2,5-Dihydroxy-3-undecyl-p-benzochinon

Bezeichnung:2,5-Dihydroxy-3-undecyl-p-benzochinon

CAS-Nr550-24-3

Englisch Name:EMBELIN

CBNumberCB7365074

SummenformelC17H26O4

Molgewicht294.39

MOL-Datei550-24-3.mol

Synonyma

2,5-Dihydroxy-3-undecyl-p-benzochinon

2,5-Dihydroxy-3-undecyl-p-benzochinon physikalisch-chemischer Eigenschaften

Schmelzpunkt	142-143°C
Siedepunkt	356.15°C (rough estimate)
Dichte	1.131
Brechungsindex	1.4230 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	DMSO: >10 mg/mL
Aggregatzustand	solid
pka	2.84±0.50(Predicted)
Farbe	Dark orange
Sensitive	Light Sensitive
Stabilität	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)

Sicherheit

WGK Germany	3
RTECS-Nr.	DK4230000

Gefahreninformationscode (GHS)

EMBELIN Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
Orange Solid
Verwenden
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.
Biologische Aktivität
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 .
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

2,5-Dihydroxy-3-undecyl-p-benzochinon Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

550-24-3, EMBELIN Verwandte Suche:

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