Centaureidin

Centaureidin is an O-methylated flavonol. It can be isolated from Tanacetum microphyllum,[1] Achillea millefolium,[2] Brickellia veronicaefolia, Bidens pilosa[3] and Polymnia fruticosa.[4]

Centaureidin

Names
IUPAC name 5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6-dimethoxychromen-4-one
Other names Desmethoxycentaureidine 5,7,3'-Trihydroxy-3,6,4'-trimethoxyflavone
Identifiers
CAS Number	17313-52-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:69356^N
ChemSpider	4474997^N
PubChem CID	5315773
UNII	548R7290J9^Y
CompTox Dashboard (EPA)	DTXSID50169530
InChI InChI=1S/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3^N Key: BZXULYMZYPRZOG-UHFFFAOYSA-N^N InChI=1/C18H16O8/c1-23-11-5-4-8(6-9(11)19)16-18(25-3)15(22)13-12(26-16)7-10(20)17(24-2)14(13)21/h4-7,19-21H,1-3H3 Key: BZXULYMZYPRZOG-UHFFFAOYAN
SMILES O=C1c3c(O)c(OC)c(O)cc3O/C(=C1/OC)c2ccc(OC)c(O)c2
Properties
Chemical formula	C18H16O8
Molar mass	360.31 g/mol
Density	1.542 g/mL
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

References

1. Abad, Maria Jose; Bermejo, Paulina; Villar, Angel (1995). "The activity of flavonoids extracted from Tanacetum microphyllum DC. (Compositae) on soybean lipoxygenase and prostaglandin synthetase". General Pharmacology: The Vascular System. 26 (4): 815–9. doi:10.1016/0306-3623(94)00242-F. PMID 7635257.
2. "Assessment Report on Achillea Millefolium L., Herba" (PDF). European Medicines Agency. 15 September 2010. Retrieved 15 October 2018.
3. Chang, Shu-Lin; Chiang, Yi-Ming; Chang, Cicero Lee-Tian; Yeh, Hsu-Hua; Shyur, Lie-Fen; Kuo, Yueh-Hsiung; Wu, Tung-Kung; Yang, Wen-Chin (2007). "Flavonoids, centaurein and centaureidin, from Bidens pilosa, stimulate IFN-γ expression". Journal of Ethnopharmacology. 112 (2): 232–6. doi:10.1016/j.jep.2007.03.001. PMID 17408892.
4. Beutler, John A.; Cardellina, John H.; Lin, Chii M.; Hamel, Ernest; Cragg, Gordon M.; Boyd, Michael R. (1993). "Centaureidin, a cytotoxic flavone from Polymnia fruticosa, inhibits tubulin polymerization". Bioorganic & Medicinal Chemistry Letters. 3 (4): 581–4. doi:10.1016/S0960-894X(01)81233-6.