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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:06 UTC
HMDB IDHMDB0000746
Secondary Accession Numbers
  • HMDB00746
Metabolite Identification
Common NameHydroxyisocaproic acid
DescriptionHydroxyisocaproic acid is an end product of leucine metabolism in human tissues such as muscle and connective tissue. It belongs to 2-hydroxycarboxylic acid group of amino acid metabolites (PMID 6434570 ). Hydroxyisocaproic acid functions as an “anti-catabolite” and is widely used in the body building community. Chronic alpha-hydroxyisocaproic acid treatment of rats has been shown to improve muscle recovery after immobilization-induced atrophy (PMID: 23757407 ). Additionally, a 4-week hydroxyisocaproic acid supplementation of 1.5 g a day was shown to lead to increases in muscle mass during an intensive training period among soccer athletes (PMID: 20051111 ). Hydroxyisocaproic acid has also shown some potential as a topical antibiotic (PMID: 22483561 ). Elevated levels of 2-hydroxyisocaproic acid have been found in the urine of patients with dihydrolipoyl dehydrogenase (E3) deficiency (PMID: 6688766 ). Hydroxyisocaproic acid is also elevated in maple syrup urine disease, a genetic disorder, and has been shown to accelerate lipid peroxidation. It may also be an indicator of oxidative stress (PMID: 11894849 ). Hydroxyisocaproic acid has been found to be a metabolite of Lactobacillus and fungal species (http://jultika.oulu.fi/files/isbn9789526211046.pdf).
Structure
Data?1582752153
Synonyms
ValueSource
(+)-2-Hydroxyisocaproic acidChEBI
(+)-alpha-Hydroxyisocaproic acidChEBI
(S)-2-Hydroxyisocaproic acidChEBI
(S)-Leucic acidChEBI
2-HYDROXY-4-methyl-pentanoIC ACIDChEBI
L-2-Hydroxy-4-methylvaleric acidChEBI
L-2-Hydroxyisocaproic acidChEBI
L-alpha-Hydroxyisocaproic acidChEBI
L-Leucic acidChEBI
(+)-2-HydroxyisocaproateGenerator
(+)-a-HydroxyisocaproateGenerator
(+)-a-Hydroxyisocaproic acidGenerator
(+)-alpha-HydroxyisocaproateGenerator
(+)-Α-hydroxyisocaproateGenerator
(+)-Α-hydroxyisocaproic acidGenerator
(S)-2-HydroxyisocaproateGenerator
(S)-LeucateGenerator
2-HYDROXY-4-methyl-pentanoateGenerator
L-2-Hydroxy-4-methylvalerateGenerator
L-2-HydroxyisocaproateGenerator
L-a-HydroxyisocaproateGenerator
L-a-Hydroxyisocaproic acidGenerator
L-alpha-HydroxyisocaproateGenerator
L-Α-hydroxyisocaproateGenerator
L-Α-hydroxyisocaproic acidGenerator
L-LeucateGenerator
HydroxyisocaproateGenerator
Hydroxy-isocaproateHMDB
(2S)-2-Hydroxy-4-methylpentanoateHMDB
(2S)-2-Hydroxy-4-methylpentanoic acidHMDB
(S)-2-Hydroxy-4-methyl-pentanoateHMDB
(S)-2-Hydroxy-4-methyl-pentanoic acidHMDB
S-2-Hydroxy-4-methylpentanoateHMDB
S-2-Hydroxy-4-methylpentanoic acidHMDB
Chemical FormulaC6H12O3
Average Molecular Weight132.1577
Monoisotopic Molecular Weight132.07864425
IUPAC Name(2S)-2-hydroxy-4-methylpentanoic acid
Traditional Name(+)-α-hydroxyisocaproate
CAS Registry Number13748-90-8
SMILES
CC(C)C[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m0/s1
InChI KeyLVRFTAZAXQPQHI-YFKPBYRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point78 - 80 °CNot Available
Boiling Point251.31 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility165500 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.710The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg126.05730932474
[M-H]-Not Available126.057http://allccs.zhulab.cn/database/detail?ID=AllCCS00000210
Predicted Molecular Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP0.5ALOGPS
logP0.78ChemAxon
logS-0.03ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity32.51 m³·mol⁻¹ChemAxon
Polarizability13.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.3231661259
DarkChem[M-H]-124.58131661259
AllCCS[M+H]+131.97632859911
AllCCS[M-H]-129.50532859911
DeepCCS[M+H]+128.30230932474
DeepCCS[M-H]-124.70630932474
DeepCCS[M-2H]-162.02630932474
DeepCCS[M+Na]+137.12830932474
AllCCS[M+H]+132.032859911
AllCCS[M+H-H2O]+127.932859911
AllCCS[M+NH4]+135.832859911
AllCCS[M+Na]+136.932859911
AllCCS[M-H]-129.532859911
AllCCS[M+Na-2H]-132.332859911
AllCCS[M+HCOO]-135.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hydroxyisocaproic acidCC(C)C[C@H](O)C(O)=O1935.3Standard polar33892256
Hydroxyisocaproic acidCC(C)C[C@H](O)C(O)=O1027.3Standard non polar33892256
Hydroxyisocaproic acidCC(C)C[C@H](O)C(O)=O1108.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hydroxyisocaproic acid,1TMS,isomer #1CC(C)C[C@H](O[Si](C)(C)C)C(=O)O1189.3Semi standard non polar33892256
Hydroxyisocaproic acid,1TMS,isomer #2CC(C)C[C@H](O)C(=O)O[Si](C)(C)C1121.8Semi standard non polar33892256
Hydroxyisocaproic acid,2TMS,isomer #1CC(C)C[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1237.3Semi standard non polar33892256
Hydroxyisocaproic acid,1TBDMS,isomer #1CC(C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O1404.6Semi standard non polar33892256
Hydroxyisocaproic acid,1TBDMS,isomer #2CC(C)C[C@H](O)C(=O)O[Si](C)(C)C(C)(C)C1356.0Semi standard non polar33892256
