What Is Guaiazulene?
Guaiazulene is a hydrocarbon derivative of azulene, an organic compound. It is classified as a bicyclic sesquiterpene with the molecular formula C15H18. Guaiazulene has a molecular weight of 198.31, a density of 0.976 g/mL, a melting point of 31-33°C, and a boiling point of 153°C. It appears as a dark blue crystal or liquid at room temperature.
It is soluble in fats, oils, paraffin, waxes, and essential oils, and slightly soluble in anhydrous ethanol. Guaiazulene is insoluble in water but soluble in concentrated sulfuric acid and phosphoric acid. Due to its low melting point of around 31°C, careful storage consideration is necessary.
Uses of Guaiazulene
Guaiazulene is utilized as a coloring agent in cosmetics and as an anti-inflammatory in pharmaceuticals. Since guaiazulene is not water-soluble, it is often used in the form of a water-soluble derivative, sodium azulene sulfonate, which incorporates a sulfonic acid group.
In cosmetics, guaiazulene is found in milky lotions and cream-type products, helping to prevent acne and rough skin, and is also used in sunscreens.
In the pharmaceutical industry, guaiazulene is indicated for various conditions such as eczema, burns, pharyngitis, tonsillitis, stomatitis, acute gingivitis, glossitis, oral wounds, gastric ulcers, gastritis, and several eye conditions including conjunctivitis and keratitis.
Properties of Guaiazulene
1. Extraction and Synthesis of Guaiazulene
Naturally, guaiazulene can be extracted from the essential oil of plants like chamomile in the Hamamelidaceae family and is also a major pigment in some soft corals. Synthetically, it can be produced through dehydrogenative oxidation of sesquiterpene compounds such as guaiol, aromadendrene, and kessyl alcohol.
2. Mechanism of Action as a Pharmaceutical Product
Guaiazulenesulfonic acid, the pharmaceutical form of guaiazulene, inhibits leukocyte migration and histamine release from mast cells. Its action is thought to have a direct effect on inflammatory tissues without involving the pituitary-adrenal system.
Types of Guaiazulene
Guaiazulene is sold primarily as a reagent for research and as an industrial raw material. It is available in various capacities such as 10g, 25g, 100g, and 500g for research and development. In the chemical industry, it is supplied as a natural active ingredient in cosmetics and pharmaceuticals, typically in units of 1 kg or 25 kg, and transported in drums.
Pharmaceutical products containing guaiazulene include ointments, gargles, eye drops, topical applications, as well as tablets and granules for oral administration.
Other Information on Guaiazulene
Chemical Uses of Guaiazulene
In synthetic chemistry, guaiazulene serves as a base for various dye molecules and compounds. Examples include 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid and 5-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid. It is also used in creating stilbazulenyl nitrones, a second-generation azulenyl nitrone functioning as a chain-breaking antioxidant, and in the synthesis of near-infrared fluorescence quenchers based on bis-azulenyl.