Isocitric acid

Isocitric acid

File:Isocitric acid.svg
Names
IUPAC name 1-Hydroxypropane-1,2,3-tricarboxylic acid
Identifiers
CAS Number	320-77-4 checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30887 checkY
ChEMBL	ChEMBL539669 checkY
ChemSpider	1161 checkY
DrugBank	DB01727 ☒N°
ECHA InfoCard
E number
KEGG	C00311 checkY
MeSH	Isocitrate
PubChem CID	1198
UNII	9RW6G5D4MQ checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13) checkY Key: ODBLHEXUDAPZAU-UHFFFAOYSA-N checkY InChI=1/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13) Key: ODBLHEXUDAPZAU-UHFFFAOYAX
SMILES O=C(O)C(CC(=O)O)C(O)C(=O)O
Properties
Chemical formula	C6H8O7
Molar mass	192.124
Melting point	105 °C (221 °F; 378 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is checkY☒N ?) Infobox references

Isocitric acid is a structural isomer of citric acid. Since citric acid and isocitric acid are structural isomers, they share similar physical and chemical properties. Due to these similar properties, it is difficult to separate the isomers. Salts and esters of isocitric acid are known as isocitrates. The isocitrate anion is a substrate of the citric acid cycle. Isocitrate is formed from citrate with the help of the enzyme aconitase, and is acted upon by isocitrate dehydrogenase.

Isocitric acid is commonly used as a marker to detect the authenticity and quality of fruit products, most often citrus juices. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. An isocitric acid value higher than this may be indicative of fruit juice adulteration.

Isocitric acid has largely been used as a biochemical agent due to limited amounts. However, isocitric acid has been shown to have pharmaceutical and therapeutic effects. Isocitric acid has been shown to effectively treat iron deficient anemia. Additionally, isocitric acid could be used to treat Parkinson's disease. Yarrowia lipolytica can be used to produce isocitric acid and is inexpensive compared to other methods. Furthermore, other methods produce unequal amounts of citric acid to isocitric acid ratio, mostly producing citric acid. Use of Yarrowia lipolytica produces a better yield, making equal amounts of citric acid to isocitric acid.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.

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TCACycle_WP78 edit

See also

• Citric acid, also fluorocitric acid and chlorocitric acid
• Tartaric acid
• Malic acid