O-Chem Question: Does l-carnitine contain cis hydroxyl groups?

[aaron_c]

From what I can tell it doesn't, but I'm hoping to hear it from someone who has some experience with chemistry. ( @JaimeS @Hip )

Boron binds to molecules with cis-hydroxyl groups like ribose. I'm trying to track down why boron gives me insomnia and whether part of the insomnia is boron interacting with something else like carnitine.

L-Carnitine, a la Wikipedia:

 

[Quemist]

Organic chemist here- there is only one hydroxyl group. It is plausible that it'll do something called chelating to the hydroxyl and the carboxyl. However, ribose is a ring and does have cis or trans hydroxyls because there are two different alcohol oxygens bound.

 

[aaron_c]

Thanks @Quemist!

 

[JaimeS]

Agreed @Quemist!

 

[Gondwanaland]

I'm trying to track down why boron gives me insomnia and whether part of the insomnia is boron interacting with something else like carnitine.

I would be curious to know if B2 helps with that.

 

[aaron_c]

I would be curious to know if B2 helps with that.

Not really? I know you know this but for the benefit of people just coming to the thread: Boron binds to B2 and together they are excreted.

Boron gives me diarrhea while B2 fixes that diarrhea. So I do try to take enough B2 to counteract the boron diarrhea. But if I took enough B2 to pull more boron out then I would start to lose the benefits of boron vs candida and just generally reverse the positive effects of boron--which I like. I'm trying to find a way to take at least enough boron to keep candida under control.

 

[Little Bluestem]

I'm trying to find a way to take at least enough boron to keep candida under control.

How much boron does it take to keep candida under control?

 

[aaron_c]

I've been using borax externally (or rather, sodium borate--I use the lab grade stuff). At first I put a tablespoon in a 30-minute foot-bath, which worked just fine.

Then, when the insomnia started I tried to get the same results with a lower dose. For this, I dissolved a heaping 1/8 teaspoon in as little water as possible while still dissolving the borax, about 1/8 cup maybe. I would then smear this on my face, scalp, and groin where the external symptoms of fungal infection were going strong (dandruff and jock itch). Then I would dry myself with a hair drier. This also worked, but I had to do more or less every day, whereas the foot baths could be skipped a little more easily.

If I take boron internally I get diarrhea, presumeably because it is stripping b2 from my guts. I've read that b2 deficiency causes problems with the brush border (shrinking?) and in any case increasing b2 has, in the past, helped make my stool healthy and reduced or eliminated my IBS. This is why external application of boron for external fungal issues appealed to me.

 

[Gondwanaland]

@aaron_c are you taking Molybdenum and eating high Molybdenum foods?

 

[aaron_c]

Not since shortly after the insomnia began. I think a molbdenum-boron interaction is probably the culprit here, but I'm concerned that it will take a long time for molybdenum levels to normalize. I have read that molybdenum's half-life in some tissues is around six months, and I can't find anything that chelates molybdenum all that well (although I see someone used EDTA once in an acute case.) But ya, I'm afraid I'm just going to have to wait.

 

[Gondwanaland]

I know Mo inhibits Cu, but don't know if the opposite is true.

 

[aaron_c]

I've read that molybdenum will bind to copper in the gut and they will be excreted together, but beyond that I am under the impression that most molybdenum in the body is already bound as part of molybdenum cofactor or maybe just part of the bone matrix (I read bones are one major place you find molybdenum stores). In which case I'm not sure how successful copper would be at pulling molybdenum out.

 

[Gondwanaland]

(dandruff and jock itch)

These can be present in Riboflavin deficiency (page 231).

 

[aaron_c]

These can be present in Riboflavin deficiency

I didn't know that.

Still, it doesn't seem to have been what caused them for me as a foot bath with boron eliminated those symptoms. Plus I take a decent-high amount of riboflavin every day.

Nice book!

 

[Gondwanaland]

@aaron_c we are all different of course, but I can get Boron toxicity pretty quickly from dietary sources causing me B2 depletion with the main signs being a slight pain in parathyroid and a rosacea-like rash in the face. Also nocturia, urinating far more than I can drink in liquids during the day. Tryptophan food sources seem to compound the problem causing stinging eye pain. All resolved by B2.

Nice book!

I'm glad you liked, but it is pretty outdated (1975). At least it presents the old research thoroughly, the kind of research that isn't done anymore.

 

[Gondwanaland]

@aaron_c I don't know if you take probiotics, but I read several reviews about Bacillus coagulans "getting rid of Candida" at online stores while researching it to lower insulin levels and help with IBS-D for my husband.

I also read long ago about Biotin helping with Candida as well.