| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H22O3 |
| Molecular Weight | 298.3762 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC\C(C)=C\COC1=CC=C2C=CC(=O)OC2=C1
InChI
InChIKey=RSDDHGSKLOSQFK-RVDMUPIBSA-N
InChI=1S/C19H22O3/c1-14(2)5-4-6-15(3)11-12-21-17-9-7-16-8-10-19(20)22-18(16)13-17/h5,7-11,13H,4,6,12H2,1-3H3/b15-11+
| Molecular Formula | C19H22O3 |
| Molecular Weight | 298.3762 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Auraptene (7-Geranyloxycoumarin) is the best known and most abundant prenyloxycoumarin present in nature. It is synthesized by various plant species, mainly those of the Rutaceae and Umbelliferae (Apiaceae) families, comprising many edible fruits and vegetables such as lemons, grapefruit, and orange. Auraptene has shown a remarkable effect in the prevention of degenerative diseases, in particular, it has been reported to be one the most promising known natural chemopreventive agents against several types of cancer. The effect in humans is not yet known.
CNS Activity
Originator
Approval Year
PubMed
Sample Use Guides
Auraptene was administrated to rats for 28 days by oral gavage in doses of 125 and 250 mg/kg.
Route of Administration:
Oral
HT29 cells were used for activity evaluation. To study the cytotoxicity of auraptene in combination with chemotherapy or ionizing radiation, thiazolyl blue (MTT) assay was used. In this regard, MTT dye (Atocel, Budapest, Hungary) was dissolved in phosphate-buffered saline (PBS; 5 mg/mL) and added to each well (20 μL/well) by the end of treatments. Afterwards, plates were incubated for 4 h at 37°C, and then medium was replaced by DMSO (150 μL/well) to dissolve produced formazan crystals, and finally, optic densities of wells were measured spectrophotometrically at 570 nm using an ELISA plate reader (Awareness Connecticut, USA).