MadSci Network: Biochemistry |
Wow, what a great question!
You are absolutely correct: while benzene is carcinogenic, most of its simple
derivatives are not. I looked at the Material Safety Data Sheets (MSDS) through
Vermont Safety Information Resources, Inc. (SIRI, go to http://www.siri.org/msds/index.html for more)
for aniline, benzoic acid, phenol, and toluene, and found none of them to be
carcinogenic. For that matter, bromobenzene and chlorobenzene weren't listed as
carcinogens; however, both benzene and nitrobenzene were. I noticed that benzene
was linked specifically to leukemia, so I went to MEDLINE (via PubMed: http://www.ncbi.nlm.nih.gov/PubMed/)
and searched for "benzene" and "leukemia". I found several articles describing
the cellular and biochemical connections between benzene and leukemia including
one very recent paper by Martyn T. Smith, et al. from Nina Holland's lab at
Berkeley goes into some detail on this. They found that it is not benzene but
one of its metabolic products, hydroquinone (also used for photographic
developers), that may be responsible for causing leukemia by interfering with
chromosomal migration during mitosis. This would explain why the substituted
forms of benzene are not carcinogens: the substituents prevent the compound from
being metabolized to hydroquinone. This may also explain why nitrobenzene is
carcinogenic, since the nitrate group is readily released to yield unsubstituted
benzene. I'm not sure why phenol wouldn't be metabolized directly to hydroquinone
to have the same effect, but it may be that the high toxicity of phenol prevents
high enough exposure to become a cancer risk. For more on the chemistry and
substitution of aromatic rings, you should consult an organic chemistry textbook:
benzene substitution is a BIG topic, and a great deal is known about its
chemistry.
Try the links in the MadSci Library for more information on Biochemistry.