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I3766

Sigma-Aldrich

Isoliquiritigenin

powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C15H12O4
Numéro CAS:
961-29-5
Poids moléculaire :
256.25
Numéro Beilstein :
1914296
Numéro MDL:
MFCD00075907
Code UNSPSC :
41106305
ID de substance PubChem :
24278037
Nomenclature NACRES :
NA.77

Forme

powder

Niveau de qualité

200

Couleur

yellow to orange

Solubilité

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

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

DXDRHHKMWQZJHT-FPYGCLRLSA-N

Informations sur le gène

rat ... Alox5(25290)

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Description générale

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

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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.

Attention

Photosensitive, hygroscopic

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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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
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
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
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
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