Tartaric acid is polar. The chemical formula for this acid is C4H6O6. Tartaric acid is a highly toxic substance. It has been found that as little as 12 grams of this acid has caused human fatality in as little as 12 hours after ingestion. Some side effects of this substance include violent vomiting and diarrhea, abdominal pain and thirst, followed by cardiovascular collapse and/or acute renal failure. This compound especially damages the muscles and the kidney, and may even cause fatal human nephropathy. Interestingly, adults with fibromyalgia and those affected by autism have been found to have elevated levels of tartaric acid in their urine. An example of this would be a young Korean child with autism who had a value of 6000 mmol/mol creatinine. This is about 600 times the median normal value. Assuming that the yeast in the intestine of the child were producing tartaric acid at a constant rate, the child would have been exposed to 4.5 grams of tartaric acid per day. This is over one third of the reported lethal dose.
Ironically, the Food and Drug administration has added tartaric acid to the GRAS list. GRAS stands for generally recognized as safe. Because of this, this product can freely be used as an additive in processed foods. Tartaric acid is a byproduct of the wine industry since a great amount of tartaric acid sludge has to be removed from the wine after yeast fermentation of the grape juice. This sludge is the primary source of tartaric acid used as a food additive. Tartaric acid is an analog of the Krebs cycle compound malic acid. An analog is a chemical compound that closely resembles but is not identical to another chemical compound. The reason an analog is important is that the analog may prevent the normal biochemical from completing its normal biochemical function.
A large percentage of patients with the disorder fibromyalgia who have high amounts of tartaric acid in their urine respond favorably to treatment with malic acid. Supplements of malic acid are able to overcome the toxic effects of tartaric acid by supplying deficient malic acid. Fifty percent of patients with fibromyalgia who also frequently have elevated yeast metabolites also suffer from hypoglycemia, even though their diet may have adequate or even excessive sugar. This reason may be due to the inhibition of the Krebs cycle by tartaric acid.
Tartaric acid is a complex compound because of the fact that it is a meso compound. A meso compound is a compound that contains chiral centers but is not chiral because it contains a mirror plane, a symmetry point or a rotoinversion axis.
There are two stereocenters in tartaric acid, so you'd suppose there are four isomers in total, two diastereomers (R,R) and (R,S) and their corresponding enantiomers (S,S) and (S,R). However, in the (R,S) isomer, there is a conformation where you can make out a mirror plane: (S,R) and (R,S), making it identical. There are three isomers of tartaric acid, one of which - the meso compound - behaves like an achiral compound, macroscopically. This is displayed in the pictures below.
Ironically, the Food and Drug administration has added tartaric acid to the GRAS list. GRAS stands for generally recognized as safe. Because of this, this product can freely be used as an additive in processed foods. Tartaric acid is a byproduct of the wine industry since a great amount of tartaric acid sludge has to be removed from the wine after yeast fermentation of the grape juice. This sludge is the primary source of tartaric acid used as a food additive. Tartaric acid is an analog of the Krebs cycle compound malic acid. An analog is a chemical compound that closely resembles but is not identical to another chemical compound. The reason an analog is important is that the analog may prevent the normal biochemical from completing its normal biochemical function.
A large percentage of patients with the disorder fibromyalgia who have high amounts of tartaric acid in their urine respond favorably to treatment with malic acid. Supplements of malic acid are able to overcome the toxic effects of tartaric acid by supplying deficient malic acid. Fifty percent of patients with fibromyalgia who also frequently have elevated yeast metabolites also suffer from hypoglycemia, even though their diet may have adequate or even excessive sugar. This reason may be due to the inhibition of the Krebs cycle by tartaric acid.
Tartaric acid is a complex compound because of the fact that it is a meso compound. A meso compound is a compound that contains chiral centers but is not chiral because it contains a mirror plane, a symmetry point or a rotoinversion axis.
There are two stereocenters in tartaric acid, so you'd suppose there are four isomers in total, two diastereomers (R,R) and (R,S) and their corresponding enantiomers (S,S) and (S,R). However, in the (R,S) isomer, there is a conformation where you can make out a mirror plane: (S,R) and (R,S), making it identical. There are three isomers of tartaric acid, one of which - the meso compound - behaves like an achiral compound, macroscopically. This is displayed in the pictures below.