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Isoliquiritigenin
Names

Preferred IUPAC name 2′,4,4′-Trihydroxychalcone
Other names 6'-Deoxychalcone 4,2',4'-Trihydroxychalcone 2',4',4-Trihydroxychalcone
Identifiers
CAS Number	961-29-5^Y
3D model (JSmol)	Interactive image
Abbreviations	ILTG
ChEBI	CHEBI:310312^N
ChEMBL	ChEMBL129795^N
ChemSpider	553829^N
ECHA InfoCard	100.202.617
EC Number	237-316-5
KEGG	C08650^N
PubChem CID	638278
UNII	B9CTI9GB8F^Y
CompTox Dashboard (EPA)
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	256.257 g·mol⁻¹
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.^[1]

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.

Isoliquiritigenin has been found to be a potent (65 times higher affinity than diazepam) GABA-A benzodiapine receptor positive allosteric modulator.^[2] It can target miR-301b/LRIG1 signaling pathways, resulting in the inhibition of melanoma growth in vitro.^[3]

^ Nerya, Ohad; Vaya, Jacob; Musa, Ramadan; Izrael, Sarit; Ben-Arie, Ruth; Tamir, Snait (2003). "Glabrene and Isoliquiritigenin as Tyrosinase Inhibitors from Licorice Roots". Journal of Agricultural and Food Chemistry. 51 (5): 1201–1207. doi:10.1021/jf020935u. PMID 12590456.
^ 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.
^ Xiang, Shijian; Chen, Huoji; Luo, Xiaojun; An, Baichao; Wu, Wenfeng; Cao, Siwei; Ruan, Shifa; Wang, Zhuxian; Weng, Lidong; Zhu, Hongxia; Liu, Qiang (2018). "Isoliquiritigenin suppresses human melanoma growth by targeting miR-301b/LRIG1 signaling". Journal of Experimental & Clinical Cancer Research. 37 (1): 184. doi:10.1186/s13046-018-0844-x. PMC 6091185. PMID 30081934.

v t e 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

This page was last edited on 3 December 2023, at 16:14