Structure via PubChem · Public domain (PubChem)
astilbin
Sign in to saveAlso known as (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one, (2R,3R)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one, dihydroquercetin-3-O-alpha-LRhap
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.
Chemical data
- Formula
- C21H22O11
- Molecular weight
- 450.4 g/mol
- 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-dihydrochromen-4-one
- SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
- InChIKey
- ZROGCCBNZBKLEL-MPRHSVQHSA-N
- XLogP
- 0.4
- Polar surface area
- 186 Ų
- H-bond donors
- 7
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- flavanone
- Mass
- 450.116212
Show 4 more facts
- found in taxon
- Eucalyptus maidenii
- chemical formula
- C₂₁H₂₂O₁₁
- isomeric SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
- canonical SMILES
- CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Natural occurrences
- Uses
- Related compounds
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477368956 | Name = Astilbin | ImageFile = Astilbin.svg | ImageSize = 250px | IUPACName = (2R,3R)-3′,4′,5,7-Tetrahydroxy-3-(α-L-rhamnopyranosyloxy)flavan-4-one | SystematicName = (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 | OtherNames = IsoastilbinNeoastilbinNeoisoastilbinTaxifolin 3-O-rhamnosideTaxifolin 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 |Section1= |Section2= |Section3= }} 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.
== 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 (Fava d'anta, Fabaceae), in the leaves of Harungana madagascariensis (Hypericaceae), in the rhizome of Astilbe thunbergii, in the root of Astilbe odontophylla (Saxifragaceae), in the rhizome of Smilax glabra (Chinaroot, Smilacaceae) and in the bark of Hymenaea martiana. In food It can be isolated from Kohki tea processed from Engelhardtia chrysolepis (huang-qui). It is also present in certain wines.
Excerpted from Wikipedia’s “astilbin” article, available under the CC BY-SA 4.0 licence.