Psoralen

Psoralen

Names
IUPAC name 7H-furo[3,2-g]chromen-7-one
Other names 7H-furo[3,2-g][1]benzopyran-7-one
Identifiers
CAS Number	66-97-7 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:27616 Y
ChEMBL	ChEMBL164660 Y
ChemSpider	5964 Y
ECHA InfoCard	100.000.581
InChI InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H Y Key: ZCCUUQDIBDJBTK-UHFFFAOYSA-N Y InChI=1/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H Key: ZCCUUQDIBDJBTK-UHFFFAOYAE
SMILES O=C1/C=C\c2cc3ccoc3cc2O1
Properties
Chemical formula	C11H6O3
Molar mass	186.16 g/mol
Melting point	158 to 161 °C (316 to 322 °F; 431 to 434 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Psoralen (also called psoralene) is the parent compound in a family of natural products known as furocoumarins. It is structurally related to coumarin by the addition of a fused furan ring, and may be considered as a derivative of umbelliferone. Psoralen occurs naturally in the seeds of Psoralea corylifolia, as well as in the common fig, celery, parsley, West Indian satinwood and in all citrus fruits. It is widely used in PUVA (psoralen + UVA) treatment for psoriasis, eczema, vitiligo, and cutaneous T-cell lymphoma. Many furocoumarins are extremely toxic to fish, and some are deposited in streams in Indonesia to catch fish.

Psoralen is a mutagen, and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form and covalent interstrand cross-links (ICL) with thymines, preferentially at 5'-TpA sites in the genome, inducing apoptosis. Psoralen plus UVA (PUVA) therapy has shown considerable clinical efficacy. Unfortunately, a side effect of PUVA treatment is a higher risk of skin cancer.

An important use of psoralen is in PUVA treatment for skin problems such as psoriasis and (to a lesser extent) eczema and vitiligo. This takes advantage of the high 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. Psoralens are also used in photopheresis, where they are mixed with the extracted leukocytes before UV radiation is applied.