Isoliquiritigenin

Modify Date: 2024-01-02 12:50:29

Isoliquiritigenin Structure
Isoliquiritigenin structure
 Common Name Isoliquiritigenin
CAS Number 961-29-5 Molecular Weight 256.253
Density 1.4±0.1 g/cm3 Boiling Point 504.0±42.0 °C at 760 mmHg
Molecular Formula C15H12O4 Melting Point 206-210°C
MSDS Chinese USA Flash Point 272.7±24.4 °C

 Use of Isoliquiritigenin


Isoliquiritigenin is an anti-tumor flavonoid from the root of Glycyrrhiza glabra, which inhibits aldose reductase with an IC50 of 320 nM.

 Names

Name isoliquiritigenin
Synonym More Synonyms

 Isoliquiritigenin Biological Activity

Description Isoliquiritigenin is an anti-tumor flavonoid from the root of Glycyrrhiza glabra, which inhibits aldose reductase with an IC50 of 320 nM.
Related Catalog
Target

IC50: 320 nM (Aldose reductase)

In Vitro Isoliquiritigenin may prevent diabetic complications through inhibiting rat lens aldose reductase with an IC50 of 320 nM and sorbitol accumulation in human red blood cells with an IC50 of 2.0 μM[1]. Isoliquiritigenin (100 μM) markedly inhibits the hypoxia-induced prolonged TPS and TR90 of cardiomyocytes. Isoliquiritigenin significantly triggers AMPK Thr172 phosphorylation as compared with vehicle group. Isoliquiritigenin treatment also induces extracellular signal-regulated kinase (ERK) signaling pathway in the cardiomyocytes. Isoliquiritigenin treatment significantly decreases the intracellular ROS levels of isolated cardiomyocytes during hypoxia/reoxygenation[3]. Isoliquiritigenin not only downregulates IL-6 expression but also significantly decreases levels of phosphorylated ERK and STAT3 and can inhibit phosphorylation levels of ERK and STAT3 induced by recombinant human IL-6, which are critical signaling proteins in IL-6 signaling regulation networks[4].
In Vivo Isoliquiritigenin shows concentration-dependent inhibition of the tonic contraction of mouse jejunum induced by various types of stimulants such as CCh (1 mM), KCl (60 mM) and BaCl2 (0.3 mM) with IC50 values of 4.96±1.97 mM, 4.03±1.34 mM and 3.70±0.58 mM, respectively[2]. Isoliquiritigenin exhibits significant anti-tumor activity in MM xenograft models and synergistically enhances the anti-myeloma activity of adriamycin[4].
References

[1]. Aida K, et al. Isoliquiritigenin: a new aldose reductase inhibitor from glycyrrhizae radix. Planta Med. 1990 Jun;56(3):254-8.

[2]. Sato Y, et al. Isoliquiritigenin, one of the antispasmodic principles of Glycyrrhiza ularensis roots, acts in the lower part of intestine. Biol Pharm Bull. 2007 Jan;30(1):145-9.

[3]. Zhang X. Natural antioxidant-isoliquiritigenin ameliorates contractile dysfunction of hypoxic cardiomyocytes via AMPK signaling pathway. Mediators Inflamm. 2013;2013:390890.

[4]. Chen X, et al. Isoliquiritigenin inhibits the growth of multiple myeloma via blocking IL-6 signaling. J Mol Med (Berl). 2012 Nov;90(11):1311-9.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 504.0±42.0 °C at 760 mmHg
Melting Point 206-210°C
Molecular Formula C15H12O4
Molecular Weight 256.253
Flash Point 272.7±24.4 °C
Exact Mass 256.073547
PSA 77.76000
LogP 3.11
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.715
Storage condition 2-8°C
Water Solubility H2O: <0.1 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FL7080000
CHEMICAL NAME :
Chalcone, 2',4,4'-trihydroxy-
CAS REGISTRY NUMBER :
961-29-5
LAST UPDATED :
199606
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C15-H12-O4
MOLECULAR WEIGHT :
256.27
WISWESSER LINE NOTATION :
QR CQ DV1U1R DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria - Salmonella typhimurium
DOSE/DURATION :
100 ug/plate
REFERENCE :
ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 3,401,1981

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS FL7080000
HS Code 2914501900

 Synthetic Route

 Customs

HS Code 2914501900
Summary 2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

 Articles38

More Articles
Isoliquiritigenin attenuates oxidative hepatic damage induced by carbon tetrachloride with or without buthionine sulfoximine.

Chem. Biol. Interact. 225 , 13-20, (2015)

Glycyrrhizae radix (G. radix) has been demonstrated to have hepatoprotective properties. This study determined the therapeutic effects of isoliquiritigenin (isoLQ) in G. radix, against liver injury in...

Effects of phytochemicals on in vitro anti-inflammatory activity of Bifidobacterium adolescentis.

Biosci. Biotechnol. Biochem. 79 , 799-807, (2015)

Probiotics have been shown to improve the condition of not only the human gastrointestinal tract but also the entire body. We found that quercetin enhances the anti-inflammatory activity of Bifidobact...

Flavonoids and Auxin Transport Inhibitors Rescue Symbiotic Nodulation in the Medicago truncatula Cytokinin Perception Mutant cre1.

Plant Cell 27 , 2210-26, (2015)

Initiation of symbiotic nodules in legumes requires cytokinin signaling, but its mechanism of action is largely unknown. Here, we tested whether the failure to initiate nodules in the Medicago truncat...

 Synonyms

iso-Liquiritigenin
Isoliquiritigenin
QR CQ DV1U1R DQ &&E Form
ISL
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
gu17
2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (2E)-
MFCD00075907
(2E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
ISOLIQUIRTIGENIN
4,2',4'-TRIHYDROXYCHALCONE
Isqliquiritigenin
2',4',4-TRIHYDROXYCHALCONE
(E)-1-(2,4-Dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
2',4,4'-Trihydroxychalcone
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