(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

• ChemBase ID: 2977
• Molecular Formular: C15H12O4
• Molecular Mass: 256.25338
• Monoisotopic Mass: 256.07355886
• SMILES: Oc1ccc(cc1)/C=C/C(=O)c1ccc(O)cc1O
• Canonical SMILES: Oc1ccc(cc1)/C=C/C(=O)c1ccc(cc1O)O
• InChI: 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+
• InChIKey: DXDRHHKMWQZJHT-FPYGCLRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
• IUPAC Traditional name: isoliquiritigenin
• Synonyms: 2',4,4'-Trihydroxychalcone; Isoliquiritigenin; Isoliquiritigenin; 2',4,4'-Trihydroxychalcone; (E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; 4,2′,4′-Trihydroxychalcone; Isoliquiritigenin; ISL; 2',4,4'-Trihydroxychalcone; GU 17; (2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one; 2',4,4'-三羟基查耳酮

Database IDs

• CAS Number: 961-29-5
• MDL Number: MFCD00075907
• PubChem SID: 24278037; 160966424; 46506198
• PubChem CID: 638278

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.1109757
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.6191914
• LogD (pH = 7.4): 3.1476436
• Log P: 3.6296294
• Molar Refractivity: 72.8197 cm^3
• Polarizability: 27.143188 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.04
• LOG S: -3.67
• Solubility (Water): 5.51e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL; H2O: <0.1 mg/mL; methanol: soluble10 mg/mL
• Apperance: Orange powder; yellow to orange powder
• Melting Point: 185-187°C

Safety Information

• Storage Condition: -20°C
• Storage Warning: Light Sensitive & Hygroscopic
• RTECS: FL7080000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: rat ... Alox5(25290)

Product Information

• Purity: 97%
• Salt Data: Free Base

DETAILS

DrugBank - DB03285

Drug information: experimental

Selleck Chemicals - S2404

Research Area: Cancer
Biological Activity:
Isoliquiritigenin (GU 17) is a strong nod gene- and glyceollin resistance-inducing flavonoid from soybean root exudate. Isoliquiritigenin (GU 17) is a licorice chalcone, a type of flavonoid. Isoliquiritigenin (GU 17)  is currently under experimentation phase testing for use as a cancer treatment as well as an aide for cocaine addiction. Isoliquiritigenin (GU 17)  is a sirtuin-activating compound. The ability of isoliquiritigenin (GU 17) to suppress metastasis was examined in a pulmonary metastasis model of mouse renal cell carcinoma. Isoliquiritigenin (GU 17) significantly reduced pulmonary metastasis, without any weight loss or leukocytopenia. Isoliquiritigenin (GU 17) suppressed in vitro proliferation of carcinoma cells, potentiated nitric oxide production by lipopolysaccharide-stimulated macrophages, and facilitated cytotoxicity of splenic lymphocytes in vitro. [1][2]

Sigma Aldrich - I3766

Biochem/physiol Actions
Soluble guanylyl cyclase activator. Possesses antitumor activity.
Caution
Photosensitive, hygroscopic
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I3766.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - I820850

Isoliquiritigenin (ISL) is a flavonoid found in licorice root and several other plants that displays antioxidant, anti-inflammatory, and antitumor activities as well as hepatoprotection against steatosis-induced oxidative stress. ISL induces quinone reduc

REFERENCES

• Yamazaki S et al. Cancer Lett. 2002 Sep 8;183(1):23-30.
• Agrawal, R., et al.: Food Chem. Toxicol., 36, 975 (1998)
• Baba, M., et al.: Biol. Pharm. Bull., 25, 247 (1998)
• Chowdhury, S., et al.: Anticancer Res., 25, 2055 (1998)