3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron
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- CAS-Nr.
- 480-19-3
- Bezeichnung:
- 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron
- Englisch Name:
- Isorhamnetin
- Synonyma:
- QUERCETIN-3-METHYLETHER;sorhamnetin;3-METHYLQUERCETIN;ISOHAMNETIN;isorhamnetol;3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one;c.i.75680;Isorhanetin;ISORHAMNETIN
- CBNumber:
- CB0472359
- Summenformel:
- C16H12O7
- Molgewicht:
- 316.26
- MOL-Datei:
- 480-19-3.mol
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3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron Eigenschaften
- Schmelzpunkt:
- 307°C
- Siedepunkt:
- 599.4±50.0 °C(Predicted)
- Dichte
- 1.634±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- L?slichkeit
- DMF: 10 mg/ml; DMSO: 20 mg/ml; DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
- pka
- 6.31±0.40(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Light yellow to Amber to Dark green
- BRN
- 44723
- Stabilit?t:
- Hygroscopic
- Major Application
- metabolomics
vitamins, nutraceuticals, and natural products
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN PROTECTING
- InChI
- InChI=1S/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3
- InChIKey
- IZQSVPBOUDKVDZ-UHFFFAOYSA-N
- SMILES
- C1(C2=CC=C(O)C(OC)=C2)OC2=CC(O)=CC(O)=C2C(=O)C=1O
- LogP
- 1.760 (est)
- CAS Datenbank
- 480-19-3(CAS DataBase Reference)
Sicherheit
- Risiko- und Sicherheitserkl?rung
- Gefahreninformationscode (GHS)
| Kennzeichnung gef?hrlicher |
Xi,Xn |
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| R-S?tze: |
36/37/38-40 |
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| S-S?tze: |
22-36-26-36/37 |
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| WGK Germany |
3 |
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| RTECS-Nr. |
LK9275450 |
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| HS Code |
29329990 |
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| Speicherklasse |
11 - Combustible Solids |
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| Bildanzeige (GHS) |
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| Alarmwort |
Warnung
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| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H351 |
Kann vermutlich Krebs verursachen. |
Karzinogenit?t |
Kategorie 2 |
Warnung |
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P201, P202, P281, P308+P313, P405,P501 |
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| Sicherheit |
| P280 |
Schutzhandschuhe/Schutzkleidung/Augenschutz tragen. |
| P281 |
Vorgeschriebene pers?nliche Schutzausrüstung verwenden. |
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3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-S?tze Betriebsanweisung:
S22:Staub nicht einatmen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
Beige to lighet yellow powder
Verwenden
Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.
Definition
ChEBI: Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It derives from a quercetin. It is a conjugate acid of an isorhamnetin(1-).
Application
Isorhamnetin is a metabolite of the flavanoid Quercetin with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.
Allgemeine Beschreibung
Isorhamnetin is one of the important flavanols found in G.biloba leaf extracts. Isorhamnetin is also found in parsley, and thereby it is a common dietary flavonoid as the metabolite of quercetin.Generally, it is well known as antagonist of peroxisome proliferator-activated receptor Y (PPARy), which inhibits adipocyte differentiation induced by the PPARy agonist rosiglitazone. Isorhamnetin is a naturally occurring compound in fruits and vegetables; recent study showed that isorhamnetin could significantly inhibit the invasion of MDA-MB-231 cells by downregulating matrix metalloproteinases(MMP-2 and MMP-9) through inhibiting p38 MAPK and STAT3. Similar results were also obtained in another study, which showed that isorhamnetin inhibited cell proliferation and led to apoptosis. In addition, isorhamnetin was found effective on Akt/mTOR/MAPKs signaling axis. It was established that isorhamnetin-induced autophagy can be reversed by the co-treatment of 3-methyl-adenine in lung cancer cells. The results indicated that isorhamnetin exerts antitumor effect in breast cancer through targeting multiple molecular targets.
