Natsudaidain

Natsudaidain
Names

IUPAC name 3-Hydroxy-3′,4′,5,6,7,8-hexamethoxyflavone
Systematic IUPAC name 2-(3,4-Dimethoxyphenyl)-3-hydroxy-5,6,7,8-tetramethoxy-4H-1-benzopyran-4-one
Identifiers
CAS Number	35154-55-3^Y
3D model (JSmol)	Interactive image
ChemSpider	2341642^N
PubChem CID	3084605
UNII	28441ILD21^Y
CompTox Dashboard (EPA)	DTXSID00188655
InChI InChI=1S/C21H22O9/c1-24-11-8-7-10(9-12(11)25-2)16-15(23)14(22)13-17(26-3)19(27-4)21(29-6)20(28-5)18(13)30-16/h7-9,23H,1-6H3^N Key: CCJBNIRSVUKABH-UHFFFAOYSA-N^N InChI=1/C21H22O9/c1-24-11-8-7-10(9-12(11)25-2)16-15(23)14(22)13-17(26-3)19(27-4)21(29-6)20(28-5)18(13)30-16/h7-9,23H,1-6H3 Key: CCJBNIRSVUKABH-UHFFFAOYAO
SMILES COC1=C(C=C(C=C1)C2=C(C(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC)O)OC
Properties
Chemical formula	C₂₁H₂₂O₉
Molar mass	418.39 g/mol
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

Natsudaidain is an O-methylated flavonol, a type of chemical compound. It can be isolated from Citrus plants^[1] (Rutaceae). The name of the molecule comes from Citrus natsudaidai (Natsumikan, lit. "summer tangerine"), a fruit of Japan developed in 1740 with a particularly tart/sour taste.

References

^ Matsui, T.; Ito, C.; Itoigawa, M.; Okada, T.; Furukawa, H. (2009). "Effect of natsudaidain isolated from Citrus plants on TNF-α and cyclooxygenase-2 expression in RBL-2H3 cells". Journal of Pharmacy and Pharmacology. 61 (1): 109–114. doi:10.1211/jpp/61.01.0015. PMID 19126304.

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Fisetin
Galangin
Gossypetin
Herbacetin
Kaempferol
Morin
Myricetin
Quercetagetin
Quercetin
Robinetin

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

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)