Isopimpinellin

{{Chembox | ImageFile = Isopimpinellin.png | ImageSize = 250px | ImageAlt = Chemical structure of isopimpinellin. | PIN = 4,9-Dimethoxy-7''H''-furo[3,2-''g''][1]benzopyran-7-one | OtherNames = 5,8-Dimethoxypsoralen<br>5,8-Dimethoxypsoralene |Section1={{Chembox Identifiers | CASNo = 482-27-9 | CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 20GCF755G6 | PubChem = 68079 | SMILES = COC1=C2C=COC2=C(C3=C1C=CC(=O)O3)OC | ChemSpiderID = 61391 | 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 | InChIKey = DFMAXQKDIGCMTL-UHFFFAOYAB | StdInChI = 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 | StdInChIKey = DFMAXQKDIGCMTL-UHFFFAOYSA-N | RTECS = | MeSHName = | ChEBI = 28853 | KEGG = C02162 }} |Section2={{Chembox Properties | Formula = C₁₃H₁₀O₅ | MolarMass = 246.21 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''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.<ref name="Kleiner1">{{cite journal|last=Kleiner|first=Heather E.|author2=Suryanarayana V.Vulimiri |author3=Matthew F.Starost |author4=Melissa J.Reed |author5=John DiGiovanni |title=Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice|journal=Carcinogenesis|year=2002|volume=23|issue=10|pages=1667–1675|doi=10.1093/carcin/23.10.1667|pmid=12376476|doi-access=free}}</ref> Several studies have looked into the effects of isopimpinellin and other furanocoumarins (such as bergamottin and imperatorin) as anticarcinogens.<ref name="Kleiner1" /><ref name="Kleiner2">{{cite journal|last=Prince|first=Misty|author2=Cheryl T.Campbell |author3=Taylor A.Robertson |author4=Amy J.Wells |author5=Heather E.Kleiner |title=Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland|journal=Carcinogenesis|year=2006|volume=27|issue=6|doi=10.1093/carcin/bgi303|pages=1204–13|pmid=16387742|doi-access=free}}</ref> These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors.<ref name="Kleiner1" /> Evidence has also been reported that links these compounds to the inhibition of breast cancers.<ref name="Kleiner2" />

== 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:<ref>{{cite book|last=Dewick|first=Paul M.|title=Medicinal Natural Products: A Biosynthetic Approach (3rd ed.)|url=https://archive.org/details/medicinalnatural0000dewi|url-access=registration|year=2009|publisher=John Wiley & Sons Ltd|location=UK|isbn=978-0-471-97478-9}}</ref>

File:CHEM257_-_2.png

== References == {{reflist}} <!--- After listing your sources please cite them using inline citations and place them after the information they cite. Please see http://en.wikipedia.org/wiki/Wikipedia:REFB for instructions on how to add citations. --->

{{coumarin}}

Category:Furanocoumarins Category:O-methylated coumarins