Milk Composition Database: Showing metabocard for Isobutyric acid (BMDB0001873)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:48:27 UTC

Update Date

2020-06-04 21:13:48 UTC

MCDB ID

BMDB0001873

Secondary Accession Numbers

BMDB01873

Metabolite Identification

Common Name

Isobutyric acid

Description

Isobutanoic acid, also known as isobutyrate or 2,2-dimethylacetate, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Isobutanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Isobutanoic acid exists in all living species, ranging from bacteria to humans. Isobutanoic acid has been found to be associated with several diseases known as nonalcoholic fatty liver disease, eosinophilic esophagitis, crohn's disease, and early preeclampsia; also isobutanoic acid has been linked to the inborn metabolic disorders including celiac disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2-Dimethylacetic acid	ChEBI
2-METHYL-propionIC ACID	ChEBI
2-Methylpropanoate	ChEBI
2-Methylpropanoic acid	ChEBI
2-Methylpropionsaeure	ChEBI
alpha-Isobutyric acid	ChEBI
alpha-Methylpropanoic acid	ChEBI
alpha-Methylpropionic acid	ChEBI
Dimethylacetic acid	ChEBI
Iso-butyric acid	ChEBI
Iso-C3H7COOH	ChEBI
Isobutanoate	ChEBI
Isobutanoic acid	ChEBI
Isobuttersaeure	ChEBI
Isobutyrate	ChEBI
Isopropylformic acid	ChEBI
2,2-Dimethylacetate	Generator
2-METHYL-propionate	Generator
a-Isobutyrate	Generator
a-Isobutyric acid	Generator
alpha-Isobutyrate	Generator
Α-isobutyrate	Generator
Α-isobutyric acid	Generator
a-Methylpropanoate	Generator
a-Methylpropanoic acid	Generator
alpha-Methylpropanoate	Generator
Α-methylpropanoate	Generator
Α-methylpropanoic acid	Generator
a-Methylpropionate	Generator
a-Methylpropionic acid	Generator
alpha-Methylpropionate	Generator
Α-methylpropionate	Generator
Α-methylpropionic acid	Generator
Dimethylacetate	Generator
Iso-butyrate	Generator
Isopropylformate	Generator
2-Methylpropionate	HMDB
2-Methylpropionic acid	HMDB
I-butyrate	HMDB
I-butyric acid	HMDB
Ammonium isobutyrate	HMDB
Isobutyric acid, ammonium salt	HMDB
Isobutyric acid, sodium salt	HMDB
2-Methpropanoic acid	HMDB
Isobutyric acid, hemiammoniate	HMDB
Sodium isobutyrate	HMDB
Isobutyric acid, calcium salt	HMDB
Isobutyric acid, nickel salt	HMDB
Isobutyric acid, potassium salt	HMDB
Isobutyric acid, sodium salt, 11C-labeled	HMDB
Isobutyric acid, sodium salt, 14C-labeled	HMDB
Isobutyric acid	KEGG

Chemical Formula

C₄H₈O₂

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

IUPAC Name

2-methylpropanoic acid

Traditional Name

isobutyric acid

CAS Registry Number

79-31-2

SMILES

CC(C)C(O)=O

InChI Identifier

InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)

InChI Key

KQNPFQTWMSNSAP-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acids

Direct Parent

Carboxylic acids

Alternative Parents

Substituents

Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain saturated fatty acid (CHEBI:16135 )
methyl-branched fatty acid (CHEBI:16135 )
short-chain fatty acid (CHEBI:16135 )
Branched fatty acids (LMFA01020071 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-46 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	167 mg/mL at 20 °C	Not Available
LogP	0.94	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	0.78	ALOGPS
logP	1.02	ChemAxon
logS	0.35	ALOGPS
pKa (Strongest Acidic)	4.87	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	1	ChemAxon
Refractivity	21.85 m³·mol⁻¹	ChemAxon
Polarizability	9.12 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)	splash10-0006-9000000000-4c977a2f823cde05363a	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-4c977a2f823cde05363a	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d3c10d617448ce79a5a1	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9100000000-80d574b59e1edc9d7535	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
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00dr-9000000000-67f1d07ca106199c76d3	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-d5e7b5664f34e843b614	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-9200000000-b18c55d6aa937214dca2	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-688272ebde48c146c6d7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-f1d1211c63775f704d72	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-af791f98a192fc352a65	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-af791f98a192fc352a65	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-b9f811f5e57b3eeeb842	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-eabd518990089acf84ca	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-9ec563a3b4f50dc2aaaf	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-eee01af90e21c20eb584	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4952a01442de6ea6ecfe	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-23cf7c0a08ac346b6bfe	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00rl-9000000000-7ca1184fbf16cfe0b735	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-97afb40e14188e82aee9	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-82e9a26713840d90625e	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f007a4a376085ff3e56a	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-17c0b668153fbfe212cb	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-ce74765d5e4785841363	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	2015-03-12	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	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	1.3 +/- 0.1 uM	PMID: 30994344	details
Detected and Quantified	1.0 +/- 0.4 uM	PMID: 30994344	details
Detected and Quantified	1.3 +/- 0.2 uM	PMID: 30994344	details
Detected and Quantified	1.2 +/- 0.4 uM	PMID: 30994344	details
Detected and Quantified	5.1 +/- 5 uM	PMID: 29642378	details
Detected and Quantified	15 +/- 15 uM	PMID: 29642378	details
Detected and Quantified	16 +/- 21 uM	PMID: 29642378	details
Detected but not Quantified	Not Applicable	PMID: 23497994	details

External Links

HMDB ID

HMDB0001873

DrugBank ID

DB02531

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isobutyric_acid

METLIN ID

106

PubChem Compound

6590

PDB ID

Not Available

ChEBI ID

16135

References

Synthesis Reference

Wang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]
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 ]
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.

Showing metabocard for Isobutyric acid (BMDB0001873)

Structure for BMDB0001873 (Isobutyric acid)