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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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10 MG
$474.00

$474.00

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10 MG
$474.00

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

$474.00

Available to ship onMay 01, 2025Details

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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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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.
Gang Chen et al.
Apoptosis : an international journal on programmed cell death, 17(1), 90-101 (2011-10-01)
Previous studies, including those from our laboratory, have demonstrated that isoliquiritigenin (ISL), a flavonoid isolated from licorice, is a promising cancer chemotherapeutic agent. However the mechanisms underlying its anticancer effects are still far from clear. We now show, for the
Quercetin-induced apoptosis prevents EBV infection
Lee M, et al.
Testing, 6(14), 12603-12603 (2015)
Isoliquiritigenin regulates the circ_0002860/miR-431-5p/RAB9A axis to function as a tumor inhibitor in melanoma.
Wu, et al.
Journal of Venomous Animals and Toxins including Tropical Diseases, 29, e20220019-e20220019 (2023)
S Yamamoto et al.
Carcinogenesis, 12(2), 317-323 (1991-02-01)
A topical application of a chalcone derivative, 4,2',4'-trihydroxychalcone (isoliquiritigenin) inhibited epidermal ornithine decarboxylase (ODC) induction and ear edema formation, i.e. inflammation, caused by a topical application of 12-O-tetradecanoylphorbol-13-acetate (TPA) in CD-1 mice. In addition, isoliquiritigenin potently inhibited 7,12-dimethylbenz[alpha]anthracene (DMBA)-initiated and
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