{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443882421 | ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile = isocitric acid.svg | ImageClass = skin-invert | ImageSize = 105px | IUPACName = 1-Hydroxypropane-1,2,3-tricarboxylic acid | OtherNames = |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 1161 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C00311 | 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) | InChIKey = ODBLHEXUDAPZAU-UHFFFAOYAX | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 539669 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ODBLHEXUDAPZAU-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 320-77-4 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9RW6G5D4MQ | PubChem = 1198 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 30887 | SMILES = O=C(O)C(CC(=O)O)C(O)C(=O)O | MeSHName = Isocitrate | DrugBank_Ref = {{drugbankcite|changed|drugbank}}° | DrugBank = DB01727 }} |Section2={{Chembox Properties | C=6 | H=8 | O=7 | MolarMass = 192.124 | Appearance = | Density = | MeltingPtC = 105 | BoilingPt = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''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.<ref name=":0">{{Cite journal |last1=Kamzolova |first1=Svetlana V. |last2=Morgunov |first2=Igor G. |date=2019-12-01 |title=Microbial production of (2R,3S)-isocitric acid: state of the arts and prospects |url=https://doi.org/10.1007/s00253-019-10207-4 |journal=Applied Microbiology and Biotechnology |language=en |volume=103 |issue=23 |pages=9321–9333 |doi=10.1007/s00253-019-10207-4 |pmid=31748825 |issn=1432-0614|url-access=subscription }}</ref> 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.<ref name=Saavedra>{{cite journal|first1=L.|last1=Saavedra|first2=A.|last2=Garcia|first3=C.|last3=Barbas|author-link3=Coral Barbas|title=Development and validation of a capillary electrophoresis method for direct measurement of isocitric, citric, tartaric and malic acids as adulteration markers in orange juice|journal=Journal of Chromatography A|date=9 June 2000|pages=395–401|volume=881|issue=1–2|pmid=10905722|doi=10.1016/s0021-9673(00)00258-2}}</ref>
Isocitric acid has largely been used as a biochemical agent due to limited amounts.<ref name=":1">{{Cite journal |last1=Yuzbasheva |first1=Evgeniya Y. |last2=Scarcia |first2=Pasquale |last3=Yuzbashev |first3=Tigran V. |last4=Messina |first4=Eugenia |last5=Kosikhina |first5=Iuliia M. |last6=Palmieri |first6=Luigi |last7=Shutov |first7=Artem V. |last8=Taratynova |first8=Maria O. |last9=Amaro |first9=Rodrigo Ledesma |last10=Palmieri |first10=Ferdinando |last11=Sineoky |first11=Sergey P. |date=2021-05-01 |title=Engineering Yarrowia lipolytica for the selective and high-level production of isocitric acid through manipulation of mitochondrial dicarboxylate–tricarboxylate carriers |url=https://www.sciencedirect.com/science/article/pii/S1096717620301671 |journal=Metabolic Engineering |language=en |volume=65 |pages=156–166 |doi=10.1016/j.ymben.2020.11.001 |pmid=33161142 |s2cid=226286865 |issn=1096-7176|hdl=11586/349079 |hdl-access=free }}</ref> However, isocitric acid has been shown to have pharmaceutical and therapeutic effects. Isocitric acid has been shown to effectively treat iron deficient anemia.<ref name=":0" /> Additionally, isocitric acid could be used to treat Parkinson's disease.<ref name=":1" /> ''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.<ref name=":1" />
== Interactive pathway map == {{TCACycle_WP78|highlight=Isocitric_acid}}
== See also == * Citric acid, also fluorocitric acid and chlorocitric acid * Tartaric acid * Malic acid
==References== {{Reflist}}
{{Citric acid cycle}}
{{DEFAULTSORT:Isocitric Acid}} Category:Alpha hydroxycarboxylic acids Category:Tricarboxylic acids Category:Citric acid cycle compounds Category:Aldols