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Oxalic Acid (Spinach crystals in your kidneys)

Category: Inorganic
Posted on: December 20, 2006 7:38 PM, by Molecule of the Day

Oxalic acid is a bifunctional carboxylic acid. Your body will make it as the result of metabolism of ethylene glycol if you ever drink antifreeze, resulting in the catastrophic precipitation of calcium oxalate in your kidneys. Some foods have (fairly low) levels of oxalate. A small portion of vitamin C/ascorbate is metabolized to oxalate, which is a very real concern if you're following Linus Pauling's lead and taking grams of the stuff per day.

InChI=1/C2H2O4/c3-1(4)2(5)6/h(H,3,4)(H,5,6)

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Comments

How much Vitamin C gets metabolised like that? My stepfather was a Pauling fanatic and made me take 2000mg per day. I wonder how much of my aches and pains are due to that.

Posted by: John Wilkins | December 20, 2006 8:21 PM

I took a macrobiotic cooking class one time. The teachers had some mooney New Ages ideas, although they were good cooks. One thing they warned us against several times was spinach. They were generally in favor of most vegetables, but "spinach has oxalic acid". They suggested kale or another leafy green as a substitute.

Later I saw on the web that while spinach does contain oxalic acid, so do many other vegetables, and the level in spinach was not unusually high.

Posted by: mesothelioma | December 20, 2006 10:19 PM

Random fact stuff about oxalic acid:

Oxalic acid is the main ingredient in the cleaner Barkeeper's Friend.

It's also present in plants in the genus Oxalis, which contains the common woodsorrel, which is an extremely common weed in theRa US and is often mistaken for clover. (When I was little my friend and I would pick them and chew on the stems. It's sort of a pleasant bitter taste.)

Posted by: The Bug | December 21, 2006 1:33 PM

Actually it's rhubarb leaves which contain extremely high levels of oxalate and can be deadly if a large dose is consumed. Admittedly a very large dose.

Posted by: Wavefunction | December 21, 2006 2:33 PM

They were generally in favor of most vegetables

Posted by: x xd xd | December 21, 2006 2:37 PM

Spinach is terrible stuff. Besides oxalate it also contains phytic acid to chelate iron and zinc. If anemia and immune deficiency are your things then spinach is your lover.

The gel method is pretty good for growing calcium oxalate. Nice white needles. In your bloodstream oxalate removes calcium (no clotting) and deposits micro needles of Caox in capillary beds. Your fingertips, toes, nose, and ears go black as your kidneys die of ischemia. It hurts a whole lot, too.

Posted by: Uncle Al | December 21, 2006 5:09 PM

Uncle Al, you seem to have some chemical knowledge but hardly any regarding molecular biology and cell biology for that matter.
Your claim is just preposterous and ludicrous. I often find people taking results from papers in the field of molbio/microbio and translate them directly into their daily diet, even though these conclusions are meant to further the field itself and thus do not explicitly mention all the other pathways and known interaction of a molecule. So the paper doesn`t have to be tens of thousands of pages long, but rather presupposes such knowledge.

Posted by: lo | December 22, 2006 1:45 PM

Ive noticed ethylene glycol in the ingredients list for various foods. I wonder if the levels are high enough to have negative results...

i.e. is it worth avoiding foods with ethylene glycol?

Posted by: Brandon | January 7, 2007 1:06 AM

I think it miht be a good idea to avoid it. See this website for details:

http://en.wikipedia.org/wiki/Ethylene_glycol

Posted by: Samantha Wimala | January 10, 2007 11:07 PM

Brandon, you are probably confusing ethelene glycol with the non-toxic propylene glycol, which has the benefit of metabolising into lactic acid instead of the aformentioned MoTD.

Posted by: Neal Lantela | January 28, 2007 4:35 PM

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