Structure via PubChem · Public domain (PubChem)
isopimpinellin
Sign in to saveAlso known as 5,8-Dimethoxypsoralen, 5,8-Dimethoxypsoralene
Isopimpinellin is a natural product synthesized by numerous plant species, especially species in the carrot family Apiaceae. The compound can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes. Several studies have looked into the effects of isopimpinellin and other furanocoumarins (such as bergamottin and imperatorin) as anticarcinogens. These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors. Evidence has also been reported that links these compounds to the inhibition of breast cancers.
Chemical data
- Formula
- C13H10O5
- Molecular weight
- 246.21 g/mol
- IUPAC name
- 4,9-dimethoxyfuro[3,2-g]chromen-7-one
- SMILES
- COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
- InChIKey
- DFMAXQKDIGCMTL-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 57.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- furanocoumarin
- Mass
- 246.053
Show 4 more facts
- found in taxon
- Dendrobium nobile
- chemical formula
- C₁₃H₁₀O₅
- canonical SMILES
- COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
- has characteristic
- bitterness
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Biosynthesis
- References
Isopimpinellin is a natural product synthesized by numerous plant species, especially species in the carrot family Apiaceae. The compound can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes. Several studies have looked into the effects of isopimpinellin and other furanocoumarins (such as bergamottin and imperatorin) as anticarcinogens. These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors. Evidence has also been reported that links these compounds to the inhibition of breast cancers.
== Biosynthesis == Isopimpinellin is a furanocoumarin thought to be synthesized through the mevalonate pathway via addition of dimethylallyl pyrophosphate (DMAPP) to a modified coumarate known as umbelliferone. The biosynthesis is shown below:
Excerpted from Wikipedia’s “isopimpinellin” article, available under the CC BY-SA 4.0 licence.