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I3766

Sigma-Aldrich

Isoliquiritigenin

powder

Synonym(s):

(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, 4,2′,4′-Trihydroxychalcone

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About This Item

Empirical Formula (Hill Notation):
C15H12O4
CAS Number:
961-29-5
Molecular Weight:
256.25
Beilstein/REAXYS Number:
1914296
MDL number:
MFCD00075907
UNSPSC Code:
41106305
PubChem Substance ID:
24278037
NACRES:
NA.77

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form

powder

Quality Level

200

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

rat ... Alox5(25290)

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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.[1]

Application

Isoliquiritigenin has been used:
  • as a bone morphogenetic protein (BMP) agonist in zebrafish embryos[2]
  • as a guanylyl cyclase activator in zebrafish embryos[3]
  • to test its antitumor and antiviral effects against Epstein-Barr virus-associated gastric carcinoma[1]

Biochem/physiol Actions

Isoliquiritigenin is a soluble guanylyl cyclase activator[3] and possesses antitumor activity.[1] It also possesses antioxidant, antiplatelet and estrogenic properties.[1]

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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Certificates of Analysis (COA)

Lot/Batch Number
0000242984
0000205312
038M4187V
106M4100V
079M4041V

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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
Small molecule modifier screen for kit-dependent functions in zebrafish embryonic melanocytes
Hultman KA, et al.
Zebrafish, 5(4), 279-287 (2008)
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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