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| | EMBELIN Basic information |
| Product Name: | EMBELIN | | Synonyms: | 2,5-dihydroxy-3-undecyl-p-benzoquinon;4-dione,2,5-dihydroxy-3-undecyl-5-cyclohexadiene-1;embelicacid;emberine;APOPTOSIS ACTIVATOR III;2,5-Cyclohexadiene-1,4-dione,2,5-dihydroxy-3-undecyl-;Embelin, >98%;Apoptosis Activator III, Embelin - CAS 550-24-3 - Calbiochem | | CAS: | 550-24-3 | | MF: | C17H26O4 | | MW: | 294.39 | | EINECS: | 208-979-8 | | Product Categories: | Inhibitors;Anthraquinones, Hydroquinones and Quinones;Caspases/Apoptosis | | Mol File: | 550-24-3.mol |  |
| | EMBELIN Chemical Properties |
| Melting point | 142-143°C | | Boiling point | 356.15°C (rough estimate) | | density | 1.131 | | refractive index | 1.4230 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | DMSO: >10 mg/mL | | form | solid | | pka | 2.84±0.50(Predicted) | | color | Dark orange | | Sensitive | Light Sensitive | | Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | | LogP | 5.024 (est) |
| WGK Germany | 3 | | RTECS | DK4230000 |
| | EMBELIN Usage And Synthesis |
| Description | Embelin (550-24-3) inhibits?the lysine acetyl transferase PCAF?in vitro and in vivo?(in vitro?IC50=7.2 mM). Inhibits H3K9 acetylation in mouse liver tissue while leaving levels of H3K14, H4K8, H4K12 unchanged.1? Also inhibits X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM, competing with Smac peptide). Binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Induces apoptosis and alters gene expression profiles in breast cancer cells.3?Possesses anti-inflammatory and analgesic activity?in vivo.4?Cell-permeable. | | Chemical Properties | Orange Solid | | Uses | Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embel
in also displays contraceptive and pro-apoptotic properties. | | Uses | Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embelin also displays contraceptive and pro-apoptotic properties. | | Definition | ChEBI: A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, an
ineoplastic and inhibitory activity towards hepatitis C protease. | | Biological Activity | Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC 50 = 4.1 μ M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC 50 4-6 μ M), but has a weaker effect on normal prostate cells (IC 50 = 19-20 μ M). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo . | | References | 1) Modak?et al. (2013),?Probing p300/CBP associated factor (PCAF)-dependent pathways with a small molecule inhibitor; ACS Chem. Biol.,?8?1311
2) Nikolovska-Coleska?et al. (2004),?Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database; J. Med. Chem.,?47?2430
3) Shah?et al.?(2016),?Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells; Pharmacol. Rep.,?68?638
4) Chitra?et al. (1994),?Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.; Chemotherapy,?40?109 |
| | EMBELIN Preparation Products And Raw materials |
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