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Hispidulin

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Name

Hispidulin

EINECS N/A
CAS No. 1447-88-7 Density 1.512 g/cm3
PSA 100.13000 LogP 2.58540
Solubility N/A Melting Point 291-292 °C
Formula C16H12O6 Boiling Point 601.506 °C at 760 mmHg
Molecular Weight 300.268 Flash Point 230.135 °C
Transport Information N/A Appearance N/A
Safety Risk Codes 22
Molecular Structure Molecular Structure of 1447-88-7 (HISPIDULIN) Hazard Symbols Xn
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;

Article Data 18

Hispidulin Synthetic route

28736-83-6

7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one

1447-88-7

hispidulin

Conditions
ConditionsYield
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%

5-hydroxy-6-methoxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one

1447-88-7

hispidulin

Conditions
ConditionsYield
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-7-O-β-D-methylglucuronopyranoside

1447-88-7

hispidulin

Conditions
ConditionsYield
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%

4'-benzyloxy-6-methoxy-5-benzyloxy-7-hydroxyflavone

1447-88-7

hispidulin

Conditions
ConditionsYield
With boron trichloride In dichloromethane at -78℃; for 1.33333h;85%
With boron trichloride In dichloromethane at -78℃; for 1.33333h;85%

4'-benzyloxy-6-methoxy-5,7-dihydroxyflavone

1447-88-7

hispidulin

Conditions
ConditionsYield
With boron trichloride In dichloromethane at -78 - 20℃; for 1h; Inert atmosphere;80%
17680-84-1

tectoridin

A

2280-44-6

D-Glucose

B

1447-88-7

hispidulin

Conditions
ConditionsYield
With hydrolysis

5,7-dihydroxy-6-methoxy-flavone-4'-O-neohesperidoside

1447-88-7

hispidulin

Conditions
ConditionsYield
With sulfuric acid for 8h;95 mg

7-benzyloxy-2-(4-benzyloxy-phenyl)-5,6-dimethoxy-chromen-4-one

1447-88-7

hispidulin

Conditions
ConditionsYield
With boron trichloride In dichloromethane at -65℃; for 1.5h;
90-24-4

2-hydroxy-4,6-dimethoxyacetophenone

1447-88-7

hispidulin

Conditions
ConditionsYield
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
1486-50-6

4-(benzyloxy)benzoic acid chloride

1447-88-7

hispidulin

Conditions
ConditionsYield
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

Hispidulin Specification

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

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