2-Hydroxyisocaproic acid

2-Hydroxyisocaproic acid
Names
	Preferred IUPAC name 2-Hydroxy-4-methylpentanoic acid
	Other names 2-Hydroxy-4-methylvaleric acid
Identifiers
CAS Number	498-36-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	83753;
ECHA InfoCard	100.007.147
PubChem CID	92779;
UNII	8RN4NSX3TY ;
CompTox Dashboard (EPA)	DTXSID80862047 ;
	InChI InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9) Key: LVRFTAZAXQPQHI-UHFFFAOYSA-N; InChI=1/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9) Key: LVRFTAZAXQPQHI-UHFFFAOYAQ;
	SMILES CC(C)CC(C(=O)O)O;
Properties
Chemical formula	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

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

^ 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.
^ ^a ^b Sakko, M.; Moore, C.; Novak-Frazer, L.; Rautemaa, V.; Sorsa, T.; Hietala, P.; Järvinen, A.; Bowyer, P.; Tjäderhane, L.; Rautemaa, R. (April 2014). "2-hydroxyisocaproic acid is fungicidal for Candida and Aspergillus species". Mycoses. 57 (4): 214–21. doi:10.1111/myc.12145. PMID 24125484. S2CID 24106682.
^ 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.
^ 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. Bibcode:2017PLoSO..1289072W. doi:10.1371/journal.pone.0189072. ISSN 1932-6203. PMC 5739422. PMID 29267346.

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[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.

[pubmed1-2] Sakko, M.; Moore, C.; Novak-Frazer, L.; Rautemaa, V.; Sorsa, T.; Hietala, P.; Järvinen, A.; Bowyer, P.; Tjäderhane, L.; Rautemaa, R. (April 2014). "2-hydroxyisocaproic acid is fungicidal for Candida and Aspergillus species". Mycoses. 57 (4): 214–21. doi:10.1111/myc.12145. PMID 24125484. S2CID 24106682.

[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. Bibcode:2017PLoSO..1289072W. doi:10.1371/journal.pone.0189072. ISSN 1932-6203. PMC 5739422. PMID 29267346.

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