2-(3,4-Dihydroxyphenyl)-3-(β-D-galaktopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-on

Bezeichnung:2-(3,4-Dihydroxyphenyl)-3-(β-D-galaktopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-on

CAS-Nr482-36-0

Englisch Name:Hyperoside

CBNumberCB9240043

SummenformelC21H20O12

Molgewicht464.38

MOL-Datei482-36-0.mol

Synonyma

2-(3,4-Dihydroxyphenyl)-3-(β-D-galaktopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-on

2-(3,4-Dihydroxyphenyl)-3-(β-D-galaktopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	225-226°C
Siedepunkt	872.6±65.0 °C(Predicted)
Dichte	1.87±0.1 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	DMSO (Slightly), Methanol (Slightly, Heated)
Aggregatzustand	Solid
pka	6.17±0.40(Predicted)
Farbe	Light Yellow to Yellow
BRN	5784795
LogP	-0.111 (est)
CAS Datenbank	482-36-0(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-40
S-Sätze:	22-45-36-24/25
WGK Germany	3
RTECS-Nr.	DJ3009200
F	10-23
HS Code	29389090

Gefahreninformationscode (GHS)

Hyperoside Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Hypericin, which is widely found in various plants, such as Hypericum, Rosaceae, Campanulaceae, Labiatae, Rhododendron, Asteraceae Kwai, Garciniaceae, Leguminosae, Euonymus, and other fruits and whole grass, is a flavonoid compound.
Chemische Eigenschaften
Yellow Solid
Physikalische Eigenschaften
Appearance: yellowish needlelike crystals. Melting point: 227–229 °C. Specific optical rotation: ?83° (c = 0.2, pyridine). Solubility: soluble in ethanol, methanol, acetone, and pyridine. Hydrochloric acid–magnesium powder reaction yielded formation of cherry red; ferric chloride reaction was green; α-naphthol reaction was positive.
History
In 1960, Nair et al. isolated hyperin from redosier dogwood, in which its content is 0.075%. Flavonoids in the treatment of cardiovascular and cerebrovascular diseases play a pivotal role, among which rutin is a typical representative. Isoquetin mainly presents in the leaves of kumquat flowers and the oleander plant kenaf, and it can also be obtained by chemical synthesis. It shows an anti-inflammatory effect through the capillary permeability test and other animal experiments. It also has a toxic effect on the larvae of Chilohabala larvae. It is one of the active ingredients of Hypericum japonicum, which is used in the treatment of hepatitis because of its inhibition of the activities of hepatic enzyme.
Verwenden
Hyperoside is used as a primary reference standard in the analysis of herbal medicinal products. It may be used as a calibration standard in method validation of polyphenols from leaf extracts using HPLC method.
Verwenden
It may be used as calibration standard solutions in method validation of polyphenols from leaf extracts using HPLC method.
Verwenden
A major flavonoid in apple peels; a bioactive constituent of apple peels
Indications
This product is available in the British Pharmacopoeia (2017) and the European Pharmacopoeia (9.0th ed.).
Monomeric compounds are currently used clinically. In clinical practice, hypericin is the main active ingredient of proprietary Chinese medicines, such as Acanthopanax capsules, of which Acanthopanax stem and leaf extract are the raw materials for the preparation. Xin’an capsules, prepared with hawthorn leaf extract, are rich in flavonoids, in which hyperoside, a kind of flavonoid, is one of the main components. Qi yue lipid-lowering tablets are prepared from the effective parts of Chinese medicinal herbs such as hawthorn (Nucleation) and Astragalus membranaceus. Flavonoid is one of the main active ingredients in hawthorn, in which hyperoside content is higher. Xinxuening tablets, containing ursolic acid, vitexin rhamnoside, hyperoside, citric acid, and others, is a preparation made from hawthorn and pueraria and other traditional Chinese medicines, in which hawthorn enhances the actions of the medicine. Clinical indications of Xinxuening tablets are coronary heart disease, angina pectoris, chest tightness, palpitations, high blood pressure, arrhythmia, hyperlipidemia, and mental depression.
Definition
ChEBI: A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity.
Allgemeine Beschreibung
Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.
Biochem/physiol Actions
Protects against peroxide-induced oxidative damage to cells by scavenging reactive oxygen species and enhancing activity of anti-oxidant enzymes, in particular, catalase and glutathione peroxidase.
Pharmakologie
Hyperoside has a protective effect against myocardial ischemia. It achieves its protective effect on the myocardium by reducing the apoptosis rate of myocardial cells, inhibiting myocardial cell lactate dehydrogenase release, enhancing anti-freeradical effect , and inhibiting calcium influx so as to .
Hyperoside has a protective effect against cerebral ischemia. Hyperoside can significantly lower oxygen-free radicals, reduce the content of malondialdehyde and NO in brain tissue, inhibit the decrease of the activity of LDH, SOD and glutathione peroxidase, and hence result in reduced brain energy, and improve the antianoxic ability . At the same time, hyperoside can reduce the degree of cerebral edema in ischemia-reperfusion rats .
Hypericin has a significant local analgesic effect that is weaker than that of morphine and stronger than that of aspirin and does not create dependency; it is a new type of local analgesic. Studies have shown that the analgesic effect of hyperoside occurs by reducing the Ca2 + of the pain nerve, thereby inhibiting high potassium-induced Ca2 + influx, which distinguishes it from morphine and aspirin .
Hyperoside has a significant anti-inflammatory effect and a strong cough effect and inhibits the role of eye aldose reductase, which may be beneficial for the prevention of diabetic cataracts. Hypericin has an obvious protective effect on liver tissue and gastric mucosa , and its mechanism is related to antioxidant activity and the promotion of a normal return of NO level and improvement of SOD activity.
Hyperoside significantly enhances immune function. In vivo, hyperoside has a significant inhibitory effect on spleen B, T lymphocyte proliferation and peritoneal macrophage phagocytosis, and mouse thymus index; in vitro hyperoside, at a concentration of 6.25–100 μg/mL, significantly enhanced B, T lymphocyte proliferation and promoted the production of interleukin 2 in T lymphocytes .
In addition, hypericin still has hypolipidemic and antidepressant pharmacological effects. Its derivative rutin has anti-inflammatory and antiviral effects. Another derivative, quercetin, is effective at inhibiting expectorant, cough, and asthma for use in the treatment of chronic bronchitis, coronary heart disease, and hypertension.

Hyperoside Upstream-Materialien And Downstream Produkte

2-(3,4-Dihydroxyphenyl)-3-(β-D-galaktopyranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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