Structure via PubChem · Public domain (PubChem)
(+)-taxifolin
Sign in to saveAlso known as (+)-(2R,3R)-dihydroquercetin, (2R,3R)-(+)-taxifolin, (2R,3R)-dihydroquercetin, Dihydroquercetin, (2R,3R)-3,3',4',5,7-pentahydroxyflavanone, (+)-dihydroquercetin, (2R,3R)-3,3',4',5,7-Pentahydroxyflavanone, (2R,3R)-Dihydroquercetin
Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle.
Chemical data
- Formula
- C15H12O7
- Molecular weight
- 304.25 g/mol
- IUPAC name
- (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
- SMILES
- C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O
- InChIKey
- CXQWRCVTCMQVQX-LSDHHAIUSA-N
- XLogP
- 1.5
- Polar surface area
- 127 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,393 papers- Taxifolin Alleviates DSS-Induced Ulcerative Colitis by Acting on Gut Microbiome to Produce Butyric Acid.Nutrients · 2022
- New Perspectives of Taxifolin in Neurodegenerative Diseases.Current neuropharmacology · 2023
- Unveiling the therapeutic potential of Taxifolin in Cancer: From molecular mechanisms to immune modulation and synergistic combinations.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- "Non-Taxifolin" Derived Flavonolignans: Phytochemistry and Biology.Current pharmaceutical design · 2015
- Advances in biochemistry and the biotechnological production of taxifolin and its derivatives.Biotechnology and applied biochemistry · 2022
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 304.058302724
Show 7 more facts
- found in taxon
- Dioscorea alata
- chemical formula
- C₁₅H₁₂O₇
- Commons category
- Taxifolin
- subject has role
- non-steroidal anti-inflammatory drug
- isomeric SMILES
- OC1=C(C([C@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)=O)C3=CC(O)=C1
- canonical SMILES
- O=C1C=2C(O)=CC(O)=CC2OC(C3=CC=C(O)C(O)=C3)C1O
- has characteristic
- bitterness
Sources (6)
via Wikidata · CC0
~5 min read
Encyclopedic overview
7 sectionsContents
- Stereocenters
- Natural occurrences
- Pharmacology
- Metabolism
- Glycosides
- Derived natural compounds
- References
Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle.
== Stereocenters == Taxifolin has two stereocenters on the C-ring, as opposed to quercetin which has none. For example, (+)-taxifolin has (2R,3R)-configuration, making it one out of four stereoisomers that comprise two pairs of enantiomers.
Excerpted from Wikipedia’s “(+)-taxifolin” article, available under the CC BY-SA 4.0 licence.