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ChemicalBook--->CAS DataBase List--->550-24-3

550-24-3

550-24-3 Structure

550-24-3 Structure
IdentificationBack Directory
[Name]

EMBELIN
[CAS]

550-24-3
[Synonyms]

EMBELIN
emberine
NSC 91874
embelicacid
EMbeliaquinone
XIAP INHIBITOR
TIMTEC-BB SBB005949
Embelin (Embelic acid)
APOPTOSIS ACTIVATOR III
embelin from embelia seeds
Apoptosis Activator III, Embelin
2,5-dihydroxy-3-undecyl-p-benzoquinon
2,5-DIHYDROXY-3-UNDECYL-P-BENZOQUINONE
2,5-DIHYDROXY-3-UNDECYL-1,4-BENZOQUINONE
2,5-DIHYDROXY-3-UNDECYL-P-BENZOQUINONE, EMBELIN
4-dione,2,5-dihydroxy-3-undecyl-5-cyclohexadiene-1
2,5-DIHYDROXY-3-UNDECYL-2,5-CYCLOHEXADIENE-1,4-DIONE
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
2,5-dihydroxy-3-undecyl-cyclohexa-2,5-diene-1,4-dione
2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl- free base
[EINECS(EC#)]

208-979-8
[Molecular Formula]

C17H26O4
[MDL Number]

MFCD00016369
[MOL File]

550-24-3.mol
[Molecular Weight]

294.39
Chemical PropertiesBack Directory
[Melting point ]

142-143°C
[Boiling point ]

356.15°C (rough estimate)
[density ]

1.131
[refractive index ]

1.4230 (estimate)
[storage temp. ]

Store at +4°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)
Hazard InformationBack Directory
[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.
[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 .
[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.
[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
Safety DataBack Directory
[WGK Germany ]

3
[RTECS ]

DK4230000
Spectrum DetailBack Directory
[Spectrum Detail]

EMBELIN(550-24-3)1HNMR
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