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EMBELIN

Basic information Safety Supplier Related

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
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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)
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Safety Information

WGK Germany 
3
RTECS 
DK4230000

MSDS

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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

EMBELINSupplier

J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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jkinfo@jkchemical.com
3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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3bsc@sina.com
Chembest Research Laboratories Limited
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021-20908456
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Wuhan Chemwish Technology Co., Ltd
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86-027-67849912
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sales@chemwish.com
Shanghai Sinch Parmaceuticals Tech. Co. Ltd.
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+86-21-54098501
Email
sales@sinch.com.cn