1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylen-7,14-dion

Bezeichnung:1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylen-7,14-dion

CAS-Nr548-04-9

Englisch Name:Hypericin

CBNumberCB2696784

SummenformelC30H16O8

Molgewicht504.44

MOL-Datei548-04-9.mol

Synonyma

1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylen-7,14-dion

1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylen-7,14-dion physikalisch-chemischer Eigenschaften

Schmelzpunkt	299-301°C
Siedepunkt	1020.3±65.0 °C(Predicted)
Dichte	1.915±0.06 g/cm3(Predicted)
RTECS-Nr.	SF8472000
storage temp.	-20°C
Löslichkeit	1 M NaOH: 10 mg/mL
Aggregatzustand	powder
pka	6.91±0.20(Predicted)
Farbe	black
Wasserlöslichkeit	Soluble in ethanol, dimethyl sulfoxide, methanol, acetone, ethylmethylketone, pyridine and sodium hydroxide. Insoluble in water.
Sensitive	Light Sensitive
Merck	14,4863
BRN	1917913
Stabilität	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
InChIKey	BTXNYTINYBABQR-UHFFFAOYSA-N
LogP	10.827 (est)
CAS Datenbank	548-04-9(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-40-43
S-Sätze:	22-36-36/37
RIDADR	2811
WGK Germany	3
F	8
HS Code	29145090

Gefahreninformationscode (GHS)

Hypericin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
An anthroquinone derivative that is naturally found in the flower of H. perforatum (St. John’s wort) and has antidepressant, antiviral, and anticancer activities. Hypericin inhibits neuronal uptake of serotonin, norepinephrine, dopamine, GABA and L-glutamate, contributing to its antidepressant effects. It exerts broad spectrum phototoxic affects (IC₅₀ = 140 - 1,570 nM) through induction of apoptotic signaling and formation of reactive oxygen species (ROS) in cancer cells. Hypericin also has in vitro activity, which can be enhanced with photo-activation, against a variety of viruses including HIV, influenza virus, hepatitis C, murine cytolomegalovirus, and herpes viruses.
Chemische Eigenschaften
Powder
Verwenden
It was used as reference standard in determining hypericins in St. John′s Wort using HPLC method.
Definition
ChEBI: Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene.
Allgemeine Beschreibung
Produced by HWI Analytik
Exact content can be found on the certificate
Biologische Aktivität
Photosensitive antiviral, anticancer and antidepressant agent derived from Hypericum perforatum (St John's wort). Inactivates enveloped viruses (including HIV), inhibits tyrosine kinases (IC 50 = 7.5 μ M) and is preferentially cytotoxic to tumor cells upon stimulation by visible light.
Biochem/physiol Actions
Primary TargetPKC
Lager
+4°C
läuterung methode
Crystallise hypericin from pyridine by addition of methanolic HCl. [Beilstein 8 IV 3761.]
Einzelnachweise
1) Kubin et al., (2005) Hypericin – the facts about a controversial agent; Current Pharm. Des., 11 233 2) Theodossiou et al., (2009) The multifaceted photocytotoxic profile of hypericin; Mol. Pharmacol., 6 1775

1,3,4,6,8,13-Hexahydroxy-10,11-dimethylphenanthro[1,10,9,8-opqra]perylen-7,14-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

548-04-9, Hypericin Verwandte Suche:

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