Chemistry and Life

Medicinal chemistry. Pharmacology. Toxicology. Environmental sciences.

Is bisguaiacol F a viable alternative to bisphenol A?

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Bisphenol A (BPA) is an ingredient in some plastic products.  It is useful in improving the properties of materials and products it is used in, but it has become a controversial subject.  BPA is used in plastic water bottles, food containers, and other materials that come in contact with what we consume.  BPA is used in small amounts and our exposure to it is probably very small. But BPA has known acute adverse health effects as an endocrine disruptor, and the human health risks associated with long term low exposure levels are difficult to assess. Figuring out how to balance the competing interests of a useful product versus the health concerns associated with its use is a messy regulatory situation.

As a precaution, BPA is has been phased out from some uses and has been banned in some jurisdictions and the search for suitable replacements is an area of active research.  One potential replacement that has been reported recently is called bisguaiacol F (BGF).  One notable aspect of BGF is that is can be produced from waste byproducts of the paper industry.  Lignans are natural chemical compounds found in wood which are removed in the production of paper.  This lignin waste is a disposal problem, so if it can be converted into a useful product (which is a replacement for a potentially harmful product) then two birds are killed with one stone.

Chemical structures of bisguaiacol F (BGF, top) and bisphenol A (BPA, bottom)

Chemical structures of bisguaiacol F (BGF, top) and bisphenol A (BPA, bottom)

So, is BGF a viable alternative to BPA?  BGF is chemically related to BPA.  Comparing the two chemical structures shown in the image, the two methyl groups (CH3) in the middle of BPA are removed and two methoxy groups (CH3O) are added on the ends.  Looking at just the first modification, removal of the two methyl groups gives a compound called bisphenol F (BPF).  BPF is a has the same endocrine disrupting concerns as BPA, so this modification alone is not sufficient to eliminate the potentially harmful effects.  Looking at the second medication, the study’s authors claim that the introduction of the two methoxy groups will prevent BPF from binding to the estrogen receptor, which is the cause of BPA’s biological effects. As far as I can tell, the researchers have only used software models to predict the biological effects of BGF, so there is certainly quite a bit more work to be done to demonstrate its safety.

It is still too early to tell whether BGF will eventually be a viable replacement for BPA, but it is research like this that is the only real hope of bypassing the current messy regulatory situation.


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