5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
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Grundinformationen
- CAS
104691-86-3- Standard-SMILES
CC(C)=CCc1c(O)cc(O)c2c(=O)c(-c3ccc(O)cc3)coc12- InChIKey
YGCCASGFIOIXIN-UHFFFAOYSA-N- Summenformel
- C20H18O5
- Durchschnittliche Molmasse
- 338,359 g/mol
- Monoisotopische Masse
- 338,11542368
Namen und Bezeichner
- Bevorzugter Name
- 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one
- IUPAC
- 5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-1-benzopyran-4-one
- Englischer Name
- 8-PRENYLGENISTEIN
- Summenformel
- C20H18O5
- Molmasse
- 338.35
Namen und Synonyme
LupiwighteoneLuncheonette8-PRENYLGENISTEIN8-IsopentenylgenisteinLupiwighteone, 10 mM in DMSO4',5,7-Trihydroxy-8-prenylisoflavone4',5,7-Trihydroxy-8-isopentenylisoflavone5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one3-(4-Hydroxyphenyl)-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one5,7-Dihydroxy-3-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
Datenbank-Bezeichner
- CAS
104691-86-3- PubChem CID
- 5317480
- DTXSID
DTXSID601132953- ChEMBL
CHEMBL3616491- ChEBI
CHEBI:185842- UNII
- S5W46B3BUM
- Nikkaji
- J397.729C
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 133 · 133-135℃
- Siedepunkt
- 583.5 · 583.5±50.0 °C(Predicted)
- Dichte
- 1.351 · 1.351±0.06 g/cm3(Predicted)
- storage temp.
- 4 °C, · 4°C, protect from light
- Löslichkeit
- 100 mg/mL · DMSO : 100 mg/mL (295.55 mM; Need ultrasonic)
- Aggregatzustand
- Powder
- pka
- 6.62 · 6.62±0.20(Predicted)
- Farbe
- Off-white to light yellow
Chemie und Industrie
Anwendungen
VerwendenLupiwighteone is a natural product derivative of Genistein (G350000). Genistein exhibits specific inhibitory activity against tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell proliferation and induces tumor cell differentiation. Produces cell-cycle arrest and apoptosis in Jurat T-leukemia cells. However, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Genistein also inhibits topoisomerase II activity in vitro. Genistein has also been shown to inhibit the action of GABA on recombinant GABAA receptors 2. uv(max)ethanol: 262.5 nm (e= 138). moderately sol. in hot alcohol.
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