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Record Information
Version1.0
Creation Date2016-07-13 19:44:01 UTC
Update Date2016-09-23 18:44:51 UTC
LmdbLMDB00176
Secondary Accession NumbersNone
Metabolite Identification
Common NameCaproic acid
DescriptionIt is a colorless oily liquid smelling of cheese. It is a fatty acid found naturally in various animal fats and oils. Caproic acid is a medium chain triglycerides (MCT). MCTs are widely used for parenteral nutrition in individuals requiring supplemental nutrition and are being more widely used in foods, drugs and cosmetics; they are essentially non-toxic. It is safe for animal dietary consumption up to levels of 1g/kg. (PMID 10685018 ).
Structure
Thumb
Synonyms
ValueSource
1-Hexanoic acidChEBI
1-Pentanecarboxylic acidChEBI
6:0ChEBI
Butylacetic acidChEBI
C6:0ChEBI
Capronic acidChEBI
CH3-[CH2]4-COOHChEBI
HexanoateChEBI
Hexoic acidChEBI
Hexylic acidChEBI
N-Caproic acidChEBI
N-Hexanoic acidChEBI
N-Hexoic acidChEBI
N-Hexylic acidChEBI
Pentanecarboxylic acidChEBI
Pentiformic acidChEBI
Pentylformic acidChEBI
1-HexanoateGenerator
1-PentanecarboxylateGenerator
ButylacetateGenerator
CapronateGenerator
Hexanoic acidGenerator
HexoateGenerator
HexylateGenerator
N-CaproateGenerator
N-HexanoateGenerator
N-HexoateGenerator
N-HexylateGenerator
PentanecarboxylateGenerator
PentiformateGenerator
PentylformateGenerator
CaproateGenerator
Hexanoic acid, calcium saltMeSH, HMDB
Hexanoic acid, sodium salt, 1-(11)C-labeledMeSH, HMDB
Hexanoic acid, nickel (2+) saltMeSH, HMDB
Hexanoic acid, sodium saltMeSH, HMDB
Bismuth(III)hexanoateMeSH, HMDB
Hexanoic acid, copper (2+) saltMeSH, HMDB
Hexanoic acid, manganese (2+) saltMeSH, HMDB
Bi(ohex)3MeSH, HMDB
Hexanoic acid, barium saltMeSH, HMDB
Hexanoic acid, potassium saltMeSH, HMDB
Hexanoic acid, rhodium (2+) saltMeSH, HMDB
FA(6:0)HMDB
Calcium N-hexanoateMeSH, HMDB
Hexanoic acid, sodium salt (1:1)MeSH, HMDB
Sodium capronateMeSH, HMDB
Calcium hexanoateMeSH, HMDB
Caproic acid sodium saltMeSH, HMDB
Sodium caproateMeSH, HMDB
Sodium hexanoateMeSH, HMDB
Chemical FormulaC6H12O2
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
IUPAC Namehexanoic acid
Traditional Namehexanoic acid
CAS Registry Number142-62-1
SMILES
CCCCCC(O)=O
InChI Identifier
InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
InChI KeyFUZZWVXGSFPDMH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.88ALOGPS
logP1.81ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)5.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.07 m³·mol⁻¹ChemAxon
Polarizability13.27 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00yi-3900000000-8d7942410dfae70c7c9dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9000000000-f4bf00b677d90d54ba69Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00yi-3900000000-8d7942410dfae70c7c9dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9ee618fa3c0bd9d56748Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9200000000-be939d8c0455d1af93a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0900000000-ba8c7078846c268d61a6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03di-0900000000-151d5971be58b6799d2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-02t9-1900000000-36096ef7dfebaa193910Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03di-9000000000-f4bf00b677d90d54ba69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f5b00c5e9d90d801ab16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-5013166dd3b692762812Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-5900000000-52b3e7f8b01498621772Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-e3af905666760ff49069Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f5b00c5e9d90d801ab16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-5013166dd3b692762812Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-5900000000-52b3e7f8b01498621772Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e3af905666760ff49069Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-01b9-6900000000-763e9a8e0f15e13fae3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-df670aaa002d77689cc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9700000000-5489131065e0934751a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-9100000000-68f7c2883fb339578aceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-8e5e925d60baa2f176c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-e877f22e42e8323f59e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9800000000-b5d583466919719819a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-791ecce51d7cdde8f0f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05tg-9000000000-b176d73a7b4fabde1ad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-08e066ae069da04a8689Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-808b7302aa744c7a1c20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-21c5ae8d52f2e0f4cd33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-3e67c250e6a67f63a0ddSpectrum
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-fe3fab44832ddab1082eSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Milk
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine
    • Park, Y. W; Juáre...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • Park, Y. W; Juáre...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Lawrence K. Cream...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine
    • H. Steinshamn, R....
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableEquine details
MilkDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected and Quantified4.6 mol/100 molNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000535
FooDB IDFDB013897
Phenol Explorer IDNot Available
KNApSAcK IDC00001218
BiGG IDNot Available
BioCyc IDHEXANOATE
METLIN ID5520
PDB IDNot Available
Wikipedia LinkHexanoic_acid
Chemspider ID8552
ChEBI ID30776
PubChem Compound ID8892
Kegg Compound IDC01585
YMDB IDYMDB01424
ECMDB IDECMDB24049
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Traul KA, Driedger A, Ingle DL, Nakhasi D: Review of the toxicologic properties of medium-chain triglycerides. Food Chem Toxicol. 2000 Jan;38(1):79-98. [10685018 ]