Milk Composition Database: Showing metabocard for Butyric acid (BMDB0000039)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:18:50 UTC

Update Date

2020-06-04 22:16:22 UTC

MCDB ID

BMDB0000039

Secondary Accession Numbers

BMDB00039

Metabolite Identification

Common Name

Butyric acid

Description

Butyric acid, also known as butyrate or butanoic acid, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. Butyric acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Butyric acid exists in all living species, ranging from bacteria to humans. Butyric acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Butanoic acid	ChEBI
1-Butyric acid	ChEBI
1-Propanecarboxylic acid	ChEBI
4:0	ChEBI
Acide butanoique	ChEBI
Acide butyrique	ChEBI
Butanic acid	ChEBI
Butanoate	ChEBI
Butanoic acid	ChEBI
Butoic acid	ChEBI
Buttersaeure	ChEBI
C4:0	ChEBI
CH3-[CH2]2-COOH	ChEBI
Ethylacetic acid	ChEBI
N-Butanoic acid	ChEBI
N-Butyric acid	ChEBI
Propanecarboxylic acid	ChEBI
Propylformic acid	ChEBI
Butyrate	Kegg
1-Butanoate	Generator
1-Butyrate	Generator
1-Propanecarboxylate	Generator
Butanate	Generator
Butoate	Generator
Ethylacetate	Generator
N-Butanoate	Generator
N-Butyrate	Generator
Propanecarboxylate	Generator
Propylformate	Generator
Honey robber	HMDB
Kyselina maselna	HMDB
Butyrate, magnesium	HMDB
Magnesium butyrate	HMDB
Acid, butyric	HMDB
Butyrate, sodium	HMDB
Dibutyrate, magnesium	HMDB
Magnesium dibutyrate	HMDB
Sodium butyrate	HMDB
Acid, butanoic	HMDB
Butyric acid magnesium salt	HMDB
Butyric acid, sodium salt	HMDB
FA(4:0)	HMDB
Butyric acid	KEGG

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

IUPAC Name

butanoic acid

Traditional Name

butyric acid

CAS Registry Number

107-92-6

SMILES

CCCC(O)=O

InChI Identifier

InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)

InChI Key

FERIUCNNQQJTOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

Substituents

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

straight-chain saturated fatty acid (CHEBI:30772 )
short-chain fatty acid (CHEBI:30772 )
Straight chain fatty acids (C00246 )
Saturated fatty acids (C00246 )
Straight chain fatty acids (LMFA01010004 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-5.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	60 mg/mL	Not Available
LogP	0.79	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	0.78	ALOGPS
logP	0.92	ChemAxon
logS	0.43	ALOGPS
pKa (Strongest Acidic)	4.91	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	2	ChemAxon
Refractivity	21.87 m³·mol⁻¹	ChemAxon
Polarizability	9.22 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 - EI-B (Non-derivatized)	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-032fc35b394786b5896a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-032fc35b394786b5896a	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-a7792b54320e7c859731	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9100000000-d125b331c4a6d37648a1	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 (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-7f461db56bfd8568ec71	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-9000000000-66f857fa612f773837bc	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-9000000000-e6689b2e6bf21570b934	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b2ffa7d67b2466dea94f	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-7467bf19c64fd3f51105	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-9ae015043b014b3c93d9	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-efbb0e35a19a1713240b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-9ae015043b014b3c93d9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-efbb0e35a19a1713240b	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-acb5cf0017a9ee680dd8	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-812e24462a71dccb0fec	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f9d30338ca1ee9409964	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-9d749b6b6cf2f93a8f85	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-9000000000-ee742730266fb4997777	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-88fc445cddcb726e93d8	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-9000000000-140190568a3f2b3c6f01	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1f7dab1fbd0179ef6d17	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-020fcfb652dc5a6f3036	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-3e4b1bc1291a3fbf86c9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1f57e9adb6de1499caf5	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-5338ff8a9c4e59150aba	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 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
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	31780 +/- 12485 uM	Total fatty acid	PMID: 16899705	details
Detected and Quantified	17138 +/- 2724 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	16798 +/- 2837 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: 23497994	details
Detected but not Quantified	Not Applicable		PMID: 23182357	details
Detected but not Quantified	Not Applicable		PMID: 14168161	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected but not Quantified	Not Applicable		PMID: 25108860	details
Detected but not Quantified	Not Applicable		PMID: 25087032	details
Detected and Quantified	6924 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	5675 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1135 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	2724 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1135 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	13393 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	14642 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	12485 uM	Total fatty acid	Fooddata+, T...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected and Quantified	33 +/- 5 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	37 +/- 2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	41 +/- 3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	42 +/- 4 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	44 +/- 16 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	35 +/- 17 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	29 +/- 5.72 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	52.55 +/- 6.31 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	56.75 +/- 5.46 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	21.84 +/- 3.36 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	20.16 +/- 5.04 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	46.08 +/- 0.72 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	44 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	0.9 (0.7 - 1.2) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.8 (0.6 - 1.1) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	1.2 (0.8 - 2.4) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	5.6 (2.4 - 9.6) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	37 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	34.9 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	24 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	27 +/- 1 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000039

DrugBank ID

DB03568

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

30772

References

Synthesis Reference

Shan, Zhiping. Preparation of butyric acid by hydrogenation of maleic anhydride. U.S. Pat. Appl. Publ. (2008), 6pp.

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 ]
Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
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 ]
Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
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.
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Butyric acid (BMDB0000039)

Structure for BMDB0000039 (Butyric acid)