroxyl radical induced deoxyribose degradation. This compound prevents the activation of NF-κB by inhibiting IKK. Embelin is an inhibitor of PCAF and XIAP and an activator of caspase-9.


References

1. Chitra, M., et al. 1994. Chemotherapy. 40: 109-113. PMID: 7510605
2. Chitra, M., et al. 2003. Fitoterapia. 74: 401-403. PMID: 12781816
3. Nikolovska-Coleska, Z., et al. 2004. J. Med. Chem. 47: 2430-2440. PMID: 15115387
4. Joshi, R., et al. 2007. Chem. Biol. Interact. 167: 125-134. PMID: 17379198

Physical State :
Solid
Derived From :
Embelia ribes
Solubility :
Soluble in DMSO (>10 mg/ml), methanol, ethanol (10 mM), and chloroform. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
142-143° C
Boiling Point :
~431.9° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.54
IC50 :
cell growth, induces apoptosis and activates caspase-9 : IC50 = 4-6 µM ( prostate cancer cells); cell growth, induces apoptosis and activates caspase-9 : IC50 = 19-20 µM (normal prostate cells); BGC-823 (Stomach adenocarcinoma cells): IC50 = 1.69 µM (human); PC-3 (Prostate carcinoma cells): IC50 = 3.7 µM (human); A549 (Lung carcinoma cells): IC50 = 1.47 µM (human); Jurkat (Acute leukemic T-cells): IC50 = 20 µM (human); Inhibitor of apoptosis protein 3: IC50 = 4.1 µM (human); LNCaP (Prostate carcinoma): IC50 = 5.70 µM (human); WI-38 5000: IC50 = 19.3 µM (human); A2780 (Ovarian carcinoma cells): IC50 = 1.79 µM (human); PrEC50: IC50 = 20.1 µM (human); Bel-7402 (Hepatoma cells): IC50 = 1.66 µM (human); WI-38 (Embryonic lung fibroblast cells): IC50 = 19.3 µM (human); SK(-)GAS Group A Streptococcus: EC5050 = 1.58 µM; Streptokinase Promotor Activity: EC5050 = 1.67 µM; Streptococcus: EC5050 = 3.32 µM; mammalian fibroblasts: EC5050 = 5.02 µM
Ki Data :
Inhibitor of apoptosis protein 3: Ki= 400 nM (human)
pK Values :
pKa: 2.84
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
DK4230000
PubChem CID :
3218
Merck Index :
14: 3555
MDL Number :
MFCD00016369
EC Number :
208-979-8
SMILES :
CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O

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Embelin  Product Citations

See how others have used Embelin. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 29113338  Chen, P. et al. 2017. Oncotarget. 8: 80709-80721.

PMID: # 23749209  Huang, X. et al. 2013. The EMBO journal. 32: 2204-16.

PMID: # 15115387  Nikolovska-Coleska, Z. et al. 2004. J. Med. Chem. 47: 2430-2440.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Good Good!
Date published: 2015-10-08
Rated 5 out of 5 by from Huang Huang, et. al. (PubMed ID 23749209) treated HCT116 cells with Embelin (purchased from SCBT) and found that it enhanced both conversion of LC3-I to LC3-II and formation of GFP-LC3 puncta in a dose and time dependent manner. However, it failed to enhance autophagy in HCT116 XIAP KO cells. -SCBT Publication Review
Date published: 2015-06-13
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