Record Information
Version2.0
Creation Date2012-07-30 14:55:00 -0600
Update Date2015-06-03 17:20:56 -0600
Secondary Accession Numbers
  • ECMDB21229
Identification
Name:Hexanoate (N-C6:0)
Description:Hexanoate (n-c6:0) belongs to the class of Carboxylic Acid Salts. These are ionic derivatives of carboxylic acid. (inferred from compound structure)Hexanoic acid (caproic acid), is the carboxylic acid derived from hexane with the general formula C5H11COOH. 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. 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. The salts and esters of this acid are known as hexanoates or caproates. Two other acids are named after goats: caprylic (C8) and capric (C10). Along with hexanoic acid, these total 15% in goat milk fat. Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other 2 are mobile liquids) are not only used for the formation of esters but also commonly used neat in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors. (WikiPedia)
Structure
Thumb
Synonyms:
  • Caproate
  • Caproic acid
  • Hexanoate
  • Hexanoate (N-C6:0)
  • Hexanoic acid
  • Hexanoic acid (N-C6:0)
Chemical Formula:C6H11O2
Weight:Average: 115.1503
Monoisotopic: 115.075904596
InChI Key:FUZZWVXGSFPDMH-UHFFFAOYSA-M
InChI:InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)/p-1
CAS number:Not Available
IUPAC Name:hexanoic acid
Traditional IUPAC Name:hexanoic acid
SMILES:CCCCCC([O-])=O
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
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00yi-3900000000-8d7942410dfae70c7c9dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-9000000000-f4bf00b677d90d54ba69View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00yi-3900000000-8d7942410dfae70c7c9dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-9ee618fa3c0bd9d56748View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9200000000-be939d8c0455d1af93a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-014i-0900000000-ba8c7078846c268d61a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-03di-0900000000-151d5971be58b6799d2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-02t9-1900000000-36096ef7dfebaa193910View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03di-9000000000-f4bf00b677d90d54ba69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-0900000000-f5b00c5e9d90d801ab16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-014i-0900000000-5013166dd3b692762812View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014i-5900000000-52b3e7f8b01498621772View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-e3af905666760ff49069View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-f5b00c5e9d90d801ab16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0900000000-5013166dd3b692762812View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-5900000000-52b3e7f8b01498621772View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-e3af905666760ff49069View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-01b9-6900000000-763e9a8e0f15e13fae3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-9700000000-5489131065e0934751a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-9100000000-68f7c2883fb339578aceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-8e5e925d60baa2f176c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-2900000000-e877f22e42e8323f59e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-9800000000-b5d583466919719819a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-791ecce51d7cdde8f0f5View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03di-9000000000-fe3fab44832ddab1082eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17120
HMDB IDHMDB0000535
Pubchem Compound ID4398339
Kegg IDC01585
ChemSpider ID3599616
WikipediaHexanoate
BioCyc IDHEXANOATE
EcoCyc IDHEXANOATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:
fadD
Uniprot ID:
P69451
Molecular weight:
62332
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoD
Uniprot ID:
P76458
Molecular weight:
23526
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in CoA-transferase activity
Specific function:
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA
Gene Name:
atoA
Uniprot ID:
P76459
Molecular weight:
22960
Reactions
Acyl-CoA + acetate = a fatty acid anion + acetyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. It has a low activity on medium or long chain fatty acids and is maximally active on C6 and C8 substrates
Gene Name:
fadK
Uniprot ID:
P38135
Molecular weight:
60773
Reactions
ATP + a short-chain carboxylic acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in acyl-CoA hydrolase activity
Specific function:
Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:
tesB
Uniprot ID:
P0AGG2
Molecular weight:
31966

Transporters

General function:
Lipid transport and metabolism
Specific function:
Responsible for the intake of short-chain fatty acids
Gene Name:
atoE
Uniprot ID:
P76460
Molecular weight:
47527
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368