Rutin
[CAS# 153-18-4]

Identification

• Classification: API >> Vitamins and minerals >> Vitamin C drugs
• Name: Rutin
• Synonyms: 3-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one; C.I. 75730
• Molecular Formula: C₂₇H₃₀O₁₆.3(H₂O)
• Molecular Weight: 664.57
• CAS Registry Number: 153-18-4
• EC Number: 205-814-1
• 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)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

Properties

• Water solubility: 12.5 g/100 mL
• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 195 °C
• Index of Refraction: 1.765, Calc.^*
• Boiling Point: 983.1±65.0 °C (760 mmHg), Calc.^*
• alpha: 23
• Flash Point: 325.4±27.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Rutin, also known as rutoside or quercetin-3-rutinoside, is a flavonoid glycoside that has garnered significant attention for its potential health benefits and applications. This compound is naturally found in various plants, including buckwheat, citrus fruits, and certain herbs. The discovery of rutin dates back to the early 19th century, with its initial isolation occurring in 1855 by the French chemist, Léon de Wurtz, who identified it in the flowering plant, Ruta graveolens, commonly known as rue. Since then, rutin has been the subject of extensive research, revealing its diverse biological activities and therapeutic applications.

The structure of rutin consists of a flavonoid moiety, quercetin, linked to a sugar moiety, specifically rutinose. This unique structure contributes to its solubility and bioavailability, influencing its effectiveness as a dietary supplement and therapeutic agent. Rutin's antioxidant properties are among its most significant attributes. As a potent scavenger of free radicals, rutin helps combat oxidative stress, which is linked to various chronic diseases, including cancer, cardiovascular diseases, and neurodegenerative disorders. Studies have shown that rutin can enhance the body’s antioxidant defense system, potentially reducing the risk of these diseases.

In addition to its antioxidant effects, rutin exhibits anti-inflammatory properties. Research indicates that rutin can modulate inflammatory pathways, reducing the production of pro-inflammatory cytokines. This characteristic makes it a promising candidate for managing inflammatory conditions such as arthritis and other chronic inflammatory diseases. Furthermore, rutin has been investigated for its potential benefits in cardiovascular health. It is known to strengthen blood vessels, improve circulation, and lower blood pressure, which can be particularly beneficial for individuals with hypertension or venous insufficiency.

Rutin is also recognized for its potential role in enhancing the effectiveness of other drugs. Studies have demonstrated that rutin can increase the absorption and efficacy of certain medications, making it a valuable adjuvant in combination therapies. This property is particularly relevant in cancer treatment, where rutin has been explored for its ability to enhance the effects of chemotherapy agents while mitigating their side effects.

The applications of rutin extend beyond medicine into the food and cosmetics industries. As a natural antioxidant, it is used as a food preservative to prolong shelf life and maintain the quality of food products. Additionally, rutin is included in various cosmetic formulations due to its skin-protective and anti-aging properties. Its ability to enhance skin hydration and elasticity makes it a popular ingredient in skincare products aimed at improving skin health.

Despite its numerous benefits, the bioavailability of rutin can be a limiting factor for its therapeutic efficacy. Researchers are actively exploring various formulations and delivery methods to enhance its absorption and bioactivity. This includes the use of nanoparticles, liposomes, and other advanced delivery systems to improve the pharmacokinetics of rutin.

In summary, rutin is a significant flavonoid with a rich history of discovery and a wide range of applications in health and wellness. Its antioxidant, anti-inflammatory, and vascular protective properties make it a valuable compound in both traditional and modern medicine. Ongoing research continues to unveil the potential of rutin in various therapeutic contexts, highlighting its importance in promoting health and preventing disease.

References

2024. Unraveling the phytochemical complexity and antimicrobial potency of introduced versus native Argania spinosa trees in Eastern Morocco. Chemical Papers, 78.
DOI: 10.1007/s11696-024-03739-1

1969. Metabolism of rutin by Polyporus versicolor PRL 572. Canadian Journal of Microbiology, 15.
DOI: 10.1139/m69-155

1979. Uncaria Elliptica a Major Source of Rutin. Planta Medica, 36.
DOI: 10.1055/s-0028-1097258