Patuletin

Patuletin
Names

IUPAC name 3,3′,4′,5,7-Pentahydroxy-6-methoxyflavone
Systematic IUPAC name 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4H-1-benzopyran-4-one
Other names 6-Methoxyquercetin Quercetagetin 6-methyl ether 2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-6-methoxy-4-benzopyrone
Identifiers
CAS Number	519-96-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75164^N
ChEMBL	ChEMBL465155^N
ChemSpider	4444997^N
ECHA InfoCard	100.007.529
EC Number	208-280-8
PubChem CID	5281678
UNII	9BNM33N01N^Y
CompTox Dashboard (EPA)	DTXSID20199864
InChI InChI=1S/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3^N Key: JMIFIYIEXODVTO-UHFFFAOYSA-N^N InChI=1/C16H12O8/c1-23-16-9(19)5-10-11(13(16)21)12(20)14(22)15(24-10)6-2-3-7(17)8(18)4-6/h2-5,17-19,21-22H,1H3 Key: JMIFIYIEXODVTO-UHFFFAOYAR
SMILES COC1=C(C=C2C(=C1O)C(=O)C(=C(O2)C3=CC(=C(C=C3)O)O)O)O
Properties
Chemical formula	C₁₆H₁₂O₈
Molar mass	332.264 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

Chemical compound

Patuletin is an O-methylated flavonol. It can be found in the genus Eriocaulon.^[1]

Glycosides

Patuletin glycosides can be found in Ipomopsis aggregata.^[2]

Patuletin-3-O-rutinoside can be isolated from the aerial parts of Echinacea angustifolia.^[3]

Patuletin acetylrhamnosides can be isolated from Kalanchoe brasiliensis.^[4]

^ Bate-Smith, E. C.; Harborne, J. B. (1969). "Quercetagetin and patuletin in Eriocaulon". Phytochemistry. 8 (6): 1035. doi:10.1016/S0031-9422(00)86351-7.
^ Smith, D. M.; Glennie, C. W.; Harborne, J. B. (1971). "Identification of eupalitin, eupatolitin and patuletin glycosides in Ipomopsis aggregata". Phytochemistry. 10 (12): 3115. doi:10.1016/S0031-9422(00)97361-8.
^ Lin, L.; Qiu, S.; Lindenmaier, M.; He, X.; Featherstone, T.; Cordell, G. A. (2002). "Patuletin-3-O-Rutinoside from the Aerial Parts of Echinacea angustifolia". Pharmaceutical Biology. 40 (2): 92. doi:10.1076/phbi.40.2.92.5839. S2CID 84855629.
^ Costa, S. S.; Jossang, A.; Bodo, B.; Souza, M. L. M.; Moraes, V. L. G. (1994). "Patuletin Acetylrhamnosides from Kalanchoe brasiliensis as Inhibitors of Human Lymphocyte Proliferative Activity". Journal of Natural Products. 57 (11): 1503–1510. doi:10.1021/np50113a005. PMID 7853000.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)