Glutaric acid is the
organic compound with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...
C
3H
6(COOH)
2 . Although the related "linear"
dicarboxylic acid
In organic chemistry, a dicarboxylic acid is an organic compound containing two carboxyl groups (). The general molecular formula for dicarboxylic acids can be written as , where R can be aliphatic or aromatic. In general, dicarboxylic acids show ...
s
adipic and
succinic acids are water-soluble only to a few percent at room temperature, the water-solubility of glutaric acid is over 50% (w/w).
Biochemistry
Glutaric acid is naturally produced in the body during the
metabolism of some
amino acids
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha am ...
, including
lysine
Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. It contains an α-amino group (which is in the protonated form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −C ...
and
tryptophan.
Defects in this metabolic pathway can lead to a disorder called
glutaric aciduria
Glutaric acidemia type 1 (GA1) is an inherited disorder in which the body is unable to completely break down the amino acids lysine, hydroxylysine and tryptophan. Excessive levels of their intermediate breakdown products (glutaric acid, glutaryl- ...
, where toxic byproducts build up and can cause severe
encephalopathy.
Production
Glutaric acid can be prepared by the ring-opening of
butyrolactone Butyrolactone may refer to:
* ''beta''-Butyrolactone
* ''gamma''-Butyrolactone (GBL)
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