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I3766

Sigma-Aldrich

Isoliquiritigenin

powder

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Synonym(s):
(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, 4,2′,4′-Trihydroxychalcone
Empirical Formula (Hill Notation):
C15H12O4
CAS Number:
Molecular Weight:
256.25
Beilstein/REAXYS Number:
1914296
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

powder

Quality Level

color

yellow to orange

solubility

H2O: <0.1 mg/mL
methanol: 10 mg/mL
DMSO: 20 mg/mL

storage temp.

2-8°C

SMILES string

Oc1ccc(cc1)\C=C\C(=O)c2ccc(O)cc2O

InChI

1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+

InChI key

DXDRHHKMWQZJHT-FPYGCLRLSA-N

Gene Information

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This Item
P045338986PHL89544
Isoliquiritigenin powder

I3766

Isoliquiritigenin

Piceatannol powder

P0453

Piceatannol

Isoliquiritigenin analytical standard

38986

Isoliquiritigenin

Isoliquiritigenin phyproof&#174; Reference Substance

PHL89544

Isoliquiritigenin

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

solubility

H2O: <0.1 mg/mL, DMSO: 20 mg/mL, methanol: 10 mg/mL

solubility

H2O: 0.5 mg/mL, DMSO: 10 mg/mL, ethanol: 10 mg/mL

solubility

-

solubility

-

color

yellow to orange

color

light tan to yellow

color

-

color

-

Gene Information

rat ... Alox5(25290)

Gene Information

human ... CDK2(1017)

Gene Information

-

Gene Information

-

General description

Isoliquiritigenin is an aromatic ketone and belongs to the chalcone group of compound. It is derived from licorice and is a component in medicine and food.

Application

Isoliquiritigenin has been used:
  • as a bone morphogenetic protein (BMP) agonist in zebrafish embryos
  • as a guanylyl cyclase activator in zebrafish embryos
  • to test its antitumor and antiviral effects against Epstein-Barr virus-associated gastric carcinoma

Biochem/physiol Actions

Isoliquiritigenin is a soluble guanylyl cyclase activator and possesses antitumor activity. It also possesses antioxidant, antiplatelet and estrogenic properties.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Caution

Photosensitive, hygroscopic

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Small molecule modifier screen for kit-dependent functions in zebrafish embryonic melanocytes
Hultman KA, et al.
Zebrafish, 5(4), 279-287 (2008)
S M Yu et al.
British journal of pharmacology, 114(8), 1587-1594 (1995-04-01)
1. The vasorelaxant activity of isoliquiritigenin, isolated from Dalbergia odorifera T, was investigated in the phenylephrine-precontracted rat aorta by measuring tension, guanylate and adenylate cyclase activities, guanosine 3':5'-cyclic monophosphate (cyclic GMP) and adenosine 3':5'-cyclic monophosphate (cyclic AMP) levels. 2. Isoliquiritigenin
Suengmok Cho et al.
Biochemical and biophysical research communications, 413(4), 637-642 (2011-09-29)
Isoliquiritigenin (ILTG) is a chalcone compound and has valuable pharmacological properties such as antioxidant, anti-inflammatory, anticancer, and antiallergic activities. Recently, the anxiolytic effect of ILTG has been reported; however, its action mechanism and hypnotic activity have not yet been demonstrated.
Wdr68 mediates dorsal and ventral patterning events for craniofacial development
Alvarado E, et al.
PLoS ONE, 11(11), e0166984-e0166984 (2016)
Lei Yang et al.
Food chemistry, 138(1), 173-179 (2012-12-26)
An ionic liquid-based ultrasonic-assisted extraction (ILUAE) method had been used for the effective extraction of isoliquiritigenin (IQ), liquiritin (LQ) and glycyrrhizic acid (GA) from licorice. The ionic liquids with different cations and anions were investigated in this work and 0.5

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