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I3766

Sigma-Aldrich

Isoliquiritigenin

powder

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C15H12O4
Numero CAS:
961-29-5
Peso molecolare:
256.25
Beilstein:
1914296
Numero MDL:
MFCD00075907
Codice UNSPSC:
41106305
ID PubChem:
24278037
NACRES:
NA.77

Stato

powder

Livello qualitativo

200

Colore

yellow to orange

Solubilità

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

Temperatura di conservazione

2-8°C

Stringa SMILE

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+
DXDRHHKMWQZJHT-FPYGCLRLSA-N

Informazioni sul gene

rat ... Alox5(25290)

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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

Caratteristiche e vantaggi

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.

Avvertenza

Photosensitive, hygroscopic

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
038M4187V
106M4100V
079M4041V
085M4018V
014M4061V

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Esculetin European Pharmacopoeia (EP) Reference Standard

Y0001611

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Beta-sitosterol

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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