10
$\begingroup$

I have heard that benzene is a dangerous chemical for humans; it causes cancer and so it's use is restricted/regulated. But many organic compounds that we use contain benzene in some form such as oils, foods, even medicines (paracetomol). So is benzene really harmful to people's health?

$\endgroup$
  • 24
    $\begingroup$ Chlorine is toxic, sodium is flammable; how can you eat NaCl? $\endgroup$ – Ivan Neretin Apr 14 '18 at 5:24
  • 4
    $\begingroup$ You should learn to understand the difference between a chemical compound and a mixture. $\endgroup$ – aventurin Apr 14 '18 at 11:35
  • 2
    $\begingroup$ Yeah, and while drinking a lot of H2O is considered very healthy, drinking a lot of H2O2 is not considered healthier. $\endgroup$ – rackandboneman Apr 14 '18 at 17:38
  • 2
    $\begingroup$ @rackandboneman - And, of course, in the US about 3800 people die every year due to overdosing on H2O. $\endgroup$ – Hot Licks Apr 14 '18 at 20:17
  • 2
    $\begingroup$ Before we discovered the toxicity of benzene, it was a widely used cheap solvent in labs. Once the toxicity was discovered benzene as a solvent was mostly replaced by toluene, which is benzene with a single methyl group attached. This apparently small change reduces toxicity by several orders of magnitude. You should not assume that single features of a molecule (like a benzene ring) determine its properties or toxicity. $\endgroup$ – matt_black Apr 14 '18 at 23:30
11
$\begingroup$

As Ivan Neretin commented, parts of a compound can never dictate its own properties to the entire molecule's properties. Additionally benzene is not a very effective functional group by itself.

In short, a restricted use is only applied when that certain chemical is exposed by itself. In paracetamol or any other thing including benzene, you will not see any benzene vapor emanating from them or something. It would also be meaningful if benzene containing compounds degradation products included benzene, like in environmental degradation of chlorobenzenes, though this is not a usual case as I see.

$\endgroup$
11
$\begingroup$

First let us make clear that the products you mentioned do not contain benzene. Likely you intended that plenty of products are aromatic compounds and, as such, contain at least a phenyl ring (or contain at least a benzene-like motif, for those less familiar with chemical nomenclature).

After reading the following, that gives some anecdotal notes as well, it will be clear that the presence of a specific part of a molecule does not necessarily dictates its properties (toxicological in the specific discussion) to the whole.

Translated from my old university notes:

.... many aromatic compounds are carcinogenic. After the London fire, a law imposing the maintenance of chimneys was promulgated. As a result it was noted that sweeper kids were at high risk of developing scrotum cancer. This was lately connected to benzo[a]pyrene present in the soot, and clearly established in the 1900s.

Benzo[c]anthracene is carcinogenic as well, and benzene is among the most powerful agents inducing leukemia.

In general strong carcinogens are strong electrophiles, such as alkylants. On the contrary, benzene is electron rich.

Again in England, around 1960, a kind of plague was causing the mass death of turkeys due to leaver cancer. It was established that as due to to a toxin present in the feeds that, once metabolized, gave epoxides as strong electrophiles.

A link to aromatic carcinogenic properties was then made and established. Rather than aromatic themselves, the real carcinogens are their epoxides formed during metabolism. They act as substrate for the nucleophilic attack by DNA bases as we will see in......

Anything altering the stability or geometry of the metabolite epoxides will therefore modulate their reacivity and in turn the hazard posed by that specific aromatic compound.

This is also the case for PAH were, at least, a particular structure (bay) is linked to strong carcinogenicity.

Edit. As this answer received a comment pointing to the fact that not all aromatics are carcinogenic I invite you to consider that the above

  • many aromatics does not mean that all aromatic compounds are carcinogenic

  • anything altering.... means that each molecule must be considered as a whole. Functionalisation of benzene by a methyl group leads to toluene, for instance. The latter does not qualify as carcinogenic and should replace benzene whenever possible

  • PAH is of course a subset of arenes. Among PAHs, again, not all compounds are carcinogens. However, in this case, a specific feature regarding the shape rather generally point to carcinogenicity (see link).

