isoliquiritin apioside Chemical Properties

Boiling point:

901.0±65.0 °C(Predicted)

Density 

1.63

storage temp. 

-20°C, protect from light

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

form 

Powder

pka

7.46±0.35(Predicted)

color 

Yellow to orange

biological source

plant

Water Solubility 

water: slightly soluble

Major Application

metabolomics
vitamins, nutraceuticals, and natural products

InChIKey

VMMVZVPAYFZNBM-KVFWHIKKSA-N

SMILES

O([C@@H]1OC[C@]([C@H]1O)(O)CO)[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC1C=CC(=CC=1)/C=C/C(C1C=CC(=CC=1O)O)=O)CO)O)O

CAS DataBase Reference

120926-46-7

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

isoliquiritin apioside Usage And Synthesis

Chemical Properties

White powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from licorice.

Uses

Isoliquiritin apioside can be used to resist myocardial ischemia and inhibit the proliferation of HIV.

Definition

ChEBI: Neolicuroside is a member of flavonoids and a glycoside.

Biological Activity

Neolicuroside modulates signaling pathways (e.g., MAPK, NF-KB), impacting vital cell processes such as proliferation, differentiation, and apoptosis. Its multitargeted mechanism includes scavenging free radicals, suppressing pro-inflammatory cytokine production, inhibiting matrix metalloproteinase (MMP) activity and hindering cancer cell growth through apoptosis and cell cycle arrest. Furthermore, it also exerts immunomodulatory effects possibly by activating toll-like receptor 4 (TLR4).

Synthesis

Dried Glycyrrhiza glabra 5.0 kg was extracted with 8 times and 6 times amount of 95% ethanol aqueous solution at reflux for 2 times, each time for 1 h. The extracts were combined, concentrated to a certain concentration under reduced pressure, and then placed on a column equipped with D101 macroporous resin, respectively, eluted with water, and 40% and 95% ethanol, and then the 40% ethanol eluent was collected, and then concentrated to a suitable concentration under reduced pressure for semi-preparative liquid chromatography, and the separation was carried out with the gradient elution of acetonitrile-water (10901000). Gradient elution of acetonitrile-water (10:90100:0) gave compounds 1 (3.9 mg), 2 (4.6 mg), 3 (3.3 mg) and 4 (3.0 mg). The 95% ethanol eluate was collected and further separated by ODS medium pressure column chromatography using 55% methanol and pure methanol solvent elution. The pure methanol eluate was collected for concentration under reduced pressure and freeze-dried to obtain dry powder (28 g). 0.43g of dried powder was dissolved in methanol and separated by semi-preparative liquid chromatography, acetonitrile-water to obtain apigenin (2.7mg).

IC 50

MMP9; NF-κB; p38 MAPK

isoliquiritin apioside(120926-46-7)Related Product Information

• Glycyroside
• 5,7-Dihydroxy-3-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-4H-1-benzopyran-4-one
• neoglycyrol
• SeMilicoisoflavone B
• Liquiritin apioside
• LICOFLAVONOL
• LICOISOFLAVONE A
• 4H-1-Benzopyran-4-one, 2-(4-(beta-D-glucopyranosyloxy)phenyl)-2,3-dihy dro-5,7-dihydroxy-, (2S)-
• Licorice glycoside C2
• 4,4'-DIHYDROXY-2-METHOXYCHALCONE
• Apigenin 7-glucoside
• Liguiritigenin-7-O-D-apiosyl-4’-O-D-glucoside
• Isoliquiritigenin
• LICOCHALCONE-A
• LIQUIRITIGENIN
• LIQUIRITIN(SH)
• ISOLIQUIRITIN
• isoliquiritin apioside