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Shape Matters! By Fcb981 (Own work) [GFDL ( copyleft/fdl.html) or CC-BY-SA-3.0 ( ons.org/licenses/by- sa/3.0/)], via Wikimedia Commons hotos/niaid/ By Angie from Sawara, Chiba-ken, Japan (Flickr) [CC BY 2.0 ( via Wikimedia Commons

Parabens Parabens have similar functionality and structures to estradiol and estrogen – two forms of estrogen found in our bodies. What do you think of when you think of estrogen? By derivative work: Leevclarke (talk) Female.svg: Gustavb Male.svg: Gustavb (Female.svg Male.svg) [Public domain], via Wikimedia Commons

“Estrogen Linked to Breast Cancer Recurrence” American Association for Cancer Research

It can be said that parabens are “estrogen mimics” –they act just like estrogen and can interfere with our bodies functions. By Ingrid Taylar from San Francisco Bay Area – California, USA [CC-BY- 2.0 ( via Wikimedia Commonshttp://creativecommons.org/licenses/by/2.0

Take a look at the following structures – can you predict which would be the best estrogen mimic? Estrogen

Butylparaben has the highest estrogenic activity – the “OH” group on one side binds to the receptor site and the size of it is similar to the size of estradiol

Take a look at the following structures – can you predict which would be the best estrogen mimic? Methylparaben is one of the most dangerous of the parabens – the small size allows it to go through skin easily. And, it is transformed in our bodies into butylparaben, which exhibits high estrogenic acitivity.

Assign the following names to the structures: Methyl paraben Butyl paraben Ethyl paraben Propyl paraben Hint: The structure in the circle is called a “paraben”.

What functional groups do you see in the paraben structures? Circle each functional group.

Alcohol Ester Benzene Alkane

Which of the following parabens are the same?

All are butylparaben, just draw in a different geometry.

Which of the following parabens are structural isomers?

Butylparaben, isobutylparaben and sec-butylparaben

There are other structural isomers that you can draw of butylparaben? Tert-butylparaben Sec-butylparaben Iso-butylparabenButylparaben (or N-butylparaben)

Size and shape matters But not always…