Apple CEO Tim Cook delivers his keynote address at the Worldwide Developers Conference in San Francisco, California June 2, 2014. Robert Galbraith/Reuters NEW YORK (Reuters) - Apple Inc has been ordered to pay $532.9 million after a federal jury found its iTunes software infringed three patents owned by Texas-based patent licensing company Smartflash LLC.

Though Smartflash had been asking for $852 million in damages, the verdict, which came late Tuesday night, was still a costly blow for the U.S. tech giant, the most valuable company in the world.

After deliberating for eight hours in the U.S. District Court for the Eastern District of Texas, the jury said that Apple not only used the Smartflash patents without permission, but did so willfully.

Apple suggested the outcome was another reason why reform is needed in the patent system to curb litigation by companies that do not make products themselves, such as Smartflash.

The case is Smartflash LLC, et al v. Apple, Inc, et al, in the U.S. District Court for the Eastern District of Texas, No. 13-cv-447.

(Editing by Stephen Coates)