hexanoic acid (YMDB01424)

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Identification

YMDB ID

YMDB01424

Name

hexanoic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Caproic acid, also known as hexanoate or hexylic acid, 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. Based on a literature review a significant number of articles have been published on Caproic acid.

Structure

MOL SDF PDB SMILES InChI

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 number

56-87-1

Weight

Average: 116.1583
Monoisotopic: 116.083729628

InChI Key

FUZZWVXGSFPDMH-UHFFFAOYSA-N

InChI

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

IUPAC Name

hexanoic acid

Traditional IUPAC Name

hexanoic acid

Chemical Formula

C₆H₁₂O₂

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:30776 )
straight-chain saturated fatty acid (CHEBI:30776 )
Straight chain fatty acids (C01585 )
Saturated fatty acids (C01585 )
Straight chain fatty acids (LMFA01010006 )

Physical Properties

State

Solid

Charge

Melting point

224.5 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1000 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	-3.05 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	9.72 g/L	ALOGPS
logP	1.88	ALOGPS
logP	1.81	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	5.09	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	31.07 m³·mol⁻¹	ChemAxon
Polarizability	13.27 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Cheese	FDB013897
Fatty	FDB013897
Sour	FDB013897
Sweat	FDB013897

SMPDB Pathways

Fatty acid biosynthesis	PW002458
lysine metabolism	PW002420

KEGG Pathways

Fatty acid biosynthesis

ec00061

SMPDB Reactions

hexanoic acid + Malonate → 3-Oxooctanoic acid

trans-Hex-2-enoic acid → hexanoic acid

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-f4bf00b677d90d54ba69	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-9ee618fa3c0bd9d56748	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9200000000-be939d8c0455d1af93a6	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0900000000-ba8c7078846c268d61a6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-03di-0900000000-151d5971be58b6799d2e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-02t9-1900000000-36096ef7dfebaa193910	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03di-9000000000-f4bf00b677d90d54ba69	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-5013166dd3b692762812	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-5900000000-52b3e7f8b01498621772	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-e3af905666760ff49069	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-5013166dd3b692762812	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-5900000000-52b3e7f8b01498621772	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e3af905666760ff49069	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-01b9-6900000000-763e9a8e0f15e13fae3c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-df670aaa002d77689cc7	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9700000000-5489131065e0934751a7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-9100000000-68f7c2883fb339578ace	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-8e5e925d60baa2f176c2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e877f22e42e8323f59e3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9800000000-b5d583466919719819a1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-791ecce51d7cdde8f0f5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05tg-9000000000-b176d73a7b4fabde1ad4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-08e066ae069da04a8689	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-808b7302aa744c7a1c20	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-3e67c250e6a67f63a0dd	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-fe3fab44832ddab1082e	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	30776
HMDB ID	HMDB00535
Pubchem Compound ID	8892
Kegg ID	C01585
ChemSpider ID	8552
FOODB ID	FDB013897
Wikipedia	Hexanoic_acid
BioCyc ID	Not Available

Structure for #<Compound:0xaf86d968>