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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:
1914296
MDL number:
MFCD00075907
UNSPSC Code:
41106305
PubChem Substance ID:
24278037
NACRES:
NA.77

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.

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Kai-Lee Wang et al.
Expert opinion on therapeutic targets, 17(4), 337-349 (2013-01-19)
Isoliquiritigenin (ISL) is a natural phenolic compound extracted from licorice. Previous studies have shown that ISL is a potent antioxidant with anti-inflammatory and antitumor activities. The anti-invasive activity of ISL was still unclear. The actual causes of death for most
M Tawata et al.
European journal of pharmacology, 212(1), 87-92 (1992-02-25)
The mechanism was studied by which isoliquiritigenin, a new aldose reductase inhibitor purified from licorice (Glycyrrhizae radix), inhibits platelet aggregation. This new agent significantly inhibited the phosphorylation of 40,000- and 20,000-dalton proteins, and inhibited the formation of 12 (S)-hydroxy-5,8,10-heptadecatrienoic acid
Xuan Yuan et al.
Journal of Asian natural products research, 14(8), 789-798 (2012-06-15)
This study focuses on the relationship between the apoptosis induced by isoliquiritigenin (ISL) and the production of reactive oxygen species (ROS). Cell viability was evaluated using sulforhodamine B assay. The apoptotic rate was determined via flow cytometry. Intracellular ROS level
Xuan Yuan et al.
Recent patents on anti-cancer drug discovery, 8(2), 191-199 (2012-09-12)
Isoliquiritigenin (ISL), a licorice chalconoid, is a bioactive agent with chemopreventive potential that has been patented for tumor treatment in China. This study investigated the mechanisms of ISL-induced apoptosis in ovarian carcinoma SKOV-3 cells. Cell viability was evaluated using a
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