AFCDB: 3-Methyl-2-butenoic acid (FDB000736)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:41 UTC

Update date

2019-11-26 02:55:18 UTC

Primary ID

FDB000736

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

3-Methyl-2-butenoic acid

Description

Senecioic acid, also known as 3-methylcrotonate or senecate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a significant number of articles have been published on Senecioic acid.

CAS Number

541-47-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	71.1 g/L	ALOGPS
logP	0.79	ALOGPS
logP	1.16	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	5.02	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	27.25 m³·mol⁻¹	ChemAxon
Polarizability	10.25 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

C5H8O2

IUPAC name

3-methylbut-2-enoic acid

InChI Identifier

InChI=1S/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)

InChI Key

YYPNJNDODFVZLE-UHFFFAOYSA-N

Isomeric SMILES

CC(C)=CC(O)=O

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

Classification

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Unsaturated 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

monounsaturated fatty acid (CHEBI:37127 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:37127 )
methyl-branched fatty acid (CHEBI:37127 )
short-chain fatty acid (CHEBI:37127 )
Branched fatty acids (LMFA01020097 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 59.98%; H 8.05%; O 31.96%	DFC
Melting Point	Mp 70°	DFC
Boiling Point	Bp40 114°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	3-Methyl-2-butenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0zgl-9100000000-fad992c9622a048041c8	Spectrum
Predicted GC-MS	3-Methyl-2-butenoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-9200000000-47cf47043dcc621a0e70	Spectrum
Predicted GC-MS	3-Methyl-2-butenoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	3-Methyl-2-butenoic 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)	splash10-0a4j-9000000000-92ace8b7ab3c75386bf2	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-052b-9000000000-ade4eabc58077e6357c8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0002-9000000000-b803e5f392f789d436dd	2012-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9200000000-ec7954ac0255b8c3e03c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052u-9000000000-b6913d6ebb6c47b8e582	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052u-9000000000-fa9b01b0a4c8a64e570a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-052b-9000000000-ad48b46e78b860433bb0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a5a-9000000000-b83dceb1bd0f86a7a491	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-9000000000-6b1083439ff18a99308e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-5289cc75fe7aae11de79	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000t-9000000000-40f2a490f543e0322242	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9000000000-52adce5593fe6ee79db3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-053r-9000000000-2154212e0fc35a7a1e81	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-7dd92e64eddf70e010a9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-9000000000-87790895b0e53b400be7	2021-09-24	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		Spectrum

External Links

ChemSpider ID

10468

ChEMBL ID

CHEMBL115725

KEGG Compound ID

Not Available

Pubchem Compound ID

10931

Pubchem Substance ID

Not Available

ChEBI ID

37127

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00509

CRC / DFC (Dictionary of Food Compounds) ID

BGP21-C:BGP21-C

EAFUS ID

2293

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

C00010280

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1035401

SuperScent ID

10931

Wikipedia ID

Not Available

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
alcohol	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
green	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dairy	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

3-Methyl-2-butenoic acid (FDB000736)

Structure for FDB000736 (3-Methyl-2-butenoic acid)