Isoliquiritigenin

HCID 638278CAS 13745-20-5
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C(/C=C/c1ccc(O)cc1)c1ccc(O)cc1O
InChIKey
DXDRHHKMWQZJHT-FPYGCLRLSA-N
Molecular formula
C15H12O4
Average molar mass
256.25 g/mol
Monoisotopic mass
256.07355886

Overview

Isoliquiritigenin is a member of the class of chalcones that is trans-chalcone hydroxylated at C-2', -4 and -4'. It has a role as a geroprotector, a metabolite, a biological pigment, an antineoplastic agent, a GABA modulator, an EC 1.14.18.1 (tyrosinase) inhibitor and a NMDA receptor antagonist. It is a member of chalcones and a member of (E)-2'-hydroxy-chalcones. It is functionally related to a trans-chalcone. It is a conjugate acid of an isoliquiritigenin(1-).

Names & identifiers

Preferred name
Isoliquiritigenin
IUPAC
(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
English name
Isoliquiritigenin
Molecular formula
C15H12O4
Molecular weight
256.25

Names & synonyms

isoliquiritigenin961-29-5(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-onetrihydroxychalcone6'-deoxychalcone2',4',4-TrihydroxychalconeChalcone, 2',4,4'-trihydroxy-GU 17B9CTI9GB8FGU-17trans-2',4,4'-trihydroxychalcone2-Propen-1-one, 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-, (E)-
Show more names
ISLISOLIQUIRTIGENIN4,2',4'-TRIHYDROXYCHALCONE(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-onegu17IsoliquiritigenIsqliquiritigeninISOLIQUIRITIGENIN(P)Isoliquiritigenin>
DTXSID2022466(E)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenoneCHEBI:310312(E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-oneRefChem:51351DTXCID202466677-489-82',4,4'-Trihydroxychalcone

Database identifiers

CAS
13745-20-5、961-29-5
PubChem CID
638278
DTXSID
DTXSID2022466
ChEMBL
CHEMBL129795
ChEBI
CHEBI:310312
UNII
B9CTI9GB8F
EC Number
237-316-5、677-489-8
Nikkaji
J120.923J、J74.686J

Properties

Computed structural properties

XLogP
3.2
Topological polar surface area
77.8 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
4
Rotatable bonds
3
Heavy atoms
19

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
LogP1.91
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point200 - 204 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
206 · 206-210°C
Boiling point
504 · 504.0±42.0 °C(Predicted)
Density
1.384 · 1.384±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: <0.1 mg/mL
form
powder

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 5 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

wgk
3
rtecs
FL7080000
hs_code
29145090
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationCompounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Cellular LocationsMembrane
Applications · 3 items

Usesaldose reductase inhibitor, antineoplastic, antiinflammatory

UsesIsoliquiritigenin (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 reductase-1, a phase II enzyme that deactivates radicals and electrophiles, with a concentration required to double activity (CD) value of 1.8 μM in murine hepatoma cells.

General DescriptionIsoliquiritigenin 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
西安久启生物科技有限公司18729366352 13186100227
Additional notes · 1 item

DefinitionChEBI: Isoliquiritigenin is a member of the class of chalcones that is trans-chalcone hydroxylated at C-2', -4 and -4'. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, a biological pigment, a NMDA receptor antagonist, a GABA modulator, a metabolite, an antineoplastic agent and a geroprotector. It is functionally related to a trans-chalcone. It is a conjugate acid of an isoliquiritigenin(1-).

Related reactions

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