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)

Safety Information

WGK Germany 

3

RTECS 

DK4230000

MSDS

• Language:English Provider:SigmaAldrich

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. 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] RAHUL MODAK. Probing p300/CBP Associated Factor (PCAF)-Dependent Pathways with a Small Molecule Inhibitor[J]. ACS Chemical Biology, 2013, 8 6: 1311-1323. DOI:10.1021/cb4000597
[2] ZANETA NIKOLOVSKA-COLESKA. 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]. Journal of Medicinal Chemistry, 2004, 47 10: 2430-2440. DOI:10.1021/jm030420+
[3] PRIYANK SHAH. Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells[J]. Pharmacological Reports, 2016, 68 3: Pages 638-644. DOI:10.1016/j.pharep.2016.01.004
[4] M CHITRA. Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.[J]. Chemotherapy, 1994, 40 2: 109-113. DOI:10.1159/000239181

EMBELIN(550-24-3)Related Product Information

• EMBELIN
• EMBELIN(P),EMBELIN(RG)
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• ACETIC ACID 4-HYDROXY-2-METHYL-5-((E)-NONADEC-14-ENYL)-3,6-DIOXO-CYCLOHEXA-1,4-DIENYL ESTER
• 2,5-DIMETHOXY-3-UNDECYL-[1,4]BENZOQUINONE
• ACETIC ACID 4-HYDROXY-3,6-DIOXO-5-UNDECYL-CYCLOHEXA-1,4-DIENYL ESTER
• 2-HYDROXY-5-METHOXY-6-METHYL-3-((E)-NONADEC-14-ENYL)-[1,4]BENZOQUINONE