Licochalcone A - Misplaced Pages

Licochalcone A
Names

Preferred IUPAC name (2E)-3--1-(4-hydroxyphenyl)prop-2-en-1-one
Other names Licochalcone a
Identifiers
CAS Number	58749-22-7
3D model (JSmol)	Interactive image
ChEBI	CHEBI:125689
ChEMBL	ChEMBL139702
ChemSpider	4477422
ECHA InfoCard	100.163.544
EC Number	635-678-2
PubChem CID	5318998
UNII	JTV5467968
CompTox Dashboard (EPA)	DTXSID10904181
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+Key: KAZSKMJFUPEHHW-DHZHZOJOSA-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	338.403 g·mol
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H332
Precautionary statements	P261, P264, P280
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Licochalcone A is a chalconoid, a type of natural phenol. It can be isolated from the root of Glycyrrhiza glabra (liquorice) or Glycyrrhiza inflata. It shows antimalarial, anticancer, antibacterial and antiviral (specifically against influenza neuraminidase) properties in vitro.

References

^ "Licochalcone A Safety Data Sheet" (PDF). Cayman Chemicals.
^ 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.
^ 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.

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

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