Hesperidin
[CAS# 520-26-3]

Identification

• Classification: API >> Circulatory system medication >> Regulating blood lipids
• Name: Hesperidin
• Synonyms: (S)-7-[[6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one; Vitamin P
• Molecular Formula: C₂₈H₃₄O₁₅
• Molecular Weight: 610.57
• CAS Registry Number: 520-26-3
• EC Number: 208-288-1
• 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=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O

Properties

• Density: ensity1.7±0.1 g/mL, Calc.^*
• Melting point: 250-255 °C (Expl.)
• alpha: -76 ° (c=2,pyridine)
• Index of Refraction: 1.695, Calc.^*
• Boiling Point: 930.1±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 305.5±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-P305+P351+P338

Discovery and Applications

Hesperidin is a flavonoid glycoside primarily found in citrus fruits, especially in oranges and lemons. Its chemical structure consists of a flavanone (a type of flavonoid) backbone bound to a rutinose sugar moiety. Hesperidin has been studied extensively due to its potential health benefits, particularly for its antioxidant, anti-inflammatory, and cardiovascular protective effects.

The compound was first identified in the late 19th century, with its name derived from *Citrus aurantiifolia* (the sweet orange), where it was initially isolated. Over the years, hesperidin has attracted significant interest from researchers due to its presence in common dietary sources and its bioactive properties. In the body, hesperidin is primarily metabolized into its aglycone form, hesperetin, which is thought to contribute to many of its biological effects.

One of the main applications of hesperidin is in the formulation of dietary supplements. It is widely used for its antioxidant properties, which help neutralize harmful free radicals in the body, potentially reducing the risk of chronic diseases such as cardiovascular diseases and certain types of cancer. Hesperidin’s antioxidant effects are also linked to its ability to improve blood circulation, which has made it a popular ingredient in products aimed at improving vascular health. Studies have shown that hesperidin may help strengthen blood vessel walls, reduce capillary permeability, and improve overall blood flow, which is beneficial for conditions such as varicose veins and hemorrhoids.

Hesperidin has also been investigated for its potential anti-inflammatory and antihypertensive (blood pressure-lowering) effects. It has been suggested that it may help reduce oxidative stress and inflammation, which are contributing factors in the development of hypertension and atherosclerosis. Clinical studies have explored its role in managing blood pressure, with some showing that hesperidin supplementation may modestly reduce systolic and diastolic blood pressure in individuals with hypertension.

In addition to its cardiovascular benefits, hesperidin is also used for its potential neuroprotective properties. It has been investigated for its role in protecting brain cells from oxidative damage and inflammation, which are associated with neurodegenerative diseases such as Alzheimer’s disease. Some research has suggested that hesperidin, through its anti-inflammatory and antioxidant effects, may help improve cognitive function and reduce the risk of neurodegeneration.

The compound is also used in the cosmetic industry, particularly in skincare products. Due to its antioxidant properties, it is included in formulations designed to protect the skin from oxidative damage caused by UV radiation and pollution. It is believed to help reduce signs of skin aging, such as wrinkles and fine lines, by neutralizing free radicals and supporting collagen production.

In terms of pharmaceutical applications, hesperidin has been used as part of combination therapies, particularly for conditions involving poor circulation, such as venous insufficiency and hemorrhoids. In these cases, it is often combined with other flavonoids, such as diosmin, to enhance its therapeutic effects.

While hesperidin is generally considered safe for use in dietary supplements and skincare products, it should be used with caution by individuals taking medications that affect blood pressure or blood clotting, as it may interact with such treatments. As with any supplement, it is recommended to consult a healthcare provider before starting hesperidin supplementation, especially for those with pre-existing medical conditions or those on medication.

In summary, hesperidin is a flavonoid with a variety of well-established applications. It is commonly used for its antioxidant, anti-inflammatory, and cardiovascular protective properties, as well as in skincare formulations. Its presence in citrus fruits, particularly oranges, has made it a readily accessible compound with significant health benefits, particularly in promoting vascular health and reducing the risk of cardiovascular diseases.

References

2018. Hesperidin: A comprehensive review of its bioactivity. Nutrients, 10(10).
DOI: 10.3390/nu10101549

2008. Synthesis and biological evaluation of hesperidin derivatives. Molecular and Cellular Biochemistry, 316(1-2).
DOI: 10.1007/s11010-008-9960-9

2003. Analytical methods for hesperidin in food samples. Journal of Agricultural and Food Chemistry, 51(15).
DOI: 10.1021/jf0304775