| Common Name |
2-Ethylacrylic acid
| Description |
2-Ethylacrylic acid is an intermediate metabolite in the conversion of R-2-methylbutyrate into 2-ethylhydracrylic acid, which is variably increased in defects of isoleucine oxidation at distal steps in the catabolic pathway (3-oxoacyl-CoA thiolase deficiency and methylmalonyl-CoA mutase deficiency) (PMID 1016232 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
2-Ethyl-2-propenoic acidChEBI
2-Ethylpropenoic acidChEBI
alpha-Methylene-butanoic acidChEBI
2-Ethyl-2-propenoateGenerator
2-EthylacrylateGenerator
2-EthylpropenoateGenerator
a-Methylene-butanoateGenerator
a-Methylene-butanoic acidGenerator
alpha-Methylene-butanoateGenerator
α-methylene-butanoateGenerator
α-methylene-butanoic acidGenerator
2-Methylene-6ci,7ci,8ci)-butyrateHMDB
2-Methylene-6ci,7ci,8ci)-butyric acidHMDB
2-MethylenebutyrateHMDB
2-Methylenebutyric acidHMDB
EthacrylateHMDB
Ethacrylic acidHMDB
Poly(2-ethylacrylic acid)MeSH
| Chemical Formlia |
C5H8O2
| Average Molecliar Weight |
100.1158
| Monoisotopic Molecliar Weight |
100.0524295
| IUPAC Name |
2-methylidenebutanoic acid
| Traditional Name |
ethacrylic acid
| CAS Registry Number |
3586-58-1
| SMILES |
CCC(=C)C(O)=O
| InChI Identifier |
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h2-3H2,1H3,(H,6,7)
| InChI Key |
WROUWQQRXUBECT-UHFFFAOYSA-N
| Chemical Taxonomy |
| Classification |
Not classified
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
| Application |
Nutrients
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Extracellliar
Membrane
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility62.6 mg/mLALOGPS
logP1.23ALOGPS
logP1.37ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.25 m3·mol-1ChemAxon
Polarizability10.26 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-0zfr-9200000000-70057d2e916fe5d099e3View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-0k96-9000000000-404d85eb01c55fd5afccView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-e2c0d6b93c24ab9497f9View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
| Name |
SMPDB Link |
KEGG Link |
Retinol MetabolismSMP00074map00830
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022716
| KNApSAcK ID |
Not Available
| Chemspider ID |
18085
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB01862
| Metagene Link |
HMDB01862
| METLIN ID |
4141
| PubChem Compound |
19166
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: MM-102 (trifluoroacetate)
References |
| Synthesis Reference |
Wang, Yan-jun; Wang, Yu-xia; Tang, Xiang-yang; Zhao, Wen-tao; Qi, Xin. Synthesis and characterization of 2-ethylacrylic acid. Shiyou Huagong (2003), 32(3), 251-253. |
| Material Safety Data Sheet (MSDS) |
Download (PDF) |
| General References |
- Mamer OA, Tjoa SS, Scriver CR, Klassen GA: Demonstration of a new mammalian isoleucine catabolic pathway yielding an Rseries of metabolites. Biochem J. 1976 Dec 15;160(3):417-26. [PubMed:1016232 ]
|
PMID: 25904744