Chemists, please check this.

[xvs]

I am getting confused about the way these compounds are named.

For example, according to Stone, androstenone is
5alpha-Androst-16-en-3-one
is this the same as
16,5a-ANDROSTEN-3-OL

Doesn\'t look it.

Again, according to Stone, androstenol is:
5alpha-Androst-16-en-3alpha-ol
is this the same as:
16, (5a)-ANDROSTEN-3a-OL

I think so, but I\'m not sure.

OK, how about some more exotic ones:

estratetraenol is apparently:
1, 3, 5(10), 16-ESTRATETRAEN-3-OL

But what is estradienol (mentioned in an abstract posted here a few days ago)?

Any help will be appreciated!

Also, any references that would explain how this naming works (though I don\'t expect to understand it without a bunch of study, so I still need some info on the above questions!).

[**DONOTDELETE**]

OK, lemme see if I can give a little insight here. First up, there are a load of numbers in the names. So for example let\'s look at

5 alpha-Androst-16-en-3-one
or -none
The 5 alpha refers to the position of the proton on the 5 carbon. It is perpendicular (axial) to the plane of the ring structure. The androst is the parent name of the compound. The 16 en is that there is a double bond (or unsaturation) at the 16 carbon, and the 3 one is that there is a keto group at carbon 3. It is a very informative name, in this case. But, the rest of the world doesn\'t care to much about the details, and takes out the numbers and alphas, betas and so on. There is also confusion on the meaning of the alpha (or beta, gamma...) You might have seen ads for moisturizers with alpha hydroxy blah blah blahs, and this refers to which carbon after the functional group the structure (hydroxy in this case) is on. If the is a number before the alpha, then it refers to the isomer. If you see a (+/-) in front of the name, it is refering to optical rotation (which usually relates to the enantiomer, but that is another can of worms.) So lets look at another one on your list and see what we can find out...

1, 3, 5(10), 16-estratetraen-3-ol
or estratetraenol

From the chemical name we get:
A load of numbers. These refer to the double bonds in the compound.

Estra, the parent name of the compound

tetraen, or tetra ene, refering to the 4 double bonds in the compound.

and finally the 3-ol, which places the hydroxy on the three carbon. I an guessing from the fact that most all of the hydroxy cmpds that we talk about are blah-3a-ol that the hydroxy is also in the axial position.

You should also note that the 3-one cmpds never have the alpha added to them , because they cannot have this kind of isomer.

OK, after putting everyone to sleep, I suppose the easy answer is, we use common names cause they are easier. images/icons/smile.gif

[xvs]

Thanks!

So is
5alpha-Androst-16-en-3alpha-ol
the same as:
16, (5a)-ANDROSTEN-3a-OL
?

And do you have any idea what the formula of estradienol is (including the numbers, etc)?

[oscar]

xvs,

I\'m no chemist, but I think it\'s:
4, 16, Estradien-3a-ol .
Its listed as C18, H26, O .
The molecular weight is 258.4.

Check out www.steraloids.com/ (\"http://www.steraloids.com/\") . There you\'ll find more Andros, Estras, etc. than you can shake a stick at! The only problem with this site is that they\'re not great at having stuff listed by \"trivial name\". But the range of their inventory is UNREAL!

Oscar images/icons/laugh.gif

[**DONOTDELETE**]

I agree with W.O. Quite honestly, if you take the time to look at the structure, you\'ll find that there are a lot of things that follow patterns. Any time you see a 5a, consider it a 5 alpha. On a philosophical note, the cmpds that we are playing with are all very similar with slight changes. Makes sense from an evolutionary point of view. Take a theme and use slight variations to get your means to an end.