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Isopimpinellin information


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
CAS Number
  • 482-27-9 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28853
ChemSpider
  • 61391
ECHA InfoCard 100.166.737 Edit this at Wikidata
KEGG
  • C02162
PubChem CID
  • 68079
UNII
  • 20GCF755G6 checkY
CompTox Dashboard (EPA)
  • DTXSID30197457 Edit this at Wikidata
InChI
  • 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
SMILES
  • COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC
Properties
Chemical formula
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).
Infobox 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.[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]

  1. ^ a b c Kleiner, Heather E.; Suryanarayana V.Vulimiri; Matthew F.Starost; Melissa J.Reed; John DiGiovanni (2002). "Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice". Carcinogenesis. 23 (10): 1667–1675. doi:10.1093/carcin/23.10.1667. PMID 12376476.
  2. ^ a b Prince, Misty; Cheryl T.Campbell; Taylor A.Robertson; Amy J.Wells; Heather E.Kleiner (2006). "Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland". Carcinogenesis. 27 (6): 1204–13. doi:10.1093/carcin/bgi303. PMID 16387742.

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Isopimpinellin

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