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Thursday, July 21, 2005

Preparation of Progesterone from Cholesterol



This is what I understand happens, following the process of production of progesterone, described on page 894, second column.
In the first two steps cholesterol is brominated in benzene, and oxidized in a solvent with acid permanganate(aq). In the last step the product is again debrominated using zinc dust.

The strong oxidizing agent potassium permanganate is used, as well as sulfuric acid. The article below describes the process of production of progesterone from cholesterol.
Progesterone has numerous physiological effects. Although primarily associated with the reproductive system, progesterone has multiple effects outside of it. This steroid hormone can act as an antiinflamatory agent, reducing the immune response; it can also assist in thyroid hormone action and bone building. Progesterone appears to prevent endometrial cancer (cancer involving the uterine lining) as well as breast cancer (1).

Article link

6 Comments:

  • I don't see that reaction in the article.

    By Blogger Jean-Claude Bradley, at 1:52 PM  

  • Also, if you describing the physiological properties of progesterone you should have a link to where you got that information.

    By Blogger Jean-Claude Bradley, at 1:53 PM  

  • I still don't see how progesterone is made in one step from cholestenone with only permanganate and sulfuric acid. Point to the page and paragraph in your citation showing this.

    By Blogger Jean-Claude Bradley, at 6:19 PM  

  • Full Marks. You make a good attempt at trying to understand every step of the process. Unfortunately this is an "old school" article so there are no hints as to the details of the chemistry but I think you have it basically right. The bromination step is a good example of chemistry that we covered but I would be interested to see if anyone can find an explanation as to why permanganate would break off an alkyl group in that position (we only saw breaking off of alkyl groups that are on an aromatic group). Also, why does the double bond migrate in the debromination step with zinc?

    By Blogger Jean-Claude Bradley, at 7:13 AM  

  • Hey, you have a great blog here! I'm definitely going to bookmark you!

    I have a ##KEYWORD## site/blog. It pretty much covers ##KEYWORD## related stuff.

    Come and check it out if you get time :-)cholesterol level

    By Blogger cholmyth, at 10:02 AM  

  • I think that even before cholesterol comes into the scene....it is acetate from where the reaction starts..please try to provide information about where the precursors come from.

    By Anonymous Sivani, at 12:26 PM  

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