Structure via PubChem · Public domain (PubChem)
psoralen
Sign in to saveAlso known as 6,7-furanocoumarin, furocoumarin, 6-hydroxy-5-benzofuranacrylic acid delta-lactone, furo[4',5':6,7]coumarin, furo[2',3':7,6]coumarin, 3-(6-hydroxy-5-benzofuranyl)-2-propenoic acid delta-lactone, 7H-furo[3,2-g][1]benzopyran-7-one
Psoralen (also called psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. 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; these applications are typically through th
Chemical data
- Formula
- C11H6O3
- Molecular weight
- 186.16 g/mol
- IUPAC name
- furo[3,2-g]chromen-7-one
- SMILES
- C1=CC(=O)OC2=CC3=C(C=CO3)C=C21
- InChIKey
- ZCCUUQDIBDJBTK-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 39.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,914 papers- Psoralen-Induced Phytophotodermatitis.Dermatitis : contact, atopic, occupational, drug · 2021
- Psoralen: a narrative review of current and future therapeutic uses.Journal of cancer research and clinical oncology · 2024
- Psoralen Derivatives: Recent Advances of Synthetic Strategy and Pharmacological Properties.Anti-inflammatory & anti-allergy agents in medicinal chemistry · 2020
- Psoralen: A Biologically Important Coumarin with Emerging Applications.Mini reviews in medicinal chemistry · 2020
- Phytochemical and Pharmacological Aspects of Psoralen - A Bioactive Furanocoumarin from Psoralea corylifolia Linn.Chemistry & biodiversity · 2023
via PubMed
~11 min read
Encyclopedic overview
11 sectionsContents
- Uses
- Chemistry
- Structure
- Synthesis
- Biosynthesis
- Plant sources
- Repair of psoralen DNA adducts
- Analysis of nucleic acids structures
- References
- Further reading
- External links
Psoralen (also called psoralene) is the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. 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; these applications are typically through the use of medications such as Methoxsalen. Many furanocoumarins are extremely toxic to fish, and some are deposited in streams in Indonesia to catch fish.
==Uses== 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 monoadducts and covalent interstrand cross-links (ICL) with thymines, preferentially at 5'-TpA sites in the genome, inducing apoptosis. Psoralen plus UVA (PUVA) therapy can be used to treat hyperproliferative skin disorders like psoriasis and certain kinds of skin cancer. Unfortunately, PUVA treatment itself leads to a higher risk of skin cancer.
Excerpted from Wikipedia’s “psoralen” article, available under the CC BY-SA 4.0 licence.