yes benzene is very harmful to human health

$\endgroup$
  • 2
    $\begingroup$ But many aromatic compounds are not toxic and it is wrong to overgeneralise. Toluene is very much less toxic than benzene, for example. And while PAHs are often bad, this is a bad generalisation for aromatic compounds as a class. $\endgroup$ – matt_black Apr 14 '18 at 23:33
  • $\begingroup$ I do not see why you should comment here. "Many is not all'. "Anything altering the stability of the potentially formed epoxides will. .. modulated the hazard posed by a specific ar. compound." "This is also the case for pah...". @matt_black. You should even remove your comment at least it does not belong to my answer! $\endgroup$ – Alchimista Apr 15 '18 at 8:13
  • $\begingroup$ The problem is you are answering a question about the general consequences of having a benzene ring in a compounds with a specific set of examples that are nasty. This doesn't help answer the general question (even after you edited the answer with caveats). $\endgroup$ – matt_black Apr 15 '18 at 12:29
  • $\begingroup$ I insist that your comment does not belong to my answer as no generalization is made. Any normal reader understand that a benzene motif itself is not responsible for harmful effects. $\endgroup$ – Alchimista Apr 15 '18 at 14:52
  • $\begingroup$ @Alchimista I would say the OP was under that impression. I edited the question to it's current form because the original was a little rough to read, but that was how I interpreted it. $\endgroup$ – Tyberius Apr 15 '18 at 19:12
9
$\begingroup$

Containing a benzene-like (phenyl) group does not make a compound have the same biological activity as benzene itself. Nearly all proteins in your body contain the amino acids phenylalanine and tyrosine, both of which have a phenyl group. Your blood constantly carries these amino acids in their free forms. However, these amino acids are not metabolized by enzymes the same way as benzene and therefore are not metabolized into the epoxide-bearing molecules (described in other answers) responsible for DNA damage.

$\endgroup$
8
$\begingroup$

Benzene is toxic to humans, it can be oxidised by enzymes in the body (might be a P450 enzyme) to form benzene oxide which is an epoxide. This is 7-oxabicyclo[4.1.0]hepta-2,4-diene which can then react with DNA or other molecules in the body. If the epoxide reacts with water to form cyclohexa-3,5-diene-1,2-diol. Then this can be oxidised again to form 7-oxabicyclo[4.1.0]hept-4-ene-2,3-diol which can react with the DNA.

As a result of this DNA damage benzene is able to cause cancer, it is important to keep in mind that many carcinogens are in fact precursors of the carcinogen. They require some metabolic activation to be able to cause cancer.

Another example is hydrazine which is converted in the liver by formaldehyde and oxidation into diazomethane. As a result the liver is damaged.

$\endgroup$
5
$\begingroup$

It is generally accepted that formation of diolepoxide-derived DNA adducts such as ones depicted in following Figure1 is the principal metabolic activation pathway leading to cancer initiation in mammals (Courtesy of https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3812823/).

Figure1

Polycyclic aromatic hydrocarbons (PAHs) are a class of environmental contaminants (Figure2) that has long been suspected for genotoxicity, metabolism and metabolic activation, DNA adduct formation, mutagenesis, and carcinogenesis. Although, PAHs are relatively non-reactive chemicals toward biological macromolecules under physiological conditions, upon entering the body, our cellular defense system attempts to “remove” these foreign substances by metabolism, which is principally done in our liver, mainly catalyzed by the cytochrome P450 enzymes. Upon metabolism, most PAHs, with multiple hydroxyl groups, become more polar and water-soluble to be excreted out of the body. However, metabolism of some PAHs generates certain reactive intermediates (see benzo[a]pyrene; [Figure 1]) that are capable of forming damaging covalent adducts with nucleic acids (e.g., free $\ce{DNA-NH2}$ groups), eventually leading to genotoxicity and cancer.

Figure2

$\endgroup$
  • 1
    $\begingroup$ PAHs are a very small subset of aromatic compounds in general and are toxic for specific reasons that don't generalise to all aromatics. $\endgroup$ – matt_black Apr 14 '18 at 23:34
  • 1
    $\begingroup$ @ matt_black: I didn't imply all aromatics in general are harmful to humans. It's too broad of field to fin point something like that. Yet, PAHs are a good example to represent benzene. For instance, unlike toluene, benzene under go similar detoxication process like a PAH such as benzo[a]pyrene by the cytochrome P450 enzymes. $\endgroup$ – Mathew Mahindaratne Apr 15 '18 at 1:48
  • 2
    $\begingroup$ The trouble with quoting a particularly nasty class of compounds as an answer to a much more general question is that you reinforce the false impression that the presence of a benzene ring in a compound inevitably makes it toxic. Nothing you say is wrong, but the answer is incredibly misleading as an answer to this specific question. $\endgroup$ – matt_black Apr 15 '18 at 12:35

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.