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Shape Matters!

Shape Matters!. 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?. “Estrogen Linked to Breast Cancer Recurrence” American Association for Cancer Research.

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Shape Matters!

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  1. Shape Matters!

  2. 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?

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

  4. It can be said that parabens are “estrogen mimics” –they act just like estrogen and can interfere with our bodies functions.

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

  6. 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

  7. 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.

  8. 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”.

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

  10. What functional groups do you see in the paraben structures? Circle each functional group. Ester Alkane Benzene Alcohol

  11. Which of the following parabens are the same?

  12. Which of the following parabens are the same? All are butylparaben, just draw in a different geometry.

  13. Which of the following parabens are structural isomers?

  14. Which of the following parabens are structural isomers? Butylparaben, isobutylparaben and sec-butylparaben

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

  16. Size and shape matters But not always…

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