:Hydroxycitric acid
{{chembox
| Watchedfields = changed
| verifiedrevid = 440298418
| ImageFile=Hydroxycitric acid.png
| ImageSize=200px
| PIN=1,2-Dihydroxypropane-1,2,3-tricarboxylic acid
| OtherNames=Hydroxycitrate (anion name)
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 110439
| InChI = 1/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13)
| InChIKey = ZMJBYMUCKBYSCP-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZMJBYMUCKBYSCP-UHFFFAOYSA-N
| CASNo=6205-14-7
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8W94T9026R
| PubChem=123908
| SMILES = O=C(O)C(O)C(O)(C(=O)O)CC(=O)O
}}
|Section2={{Chembox Properties
| C=6 | H=8 | O=8
| Appearance=
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|Section3={{Chembox Hazards
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Hydroxycitric acid (HCA) is a derivative of citric acid that is found in a variety of tropical plants including Garcinia cambogia and Hibiscus sabdariffa.
There are four isomers, (+)- and (-)-hydroxycitric acid, and (+)- and (-)-allo-hydroxycitric acid. The (-)-hydroxycitric acid isomer is the one found in Garcinia.{{cite journal |last1=Jena |first1=BS |last2=Jayaprakasha |first2=GK |last3=Singh |first3=RP |last4=Sakariah |first4=KK |title=Chemistry and biochemistry of (-)-hydroxycitric acid from Garcinia. |journal=Journal of Agricultural and Food Chemistry |date=2002-01-02 |volume=50 |issue=1 |pages=10–22 |doi=10.1021/jf010753k |pmid=11754536}}
Chemistry
Hydroxycitric acid as such cannot be isolated from garcinia fruits or hibiscus sabdariffa fruits. It exists in both the open and lactone forms. The presence of two chiral centres in the molecule is exploited to construct molecular skeletons that are otherwise difficult to synthesize, thus demonstrating the lactones use as chirons.{{Cite journal|last1=Habel|first1=Deenamma|last2=Nair|first2=Divya S.|last3=Kallingathodi|first3=Zabeera|last4=Mohan|first4=Chithra|last5=Pillai|first5=Sarath M.|last6=Nair|first6=Rani R.|last7=Thomas|first7=Grace|last8=Haleema|first8=Simimole|last9=Gopinath|first9=Chithra|last10=Abdul|first10=Rinshad V.|last11=Fritz|first11=Matthew|date=2020-07-24|title=Natural Product-Derived Chiral Pyrrolidine-2,5-diones, Their Molecular Structures and Conversion to Pharmacologically Important Skeletons|url=https://pubs.acs.org/doi/10.1021/acs.jnatprod.0c00211|journal=Journal of Natural Products|language=en|volume=83|issue=7|pages=2178–2190|doi=10.1021/acs.jnatprod.0c00211|pmid=32584573|s2cid=220079442 |issn=0163-3864|url-access=subscription}}
Biological effects
(-)-HCA is a competitive inhibitor of ATP citrate lyase, which converts citrate into oxaloacetate and acetyl CoA. The reverse of this conversion is a step in the citric acid cycle.
Laboratory and animal studies of HCA have produced results that indicate a potential for modulation of lipid metabolism. A meta-analysis published in 2010 revealed that gastrointestinal adverse effects were twice as likely for users of hydroxycitric acid. The use of HCA is contraindicated in people with colitis or inflammatory bowel disease.
=Potential for liver damage=
A 2024 review indicated that consuming foods or dietary supplements containing hydroxycitric acid, such as Garcinia products, may cause liver disease.{{cite journal |vauthors=Philips CA, Theruvath AH |title=A comprehensive review on the hepatotoxicity of herbs used in the Indian (Ayush) systems of alternative medicine |journal=Medicine (Baltimore) |volume=103 |issue=16 |pages=e37903 |date=April 2024 |pmid=38640296 |pmc=11029936 |doi=10.1097/MD.0000000000037903}}
References
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