Isopimpinellin

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28853;
ChemSpider	61391;
ECHA InfoCard	100.166.737
KEGG	C02162;
PubChem CID	68079;
UNII	20GCF755G6 ;
CompTox Dashboard (EPA)	DTXSID30197457 ;
	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]

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]

References

^ ^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.
^ ^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.
^ Dewick, Paul M. (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). UK: John Wiley & Sons Ltd. ISBN 978-0-471-97478-9.

[Kleiner1-1] 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.

[Kleiner2-2] 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.

[3] Dewick, Paul M. (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). UK: John Wiley & Sons Ltd. ISBN 978-0-471-97478-9.

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[2]

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