Troxerutin
[CAS# 7085-55-4]

Identification

• Classification: API >> Vitamins and minerals >> Vitamin C drugs
• Name: Troxerutin
• Synonyms: Trihydroxyethylrutin; 3',4',7-Tris[O-(2-hydroxyethyl)]rutin
• Molecular Formula: C₃₃H₄₂O₁₉
• Molecular Weight: 742.68
• CAS Registry Number: 7085-55-4
• EC Number: 230-389-4
• SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OCCO)C5=CC(=C(C=C5)OCCO)OCCO)O)O)O)O)O)O

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.690, Calc.^*
• Boiling Point: 1058.4±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 332.0±27.8 °C, Calc.^*

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

Safety Data

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

Hazard Classification

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

Discovery and Applications

Troxerutin (C21H20O11) is a flavonoid compound derived from rutin, a common flavonoid found in various plants, such as buckwheat, citrus fruits, and apples. It is a glycoside of quercetin and has garnered attention due to its numerous biological activities, which make it a valuable substance in both medical and cosmetic applications. Troxerutin's discovery and applications have expanded as research into its pharmacological and therapeutic properties has progressed, particularly in the areas of vascular health, antioxidant effects, and inflammation management.

The compound was first isolated in the mid-20th century, and its molecular structure was confirmed as a derivative of rutin. Troxerutin differs from rutin in the position of its hydroxyl group, which influences its biological activity. Although rutin itself has been studied for a variety of health benefits, troxerutin has emerged as a more potent variant with enhanced bioavailability, making it a more effective agent in medical applications.

Troxerutin has gained popularity for its therapeutic effects on the vascular system. Research has demonstrated that it possesses a variety of beneficial properties, including the ability to improve blood circulation, reduce capillary permeability, and strengthen blood vessel walls. These effects are particularly useful in treating conditions such as chronic venous insufficiency (CVI), varicose veins, and hemorrhoids, all of which are associated with poor blood flow and weak blood vessel walls. Troxerutin's ability to improve endothelial function and reduce inflammation in the vascular walls has made it a key ingredient in treatments aimed at alleviating the symptoms of these conditions. In many cases, troxerutin is used topically or orally as part of a therapeutic regimen to improve circulation and reduce swelling.

In addition to its vascular benefits, troxerutin is recognized for its antioxidant properties. The compound scavenges free radicals and reduces oxidative stress, which can otherwise contribute to aging, tissue damage, and the development of chronic diseases. As a result, troxerutin is frequently included in dietary supplements, skin care products, and anti-aging treatments. In cosmetics, it is often added to formulations designed to protect the skin from environmental damage, improve skin tone, and reduce signs of aging, such as wrinkles and age spots.

Troxerutin's anti-inflammatory effects also extend to its use in treating various inflammatory conditions, including osteoarthritis and other musculoskeletal disorders. Its ability to modulate the inflammatory response by inhibiting pro-inflammatory cytokines and reducing swelling makes it a valuable agent in the management of pain and inflammation. This property of troxerutin has led to its inclusion in formulations aimed at reducing joint pain, improving mobility, and promoting overall musculoskeletal health.

Beyond its use in vascular health, antioxidant, and anti-inflammatory treatments, troxerutin has been studied for its potential neuroprotective effects. Preliminary research suggests that it may have applications in protecting the brain and nervous system from oxidative damage and neurodegenerative conditions, such as Alzheimer's disease. Although further studies are needed to confirm its role in these areas, the compound's antioxidant and anti-inflammatory properties make it a promising candidate for future research in the neurodegenerative field.

Troxerutin has also been investigated for its potential as an adjunct therapy in diabetes management. It has been shown to reduce the formation of advanced glycation end products (AGEs), which are implicated in diabetic complications such as retinopathy and nephropathy. By inhibiting AGE formation, troxerutin may help to reduce the risk of long-term complications in diabetic patients.

In summary, troxerutin is a versatile and bioactive compound with a wide range of applications. Its discovery and subsequent research have revealed its potential as a therapeutic agent for improving vascular health, reducing inflammation, and protecting against oxidative stress. As research continues, troxerutin's role in treating various health conditions is expected to expand, solidifying its place in both pharmaceutical and cosmetic industries.

References

2024. Dissecting the antidepressant effect of troxerutin: modulation of neuroinflammatory and oxidative stress biomarkers in lipopolysaccharide-treated mice. Naunyn-Schmiedeberg's Archives of Pharmacology, 397(12).
DOI: 10.1007/s00210-024-03252-y

2024. Coumarin—Synthetic Methodologies, Pharmacology, and Application as Natural Fluorophore. Topics in current chemistry (Cham), 382(3).
DOI: 10.1007/s41061-024-00462-z

2024. Efficient regioselective enzymatic acylation of troxerutin: difference characterization of in vitro cellular uptake and cytotoxicity. Food & Function, 15(10).
DOI: 10.1039/d4fo00906a