Why do people use castor oil topically?

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monoid

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Recalling my high-school chemistry, I know that most fats/oils are in the chemical form of triglycerides. That is, it is an ester formed by 3 fatty acid molecules and one glycerol molecules. Each glycerol molecule (CH2OH-CHOH-CH2OH) contains 3 hydroxyls (-OH); and each of them will react with the carboxylic -COOH radical in a fatty acid molecule.

What we want from castor oil is ricinoleic acid (which is a PGE2 agonist).
512px-Ricinoleic_acid.svg.png

This is a fatty acid, and is present in castor oil in the triglyceride form called ricinolein:
512px-Ricinolein.svg.png

See? Three ricinoleic acid forming an ester with a glycerol in the middle.

However, two problems arise:

(1) Ricinoleic acid has a molar mass of 298. THREE ricinoleic acid plus a glycerol minus 3 water is 933, which exceeds the human absorption limit of 500g/mol by a large margin. How could castor oil be absorbed by human skin?

(2) Even if it is absorbed, how can this molecule be properly hydrolyzed to produce isolated ricinoleic acid molecules instead of triglycerides?

Therefore I think that oral is the way to go if we want to use castor oil. Oil can be hydrolyzed to produce glycerol and fatty acids in the stomach because of the presence of lipase (fat enzyme).

OR

We could hydrolyze castor oil (ricinolein) in vitro into ricinoleic acid (by lipase? or other hydrolysis agent?) and made it into a topical.
 
Norwood One

Norwood One

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Apply with DMSO for penetration, by itself, it just sits there like you said because the high molar mass.
 
Jeca Tatu

Jeca Tatu

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Hey monoid, thank you.

I was waiting for a long time to post the exact same thing in the alternative section but postponed it due the lack of time. So this is really appreciated.
In the thread I was going to open I would suggest us to think about applying pure ricinoleic acid, which at least where I live is very easy to find. My guess is it would be harsh to the skin in some degree, so I think we could try it in a composite vehicle, with a carrier and some light moisturizer or even balancing the pH of the solution to saturate the solution only with the essencial stuff.

will be back here to elaborate on this as soon as possible :)
 
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deniak

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Good post. From my experience topical castor is big no-no from practical standpoint, however after few weeks of regular use, orally and topically, I really noticed hypertrichosis between eyebrows and temples. I ditched it, because I noticed stomach sensations and slight bloating. It turns out that long term using of castor oil, even small approved doses, can have very unpleasant and serious side effects.
It might be similiar situation to using fatty acids as reductase blockers, it may work but only in specific (free) form which is very hard to obtain. Im biased more and more to ditch all this promising "new age" angles and stick to few treatments that are proved to work in vivo.
 
Giiizmo

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I too would like to know what kind of "serious side effects" castor oil can induce as it's the second time I read a poster on this forum making such claims.

If it's about the supposed ricin content, it's a protein that gets denatured during the heat-extraction of the oil. Furthermore, it is not oil soluble so contamination is rather unlikely. Also, according to Wikipedia, "In India, Pakistan and Nepal food grains are preserved by the application of castor oil. It stops rice, wheat, and pulses from rotting. For example, the legume pigeon pea is commonly available coated in oil for extended storage." so people have been consuming minute quantities of castor oil for centuries without any apparent side-effects.

The one side-effect that I can think of is a possible loss of potassium due to castor oil induced diarrhea. In that case, just consume less of the stuff so you can stop crapping yourself.

I do consume about 1ml of the stuff daily and don't suffer from any side effects if maybe some increased body hair and coarser beard hair. I'm not expecting much from it but it doesn't seem to do any harm either. Maybe I'll get bored of it at some point and drop it.
 
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deniak

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Ok guys, Im no pharmacist but I try to translate info from bottle sticker:)
"... even with therapeutic dose it iritiate small intestine, may lead to organ vasocongestion in abdominal cavity and pelvis area, which may lead to intensified inflammation..."
I call it serious if you consider still non proved impact on hairs in balding area. There is also info about using it only intermittently.
Also, its from bottle of legit castor oil from pharmacy store.

Vincent - abdomen bloat. Maybe its not connected but with "sensations" I noticed bloat. After stopping castor Im free of both.
 
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monoid

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I found out that we can get sodium ricinoleate salt from here: http://www.alibaba.com/product-detail/SODIUM-RICINOLEATE_117262334.html?spm=a2700.7724838.0.0.8TlF1N .
Adding a little acid to this salt and it yields isolated ricinoleic acid.

Sodium Ricinoleate + Hydrochloric acid (HCl) ==> Sodium chloride (table salt) + Ricinoleic acid

Anyone thinking that this is possible?

- - - Updated - - -

Or, we could use the saponification process of castor oil to produce ricinoleic acid:

Ricinolein (Castor oil) heated together with NaOH ==> Ricinoleic acid + H[SUB]2[/SUB]O
Then use HCl to tune the pH to neutral.
 
hellouser

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monoid said:
(1) Ricinoleic acid has a molar mass of 298. THREE ricinoleic acid plus a glycerol minus 3 water is 933, which exceeds the human absorption limit of 500g/mol by a large margin. How could castor oil be absorbed by human skin?
Click to expand...

Dermaroll, wash off sebum from scalp, exfoliate and dermaroll. Dermarolling alone will allow much larger compounds to pass through with ease.
 
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monoid

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hellouser said:
Dermaroll, wash off sebum from scalp, exfoliate and dermaroll. Dermarolling alone will allow much larger compounds to pass through with ease.
Click to expand...
This does not answer my second problem:
monoid said:
(2) Even if it is absorbed, how can this molecule be properly hydrolyzed to produce isolated ricinoleic acid molecules instead of triglycerides?
Click to expand...


Caster oil contains ricinolein, which is a triglyceride formed by a glycerin molecule and 3 ricinoleic acid molecules. What we want is isolated ricinoleic acid (the actual PGE2 agonist). These two are different.
 
Armando Jose

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Lipases are present in skin and transform triglycerides in free fatty acids. Dont worry, only fats must be enough time in the area
 
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monoid

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Armando Jose said:
Lipases are present in skin and transform triglycerides in free fatty acids. Dont worry, only fats must be enough time in the area
Click to expand...

Oh really? Good to know.

But I still think that applying isolated ricinoleic acid may be better?
 
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