Isocitric acid

Isocitric acid
Names
	IUPAC name 1-Hydroxypropane-1,2,3-tricarboxylic acid
Identifiers
CAS Number	320-77-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30887 ;
ChEMBL	ChEMBL539669 ;
ChemSpider	1161 ;
DrugBank	DB01727 °;
ECHA InfoCard	100.005.713
KEGG	C00311 ;
MeSH	Isocitrate
PubChem CID	1198;
	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) Key: ODBLHEXUDAPZAU-UHFFFAOYSA-N ; 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).
	verify (what is ?)
	Infobox references

Isocitric acid is a structural isomer of citric acid. 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.[1]

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles. [§ 1]

[[File:

[[<div style="display:block; width:30.1834671470831px; height:0px; overflow:hidden; position:relative; left:374.23731182425786px; top:602.398967699498px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:30.9999999999983px; height:0px; overflow:hidden; position:relative; left:466.4486251180706px; top:631.168519171318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:29.1504661757638px; height:0px; overflow:hidden; position:relative; left:816.8495338242362px; top:541.621487793808px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:41.841620626151px; height:0px; overflow:hidden; position:relative; left:649.9875435628912px; top:278.04945206398px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:33.7681761528873px; height:0px; overflow:hidden; position:relative; left:330.70153294231534px; top:297.610619807187px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:32.582089552239px; height:0px; overflow:hidden; position:relative; left:177.09689795536426px; top:425.87537485759px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:538.689173119075px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:88px; height:0px; overflow:hidden; position:relative; left:715.2163009404388px; top:401px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:80px; height:0px; overflow:hidden; position:relative; left:503.0px; top:670.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:84.9238578680197px; height:0px; overflow:hidden; position:relative; left:692.0761421319803px; top:573.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:304.2323578810314px; top:716.549820282624px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:33.621221037988px; height:0px; overflow:hidden; position:relative; left:367.5646397813722px; top:175.627991937516px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:720.2375300176794px; top:702.001875326864px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:720.2375300176792px; top:682.337193696082px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:73.3148283021269px; height:0px; overflow:hidden; position:relative; left:258.0px; top:207.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:853.3602503491594px; top:486.042093313318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:853.3602503491594px; top:466.042093313318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:304.2323578810314px; top:696.549820282624px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:498.689173119076px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:48.2984700306043px; height:0px; overflow:hidden; position:relative; left:180.0px; top:310.519900497513px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:853.3602503491594px; top:506.042093313318px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:720.2375300176792px; top:662.337193696082px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:70px; height:0px; overflow:hidden; position:relative; left:216.0px; top:374.674493554328px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:82px; height:0px; overflow:hidden; position:relative; left:264.0px; top:272.330227037402px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:61.4143272597748px; height:0px; overflow:hidden; position:relative; left:221.89453081488801px; top:475.826018808777px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:558.689173119075px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:52.4198466377163px; height:0px; overflow:hidden; position:relative; left:487.5801533622837px; top:199.5px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:47.2000923036619px; height:0px; overflow:hidden; position:relative; left:664.7999076963381px; top:198.406955168477px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:66px; height:0px; overflow:hidden; position:relative; left:277.0px; top:578px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:60px; height:0px; overflow:hidden; position:relative; left:68.73658375472704px; top:518.689173119076px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:174.797362167969px; height:0px; overflow:hidden; position:relative; left:111.0px; top:654.04700332349px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:154.310540655952px; height:0px; overflow:hidden; position:relative; left:575.6894593440477px; top:135.269018473869px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:170px; height:0px; overflow:hidden; position:relative; left:152.0px; top:124.074190177638px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:76px; height:0px; overflow:hidden; position:relative; left:682.0px; top:308.556556257706px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:46.2956622035883px; height:0px; overflow:hidden; position:relative; left:808.7043377964117px; top:363.951733482022px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:39px; height:0px; overflow:hidden; position:relative; left:813.9382716049388px; top:422.40772328832px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:36.5px; height:0px; overflow:hidden; position:relative; left:775.7640561670411px; top:541.621487793808px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:44.2885215390222px; height:0px; overflow:hidden; position:relative; left:670.9877017410322px; top:485.86403074685px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:41.8532982134678px; height:0px; overflow:hidden; position:relative; left:681.1902406172646px; top:427.288869264805px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:42.6019239578559px; height:0px; overflow:hidden; position:relative; left:692.5039932478962px; top:536.621487793808px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:28.5478699038022px; height:0px; overflow:hidden; position:relative; left:677.2474233020198px; top:598.540271103061px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:31.2611679545706px; height:0px; overflow:hidden; position:relative; left:642.4000247852737px; top:598.540271103061px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:32.9824561403508px; height:0px; overflow:hidden; position:relative; left:630.1160862354895px; top:693.89597205691px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:30.9999999999982px; height:0px; overflow:hidden; position:relative; left:466.4486251180698px; top:616.797517039126px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:30.1834671470831px; height:0px; overflow:hidden; position:relative; left:374.23731182425786px; top:588.027965567302px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:29.6136269214791px; height:0px; overflow:hidden; position:relative; left:289.5220258089487px; top:624.295539263445px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:70.9637798844278px; height:0px; overflow:hidden; position:relative; left:302.78215871956456px; top:542.264367816092px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:71.0094500492967px; height:0px; overflow:hidden; position:relative; left:302.75932363713014px; top:493.666666666667px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:39.3831123868514px; height:0px; overflow:hidden; position:relative; left:278.6168876131486px; top:422.876981279349px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:29.7294003600621px; height:0px; overflow:hidden; position:relative; left:203.66666666666663px; top:343.688918684141px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:35.0113378684808px; height:0px; overflow:hidden; position:relative; left:290.45787084901383px; top:243.69018283712px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:28.2086167800452px; height:0px; overflow:hidden; position:relative; left:454.45588384607703px; top:173.001159642582px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:151px; height:0px; overflow:hidden; position:relative; left:103.0px; top:152.25px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:183px; height:0px; overflow:hidden; position:relative; left:310.0px; top:92px; background:transparent; border-top:3px green solid"></div>]]

[[<div style="display:block; width:29.2970776041057px; height:0px; overflow:hidden; position:relative; left:659.0px; top:536.621487793808px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:27.0336779387258px; height:0px; overflow:hidden; position:relative; left:599.0px; top:693.89597205691px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:19.5546565671207px; height:0px; overflow:hidden; position:relative; left:466.350105337641px; top:690.298609635293px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:41.841620626151px; height:0px; overflow:hidden; position:relative; left:780.9875435628912px; top:330.04945206398px; background:transparent; border-top:3px blue solid"></div>]]

[[<div style="display:block; width:81px; height:12px; overflow:hidden; position:relative; left:715.2163009404388px; top:384px; background:transparent; border:4px black solid"></div>]]

|{{{bSize}}}px|alt=TCA Cycle edit]]

TCA Cycle edit

The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

References

Saavedra, L.; Garcia, A.; Barbas, C. (9 June 2000). "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 of Chromatography A. 881 (1–2): 395–401. doi:10.1016/s0021-9673(00)00258-2. PMID 10905722.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[WikiPathways-2] The interactive pathway map can be edited at WikiPathways: "TCACycle_WP78".

[Saavedra-1] Saavedra, L.; Garcia, A.; Barbas, C. (9 June 2000). "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 of Chromatography A. 881 (1–2): 395–401. doi:10.1016/s0021-9673(00)00258-2. PMID 10905722.

Isocitric acid

Interactive pathway map

See also

References