Skip to Content
Merck
CN

I3766

Isoliquiritigenin

powder

Synonym(s):

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C15H12O4
CAS Number:
961-29-5
Molecular Weight:
256.25
UNSPSC Code:
41106305
NACRES:
NA.77
PubChem Substance ID:
24278037
MDL number:
MFCD00075907
Beilstein/REAXYS Number:
1914296
Form:
powder
Quality level:
200

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI key

DXDRHHKMWQZJHT-FPYGCLRLSA-N

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+

form

powder

color

yellow to orange

solubility

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

storage temp.

2-8°C

Quality Level

200

Gene Information

rat ... Alox5(25290)

Looking for similar products? Visit Product Comparison Guide

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.

Disclaimer

Photosensitive, hygroscopic

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000205312
0000242984
0000242984
0000205312
038M4187V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
Wdr68 mediates dorsal and ventral patterning events for craniofacial development
Alvarado E, et al.
PLoS ONE, 11(11), e0166984-e0166984 (2016)
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
View All Related Papers

Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service