Alcohol used in the production of testosterone esters?

[Kettlebells]

I am assuming that testosterone esters are testosterone bound to an ester. From organic chemistry, we know that an ester is an alcohol bound to a carboxylic acid, which is an organic acid that contains a carboxyl group (i.e., an acid with a chemical formula that ends in COOH). In the case of testosterone cypionate, the carboxylic acid is cypionic acid. Is ethanol the alcohol?

 

[Jinzang]

The "alcohol" is testosterone, which has a hydroxyl group on the five carbon ring. This is where the acid which forms an ester binds to the testosterone.

 

[Kettlebells]

So the condensation reaction for testosterone cypionate is between testosterone and cypionic acid?

C19H28O2 + C8H14O2 -> C27H40O3 + H2O

The five carbon ring with the hydroxyl (OH) group is easy to see in the image below on the right.


My knowledge of organic chemistry was obtained from studying the subject as it applies to brewing science; therefore, I am used to seeing esters that are formed from an alcohol and a carboxylic acid such as ethyl acetate or isoamyl acetate.

 

[Country23030]

right on, nice discussion.....

 

[Kettlebells]

The body just reverses the condensation reaction via hydrolysis by inserting an H2O molecule to free the testosterone molecule from the cypionic acid molecule.

C27H40O3 + H2O -> C19H28O2 + C8H14O2

My next question is what enzyme serves as the hydrolysis reaction catalyst?

 

[Jinzang]

A few chemical diagrams might make this clearer. Here's a diagram of testosterone.



and here's a diagram of propionic acid. I've flipped the image to make it align with the final image.



When they chemically combine, they form the ester testosterone propionate:

 

[Jinzang]

My next question is what enzyme serves as the hydrolysis reaction catalyst?

The esters are manufactured chemically, outside the body. I don't know the details of the process, except what I read on the Internet:

Today almost all steroid hormones are produced by stigmasterol, an inexpensive component of soybeans, or from cholesterol, which is available in tons quantities from wool fat. Stigmasterol is chemically converted to progesterone, by a pathway unrelated to synthesis in the body. Stigmasterol may also be converted through a microbial process to make other steroids, including estrone or testosterone.

Inside the body the the ester is split off of the testosterone molecule by an enzyme called, unsurprisingly, esterase.

 

[Kettlebells]

That is interesting. The hydroxyl group from testosterone is lost along with a hydrogen atom from the hydroxyl group in propionic acid, forming the H2O molecule residue during the condensation reaction that results in testosterone propionate. So esterase is responsible for catalyzing the reaction that re-inserts the water molecule that was lost during the creation of testosterone propionate; thereby, leaving testosterone and propionic acid in the body.