Chemistry:2-Hydroxyisocaproic acid

From HandWiki
2-Hydroxyisocaproic acid
Leucic acid.svg
Names
Preferred IUPAC name
2-Hydroxy-4-methylpentanoic acid
Other names
2-Hydroxy-4-methylvaleric acid
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C6H12O3
Molar mass 132.159 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

2-Hydroxyisocaproic acid (HICA or leucic acid) is a metabolite of the branched-chain amino acid leucine.[1] It is commonly sold as a purported muscle building supplement.[2] It also has fungicidal properties.[2] HICA was shown to increase protein synthesis and muscle mass in rats who were recovering from a period of induced atrophy.[3]

HICA is also produced by several protozoans it has been reported to show anti- inflammatory activities.[4]

References

  1. Ehling, Stefan; Reddy, Todime M. (February 2014). "Investigation of the presence of β-hydroxy-β-methylbutyric acid and α-hydroxyisocaproic acid in bovine whole milk and fermented dairy products by a validated liquid chromatography-mass spectrometry method.". Journal of Agricultural and Food Chemistry 62 (7): 1506–11. doi:10.1021/jf500026s. PMID 24495238. 
  2. 2.0 2.1 Sakko, M.; Moore, C.; Novak-Frazer, L.; Rautemaa, V.; Sorsa, T.; Hietala, P.; Järvinen, A.; Bowyer, P. et al. (April 2014). "2-hydroxyisocaproic acid is fungicidal for Candida and Aspergillus species.". Mycoses 57 (4): 214–21. doi:10.1111/myc.12145. PMID 24125484. 
  3. Lang, Charles H.; Pruznak, Anne; Navaratnarajah, Maithili; Rankine, Kristina A.; Deiter, Gina; Magne, Hugues; Offord, Elizabeth A.; Breuillé, Denis (August 2013). "Chronic α-hydroxyisocaproic acid treatment improves muscle recovery after immobilization-induced atrophy.". American Journal of Physiology 305 (3): E416–28. doi:10.1152/ajpendo.00618.2012. PMID 23757407. 
  4. Westrop, Gareth D.; Wang, Lijie; Blackburn, Gavin J.; Zhang, Tong; Zheng, Liang; Watson, David G.; Coombs, Graham H. (2017-12-21). "Metabolomic profiling and stable isotope labelling of Trichomonas vaginalis and Tritrichomonas foetus reveal major differences in amino acid metabolism including the production of 2-hydroxyisocaproic acid, cystathionine and S-methylcysteine". PLOS ONE 12 (12): e0189072. doi:10.1371/journal.pone.0189072. ISSN 1932-6203. PMID 29267346. Bibcode2017PLoSO..1289072W.