Licochalcone A

Licochalcone A
Names

IUPAC name (E)-3-[4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Other names Licochalcone a
Identifiers
CAS Number	58749-22-7^Y
ChemSpider	4477422^N
Jmol interactive 3D	Image
PubChem	5318998
InChI InChI=1S/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+^N Key: KAZSKMJFUPEHHW-DHZHZOJOSA-N^N InChI=1/C21H22O4/c1-5-21(2,3)17-12-15(20(25-4)13-19(17)24)8-11-18(23)14-6-9-16(22)10-7-14/h5-13,22,24H,1H2,2-4H3/b11-8+ Key: KAZSKMJFUPEHHW-DHZHZOJOBU
SMILES CC(C)(C=C)c1cc(c(cc1O)OC)/C=C/C(=O)c2ccc(cc2)O
Properties
Chemical formula	C₂₁H₂₂O₄
Molar mass	338.39 g/mol
Hazards
R-phrases	R20, R21, R22
S-phrases	S36
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

Licochalcone A is a chalconoid, a type of natural phenols. It can be isolated from root of Glycyrrhiza glabra^[1] (liquorice) or Glycyrrhiza inflata.^[2] It shows antimalarial, anticancer, antibacterial and antiviral (specifically against influenza neuraminidase) properties in vitro.^[1]^[2]^[3]^[4]

References

1 2 Fu, Y.; Hsieh, T. C.; Guo, J.; Kunicki, J.; Lee, M. Y. W. T.; Darzynkiewicz, Z.; Wu, J. M. (2004). "Licochalcone-A, a novel flavonoid isolated from licorice root (Glycyrrhiza glabra), causes G2 and late-G1 arrests in androgen-independent PC-3 prostate cancer cells". Biochemical and Biophysical Research Communications 322 (1): 263–270. doi:10.1016/j.bbrc.2004.07.094. PMID 15313200.
1 2 Friis-Møller, A.; Chen, M.; Fuursted, K.; Christensen, S. R. B. G.; Kharazmi, A. (2002). "In Vitro Antimycobacterial and Antilegionella Activity of Licochalcone a from Chinese Licorice Roots". Planta Medica 68 (5): 416–419. doi:10.1055/s-2002-32087. PMID 12058317.
↑ Chen, M.; Theander, T. G.; Christensen, S. B.; Hviid, L.; Zhai, L.; Kharazmi, A. (1994). "Licochalcone A, a new antimalarial agent, inhibits in vitro growth of the human malaria parasite Plasmodium falciparum and protects mice from P. Yoelii infection". Antimicrobial Agents and Chemotherapy 38 (7): 1470–1475. doi:10.1128/aac.38.7.1470. PMC 284578. PMID 7979274.
↑ Dao, TT; Nguyen, PH; Lee, HS; Kim, E; Park, J; Lim, SI; Oh, WK (January 2011). "Chalcones as novel influenza A (H1N1) neuraminidase inhibitors from Glycyrrhiza inflata.". Bioorganic & Medicinal Chemistry Letters 21 (1): 294–8. doi:10.1016/j.bmcl.2010.11.016. PMID 21123068.

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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