| Stereochemistry | ACHIRAL |
| Molecular Formula | C45H74O |
| Molecular Weight | 631.0685 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 8 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CO
InChI
InChIKey=AFPLNGZPBSKHHQ-MEGGAXOGSA-N
InChI=1S/C45H74O/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)33-18-34-45(10)35-36-46/h19,21,23,25,27,29,31,33,35,46H,11-18,20,22,24,26,28,30,32,34,36H2,1-10H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-33+,45-35+
Solanesol is a naturally occurring isoprenoid and the most abundant lipid in tobacco leaves. It is also found in tomato, potato, eggplant, and pepper plants. Solanesol is widely used in the pharmaceutical industry as an intermediate for the synthesis of ubiquinone drugs, such as coenzyme Q10 and vitamin K2. Solanesol possesses antibacterial, antifungal, antiviral, anticancer, anti-inflammatory, and anti-ulcer activities, and solanesol derivatives also have anti-oxidant and antitumor activities. Solanesol has been shown to increase the expression of HO-1 and Hsp70 which may contribute to the prevention of ethanol-induced cell damage. Solanesol is readily introduced into the body as a component of tobacco smoke.
Originator
Approval Year
Sample Use Guides
Ten cigaret smokers took seven puffs from a 10 mg 'tar' yield test cigaret and a fixed volume of air (0, 75, 250, 500 or 1000 mL) to give controlled depth of inhalation. Subjects exhaled normally after a 2-second breath hold with exhalation passing through a filter pad for the collection of non-retained nicotine and solanesol. Blood samples were taken before and at intervals during and after smoking. A second series of experiments was conducted with a fixed inhalation volume (500 mL) and three breath hold durations (0, 2, and 10 seconds). Solanesol retention increased from 34.2% at zero inhalation volume to 71.9% at 1000 mL inhalation volume ( for 2-second breath hold) and from 51.8% at zero breath hold to 87.6% at 10-second breath hold (500 mL inhalation).
Route of Administration:
Respiratory
Normal human hepatic cell L02 was cultured in DMEM media containig 10% (v/v) fetal bovine serum, 100 U/mL penicillin and 100 micro-g/mL streptomycin at 37 deg-C ina 5% CO2 atmosphere. Cells were cultured with different concentrations of solanesol (0 - 80 micro-M) for 12 hours. Relative HO-1 and Hsp70 mRNA expressions were determined using real-time polymer chain reaction and calculated by subtracting the Ct value for GAPDH from the Ct value for HO-1 or Hsp70. Solanesol increased mRNA and protein levels of HO-1 and Hsp70 in a dose-dependent manner.
SUBSTANCE RECORD
