Taxifolin
[CAS# 480-18-2]

Identification

• Classification: Biochemical >> Natural biochemical product
• Name: Taxifolin
• Synonyms: (2R,3R)-3,3',4',5,7-Pentahydroxyflavanone; (2R,3R)-Dihydroquercetin
• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25
• CAS Registry Number: 480-18-2 (98006-93-0)
• EC Number: 207-543-4
• SMILES: C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 687.6±55.0 ºC 760 mmHg (Calc.)^*
• Flash point: 264.2±25.0 ºC (Calc.)^*
• Index of refraction: 1.763 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

Taxifolin, also known as dihydroquercetin, is a naturally occurring flavanonol widely distributed in plants such as Silybum marianum, Larix species, and various fruits including onions and grapes. Chemically, it is a flavonoid characterized by a 3-hydroxyflavanone backbone with multiple hydroxyl groups on the aromatic rings, which confer potent antioxidant properties. Taxifolin has attracted attention due to its diverse pharmacological activities, including antioxidant, anti-inflammatory, cardioprotective, neuroprotective, and anticancer effects.

The discovery of taxifolin dates back to studies of plant polyphenols in the early 20th century, when researchers were investigating the bioactive constituents responsible for the health benefits of fruits, vegetables, and medicinal plants. Isolation and structural elucidation were accomplished using chromatographic separation and spectroscopic methods, enabling further investigation into its biological activities and therapeutic potential.

Pharmacologically, taxifolin exhibits strong antioxidant activity. Its multiple hydroxyl groups allow it to scavenge reactive oxygen species (ROS), chelate metal ions, and inhibit lipid peroxidation, protecting cellular components from oxidative damage. These properties contribute to its potential in preventing oxidative stress–related diseases, such as cardiovascular and neurodegenerative disorders.

Taxifolin also demonstrates anti-inflammatory effects. It can suppress the production of pro-inflammatory cytokines and inhibit key enzymes such as cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS), thereby modulating inflammatory pathways like NF-κB and MAPK. These mechanisms underlie its therapeutic potential in conditions associated with chronic inflammation, including arthritis, metabolic disorders, and neuroinflammation.

In addition, taxifolin exhibits cardioprotective activity. It can improve endothelial function, reduce oxidative stress in cardiac tissues, and inhibit platelet aggregation, which supports its role in preventing atherosclerosis and other cardiovascular diseases. Its neuroprotective effects are also significant, as it reduces oxidative damage and inflammation in neuronal cells, mitigates apoptosis, and modulates signaling pathways involved in neurodegenerative diseases such as Alzheimer’s and Parkinson’s.

Taxifolin has shown anticancer activity in vitro and in vivo. It can induce apoptosis, inhibit cell proliferation, and interfere with cell cycle progression in various cancer cell lines. These effects are mediated through modulation of signaling pathways including PI3K/Akt, p53, and MAPK, suggesting potential applications as a chemopreventive or adjuvant therapeutic agent.

Despite its promising pharmacological profile, taxifolin has limited water solubility, which may restrict its bioavailability. Researchers are investigating formulation strategies, such as nanoparticle encapsulation, liposomal delivery, and complexation with cyclodextrins, to enhance solubility, absorption, and systemic distribution, thereby improving its therapeutic efficacy.

Overall, taxifolin is a bioactive flavanonol with a wide range of pharmacological activities, including antioxidant, anti-inflammatory, cardioprotective, neuroprotective, and anticancer effects. Its historical use in medicinal plants, combined with modern studies on its molecular mechanisms and potential applications, underscores its value as a therapeutic compound.

References

2021. Taxifolin, a novel food, attenuates acute alcohol-induced liver injury in mice through regulating the NF-κB-mediated inflammation and PI3K/Akt signalling pathways. Pharmaceutical Biology, 59(1).
DOI: 10.1080/13880209.2021.1942504

2018. Taxifolin, a natural flavonoid interacts with cell cycle regulators causes cell cycle arrest and causes tumor regression by activating Wnt/β-catenin signaling pathway. BMC Cancer, 18(1).
DOI: 10.1186/s12885-018-4959-4

2019. In Vitro and in Vivo Anti-Hyperglycemic Activities of Taxifolin and Its Derivatives Isolated from Pigmented Rice (Oryzae sativa L. cv. Superhongmi). Journal of Agricultural and Food Chemistry, 68(3).
DOI: 10.1021/acs.jafc.9b04962