What Is Xanthone?
Xanthone is an organic compound with the chemical formula C13H8O2 and a three-ring structure in which two benzene rings are bridged by an ether and a ketone.
Its CAS number is 90-47-1 and its other names include “genicid” and “benzophenone oxide.” Xanthone can be synthesized by heating phenyl salicylate. It is also known to occur naturally in Harungana and Garcinia.
Uses of Xanthone
Xanthone has been used since 1939 as an insecticide, especially for the control of codling moth eggs and larvae. It is also the raw material for xanthidolol, which is used to measure urea levels in the blood. The reduction of xanthone yields xantidrol.
Properties of Xanthone
Xanthone has a specific gravity (density) of approximately 1.1607, a melting point of 173-177°C, and a boiling point of 349-350°C. It is almost insoluble in water. It is almost insoluble in water, insoluble in ethanol and ether, and soluble in chloroform.
It exists in solid form at room temperature and is white to light brown or light red. Under normal conditions, it is highly stable. However, because it is an organic compound, it is very dangerous when mixed with strong oxidizers. It is possible that it may be altered by light, so it should be shielded from light when stored.
Other Information on Xanthone
1. Toxicity, Hazards and Applicable Laws and Regulations
Xanthone is orally toxic. It is classified as a poisonous or toxic substance under the Regulations on the Transport and Storage of Dangerous Goods by Ships and the Civil Aeronautics Law, and as a toxic solid (organic substance) under UN2811, the UN number related to transportation.
2. Xanthone Derivatives (Xanthones and Xanthonoids)
There is a group of xanthone derivatives called mangostin (α-mangostin and γ-mangostin), which have been suggested to have a variety of physiological effects, including antibacterial activity, anticancer activity, antioxidant activity, and anti-inflammatory effects. As the name suggests, these are found in the rind of the mangosteen plant.
These unique plant-derived chemicals are called phytochemicals. Many other xanthone derivatives and their glycosides are also known to be biologically active phytochemicals. Some of these are commercialized as supplements, such as mangosteen extract derived from the mangosteen plant.
Although the term “xanthones” is sometimes used to include all phytochemicals with the xanthone structure, they should be referred to as xanthones. They are sometimes called xanthonoids. It is important to note that these phytochemicals are not xanthones themselves.
3. Biosynthesis of Xanthonoids
Benzoyl coenzyme A is first produced from benzoic acid. In the raw material stage, there is one benzene ring derived from benzoic acid.
Three molecules of malonyl coenzyme A react with it to form 2,4,6-trihydroxybenzophenone. A new ring is formed using three molecules of malonyl coenzyme A, with a ketone group between the two rings.
Next, 2,3′,4,6-tetrahydroxybenzophenone is formed by the action of benzophenone-3′-hydroxylase and cytochrome P450 monooxygenase. This is the state to which the hydroxyl group is added.
From this state, a third ring is formed by the action of xanthone synthase to form the xanthone structure. As shown in this example, most naturally occurring xanthonoids have hydroxyl groups, and only a few are pure xanthone.