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CAS No.: | 1447-88-7 |
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Name: | HISPIDULIN |
Article Data: | 18 |
Molecular Structure: | |
Formula: | C16H12O6 |
Molecular Weight: | 300.268 |
Synonyms: | 6-Methylscutellarein;6-O-Methylapigenin;6-O-Methylscutellarein;Dinatin;Hispedulin;NSC122415;Salvitin;Scutellarein 6-methyl ether;Flavone,4',5,7-trihydroxy-6-methoxy- (7CI,8CI);4',5,7-Trihydroxy-6-methoxyflavone;5,7,4'-Trihydroxy-6-methoxyflavone;6-Methoxy-5,7,4'-trihydroxyflavone;6-Methoxyapigenin; |
Density: | 1.512 g/cm3 |
Melting Point: | 291-292 °C |
Boiling Point: | 601.506 °C at 760 mmHg |
Flash Point: | 230.135 °C |
Hazard Symbols: | Xn |
Risk Codes: | 22 |
PSA: | 100.13000 |
LogP: | 2.58540 |
7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one
hispidulin
Conditions | Yield |
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With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol under 760.051 Torr; for 8h; Inert atmosphere; | 96% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol under 760.051 Torr; for 8h; | 96% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol for 8h; | 96.1% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 20℃; for 8h; | 96% |
hispidulin
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether; dichloromethane at 0 - 25℃; for 1h; | 92% |
With hydrogenchloride In diethyl ether; dichloromethane; water at 0 - 25℃; for 1h; |
hispidulin
Conditions | Yield |
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With sulfuric acid In ethanol; water at 20 - 100℃; Solvent; Temperature; Reagent/catalyst; | 91% |
With sulfuric acid In ethanol; water at 100℃; Inert atmosphere; | 90% |
hispidulin
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -78℃; for 1.33333h; | 85% |
With boron trichloride In dichloromethane at -78℃; for 1.33333h; | 85% |
hispidulin
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -78 - 20℃; for 1h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With hydrolysis |
hispidulin
Conditions | Yield |
---|---|
With sulfuric acid for 8h; | 95 mg |
hispidulin
Conditions | Yield |
---|---|
With boron trichloride In dichloromethane at -65℃; for 1.5h; |
Conditions | Yield |
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Multi-step reaction with 8 steps 1: 60 percent / aluminium chloride / chlorobenzene / 1 h / Heating 2: 99 percent / K2CO3 / acetone / Heating 3: 29 percent / NaOH; K2S2O8; pyridine / H2O / 24 h / 20 °C 4: 59 percent / K2CO3 / acetone / Heating 5: pyridine / 3 h / 20 °C 6: KOH / pyridine / 4 h / 60 °C 7: sulfuric acid / acetic acid / 1.5 h / 60 °C 8: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: pyridine / 3 h / 20 °C 2: KOH / pyridine / 4 h / 60 °C 3: sulfuric acid / acetic acid / 1.5 h / 60 °C 4: BCl3 / CH2Cl2 / 1.5 h / -65 °C View Scheme |
The IUPAC name of Hispidulin is 5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxychromen-4-one. With the CAS registry number 1447-88-7, it is also named as 4',5,7-Trihydroxy-6-methoxyflavone. The product's category is Miscellaneous Natural Products. In addition, this chemical is partial positive allosteric modulator at the benzodiazepine receptor. It is used as brain penetrant. And it also has antifungal, antiproliferative, antioxidant and antithrombotic properties.
The other characteristics of Hispidulin can be summarized as: (1)ACD/LogP: 1.60; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.54; (4)ACD/LogD (pH 7.4): 0.39; (5)ACD/BCF (pH 5.5): 8.4; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 153.57; (8)ACD/KOC (pH 7.4): 11; (9)H bond acceptors: 6; (10)H bond donors: 3; (11)Freely Rotating Bonds: 5; (12)Polar Surface Area: 63.22 Å2; (13)Index of Refraction: 1.697; (14)Molar Refractivity: 76.53 cm3; (15)Molar Volume: 198.5 cm3; (16)Polarizability: 30.33×10-24cm3; (17)Surface Tension: 72.8 dyne/cm; (18)Density: 1.512 g/cm3; (19)Flash Point: 230.1 °C; (20)Enthalpy of Vaporization: 92.8 kJ/mol; (21)Boiling Point: 601.5 °C at 760 mmHg; (22)Vapour Pressure: 4.61E-15 mmHg at 25 °C
People can use the following data to convert to the molecule structure.
(1)SMILES:O=C\1c3c(O)c(OC)c(O)cc3O/C(=C/1)c2ccc(O)cc2
(2)InChI:InChI=1/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
(3)InChIKey:IHFBPDAQLQOCBX-UHFFFAOYAV
(4)Std. InChI:InChI=1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
(5)Std. InChIKey:IHFBPDAQLQOCBX-UHFFFAOYSA-N