Neohesperidin

Orange juice UHPLC UV chromatogram

Neohesperidin is a flavonoid compound predominantly found in citrus fruits. It is particularly abundant in the bitter oranges of the species Citrus aurantium. Neohesperidin is known for its intense bitterness and is used in the food and pharmaceutical industries primarily as a precursor for the synthesis of neohesperidin dihydrochalcone (NHDC), a potent artificial sweetener. The compound belongs to the class of bioflavonoids, which are recognized for their antioxidant, anti-inflammatory, and potential health-benefiting properties.

Chemical Properties

Neohesperidin is a flavanone glycoside, consisting of the flavanone hesperetin bound to a disaccharide moiety. Its chemical structure allows it to act as an antioxidant, scavenging free radicals and potentially mitigating oxidative stress in biological systems. The compound's bitterness has limited its direct use as a flavoring agent, but its conversion to NHDC, which is roughly 1500-1800 times sweeter than sucrose, has made it valuable in creating low-calorie sweeteners.

Extraction and Synthesis

Neohesperidin is extracted from the peels of bitter oranges using a variety of methods, including solvent extraction and enzymatic treatments. The conversion of neohesperidin to NHDC involves a chemical reaction known as hydrogenation, which modifies the compound's structure to reduce its bitterness and significantly increase its sweetness.

Applications

Food Industry

In the food industry, NHDC derived from neohesperidin is used as a sweetening agent in a wide range of products, including beverages, confectioneries, and dairy products. Its high sweetness level allows it to be used in very small quantities, making it an effective tool for reducing sugar content and lowering the caloric value of foods and drinks.

Pharmaceuticals

Neohesperidin and its derivatives have been studied for their potential health benefits, including antioxidant and anti-inflammatory effects. While research is ongoing, there is interest in the use of neohesperidin in dietary supplements and potential therapeutic agents.

Cosmetics

The antioxidant properties of neohesperidin have also made it a candidate for use in cosmetic formulations, where it can help to protect the skin from oxidative damage and support skin health.

Health Benefits and Risks

Research into the health effects of neohesperidin and NHDC is ongoing. Studies suggest that these compounds may have several beneficial effects, including lowering blood pressure, reducing inflammation, and potentially having anti-cancer properties. However, as with any bioactive compound, the effects can vary depending on the dose and the individual's health status. It is important for consumers to use products containing neohesperidin or NHDC as directed and to consult healthcare professionals with any concerns.

Regulatory Status

The regulatory status of NHDC varies by country, but it has been approved for use as a sweetener in many regions, including the European Union and the United States. Regulatory bodies have assessed NHDC for safety and have established acceptable daily intake levels to ensure consumer safety.