Record Information
Version1.0
Creation date2010-04-08 22:10:58 UTC
Update date2019-11-26 03:09:15 UTC
Primary IDFDB013897
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHexanoic acid
DescriptionPresent in apple, wine grapes, butter, licorice and cheeses, e.g. blue cheeses, Cheddar cheese, Swiss cheese, feta cheese, gruyere de comte cheese, etcand is) also present in a few essential oils and fruital aromas. Secondary product of butyric acid fermentation. Flavouring ingredient Hexanoic acid (common name caproic acid), is the carboxylic acid derived from hexane with the general formula C5H11COOH. It is a colorless oily liquid with an odor reminiscent 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 gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. Hexanoic acid is found in many foods, some of which are tapioca pearl, meat bouillon, pecan nut, and oval-leaf huckleberry.
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 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
Caproic aciddb_source
FEMA 2559db_source
Pentane-1-carboxylic aciddb_source
Predicted PropertiesNot Available
Chemical FormulaC6H12O2
IUPAC name
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 62.04%; H 10.41%; O 27.55%DFC
Melting PointFp -1.5°DFC
Boiling PointBp 205°DFC
Experimental Water Solubility10.3 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP1.92HANSCH,C ET AL. (1995)
Experimental pKapKa1 4.8 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 0.93DFC
Refractive Indexn20D 1.4164DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-fe3fab44832ddab1082e2014-09-20View Spectrum
GC-MSSedanoic acid, 1 TMS, GC-MS Spectrumsplash10-00yi-3900000000-8d7942410dfae70c7c9dSpectrum
GC-MSSedanoic acid, non-derivatized, GC-MS Spectrumsplash10-03di-9000000000-f4bf00b677d90d54ba69Spectrum
GC-MSSedanoic acid, non-derivatized, GC-MS Spectrumsplash10-00yi-3900000000-8d7942410dfae70c7c9dSpectrum
Predicted GC-MSSedanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-9ee618fa3c0bd9d56748Spectrum
Predicted GC-MSSedanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-9200000000-be939d8c0455d1af93a6Spectrum
Predicted GC-MSSedanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSedanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSSedanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0900000000-ba8c7078846c268d61a62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03di-0900000000-151d5971be58b6799d2e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-02t9-1900000000-36096ef7dfebaa1939102012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03di-9000000000-f4bf00b677d90d54ba692012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f5b00c5e9d90d801ab162012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-5013166dd3b6927628122012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-5900000000-52b3e7f8b014986217722012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-e3af905666760ff490692012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f5b00c5e9d90d801ab162017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-5013166dd3b6927628122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-5900000000-52b3e7f8b014986217722017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e3af905666760ff490692017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-01b9-6900000000-763e9a8e0f15e13fae3c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0002-9000000000-df670aaa002d77689cc72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9700000000-5489131065e0934751a72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-9100000000-68f7c2883fb339578ace2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-8e5e925d60baa2f176c22016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-e877f22e42e8323f59e32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9800000000-b5d583466919719819a12016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-791ecce51d7cdde8f0f52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05tg-9000000000-b176d73a7b4fabde1ad42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9000000000-08e066ae069da04a86892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-808b7302aa744c7a1c202021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-21c5ae8d52f2e0f4cd332021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000000000-3e67c250e6a67f63a0dd2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID8552
ChEMBL IDCHEMBL14184
KEGG Compound IDC01585
Pubchem Compound ID8892
Pubchem Substance IDNot Available
ChEBI ID30776
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00535
CRC / DFC (Dictionary of Food Compounds) IDJJQ79-J:JJQ79-J
EAFUS ID1629
Dr. Duke IDCAPRONIC-ACID|CAPROIC-ACID|HEXOIC-ACID|HEXANOIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001218
HET ID6NA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID142-62-1
GoodScent IDrw1008541
SuperScent ID8892
Wikipedia IDHexanoic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acidulant64047 Any substance which is added to food to preserve or enhance its flavour and/or appearance.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
Enzymes
NameGene NameUniProt ID
Peroxisomal carnitine O-octanoyltransferaseCROTQ9UKG9
Carnitine O-palmitoyltransferase 2, mitochondrialCPT2P23786
Mitochondrial carnitine/acylcarnitine carrier proteinSLC25A20O43772
Pathways
NameSMPDB LinkKEGG Link
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052 map01040
Fatty Acid BiosynthesisSMP00456 Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cheese
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sour
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.