Canmetcon
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Identification
YMDB IDYMDB01424
Namehexanoic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionHexanoic acid (caproic acid) 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. It is one of the major volatile compounds found in Napa Gamay wine and produced during fermentation.
Structure
Thumb
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 + Malonate3-Oxooctanoic acid
trans-Hex-2-enoic acidhexanoic acid
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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