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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:31 UTC
Update Date2017-12-07 03:18:51 UTC
HMDB IDHMDB0032385
Secondary Accession Numbers
  • HMDB32385
Metabolite Identification
Common NameMethyl methacrylate
DescriptionMethyl methacrylate, also known as MMA or methylmethacrylic acid, belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position. Methyl methacrylate exists as a liquid, soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, methyl methacrylate is primarily located in the cytoplasm. Methyl methacrylate can be biosynthesized from methacrylic acid. Methyl methacrylate has an acrylic, aromatic, and fruity taste.
Structure
Thumb
Synonyms
ValueSource
2-(Methoxycarbonyl)-1-propeneChEBI
2-Methyl-2-propenoic acid methyl esterChEBI
2-Methylacrylic acid methyl esterChEBI
Methacrylate de methyleChEBI
Methacrylic acid methyl esterChEBI
Methacrylsaeuremethyl esterChEBI
Methyl 2-methyl-2-propenoateChEBI
Methyl 2-methylacrylateChEBI
Methyl 2-methylpropenoateChEBI
Methyl alpha-methylacrylateChEBI
Methyl methylacrylateChEBI
Methyl-methacrylatChEBI
MethylmethacrylateChEBI
MMAChEBI
Polymethyl methacrylic acidGenerator
2-Methyl-2-propenoate methyl esterGenerator
2-Methylacrylate methyl esterGenerator
Methacrylic acid de methyleGenerator
Methacrylate methyl esterGenerator
Methyl 2-methyl-2-propenoic acidGenerator
Methyl 2-methylacrylic acidGenerator
Methyl 2-methylpropenoic acidGenerator
Methyl a-methylacrylateGenerator
Methyl a-methylacrylic acidGenerator
Methyl alpha-methylacrylic acidGenerator
Methyl α-methylacrylateGenerator
Methyl α-methylacrylic acidGenerator
Methyl methylacrylic acidGenerator
Methylmethacrylic acidGenerator
2-Methyl-acrylic acid methyl esterHMDB
2-Propenoic acid, 2-methyl-, methyl esterHMDB
Acrylic acid, 2-methyl-, methyl esterHMDB
Methyl ester OF 2-methyl-2-propenoic acidHMDB
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Namemethyl 2-methylprop-2-enoate
Traditional Namemethyl methacrylate
CAS Registry Number80-62-6
SMILES
COC(=O)C(C)=C
InChI Identifier
InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3
InChI KeyVVQNEPGJFQJSBK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as enoate esters. These are an alpha,beta-unsaturated carboxylic ester of general formula R1C(R2)=C(R3)C(=O)OR4 (R4= organyl compound) in which the ester C=O function is conjugated to a C=C double bond at the alpha,beta position.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentEnoate esters
Alternative Parents
Substituents
  • Enoate ester
  • Methyl ester
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Environmental role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-48 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility15 mg/mL at 25 °CNot Available
LogP1.38Not Available
Predicted Properties
PropertyValueSource
Water Solubility50.5 g/LALOGPS
logP1.1ALOGPS
logP1.31ChemAxon
logS-0.3ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.47 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-77a257ba815641d19301View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-88f058bfbf5b9ed8387eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9200000000-598b3051ae73088545daView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-77a257ba815641d19301View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-88f058bfbf5b9ed8387eView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-9200000000-598b3051ae73088545daView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-c7de093e2ae146122642View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-2413b648229b3e94869aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udl-9700000000-81822add10a210995745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-23cdc552bf98ca51da6fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-4484d04b7eb3d4bfc616View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9000000000-790ff6ef8153c5b6c655View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gba-9000000000-5bccf026b5962d862db1View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009805
KNApSAcK IDNot Available
Chemspider ID6406
KEGG Compound IDC19504
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPoly(methyl methacrylate)
METLIN IDNot Available
PubChem Compound6658
PDB IDNot Available
ChEBI ID34840
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Polly DW Jr, Kuklo TR, Doukas WC, Scoville C: Advanced medical care for soldiers injured in Iraq and Afghanistan. Minn Med. 2004 Nov;87(11):42-4. [PubMed:15615201 ]
  2. (). EAFUS: Everything Added to Food in the United States.. .