Herbacetin Chemical Properties

Melting point:

284℃

Boiling point:

618.7±55.0 °C(Predicted)

Density 

1.799

storage temp. 

-20°C

solubility 

DMF:30.0(Max Conc. mg/mL);99.26(Max Conc. mM)
DMSO:30.0(Max Conc. mg/mL);99.26(Max Conc. mM)
DMSO:PBS(pH 7.2) (1:4):1.0(Max Conc. mg/mL);3.31(Max Conc. mM)
Ethanol:2.0(Max Conc. mg/mL);6.62(Max Conc. mM)

form 

A crystalline solid

pka

6.49±0.40(Predicted)

color 

Light yellow to yellow

Major Application

metabolomics
vitamins, nutraceuticals, and natural products

InChI

InChI=1S/C15H10O7/c16-7-3-1-6(2-4-7)14-13(21)12(20)10-8(17)5-9(18)11(19)15(10)22-14/h1-5,16-19,21H

InChIKey

ZDOTZEDNGNPOEW-UHFFFAOYSA-N

SMILES

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

LogP

1.140 (est)

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

Herbacetin Usage And Synthesis

Chemical Properties

Soluble in methanol, ethanol, DMSO and other organic solvents, derived from the aerial part of Equisetum, Rhodiola rosea.

Uses

Herbacetin is a flavonol compound, and a natural inhibitor of E.coli β-glucuronidase. Herbacetin inhibits inducible nitric oxide synthase via JNK and nuclear factor-κB in LPS-stimulated RAW264.7 cells. Molecular docking study of flavonoid compounds as an inhibitor of β-ketoacyl acyl carrier proteinsynthase II of Pseudomonas aeruginosa.

Definition

ChEBI: Herbacetin is a pentahydroxyflavone that is kaempferol substituted by a hydroxy group at position 8. It is a natural flavonoid from flaxseed which exerts antioxidant, anti-inflammatory and anticancer activities. It has a role as an EC 4.1.1.17 (ornithine decarboxylase) inhibitor, an antineoplastic agent, an apoptosis inducer, an angiogenesis inhibitor, a plant metabolite, an antilipemic drug, an anti-inflammatory agent and an EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is functionally related to a kaempferol.

Biological Activity

Herbacetin is a natural flavonoid in flaxseed with a variety of pharmacological activities, including antioxidant, anti-inflammatory and anticancer effects. Gluprotamine is an allosteric inhibitor of Ornithine decarboxylase (ODC), which directly binds to Asp44, Asp243 and Glu384 on ODC.

Synthesis

Method of extracting Herbacetin from Rhodiola rosea, comprising the following steps;
1) extracting crushed Rhodiola rosea herbs with an extraction solvent, and concentrating the extract under reduced pressure to obtain an extract infusion;
2) extract the extract extract, the extracted aqueous layer and then acid hydrolysis;
3) The solution after acid hydrolysis is extracted with organic solvent, the extract is combined and concentrated under reduced pressure to obtain herbaceous extract;
4) the oxalic acid extract is processed by polyamide column chromatography, the stream fraction containing oxalic acid is collected, concentrated to dryness, and the crude oxalic acid is obtained;
5) The crude herbaceous material was processed by reversed-phase silica gel column chromatography, the flow fraction containing herbaceous material was collected, concentrated to dryness, and recrystallized to obtain the pure product of herbacetin material.

in vivo

Herbacetin(527-95-7)Related Product Information

• Quercetin-7-O-β-D-glucopyranoside
• Naringenin 7-O-β-D-Glucuronide (Mixture of Diastereomers)
• ROSARIN
• Herbacetin 7-rhamnoside
• Leucoside
• 7,8-Dihydroxycoumarin
• Kaempferol
• Phloretin
• 3,7,3',4'-TETRAMETHYLGOSSYPETIN
• GOSSYPIN
• 5,3',4'-trihydroxy-3,6,7,8-tetramethoxyflavone
• GOSSYPETIN
• HERBACETIN-3,8-DIGLUCOPYRANOSIDE
• Herbacetin
• 3,3',4',5,6,7,8-heptamethoxyflavone
• HERBACETIN 8-GLUCOSIDE-3-SOPHORISIDE
• HEPTAMETHOXYFLAVONE
• HERBACETIN-7-O-GLUCORHAMNOSIDE