butanoic acid (YMDB01392)

Identification

YMDB ID

YMDB01392

Name

butanoic acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

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

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-butanoate
1-butanoic acid
1-Butyrate
1-Butyric acid
1-Propanecarboxylate
1-Propanecarboxylic acid
acide butanoique
acide butyrique
BUA
Butanate
Butanic acid
butanoate
Butanoic acid
butoic acid
Buttersaeure
Butyrate
butyric acid
C4:0
Ethylacetate
Ethylacetic acid
Honey robber
Kyselina maselna
n-Butanoate
n-Butanoic acid
n-Butyrate
n-Butyric acid
n-C3H7COOH
Propanecarboxylate
Propanecarboxylic acid
Propylformate
Propylformic acid
4:0
CH3-[CH2]2-COOH
Butoate
Butyrate, magnesium
Magnesium butyrate
Acid, butyric
Butyrate, sodium
Dibutyrate, magnesium
Magnesium dibutyrate
Sodium butyrate
Acid, butanoic
Butyric acid magnesium salt
Butyric acid, sodium salt
FA(4:0)

CAS number

107-92-6

Weight

Average: 88.1051
Monoisotopic: 88.0524295

InChI Key

FERIUCNNQQJTOY-UHFFFAOYSA-N

InChI

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

IUPAC Name

butanoic acid

Traditional IUPAC Name

butyric acid

Chemical Formula

C₄H₈O₂

SMILES

[H]OC(=O)C([H])([H])C([H])([H])C([H])([H])[H]

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

Charge

Melting point

-5.7 °C

Experimental Properties

Property	Value	Reference
Water Solubility	60 mg/mL at 25 oC [HEMPHILL,L & SWANSON,WS (1964)]	PhysProp
LogP	0.79 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	239 g/L	ALOGPS
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

extracellular

Organoleptic Properties

Flavour/Odour	Source
Acetic	FDB031031
Butter	FDB031031
Cheese	FDB031031
Fruit	FDB031031
Rancid	FDB031031
Sharp	FDB031031
Sweat	FDB031031

SMPDB Pathways

Fatty acid biosynthesis

PW002458

KEGG Pathways

Butanoate metabolism	ec00650
Fatty acid biosynthesis	ec00061

SMPDB Reactions

butanoic acid + Malonate → 3-Oxohexanoic acid

But-2-enoic acid → butanoic 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 - EI-B (Non-derivatized)	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-032fc35b394786b5896a	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-032fc35b394786b5896a	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-a7792b54320e7c859731	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9100000000-d125b331c4a6d37648a1	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)	splash10-000i-9000000000-7f461db56bfd8568ec71	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-9000000000-66f857fa612f773837bc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-9000000000-e6689b2e6bf21570b934	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b2ffa7d67b2466dea94f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-7467bf19c64fd3f51105	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-9ae015043b014b3c93d9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-efbb0e35a19a1713240b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-9ae015043b014b3c93d9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-efbb0e35a19a1713240b	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-acb5cf0017a9ee680dd8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-812e24462a71dccb0fec	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f9d30338ca1ee9409964	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-9d749b6b6cf2f93a8f85	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-9000000000-ee742730266fb4997777	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-88fc445cddcb726e93d8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-9000000000-140190568a3f2b3c6f01	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1f7dab1fbd0179ef6d17	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-020fcfb652dc5a6f3036	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-3e4b1bc1291a3fbf86c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1f57e9adb6de1499caf5	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-5338ff8a9c4e59150aba	JSpectraViewer \| MoNA
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
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

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
Kogan, G. L., Filipp, D., Arman, I. P., Leibovich, B. A., Beliaeva, E. S. (1991). "[Cloning of segments of the Drosophila melanogaster genome using artificial chromosomes of the yeast Saccharomyces cerevisiae]." Genetika 27:1316-1323.1761208

Synthesis Reference:

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

External Links:

Resource	Link
CHEBI ID	30772
HMDB ID	HMDB00039
Pubchem Compound ID	264
Kegg ID	C00246
ChemSpider ID	259
FOODB ID	FDB031031
Wikipedia	Butyric_acid
BioCyc ID	BUTYRIC_ACID

Structure for #<Compound:0xa0f1d858>