Isoliquiritigenin

Isoliquiritigenin
Names

IUPAC name (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
Other names 6'-deoxychalcone 2',4,4'-Trihydroxychalcone 4,2',4'-Trihydroxychalcone 4'2'4'-trihydroxychalcone 2',4',4-Trihydroxychalcone
Identifiers
CAS Number	961-29-5^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:310312^N
ChEMBL	ChEMBL129795^N
ChemSpider	553829^N
ECHA InfoCard	100.202.617
EC Number	237-316-5
KEGG	C08650^N
PubChem	638278
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+^N Key: DXDRHHKMWQZJHT-FPYGCLRLSA-N^N InChI=1/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+ Key: DXDRHHKMWQZJHT-FPYGCLRLBB
SMILES C1=CC(=CC=C1C=CC(=O)C2=C(C=C(C=C2)O)O)O
Properties
Chemical formula	C₁₅H₁₂O₄
Molar mass	256.25 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Isoliquiritigenin is a phenolic chemical compound found in licorice. It is under experimentation phase testing for use as a cancer treatment and as an aide for cocaine addiction. It is a sirtuin-activating compound.

Metabolism

The enzyme 6'-deoxychalcone synthase uses malonyl-CoA, 4-coumaroyl-CoA, NADPH, and H⁺ to produce CoA, isoliquiritigenin, CO₂, NADP⁺, and H₂O.

The enzyme isoliquiritigenin 2'-O-methyltransferase further transforms isoliquiritigenin into 2'-O-methylisoliquiritigenin.

Mechanism of action

Isoliquiritigenin has been found to potent (65 times higher affinity than diazepine) GABA-A benzodiapine receptor positive allosteric modulator.^[1]

References

↑ Cho, S; Kim, S; Jin, Z; Yang, H; Han, D; Baek, N. I.; Jo, J; Cho, C. W.; Park, J. H.; Shimizu, M; Jin, Y. H. (2011). "Isoliquiritigenin, a chalcone compound, is a positive allosteric modulator of GABAA receptors and shows hypnotic effects". Biochemical and Biophysical Research Communications. 413 (4): 637–42. doi:10.1016/j.bbrc.2011.09.026. PMID 21945440.

Chalconoids and their glycosides

Chalconoids	Butein Isoliquiritigenin Methyl hydroxychalcone Okanin

Chalconoid glycosides	Carthamin Marein okanin 3,4,3′-trimethyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside okanin 4-methyl ether 4′-glucoside monoacetate Okanin 3,4-dimethyl ether 4′-glucoside

Acylated chalconoids	Licochalcone A Sophoradin (prenylated) Tephrospinosin (3′,5′-diisopentenyl-2′,4′-dihydroxychalcone) (prenylated) Xanthohumol (prenylated)

O-methylated chalconoids	Cardamomin Flavokawin B Okanin 3,4,3′,4′-tetramethyl ether Pashanone (2',6'-Dihydroxy-3',4'-dimethoxychalcone)

Flavokavains	Flavokavain A Flavokavain B Flavokavain C

Synthetic	Sofalcone

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