AFCDB: Butanoic acid (FDB012062)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:58 UTC

Update date

2020-04-21 18:03:35 UTC

Primary ID

FDB012062

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Butanoic acid

Description

Found in fresh and cooked apples, banana, sour cherry, papaya, strawberries, wheat bread, cheeses, butter and coffee. Flavouring agent Butyric acid (from Greek ???????? = butter), also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Salts and esters of butyric acid are known as butyrates or butanoates. Butyric acid is found in rancid butter, parmesan cheese, vomit, and body odor and has an unpleasant smell and acrid taste, with a sweetish aftertaste (similar to ether). It can be detected by mammals with good scent detection abilities (such as dogs) at 10 ppb, whereas humans can detect it in concentrations above 10 ppm.; Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. The triglyceride of butyric acid makes up 3% to 4% of butter. When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis leading to the unpleasant odor. It is an important member of the fatty acid sub-group called short chain fatty acids. Butyric acid is a weak acid with a pKa of 4.82, similar to acetic acid which has pKa 4.76. The similar strength of these acids results from their common -CH2COOH terminal structure. Pure butyric acid is 10.9 molar.; Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC). Butyrate has diverse and apparently paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate and the intracellular milieu. In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis. Perhaps not surprisingly, results of these investigations have been mutually contradictory. The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results. In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon. (PMID: 16460475) Butyric acid is a carboxylic acid found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.; The acid is an oily colorless liquid that is easily soluble in water, ethanol, and ether, and can be separated from an aqueous phase by saturation with salts such as calcium chloride. Potassium dichromate and sulfuric acid oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide. The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold.

CAS Number

107-92-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C4H8O2

IUPAC name

butanoic acid

InChI Identifier

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

InChI Key

FERIUCNNQQJTOY-UHFFFAOYSA-N

Isomeric SMILES

CCCC(O)=O

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

Classification

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 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 54.53%; H 9.15%; O 36.32%	DFC
Melting Point	Mp -8°	DFC
Boiling Point	Bp 163.5°	DFC
Experimental Water Solubility	60 mg/mL at 25 oC	HEMPHILL,L & SWANSON,WS (1964)
Experimental logP	0.79	HANSCH,C ET AL. (1995)
Experimental pKa	pKa 4.82 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d204 0.96	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03di-9000000000-5338ff8a9c4e59150aba	2014-09-20	View Spectrum
GC-MS	Butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	Spectrum
GC-MS	Butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-032fc35b394786b5896a	Spectrum
GC-MS	Butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-6dc57ea0c6b21d3f8aa1	Spectrum
GC-MS	Butanoic acid, non-derivatized, GC-MS Spectrum	splash10-03dl-9000000000-032fc35b394786b5896a	Spectrum
Predicted GC-MS	Butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002f-9000000000-a7792b54320e7c859731	Spectrum
Predicted GC-MS	Butanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00fr-9100000000-d125b331c4a6d37648a1	Spectrum
Predicted GC-MS	Butanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Butanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-9000000000-7f461db56bfd8568ec71	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-000i-9000000000-66f857fa612f773837bc	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-000i-9000000000-e6689b2e6bf21570b934	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b2ffa7d67b2466dea94f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-7467bf19c64fd3f51105	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-9ae015043b014b3c93d9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-efbb0e35a19a1713240b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-9ae015043b014b3c93d9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-e30b3c6bd6218b9b49e1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-efbb0e35a19a1713240b	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-acb5cf0017a9ee680dd8	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-812e24462a71dccb0fec	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-f9d30338ca1ee9409964	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-9d749b6b6cf2f93a8f85	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00ku-9000000000-ee742730266fb4997777	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-88fc445cddcb726e93d8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-9000000000-140190568a3f2b3c6f01	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-1f7dab1fbd0179ef6d17	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-9000000000-020fcfb652dc5a6f3036	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-3e4b1bc1291a3fbf86c9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1f57e9adb6de1499caf5	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30772

Phenol-Explorer ID

Not Available

DrugBank ID

DB03568

HMDB ID

HMDB00039

CRC / DFC (Dictionary of Food Compounds) ID

HCX15-D:HCX15-D

EAFUS ID

438

Dr. Duke ID

1-BUTYRIC-ACID|BUTYRIC-ACID|BUTANOIC-ACID|N-BUTYRIC-ACID

BIGG ID

34376

KNApSAcK ID

C00001180

HET ID

BUA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
anti cancer	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
apoptotic			DUKE
bruchifuge	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
nematistat			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Cholinesterase	BCHE	P06276
Peroxisome proliferator-activated receptor gamma	PPARG	P37231
Tumor necrosis factor	TNF	P01375
Histone deacetylase 4	HDAC4	P56524
Histone deacetylase 9	HDAC9	Q9UKV0

Pathways

Name	SMPDB Link	KEGG Link
Butyrate Metabolism	SMP00073	map00650
Fatty Acid Biosynthesis	SMP00456	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
rancid	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
cheese	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweat	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sharp	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
acetic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
butter	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruit	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Butanoic acid (FDB012062)

Structure for FDB012062 (Butanoic acid)