Milk Composition Database: Showing metabocard for Caproic acid (BMDB0000535)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:32:21 UTC

Update Date

2020-06-04 21:45:49 UTC

MCDB ID

BMDB0000535

Secondary Accession Numbers

BMDB00535
BMDB0061883
BMDB61883

Metabolite Identification

Common Name

Caproic acid

Description

Caproic acid, also known as hexanoate or caproate, 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 exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Caproic acid exists in all living species, ranging from bacteria to humans. In cattle, caproic acid is involved in the metabolic pathway called the mitochondrial Beta-oxidation OF short chain saturated fatty acids pathway. Caproic acid is a potentially toxic compound. Caproic acid has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, nonalcoholic fatty liver disease, ulcerative colitis, and crohn's disease; also caproic acid has been linked to the inborn metabolic disorders including medium chain acyl-coa dehydrogenase deficiency.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexanoic acid	ChEBI
1-Pentanecarboxylic acid	ChEBI
6:0	ChEBI
Butylacetic acid	ChEBI
C6:0	ChEBI
Capronic acid	ChEBI
CH3-[CH2]4-COOH	ChEBI
Hexanoate	ChEBI
Hexoic acid	ChEBI
Hexylic acid	ChEBI
N-Caproic acid	ChEBI
N-Hexanoic acid	ChEBI
N-Hexoic acid	ChEBI
N-Hexylic acid	ChEBI
Pentanecarboxylic acid	ChEBI
Pentiformic acid	ChEBI
Pentylformic acid	ChEBI
1-Hexanoate	Generator
1-Pentanecarboxylate	Generator
Butylacetate	Generator
Capronate	Generator
Hexanoic acid	Generator
Hexoate	Generator
Hexylate	Generator
N-Caproate	Generator
N-Hexanoate	Generator
N-Hexoate	Generator
N-Hexylate	Generator
Pentanecarboxylate	Generator
Pentiformate	Generator
Pentylformate	Generator
Caproate	Generator
Hexanoic acid, calcium salt	MeSH, HMDB
Hexanoic acid, sodium salt, 1-(11)C-labeled	MeSH, HMDB
Hexanoic acid, nickel (2+) salt	MeSH, HMDB
Hexanoic acid, sodium salt	MeSH, HMDB
Bismuth(III)hexanoate	MeSH, HMDB
Hexanoic acid, copper (2+) salt	MeSH, HMDB
Hexanoic acid, manganese (2+) salt	MeSH, HMDB
Bi(ohex)3	MeSH, HMDB
Hexanoic acid, barium salt	MeSH, HMDB
Hexanoic acid, potassium salt	MeSH, HMDB
Hexanoic acid, rhodium (2+) salt	MeSH, HMDB
FA(6:0)	HMDB
Calcium N-hexanoate	MeSH, HMDB
Hexanoic acid, sodium salt (1:1)	MeSH, HMDB
Sodium capronate	MeSH, HMDB
Calcium hexanoate	MeSH, HMDB
Caproic acid sodium salt	MeSH, HMDB
Sodium caproate	MeSH, HMDB
Sodium hexanoate	MeSH, HMDB

Chemical Formula

C₆H₁₂O₂

Average Molecular Weight

116.1583

Monoisotopic Molecular Weight

116.083729628

IUPAC Name

hexanoic acid

Traditional Name

hexanoic acid

CAS Registry Number

142-62-1

SMILES

CCCCCC(O)=O

InChI Identifier

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

InChI Key

FUZZWVXGSFPDMH-UHFFFAOYSA-N

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

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	10.3 mg/mL	Not Available
LogP	1.92	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
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	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03di-9000000000-f4bf00b677d90d54ba69	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00yi-3900000000-8d7942410dfae70c7c9d	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-9ee618fa3c0bd9d56748	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9200000000-be939d8c0455d1af93a6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-014i-0900000000-ba8c7078846c268d61a6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-03di-0900000000-151d5971be58b6799d2e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-02t9-1900000000-36096ef7dfebaa193910	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03di-9000000000-f4bf00b677d90d54ba69	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-014i-0900000000-5013166dd3b692762812	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-014i-5900000000-52b3e7f8b01498621772	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-e3af905666760ff49069	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-f5b00c5e9d90d801ab16	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-5013166dd3b692762812	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-5900000000-52b3e7f8b01498621772	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-e3af905666760ff49069	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-01b9-6900000000-763e9a8e0f15e13fae3c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0002-9000000000-df670aaa002d77689cc7	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-9700000000-5489131065e0934751a7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-9100000000-68f7c2883fb339578ace	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-8e5e925d60baa2f176c2	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-2900000000-e877f22e42e8323f59e3	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01b9-9800000000-b5d583466919719819a1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-791ecce51d7cdde8f0f5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05tg-9000000000-b176d73a7b4fabde1ad4	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-9000000000-08e066ae069da04a8689	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-808b7302aa744c7a1c20	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-21c5ae8d52f2e0f4cd33	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-9000000000-3e67c250e6a67f63a0dd	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-fe3fab44832ddab1082e	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	11192 +/- 5165 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected and Quantified	7662 +/- 1463 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	7404 +/- 1291 uM	Total fatty acid	M. Ferrand et al....	details
Detected but not Quantified	Not Applicable		PMID: 1779072	details
Detected but not Quantified	Not Applicable		PMID: 14168161	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected and Quantified	3616 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	3444 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	602 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1894 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	602 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	6543 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	7490 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	6887 uM	Total fatty acid	Fooddata+, T...	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected and Quantified	20.39 +/- 1.9 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	19.11 +/- 2.55 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	7.65 +/- 1.91 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	8.92 +/- 1.27 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	17.48 +/- 0.03 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	25 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	0.7 (0.3 - 14) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.8 (0.3 - 15) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	1.0 (0.4 - 18) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	6.0 (2.2 - 8.9) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	12.8 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	14.3 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	10.5 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	11.8 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000535

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hexanoic_acid

METLIN ID

5520

PubChem Compound

8892

PDB ID

Not Available

ChEBI ID

30776

References

Synthesis Reference

Gao, Fei; Wu, Zongwei. Process for preparation of hexanoic acid by oxidation of 2-octanol with nitric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
Antunes-Fernandes EC, van Gastelen S, Dijkstra J, Hettinga KA, Vervoort J: Milk metabolome relates enteric methane emission to milk synthesis and energy metabolism pathways. J Dairy Sci. 2016 Aug;99(8):6251-6262. doi: 10.3168/jds.2015-10248. Epub 2016 May 26. [PubMed:27236769 ]
van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Caproic acid (BMDB0000535)

Structure for BMDB0000535 (Caproic acid)