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hexanoic acid (YMDB01424)

Identification
YMDB IDYMDB01424
Namehexanoic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionCaproic acid, also known as hexanoate or 6:0, 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. Caproic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Caproic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (+)-S-Lysine
  • (S)-2,6-diamino-Hexanoate
  • (S)-2,6-diamino-Hexanoic acid
  • (S)-2,6-Diaminohexanoate
  • (S)-2,6-Diaminohexanoic acid
  • (S)-a,e-Diaminocaproate
  • (S)-a,e-Diaminocaproic acid
  • (S)-alpha,epsilon-diaminocaproic acid
  • (S)-Lysine
  • 2,6-Diaminohexanoate
  • 2,6-diaminohexanoic acid
  • 6-amino-Aminutrin
  • 6-amino-L-Norleucine
  • a-Lysine
  • alpha-Lysine
  • Aminutrin
  • Hexanoic acid, 2,6-diamino-, (S)-
  • K
  • L-(+)-Lysine
  • L-2,6-Diainohexanoate
  • L-2,6-Diainohexanoic acid
  • L-2,6-Diaminocaproate
  • L-2,6-Diaminocaproic acid
  • L-H2N(CH2)4CH(NH2)COOH
  • L-Lys
  • L-Lysin
  • L-Lysine
  • Lys
  • Lysine
  • Lysine acid
  • Lysine, L-
  • 1-Hexanoic acid
  • 1-Pentanecarboxylic acid
  • 6:0
  • Butylacetic acid
  • C6:0
  • Capronic acid
  • CH3-[CH2]4-COOH
  • Hexanoate
  • Hexoic acid
  • Hexylic acid
  • N-Caproic acid
  • N-Hexanoic acid
  • N-Hexoic acid
  • N-Hexylic acid
  • Pentanecarboxylic acid
  • Pentiformic acid
  • Pentylformic acid
  • 1-Hexanoate
  • 1-Pentanecarboxylate
  • Butylacetate
  • Capronate
  • Hexanoic acid
  • Hexoate
  • Hexylate
  • N-Caproate
  • N-Hexanoate
  • N-Hexoate
  • N-Hexylate
  • Pentanecarboxylate
  • Pentiformate
  • Pentylformate
  • Caproate
  • Hexanoic acid, calcium salt
  • Hexanoic acid, sodium salt, 1-(11)C-labeled
  • Hexanoic acid, nickel (2+) salt
  • Hexanoic acid, sodium salt
  • Bismuth(III)hexanoate
  • Hexanoic acid, copper (2+) salt
  • Hexanoic acid, manganese (2+) salt
  • Bi(ohex)3
  • Hexanoic acid, barium salt
  • Hexanoic acid, potassium salt
  • Hexanoic acid, rhodium (2+) salt
  • FA(6:0)
  • Calcium N-hexanoate
  • Hexanoic acid, sodium salt (1:1)
  • Sodium capronate
  • Calcium hexanoate
  • Caproic acid sodium salt
  • Sodium caproate
  • Sodium hexanoate
CAS number56-87-1
WeightAverage: 116.1583
Monoisotopic: 116.083729628
InChI KeyFUZZWVXGSFPDMH-UHFFFAOYSA-N
InChIInChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)
IUPAC Namehexanoic acid
Traditional IUPAC Namehexanoic acid
Chemical FormulaC6H12O2
SMILESCCCCCC(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
StateSolid
Charge0
Melting point224.5 °C
Experimental Properties
PropertyValueReference
Water Solubility1000 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP-3.05 [HANSCH,C ET AL. (1995)]PhysProp
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
  • extracellular
Organoleptic Properties
Flavour/OdourSource
CheeseFDB013897
FattyFDB013897
SourFDB013897
SweatFDB013897
SMPDB Pathways
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
lysine metabolismPW002420 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
hexanoic acid + Malonate → 3-Oxooctanoic acid
trans-Hex-2-enoic acid → hexanoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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
References
References:
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
  • Nookaew, I., Jewett, M. C., Meechai, A., Thammarongtham, C., Laoteng, K., Cheevadhanarak, S., Nielsen, J., Bhumiratana, S. (2008). "The genome-scale metabolic model iIN800 of Saccharomyces cerevisiae and its validation: a scaffold to query lipid metabolism." BMC Syst Biol 2:71.18687109
  • Shimazu, M., Sekito, T., Akiyama, K., Ohsumi, Y., Kakinuma, Y. (2005). "A family of basic amino acid transporters of the vacuolar membrane from Saccharomyces cerevisiae." J Biol Chem 280:4851-4857.15572352
  • Bhattacharjee, J. K. (1985). "alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes." Crit Rev Microbiol 12:131-151.3928261
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30776
HMDB IDHMDB00535
Pubchem Compound ID8892
Kegg IDC01585
ChemSpider ID8552
FOODB IDFDB013897
WikipediaHexanoic_acid
BioCyc IDNot Available