As I said earlier, I don't know anything about iTunes....but here's some ideas to try anyway (gleaned from the web).
Have you tried turning off the iTunes normaliser (Preferences > Effects > Sound Check)?
Try changing the QuickTime Sound Out Setting to improve the quality:
QuickTime 6
1. Click the Start button and point to Control Panel.
2. From the menu at the top of the QuickTime Settings window, choose Sound Out.
3. Select a different option in the "Choose a device for playback" menu.
QuickTime 7
1. Click the Start button and point to Control Panel.
2. Open the QuickTime control panel.
3. Click the "Safe mode (waveOut only)" checkbox.
Some PC audio hardware has audio-enhancing effects that can conflict with iTunes' Sound Enhancer feature.
To resolve these conflicts, do one of the following:
* Turn off the effects for your PC's audio hardware using the configuration software that came with your hardware.
* Disable the Sound Enhancer feature in iTunes:
1. Open iTunes.
2. From the Edit menu, choose Preferences.
3. Click the Effects tab.
4. Deselect Sound Enhancer.
If none of the above works, it's a long shot but take a look at this
thread. Give the tool a go and report back.