Astilbin

Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer.^[2]

Astilbin

Names
IUPAC name (2R,3R)-3′,4′,5,7-Tetrahydroxy-3-(α-L-rhamnopyranosyloxy)flavan-4-one
Systematic IUPAC name (2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2,3-dihydro-4H-1-benzopyran-4-one
Other names Isoastilbin Neoastilbin Neoisoastilbin Taxifolin 3-O-rhamnoside Taxifolin 3-rhamnoside (2R-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one[1]
Identifiers
CAS Number	54141-72-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:38200 Y
ChEMBL	ChEMBL486017 Y
ChemSpider	106533 Y
ECHA InfoCard	100.222.924
KEGG	C17449
PubChem CID	119258
UNII	KA92CW3M68 Y
CompTox Dashboard (EPA)	DTXSID501019948
InChI InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 Y Key: ZROGCCBNZBKLEL-MPRHSVQHSA-N Y InChI=1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 Key: ZROGCCBNZBKLEL-MPRHSVQHBV
SMILES O=C3c4c(O)cc(O)cc4O[C@H](c1ccc(O)c(O)c1)[C@H]3O[C@@H]2O[C@H]([C@H](O)[C@@H](O)[C@H]2O)C
Properties
Chemical formula	C21H22O11
Molar mass	450.39 g/mol
Appearance	brown powder[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

Natural occurrences

Astilbin can be found in St John's wort (Hypericum perforatum, Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in Dimorphandra mollis^[3] (Fava d'anta, Fabaceae), in the leaves of Harungana madagascariensis (Hypericaceae),^[4] in the rhizome of Astilbe thunbergii,^[5] in the root of Astilbe odontophylla^[6] (Saxifragaceae), in the rhizome of Smilax glabra^[7] (Chinaroot, Smilacaceae) and in the bark of Hymenaea martiana.^[8]

In food

It can be isolated from Kohki tea processed from Engelhardtia chrysolepis (huang-qui).^[2] It is also present in certain wines.^[9]

Uses

Astilbin can act as an insecticide against Anticarsia gemmatalis and Spodoptera frugiperda.^[3] It shows in vitro antibacterial activity^[4] and activity on burn wound healing.^[5] Astilbin is used in traditional Chinese medicine.^[6]

Related compounds

3'-O-Methylastilbin shows an immunosuppressive activity against contact dermatitis.^[7]