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Isopimpinellin

Chemical compound From Wikipedia, the free encyclopedia

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.[1] Several studies have looked into the effects of isopimpinellin and other furanocoumarins (such as bergamottin and imperatorin) as anticarcinogens.[1][2] These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors.[1] Evidence has also been reported that links these compounds to the inhibition of breast cancers.[2]

Quick facts Names, Identifiers ...
Isopimpinellin
Chemical structure of isopimpinellin.
Names
Preferred IUPAC name
4,9-Dimethoxy-7H-furo[3,2-g][1]benzopyran-7-one
Other names
5,8-Dimethoxypsoralen
5,8-Dimethoxypsoralene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.166.737 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
    Key: DFMAXQKDIGCMTL-UHFFFAOYSA-N
  • InChI=1/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3
    Key: DFMAXQKDIGCMTL-UHFFFAOYAB
  • COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
Properties
C13H10O5
Molar mass 246.21 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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:[3]

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