Record Information
Version1.0
Creation date2010-04-08 22:06:02 UTC
Update date2019-11-26 02:59:43 UTC
Primary IDFDB003982
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSedanoic acid
DescriptionHexanoic acid, also known as hexanoate or caproic acid, is a member of the class of compounds known as medium-chain fatty acids. Medium-chain fatty acids are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Thus, hexanoic acid is considered to be a fatty acid lipid molecule. Hexanoic acid is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Hexanoic acid can be found in a number of food items such as lettuce, squashberry, yellow pond-lily, and cabbage, which makes hexanoic acid a potential biomarker for the consumption of these food products. Hexanoic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), saliva, feces, and sweat. Hexanoic acid exists in all living species, ranging from bacteria to humans. In humans, hexanoic acid is involved in a couple of metabolic pathways, which include beta oxidation of very long chain fatty acids and fatty acid biosynthesis. Hexanoic acid is also involved in a couple of metabolic disorders, which include mitochondrial beta-oxidation of short chain saturated fatty acids and short-chain 3-hydroxyacyl-coa dehydrogenase deficiency (SCHAD). Moreover, hexanoic acid is found to be associated with medium Chain Acyl-CoA Dehydrogenase Deficiency. Hexanoic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Hexanoic acid (caproic acid) is the carboxylic acid derived from hexane with the chemical formula CH 3(CH 2) 4COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that give the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. It is also one of the components of vanilla. The primary use of hexanoic acid is in the manufacture of its esters for artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols .
CAS Number142-62-1
Structure
Thumb
Synonyms
SynonymSource
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 saltHMDB
Hexanoic acid, sodium salt, 1-(11)C-labeledHMDB
Hexanoic acid, nickel (2+) saltHMDB
Hexanoic acid, sodium saltHMDB
Bismuth(III)hexanoateHMDB
Hexanoic acid, copper (2+) saltHMDB
Hexanoic acid, manganese (2+) saltHMDB
Bi(ohex)3HMDB
Hexanoic acid, barium saltHMDB
Hexanoic acid, potassium saltHMDB
Hexanoic acid, rhodium (2+) saltHMDB
FA(6:0)HMDB
Calcium N-hexanoateHMDB
Hexanoic acid, sodium salt (1:1)HMDB
Sodium capronateHMDB
Calcium hexanoateHMDB
Caproic acid sodium saltHMDB
Sodium caproateHMDB
Sodium hexanoateHMDB
Predicted Properties
PropertyValueSource
Water Solubility9.72 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H12O2
IUPAC namehexanoic acid
InChI IdentifierInChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
InChI KeyFUZZWVXGSFPDMH-UHFFFAOYSA-N
Isomeric SMILESCCCCCC(O)=O
Average Molecular Weight116.1583
Monoisotopic Molecular Weight116.083729628
Classification
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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00yi-3900000000-8d7942410dfae70c7c9dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9000000000-f4bf00b677d90d54ba69JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00yi-3900000000-8d7942410dfae70c7c9dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9ee618fa3c0bd9d56748JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9200000000-be939d8c0455d1af93a6JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0900000000-ba8c7078846c268d61a6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03di-0900000000-151d5971be58b6799d2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-02t9-1900000000-36096ef7dfebaa193910JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03di-9000000000-f4bf00b677d90d54ba69JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f5b00c5e9d90d801ab16JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-5013166dd3b692762812JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-5900000000-52b3e7f8b01498621772JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-e3af905666760ff49069JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f5b00c5e9d90d801ab16JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-5013166dd3b692762812JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-5900000000-52b3e7f8b01498621772JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e3af905666760ff49069JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-01b9-6900000000-763e9a8e0f15e13fae3cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9700000000-5489131065e0934751a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-9100000000-68f7c2883fb339578aceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-8e5e925d60baa2f176c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-e877f22e42e8323f59e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9800000000-b5d583466919719819a1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-791ecce51d7cdde8f0f5JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-fe3fab44832ddab1082eJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDSEDANOIC-ACID
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).