3-METHYLCROTONIC ACID (CHEM006544)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:15:03 UTC
Update Date2016-11-09 01:09:45 UTC
Accession NumberCHEM006544
Identification
Common Name3-METHYLCROTONIC ACID
ClassSmall Molecule
DescriptionA methyl-branched fatty acid that is but-2-enoic acid bearing a methyl substituent at position 3.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,3-Dimethylacrylic acidChEBI
3-Methyl-2-butenoic acidChEBI
3-Methylcrotonic acidChEBI
beta,beta-Dimethacrylic acidChEBI
beta,beta-Dimethylacrylic acidChEBI
beta-Methylcrotonic acidChEBI
SENECIC ACIDChEBI
3,3-DimethylacrylateGenerator
3-Methyl-2-butenoateGenerator
3-MethylcrotonateGenerator
b,b-DimethacrylateGenerator
b,b-Dimethacrylic acidGenerator
beta,beta-DimethacrylateGenerator
Β,β-dimethacrylateGenerator
Β,β-dimethacrylic acidGenerator
b,b-DimethylacrylateGenerator
b,b-Dimethylacrylic acidGenerator
beta,beta-DimethylacrylateGenerator
Β,β-dimethylacrylateGenerator
Β,β-dimethylacrylic acidGenerator
b-MethylcrotonateGenerator
b-Methylcrotonic acidGenerator
beta-MethylcrotonateGenerator
Β-methylcrotonateGenerator
Β-methylcrotonic acidGenerator
SENECateGenerator
SenecioateGenerator
3-Methyl-crotonateHMDB
3-Methyl-crotonic acidHMDB
3-Methylbut-2-enoateHMDB
3-Methylbut-2-enoic acidHMDB
b,b-Dimethyl acrylateHMDB
b,b-Dimethyl acrylic acidHMDB
beta,beta-Dimethyl acrylateHMDB
Β,β-dimethyl acrylateHMDB
Β,β-dimethyl acrylic acidHMDB
Senecioic acidChEBI
Chemical FormulaC5H8O2
Average Molecular Mass100.116 g/mol
Monoisotopic Mass100.052 g/mol
CAS Registry Number541-47-9
IUPAC Name3-methylbut-2-enoic acid
Traditional Nameβ,β-dimethacrylate
SMILESCC(C)=CC(O)=O
InChI IdentifierInChI=1S/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)
InChI KeyYYPNJNDODFVZLE-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-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 FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility71.1 g/LALOGPS
logP0.79ALOGPS
logP1.16ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)5.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.25 m³·mol⁻¹ChemAxon
Polarizability10.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zgl-9100000000-fad992c9622a048041c8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9200000000-47cf47043dcc621a0e70Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4j-9000000000-92ace8b7ab3c75386bf2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-052b-9000000000-ade4eabc58077e6357c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0002-9000000000-b803e5f392f789d436ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9200000000-ec7954ac0255b8c3e03cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-9000000000-b6913d6ebb6c47b8e582Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-9000000000-fa9b01b0a4c8a64e570aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-9000000000-ad48b46e78b860433bb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5a-9000000000-b83dceb1bd0f86a7a491Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-6b1083439ff18a99308eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-5289cc75fe7aae11de79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-9000000000-40f2a490f543e0322242Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-52adce5593fe6ee79db3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-053r-9000000000-2154212e0fc35a7a1e81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-7dd92e64eddf70e010a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9000000000-87790895b0e53b400be7Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000509
FooDB IDFDB000736
Phenol Explorer IDNot Available
KNApSAcK IDC00010280
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5495
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID10468
ChEBI ID37127
PubChem Compound ID10931
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17200891
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=5370660
3.
4. Iordache, Florin; Badica, Sonia; Ionescu, Alina; Badea, Florin. Synthesis of b,b-dimethylacrylic acid and its methyl and ethyl esters. Revistade Chimie (Bucharest, Romania) (1979), 30(7), 629-32.
5. Duran M, Ketting D, Wadman SK, Jakobs C, Schutgens RB, Veder HA: Organic acid excretion in a patient with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency: facts and artefacts. Clin Chim Acta. 1978 Dec 1;90(2):187-93.
6. Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406.
7. Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35.
8. Jakobs C, Bojasch M, Duran M, Ketting D, Wadman SK, Leupold D: 3-methyl-3-butenoic acid: an artefact in the urinary metabolic pattern of patients with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency. Clin Chim Acta. 1980 Sep 8;106(1):85-9.