Psoralen



Psoralen
Chemical name 7H-furo[3,2-g]chromen-7-one or
7H-furo[3,2-g]benzopyran-7-one
Chemical formula C11H6O3
Molecular mass 186.17 g/mol
Melting point 158-161 °C
Density x.xxx g/cm3
CAS number [66-97-7]
SMILES O=C1OC2=CC3=C
(C=CO3)C=C2C=C1
Disclaimer and references

Psoralen (also called psoralene) is the parent compound in a family of natural products known as PUVA (=Psoralen +UVA) treatment for psoriasis, eczema and vitiligo. Although safe to mammals, it should be used with care since many furocoumarins are extremely toxic to fish, and some are indeed used in streams in Indonesia to catch fish.

Uses

An important use of psoralen is in UV absorbance of psoralen. The psoralen is applied first to sensitise the skin, then UVA light is applied to clean up the skin problem. Psoralen has also been recommended for treating alopecia.

Psoralen is a significant mutagen and is used for this purpose in molecular biology research.

Chemistry

One isomer of psoralen is angelicin, and most furocoumarins can be regarded as derivatives of psoralen or angelicin. Some important psoralen derivatives are xanthotoxin, bergapten and nodekenetin.

Another important feature of this class of compounds is its ability in generating singlet oxygen.

Structure

The structure of psoralen was originally deduced using its degradation reactions. It exhibits the normal reactions of the Potassium permanganate causes oxidation of the furan ring, while other methods of oxidation produce furan-2,3-carboxylic acid.

Synthesis

Psoralen synthesis is challenging, due the fact that acetic anhydride. The synthesis is then completed by dehydrogenation of the five-membered ring to produce the furan ring.

References

  1. F. M. Dean Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963.
  2. The Merck Index, 7th edition, Merck & Co, Rahway, New Jersey, USA, 1960.
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Types of Furanocoumarin • Lignans • Lignins • Suberins
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Psoralen". A list of authors is available in Wikipedia.