Taxifolin

Taxifolin

Names
IUPAC name (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Other names Dihydroquercetin Taxifoliol Distylin Catechin hydrate (+)-Taxifolin trans-Dihydroquercetin (+)-Dihydroquercetin
Identifiers
CAS Number	480-18-2 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17948 N
ChEMBL	ChEMBL66 N
ChemSpider	388626 N
ECHA InfoCard	100.006.859
EC Number	207-543-4
KEGG	C01617 N
PubChem	439533
UNII	9SOB9E3987 N
InChI InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1 N Key: CXQWRCVTCMQVQX-LSDHHAIUSA-N N InChI=1/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1 Key: CXQWRCVTCMQVQX-LSDHHAIUBE
SMILES OC1=C(C([C@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)=O)C3=CC(O)=C1
Properties
Chemical formula	C15H12O7
Molar mass	304.25 g·mol−1
Appearance	Brown powder
UV-vis (λmax)	290, 327 nm (methanol)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Taxifolin (5,7,3',4'-flavanonol) is a flavan-on-ol, a type of flavonoid.

It can be found in conifers like the Siberian larch, Larix sibirica, in Russia, in Pinus roxburghii, in Cedrus deodara and in the Chinese yew, Taxus chinensis var. mairei.

It is also found in the silymarin extract from the milk thistle seeds.

Taxifolin is present in vinegars aged in cherry wood.

Taxifolin is not mutagenic and less toxic than the related compound quercetin. It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism. Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner. There is also a strong correlation (with a correlation coefficient of 0.93) between the antiproliferative effects of dihydroquercetin (DHQ, Taxifolin) derivatives on murine skin fibroblasts and human breast cancer cells.

The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine. Also taxifolin inhibited the cellular melanogenesis as effectively as arbutin, one of the most widely used hypopigmenting agents in cosmetics. However, arbutin acts as quercetin extremely mutagenic, carcinogenic and toxic.