Umbelliferone

Umbelliferone, also known as 7-hydroxycoumarin, is a natural chemical compound with the formula C9H6O3. It is a phenolic compound that belongs to the class of organic compounds known as coumarins. Umbelliferone is notable for its presence in many plants, where it serves various ecological roles, including acting as a phytoalexin, a substance produced by plants to deter herbivores and pathogens. This compound is also of interest in the pharmaceutical and cosmetic industries due to its unique properties, including its ability to absorb ultraviolet light.

Chemical Properties

Umbelliferone has a molecular weight of 162.14 g/mol and appears as a white crystalline substance. It is sparingly soluble in water but highly soluble in organic solvents such as ethanol and ether. The compound's structure features a benzopyrone ring, which is characteristic of the coumarin family. This structure is responsible for its UV absorption properties, making it a common ingredient in sunscreen formulations.

Biosynthesis

The biosynthesis of umbelliferone in plants involves the transformation of cinnamic acid into 7-hydroxycoumarin through a series of enzymatic reactions. This process begins with the hydroxylation of cinnamic acid, which is then followed by lactonization to form the coumarin structure. The enzymes involved in this pathway are part of the plant's secondary metabolism, which contributes to the plant's defense mechanisms and other ecological functions.

Natural Occurrence

Umbelliferone is widely distributed in the plant kingdom, particularly in the family Apiaceae (also known as Umbelliferae), from which its name is derived. It is found in significant amounts in plants such as Angelica, Anthriscus, and Ferula, among others. The compound's presence is not limited to the Apiaceae family, as it can also be found in other plant families, including the Fabaceae and Poaceae.

Applications

1. 1. 1. Pharmaceutical###

Umbelliferone has been studied for its potential therapeutic effects, including anti-inflammatory, antioxidant, and antimicrobial activities. Its ability to absorb UV light also suggests potential applications in protecting the skin from UV-induced damage, making it a candidate for inclusion in sunscreen and other skincare products.

1. 1. 1. Cosmetic###

In the cosmetic industry, umbelliferone is valued for its fragrance and its role in protecting products from UV degradation. Its use in perfumes and scented products is due to its pleasant, subtle aroma.

1. 1. 1. Scientific Research###

Researchers have explored umbelliferone's role in scientific studies, particularly its fluorescence properties. When exposed to ultraviolet light, umbelliferone emits a blue fluorescence, making it useful as a fluorescent marker in various biochemical assays.

Safety and Toxicology

While umbelliferone is generally considered safe for use in cosmetics and pharmaceuticals, its safety profile depends on the concentration and mode of application. High doses may pose risks, and as with all chemical compounds, it is essential to adhere to regulatory guidelines and safety standards.

See Also

• Coumarin
• Phytoalexin
• Cinnamic acid
• Apiaceae