HISPIDULIN Chemical Properties

Melting point:

291-292 °C

Boiling point:

601.5±55.0 °C(Predicted)

Density 

1.512±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: soluble20mg/mL, clear

pka

6.51±0.40(Predicted)

form 

powder

color 

white to beige

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

InChIKey

IHFBPDAQLQOCBX-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(O)C=C2)OC2=CC(O)=C(OC)C(O)=C2C(=O)C=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

RTECS 

DJ2996000

HISPIDULIN Usage And Synthesis

Chemical Properties

Yellow crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, from the lychee grass extracted from the inside of the Asteraceae plant ragweed whole grass, snow lotus.

Uses

Hispidulin has been used as a calibration standard:

• in high-performance liquid chromatography (HPLC) for quantification of Clerodendrum petasites flavonoids
• in liquid chromatography/electrospray ionization mass spectrometry (LC/ESI-MS) analysis
• in reverse-phase high-performance liquid chromatography with a diode-array detector (HPLC-DAD) and high-performance thin-layer chromatography (HPTLC)

Definition

ChEBI: A monomethoxyflavone that is scutellarein methylated at position 6.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Biological Activity

Partial positive allosteric modulator at the benzodiazepine receptor (IC 50 = 1.3 μ M for inhibition of flumazenil binding); natural sage flavone. Stimulates GABA-induced chloride currents in Xenopus oocytes expressing α 1 α 2-, α 3-, α 5- or α 6- β 2 γ 2S GABA A receptors. Brain penetrant; oral administration reduces seizures in a gerbil model of epilepsy. Also has antifungal, antiproliferative, antioxidant and antithrombotic properties.

Biochem/physiol Actions

Hispidulin is a bioactive flavonoid with a variety of effects including antiproliferative, antifungal, anti-inflammatory, antioxidative and antiepileptic activity. Like EGCG, hispidulin appears to activate AMPK and inhibit the PI3K/Akt/mTOR pathway. The antiepileptic activity may be due to additional activity as a benzodiazepine (BZD) receptor ligand.

HISPIDULIN(1447-88-7)Related Product Information

• APIGENIN 6-GLUCOSYL-7-O-METHYL ETHER
• cirsimaritin
• 6,7-DIMETHOXY-3',4',5-TRIHYDROXYFLAVONE
• 3'-BENZYLOXY-4',5,6,7-TETRAMETHOXYFLAVONE
• 3',4',5',5,6,7-HEXAMETHOXYFLAVONE
• 6-METHOXYLUTEOLIN
• 3',4',5',6,7,8-HEXAMETHOXY-5-HYDROXYFLAVONE
• HISPIDULIN
• CASTICIN
• HINOKIFLAVONE
• 3',5-DIHYDROXY-4',6,7-TRIMETHOXYFLAVONE
• EUPATORIN-5-METHYL ETHER
• SCUTELLAREIN TETRAMETHYL ETHER
• SCUTELLAREIN
• Tangeretin
• 3,3',4',5,6,7,8-heptamethoxyflavone
• salvigenin
• SINENSETIN