AFCDB: 2-Methylpropanoic acid (FDB003277)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:44 UTC

Update date

2019-11-26 02:58:47 UTC

Primary ID

FDB003277

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

2-Methylpropanoic acid

Description

Present in apple, morello cherry, guava fruit, wine grapes, pineapple, crispbread, other breads, cheeses, wines, scallop and several essential oils, e.g. Roman chamomile. Acid and simple esters used as flavouring agents Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.; Isobutyric acid is an isomer of n-butyric acid; they have the same chemical formula C4H8 O2 but a different structure.; Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2-CH-COOH. It is found in the free state in carobs (Ceratonia siliqua) and in the root of Arnica dulcis, and as an ethyl ester in croton oil.

CAS Number

79-31-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	197 g/L	ALOGPS
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	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

2-methylpropanoic acid

InChI Identifier

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

InChI Key

KQNPFQTWMSNSAP-UHFFFAOYSA-N

Isomeric SMILES

CC(C)C(O)=O

Average Molecular Weight

88.1051

Monoisotopic Molecular Weight

88.0524295

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Fibroblast

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	Fp -47°	DFC
Boiling Point	Bp35 118-119°	DFC
Experimental Water Solubility	167 mg/mL at 20 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	0.94	SANGSTER (1993)
Experimental pKa	pKa 4.79 (4.85)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	d154 0.95	DFC
Refractive Index	n20D 1.3930	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-ce74765d5e4785841363	2015-03-01	View Spectrum
GC-MS	2-Methylpropanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4c977a2f823cde05363a	Spectrum
GC-MS	2-Methylpropanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	Spectrum
GC-MS	2-Methylpropanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-4c977a2f823cde05363a	Spectrum
GC-MS	2-Methylpropanoic acid, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-e8e4dc7f7f3f492ec19c	Spectrum
Predicted GC-MS	2-Methylpropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-d3c10d617448ce79a5a1	Spectrum
Predicted GC-MS	2-Methylpropanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0076-9100000000-80d574b59e1edc9d7535	Spectrum
Predicted GC-MS	2-Methylpropanoic acid, non-derivatized, 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, Positive (Annotated)	splash10-00dr-9000000000-67f1d07ca106199c76d3	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-9000000000-d5e7b5664f34e843b614	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0f79-9200000000-b18c55d6aa937214dca2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0006-9000000000-688272ebde48c146c6d7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-0006-9000000000-f1d1211c63775f704d72	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-000i-9000000000-af791f98a192fc352a65	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-d5f9008f8738e9ee1206	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-3b1bc720943b7b4b9b7b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-9000000000-af791f98a192fc352a65	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-9000000000-b9f811f5e57b3eeeb842	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-eabd518990089acf84ca	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-9ec563a3b4f50dc2aaaf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-eee01af90e21c20eb584	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4952a01442de6ea6ecfe	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-23cf7c0a08ac346b6bfe	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00rl-9000000000-7ca1184fbf16cfe0b735	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-4b3590a18d40d4d58a01	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000f-9000000000-97afb40e14188e82aee9	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-82e9a26713840d90625e	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-f007a4a376085ff3e56a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-17c0b668153fbfe212cb	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, 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

16135

Phenol-Explorer ID

Not Available

DrugBank ID

DB02531

HMDB ID

HMDB01873

CRC / DFC (Dictionary of Food Compounds) ID

CVK55-C:CVK55-C

EAFUS ID

1884

Dr. Duke ID

2-METHYL-PROPIONIC-ACID|ISOBUTYRIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00029462

HET ID

ALQ

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
irritant			DUKE
transdermal			DUKE

Enzymes

Not Available

Pathways

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
butter	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
strawberry	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

2-Methylpropanoic acid (FDB003277)

Structure for FDB003277 (2-Methylpropanoic acid)