Taxifolin

Names

[ CAS No. ]:
480-18-2

[ Name ]:
Taxifolin

[Synonym ]:
EINECS 207-543-4
Dihydroquercetin
(3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one
(2R,3R)-3,3',4',5,7-Pentahydroxyflavanone
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
Distylin
(+)-Taxifolin
(2S,3S)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-trans)-
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2S,3S)-
Taxifolin
MFCD00006845
(-)-taxifolin
Taxifoliol
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-chromen-4-one

Biological Activity

[Description]:

Taxifolin exhibits important anti-tyrosinase activity. Taxifolin exhibits significant inhibitory activity against collagenase with an IC50 value of 193.3 μM.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

Research Areas >> Cancer

Natural Products >> Flavonoids

[Target]

IC50: 193.3 μM (Collagenase)[1] Tyrosinase[1]

[In Vitro]

This is confirmed by the investigation of pure Taxifolin and (+)-Catechin against collagenase activity. Taxifolin exhibits significant inhibitory activity with an IC50 value of 193.3 μM while (+)-Catechin is not active[1]. Taxifolin is a ubiquitous bioactive constituent of foods and herbs. Taxifolin (dihydroquercetin) is a bioactive flavanonol commonly found in grapes, citrus fruits, onions, green tea, olive oil, wine, and many other foods, as well as several herbs (such as milk thistle, French maritime bark, Douglas fir bark, and Smilacis Glabrae Rhizoma)[2].

[In Vivo]

Taxifolin may be easily metabolized and that its metabolites are the prevalent form in vivo, although limited information is available on metabolism of Taxifolin in vivo[2].

[Animal admin]

Rats[2] Twelve male Sprague-Dawley rats (weighing 180-220 g) are used. The rats are randomly divided into two groups (six rats per group), a drug group and a blank group. Taxifolin is suspended in 0.5% CMC-Na solution and orally administered to the drug group at a dose of 200 mg/kg body weight, while blank group rats are orally administered 0.5% CMC-Na solution at the same volume. All rats are dosed once a day (at 9:00 a.m.) for 3 days.

[References]

[1]. Angelis A, et al. Bio-Guided Isolation of Methanol-Soluble Metabolites of Common Spruce (Picea abies) Bark by-Products and Investigation of Their Dermo-Cosmetic Properties. Molecules. 2016 Nov 21;21(11). pii: E1586.

[2]. Yang P, et al. Detection of 191 Taxifolin Metabolites and Their Distribution in Rats Using HPLC-ESI-IT-TOF-MS(n). Molecules. 2016 Sep 13;21(9). pii: E1209.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
687.6±55.0 °C at 760 mmHg

[ Melting Point ]:
230-233°C (dec.)

[ Molecular Formula ]:
C₁₅H₁₂O₇

[ Molecular Weight ]:
304.252

[ Flash Point ]:
264.2±25.0 °C

[ Exact Mass ]:
304.058289

[ PSA ]:
127.45000

[ LogP ]:
1.82

[ Vapour Pressure ]:
0.0±2.3 mmHg at 25°C

[ Index of Refraction ]:
1.763

[ Storage condition ]:
-20?C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK6920000

CHEMICAL NAME :: Flavanone, 3,3',4',5,7-pentahydroxy-

CAS REGISTRY NUMBER :: 480-18-2

BEILSTEIN REFERENCE NO. :: 0093548

LAST UPDATED :: 199701

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C15-H12-O7

MOLECULAR WEIGHT :: 304.27

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1200 mg/kg

TOXIC EFFECTS :: Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 985 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Fibroblast

DOSE/DURATION :: 1 gm/L/48H

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 48,337,1977

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
LK6920000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Combined experimental and in silico approaches for exploring antiperoxidative potential of structurally diverse classes of antioxidants on docetaxel-induced lipid peroxidation using 4-HNE as the model marker.

Bioorg. Chem. 56 , 1-7, (2014)

The objective of the present work was tantamount to explain the antiperoxidative potential and structural requirements of twenty-eight structurally diverse classes of antioxidants on docetaxel-induced...

In vitro effects of myricetin, morin, apigenin, (+)-taxifolin, (+)-catechin, (-)-epicatechin, naringenin and naringin on cytochrome b5 reduction by purified NADH-cytochrome b5 reductase.

Toxicology 308 , 34-40, (2013)

The microsomal NADH-dependent electron transport system consisting of cytochrome b5 reductase and cytochrome b5 participates in a number of physiologically important processes including lipid metaboli...

Chemical profiling and quantification of Gua-Lou-Gui-Zhi decoction by high performance liquid chromatography/quadrupole-time-of-flight mass spectrometry and ultra-performance liquid chromatography/triple quadrupole mass spectrometry.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 986-987 , 69-84, (2015)

Gua-Lou-Gui-Zhi decoction (GLGZD) is a classical formula of traditional Chinese medicine, which has been commonly used to treat dysfunction after stroke, epilepsy and spinal cord injury. In this study...

Related Compounds

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