TRIHYDROXYCHALCONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H12O4
Molecular Weight	256.2534
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=CC=C(\C=C\C(=O)C2=CC=C(O)C=C2O)C=C1

InChI

InChIKey=DXDRHHKMWQZJHT-FPYGCLRLSA-N

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+

HIDE SMILES / InChI

Molecular Formula	C15H12O4
Molecular Weight	256.2534
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18824345 | https://www.ncbi.nlm.nih.gov/pubmed/20412384

Trihydroxychalcone (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. Trihydroxychalcone is a potent antimetastatic agent, which can markedly inhibit the metastatic and invasive capacity of prostate cancer cells. The inhibition of JNK/AP-1 signaling may be one of the mechanisms by which ISL inhibits cancer cell invasion and migration. Trihydroxychalcone has been shown to be a BACE1 inhibitor, which could ameliorate memory impairment in mice, and is expected to be potentially used as a lead compound for further anti-AD reagent development.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cytochrome P450 1A 1 Target ID: CHEMBL3544905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15664435	Inhibitor 8504
Aldose reductase 45 Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11370705 \| https://www.ncbi.nlm.nih.gov/pubmed/10220294	Inhibitor 8504	320.0 nM [IC50]
Monoamine oxidase A 52 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11501051	Inhibitor 8504	13.9 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11501051	Inhibitor 8504	47.2 µM [IC50]
Beta-secretase 1 21 Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20412384	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 278 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20412384	Primary		Preclinical	Unknown Approved Use Unknown
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068129 https://www.ncbi.nlm.nih.gov/pubmed/1899810	Preventing		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Isoliquiritigen enhances the antitumour activity and decreases the genotoxic effect of cyclophosphamide.	2013-07-24	23887720
Isoliquiritigenin inhibits cell proliferation and induces apoptosis in human hepatoma cells.	2005-02	15729620
Studies on cancer chemoprevention by traditional folk medicines XXV. Inhibitory effect of isoliquiritigenin on azoxymethane-induced murine colon aberrant crypt focus formation and carcinogenesis.	2002-02	11853176
The potent anti-tumor-promoting agent isoliquiritigenin.	1991-02	1899810
Metabolism and excretion of butein, 2',3,4-trihydroxychalcone, 3-O-methylbutein, 4-O-methylbutein and 2',4',4-trihydroxychalcone in the rat.	1983-11	6673378

Patents

Sample Use Guides

In Vivo Use Guide

In APP-PS1 double transgenic mice model the treatment of 9 mg/kg/day of Trihydroxychalcone could obviously decrease Abeta production and Abeta plaque formation, while efficiently improve the memory impairment based on Morris water maze test.

Route of Administration: Intraperitoneal

In Vitro Use Guide

DU145 cells were cultured in the presence of 0-20 umol/L Trihydroxychalcone with or without 10 ug/L epidermal growth factor (EGF). Trihydroxychalcone inhibited basal and EGF-induced cell migration, invasion and adhesion dose dependently. Trihydroxychalcone decreased EGF-induced secretion of urokinase-type plasminogen activator (uPA), matrix metalloproteinase (MMP)-9, tissue inhibitor of metalloproteinase-1 (TIMP-1), and vascular endothelial growth factor (VEGF), but increased TIMP-2 secretion in a concentration-dependent manner.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:00:33 GMT 2025` Edited by `admin` on `Mon Mar 31 19:00:33 GMT 2025`
Record UNII	B9CTI9GB8F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ILG

Preferred Name

English

TRIHYDROXYCHALCONE

Official Name

English

GU 17

Code

English

2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (2E)-

Systematic Name

English

2-PROPEN-1-ONE, 1-(2,4-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-, (E)-

Systematic Name

English

ISOLIQUIRITIGEN

Common Name

English

ISOLIQUIRITIGENIN

Common Name

English

CHALCONE, 2',4,4'-TRIHYDROXY-

Systematic Name

English

2',4,4'-TRIHYDROXYCHALCONE

Systematic Name

English

Code System Code Type Description

CAS

13745-20-5