Chalepensin

Chalepensin is a chemical compound of the furanocoumarin class. Originally isolated in 1967 from fringed rue (Ruta chalepensis),^[1] from which it derives its name, it has also been found in other plants of the genus Ruta including common rue (Ruta graveolens)^[2] and mountain rue (Ruta montana).^[3]

Chalepensin

Names
IUPAC name 6-(2-Methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one
Other names Xyloltenin; 3-(α,α-dimethylallyl)psoralen
Identifiers
CAS Number	13164-03-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:3572
ChEMBL	ChEMBL1333931
ChemSpider	114167
KEGG	C09165
PubChem CID	128834
CompTox Dashboard (EPA)	DTXSID90157153
InChI InChI=1S/C16H14O3/c1-4-16(2,3)12-8-11-7-10-5-6-18-13(10)9-14(11)19-15(12)17/h4-9H,1H2,2-3H3 Key: FYCCCUNGXGKNJV-UHFFFAOYSA-N
SMILES CC(C)(C=C)C1=CC2=C(C=C3C(=C2)C=CO3)OC1=O
Properties
Chemical formula	C16H14O3
Molar mass	254.285 g·mol−1
Melting point	82–83 °C (180–181 °F; 355–356 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical properties

Chalepensin forms colorless crystalline needles with a melting point of 82-83 °C.^[4]

Research

Chalepensin has been shown to have antifertility effects in female rats.^[2][5][6] This may be the result of toxic effects chalepensin has on the ovaries.^[5] This antifertility effect may provide some scientific evidence in support of the traditional uses of fringed rue^[6] and modern use of rue oil (oil from plants of the genus Ruta) in South America^[7] as an abortifacient.

Chalepensis has also been shown to have antibacterial activity against Streptococcus mutans and methicillin-resistant Staphylococcus aureus (MRSA).^[8]

Related compounds

Several chemical compounds that have the same core chemical structure as chalepensin are known, including chalepin, rutamarin, 5-methoxychalepensin, and 5,8-dimethoxychalepensin.

• 
  Chalepin
• 
  Rutamarin
• 
  5-Methoxychalepensin
• 
  5,8-Dimethoxychalepensin