Structure via PubChem · Public domain (PubChem)
bergapten
Sign in to saveAlso known as 5-methoxypsoralene, Majudin, Bergaptene, Heraclin, 4-methoxy-7H-furo[3,2-g][1]benzopyran-7-one, 4-methoxyfuro[3,2-g]chromen-7-one, 4-methoxy-7-furo[3,2-g][1]benzopyranone, 5-methoxypsoralen
Bergapten (5-methoxypsoralen) is a naturally occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.
In the Vinony graph
Within Vinony's link graph, bergapten is referenced by 72 other articles, and connects out to psoriasis, trioxsalen and ultraviolet radiation.
It sits within the topics ECHA InfoCard ID from Wikidata, Furanocoumarins and IARC Group 2A carcinogens.
Its subject is documented across 13 Wikipedia language editions.
Chemical data
- Formula
- C12H8O4
- Molecular weight
- 216.19 g/mol
- IUPAC name
- 4-methoxyfuro[3,2-g]chromen-7-one
- SMILES
- COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
- InChIKey
- BGEBZHIAGXMEMV-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 48.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- atopic eczema, psoriasis
via ChEMBL · EBI
Research
882 papers- Bergapten inhibits NLRP3 inflammasome activation and pyroptosis via promoting mitophagy.Acta pharmacologica Sinica · 2023
- Bergapten: A review of its pharmacology, pharmacokinetics, and toxicity.Phytotherapy research : PTR · 2021
- Bergapten ameliorates combined allergic rhinitis and asthma syndrome after PM2.5 exposure by balancing Treg/Th17 expression and suppressing STAT3 and MAPK activation in a mouse model.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2023
- Natural small molecule bergapten ameliorates rheumatoid arthritis by targeting STAT3.Pharmacological research · 2025
- Inhalable and bioactive lipid-nanomedicine based on bergapten for targeted acute lung injury therapy via orchestrating macrophage polarization.Bioactive materials · 2025
via PubMed
Wikidata facts
- Subclass of
- furanocoumarin
- Mass
- 216.042259
Show 5 more facts
- chemical formula
- C₁₂H₈O₄
- canonical SMILES
- COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
- subject has role
- carcinogen
- Commons category
- Bergapten
- has characteristic
- bitterness
via Wikidata · CC0
~6 min read
Encyclopedic overview
4 sectionsContents
- Toxicity
- Medical usages
- Synthesis
- References
Bergapten (5-methoxypsoralen) is a naturally occurring organic chemical compound produced by numerous plant species, especially from the carrot family Apiaceae and the citrus family Rutaceae. For example, bergapten has been extracted from 24 species of the genus Heracleum in the family Apiaceae. In the family Rutaceae, various Citrus species contain significant amounts of bergapten, especially the bergamot orange, the micrantha, and certain varieties of lime and bitter orange.
Bergapten belongs to a class of chemical compounds known as the furanocoumarins. In 1834, Kalbrunner isolated 5-methoxypsoralen from bergamot essential oil, hence the common name "bergapten". It was the first furanocoumarin to be isolated and identified.
Excerpted from Wikipedia’s “bergapten” article, available under the CC BY-SA 4.0 licence.