I'm wondering if the information lost by rearranging the letters of a book is measurable as a difference in its initial and final mass.
Choose a long, random string over an alphabet, say $\{0,1\}$, of length $N$. It should be random in the sense that it is incompressible. You might also choose a big book, at random, and compress it.
Once you have the book, or have written down the string in a book, measure the book's mass $m_0$.
Convert the letters into a standard alphabet by using, say, the ASCII encoding scheme. The letters should be more or less distributed uniformly, unlike English which has a rank-frequency distribution for the letters. Rearrange the letters into the complete works of Shakespeare, or as much literature as you possibly can. Then apply the encoding to get a bitstring. This process can be represented by a 0/1 permutation matrix $\sigma_1$ which acts on the bitstring.
Finally, move all the 0's to the left, and 1's to the right. This can be represented as another permutation matrix $\sigma_2$. Measure the mass of the book to get $m_2$.
It appears that the information content of the book at the beginning is $S_0=N$ bits. The information content $S_1$ of the complete works of Shakespeare is around 1.98MB (less than really, size of zipped text file). The last state is very compressible, and $S_2 \approx 2\log_2(N/2)$.
Suppose $N$ is large, say Avagadros' number $N=N_{A}=6.02214076*10^{23}$, more than a zetta and less than a yotta. Then $\triangle S = S_0 - S_2 \approx N_A$. If 1 bit represents about $10^{-23} J/K$, then at $300K$ the information lost corresponds to $~20.1$ picograms.
I suppose the lost information is carried away by the matrices $\sigma_1$, $\sigma_2$ if no one watches or records the rearrangement as it occurs. Is that correct?