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 428)Lieferanten
480-19-3(3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron)Verwandte Suche:
4-Methoxyphenylaceton
L-Rhamnose monohydrate
2,3-Diphenylcycloprop-2-en-1-on
2'-Hydroxyacetophenone
Tetrahydro-4H-pyran-4-on
3,6-Bis[(4-chlor-2-phosphonophenyl)azo]-4,5-dihydroxynaphthalin-2,7-disulfonsure
4'-Hydroxyacetophenon
3,3',4',5-Tetrahydroxy-7-methoxyflavon
1,4:3,6-Dianhydro-D-glucitol
Triethoxy(3-isocyanatopropyl)silan
4H-pyran-4-on
Flavon
2-(3,4-Dimethoxyphenyl)-5-hydroxy-3,7-dimethoxy-4-benzopyron
3-[[6-O-(6-Desoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-on, Tris(2-hydroxyethyl)ether
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyron
- IsorhaMnetin, froM Hippophae fhaMnoides L.
- sorhamnetin
3,5,7-Trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on
- 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-
- 3,5,7-Trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-one
- 3'-Methoxy-3,4',5,7-tetrahydroxyflavone
3,5,7-Trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on
3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one
- 3'-METHOXY-3,4',5,7-TETRAHYDROXYFLAVONE
- 3'-METHOXY-3,5,7,4'-TETRAHYDROXYFLAVONE
- 3,5,7,4'-TETRAHYDROXY-3'-METHOXYFLAVONE
- 3,5,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-4-BENZOPYRONE
- 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-1-benzopyran-4-one
- 3,5,7-trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on
- ISORHAMNETIN
- 2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-4h-1-benzopyran-4-on
- 3,4’,5,7-tetrahydroxy-3’-methoxy-flavon
- 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4h-1-benzopyran-4-on
- 3’-methoxy-3,4’,5,7-tetrahydroxy-flavon
- 3’-methoxyquercetin
- c.i.75680
- I3,6,7-TRIHYDROXY-2-(4-HYDROXY-3-METHOXYPHENYL)-4H-CHROMEN-4-ONE
- ISORHAMNETIN WITH HPLC
- Flavone, 3,4',5,7-tetrahydroxy-3'-methoxy-
- 3'-Methoxy-3,4',5,7-tetrahydroxyflavone
3,5,7-Trihydroxy-2-(4-hydroxy-3-metoxyphenyl)benzopyran-4-on
- Isorhanetin
- ISOHAMNETIN:3'-METHOXY-3,4',5,7-TETRAHYDRO-XY-FLAVONE
- QUERCETIN-3-ORTHO-METHYLETHER
- ISORHAMNETIN hplc
- Isorhamnetin (15 mg)
- 3,3',5,7-Tetrahydroxy-3'-Methoxyflavone
- Isorhamnetin USP/EP/BP
- Isorhamnetin, ≥95% (HPLC)
- 2'-0xydiethanol
- 2'-Oxybisethanol
- Isorhamnetin, 98%, from Hippophae fhamnoides L.
- Isorhamnetin 480-19-3
- 3,6,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyran-4-one
- Isorhamnetin, >98%（HPLC)
- 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one
- 3,5,7-trihydroxy-2- (4-hydroxy-3-methoxyphenyl) -4H-benzopyran-4-one
- 3-methylquercetin|||3'-Methylquercetin|||Isorhamnetol|||3'-Methoxyquercetin
- Isorhamnetin, 10 mM in DMSO
- 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)benzenebenzopyran-4-one
- isorhamnetol
- 3-METHYLQUERCETIN
- Isorhamnetin (Standard)
- 3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one
- ISOHAMNETIN
- QUERCETIN-3-METHYLETHER
- sorhamnetin
- 480-19-3
- 418-19-3
- Natural Dyes
- Biochemicals and Reagents
- BioChemical
- Penta-substituted Flavones
- Flavanols
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
