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Hydroxycitric acid

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Hydroxycitric acid
Names
IUPAC name 1,2-dihydroxypropane-1,2,3-tricarboxylic acid
Other names Hydroxycitrate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=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)Key: ZMJBYMUCKBYSCP-UHFFFAOYSA-N
  • 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)Key: ZMJBYMUCKBYSCP-UHFFFAOYAQ
SMILES
  • O=C(O)C(O)C(O)(C(=O)O)CC(=O)O
Properties
Chemical formula C6H8O8
Molar mass 208.12292
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Hydroxycitric acid (HCA) is a derivative of citric acid that is found in a variety of tropical plants including Garcinia cambogia and Hibiscus subdariffa. Laboratory and animal studies of HCA have produced results that indicate a potential for modulation of lipid metabolism; consequently HCA is an ingredient in some weight loss products and dietary supplements. However, a clinical study has demonstrated that HCA has no effect in terms of weight loss or reduction of fat mass.

One isomer of HCA, known as (2S,3R)-HCA, inhibits pancreatic alpha-amylase and intestinal alpha-glucosidase, leading to a reduction in carbohydrate metabolism in vitro. In a study in Zucker rats, which are genetically predisposed to obesity, Garcinia cambogia extract containing HCA showed that high doses led to significant suppression of epididymal fat accumulation, but also caused potent testicular atrophy and toxicity. However, this study has been criticized because of possible contamination of the HCA used and various design flaws.

References

  1. ^ Yamada T, Hida H, Yamada Y (2007). "Chemistry, physiological properties, and microbial production of hydroxycitric acid". Appl. Microbiol. Biotechnol. 75 (5): 977–82. doi:10.1007/s00253-007-0962-4. PMID 17476502.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. Shara M, Ohia SE, Yasmin T; et al. (2003). "Dose- and time-dependent effects of a novel (-)-hydroxycitric acid extract on body weight, hepatic and testicular lipid peroxidation, DNA fragmentation and histopathological data over a period of 90 days". Mol. Cell. Biochem. 254 (1–2): 339–46. doi:10.1023/A:1027358106407. PMID 14674714. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  3. Heymsfield SB, Allison DB, Vasselli JR, Pietrobelli A, Greenfield D, Nunez C. (1998). "Garcinia cambogia (hydroxycitric acid) as a potential antiobesity agent: a randomized controlled trial". JAMA. 280 (18): 1596–600. doi:10.1001/jama.280.18.1596. PMID 9820262.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. Saito M, Ueno M, Ogino S, Kubo K, Nagata J, Takeuchi M (2005). "High dose of Garcinia cambogia is effective in suppressing fat accumulation in developing male Zucker obese rats, but highly toxic to the testis". Food Chem. Toxicol. 43 (3): 411–9. doi:10.1016/j.fct.2004.11.008. PMID 15680676.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Madhusudan Soni Burdock Group (2005). "Garcinia cambogia toxicity is misleading". Food and Chemical Toxicology. 43 (11): 1683–1684. doi:10.1016/j.fct.2005.05.011. PMID 15993998.
  6. Hayamizu, K; Tomi, H; Kaneko, I; Shen, M; Soni, MG; Yoshino, G (2008). "Effects of Garcinia cambogia extract on serum sex hormones in overweight subjects". Fitoterapia. 79 (4): 255–61. doi:10.1016/j.fitote.2007.12.003. PMID 18316163.
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