Hydroxyisocaproic acid,2TBDMS,isomer #1CC(C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1676.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-866999574fff80fabad12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (2 TMS) - 70eV, Positivesplash10-02gc-9440000000-7fffd162011678b17f4a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hydroxyisocaproic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyisocaproic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-001r-7900000000-716c5f55d60f6894323b2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyisocaproic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-014s-9000000000-9c50133cdf095ca16a2e2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Hydroxyisocaproic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-00kb-9100000000-dc2c3e9343c9a8e307c32012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 10V, Positive-QTOFsplash10-0159-5900000000-01e9c211c49cea6fc5c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 20V, Positive-QTOFsplash10-0ap0-9300000000-a1f6fc289aa530d63fd82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-eb5a5d102c8e756f68342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 10V, Negative-QTOFsplash10-001i-2900000000-1a66b9767516fbd456302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 20V, Negative-QTOFsplash10-06s9-9400000000-cf71f1c20e2a87bbb2b02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-11e049c8df5b1a6268c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 10V, Negative-QTOFsplash10-0019-9700000000-a7d0b1ce1c211b31bc0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 20V, Negative-QTOFsplash10-00kr-9100000000-504826b66e199a65ef092021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 40V, Negative-QTOFsplash10-014l-9000000000-ccecb4a470c359949fec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 10V, Positive-QTOFsplash10-014i-9000000000-3019a9d0620e7da019632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 20V, Positive-QTOFsplash10-00kf-9000000000-e587d44396e53f2409fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxyisocaproic acid 40V, Positive-QTOFsplash10-0006-9000000000-457ece1d510dad645c892021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.7 uMNewborn (0-30 days old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified<0.7 uMNewborn (0-30 days old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified6.17 +/- 7.65 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14 uMNewborn (0-30 days old)FemaleMaple syrup urine disease details
Cerebrospinal Fluid (CSF)Detected and Quantified12.9 uMNewborn (0-30 days old)FemaleMaple syrup urine disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleSupragingival Plaque details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)MaleTooth Decay details
UrineDetected and Quantified1.855 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified41.5 (3.00-80.00) umol/mmol creatinineChildren (1-13 years old)BothMaple syrup urine disease (MSUD)
    • MetaGene: Metabol...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Supragingival Plaque
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Tooth Decay
  1. Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Maple syrup urine disease
  1. Shigematsu Y, Kikuchi K, Momoi T, Sudo M, Kikawa Y, Nosaka K, Kuriyama M, Haruki S, Sanada K, Hamano N, et al.: Organic acids and branched-chain amino acids in body fluids before and after multiple exchange transfusions in maple syrup urine disease. J Inherit Metab Dis. 1983;6(4):183-9. [PubMed:6422161 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022218
KNApSAcK IDNot Available
Chemspider ID75520
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hydroxyisocaproic acid
METLIN ID5714
PubChem Compound83697
PDB IDNot Available
ChEBI ID44510
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000243
Good Scents IDrw1136521
References
Synthesis ReferenceSchmidt, E. G.; Peterson, W. H.; Fred, E. B. The formation of l-leucic acid in the acetone-butyl alcohol fermentation. Journal of Biological Chemistry (1924), 61 163-75.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kuhara T, Shinka T, Inoue Y, Matsumoto M, Yoshino M, Sakaguchi Y, Matsumoto I: Studies of urinary organic acid profiles of a patient with dihydrolipoyl dehydrogenase deficiency. Clin Chim Acta. 1983 Sep 30;133(2):133-40. [PubMed:6688766 ]
  2. Liebich HM, Forst C: Hydroxycarboxylic and oxocarboxylic acids in urine: products from branched-chain amino acid degradation and from ketogenesis. J Chromatogr. 1984 Aug 10;309(2):225-42. [PubMed:6434570 ]
  3. Fontella FU, Gassen E, Pulrolnik V, Wannmacher CM, Klein AB, Wajner M, Dutra-Filho CS: Stimulation of lipid peroxidation in vitro in rat brain by the metabolites accumulating in maple syrup urine disease. Metab Brain Dis. 2002 Mar;17(1):47-54. [PubMed:11894849 ]
  4. Lang CH, Pruznak A, Navaratnarajah M, Rankine KA, Deiter G, Magne H, Offord EA, Breuille D: Chronic alpha-hydroxyisocaproic acid treatment improves muscle recovery after immobilization-induced atrophy. Am J Physiol Endocrinol Metab. 2013 Aug 1;305(3):E416-28. doi: 10.1152/ajpendo.00618.2012. Epub 2013 Jun 11. [PubMed:23757407 ]
  5. Mero AA, Ojala T, Hulmi JJ, Puurtinen R, Karila TA, Seppala T: Effects of alfa-hydroxy-isocaproic acid on body composition, DOMS and performance in athletes. J Int Soc Sports Nutr. 2010 Jan 5;7:1. doi: 10.1186/1550-2783-7-1. [PubMed:20051111 ]
  6. Sakko M, Tjaderhane L, Sorsa T, Hietala P, Jarvinen A, Bowyer P, Rautemaa R: 2-Hydroxyisocaproic acid (HICA): a new potential topical antibacterial agent. Int J Antimicrob Agents. 2012 Jun;39(6):539-40. doi: 10.1016/j.ijantimicag.2012.02.006. Epub 2012 Apr 5. [PubMed:22483561 ]