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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:49:31 UTC

Update Date

2023-02-21 17:22:01 UTC

HMDB ID

HMDB0032385

Secondary Accession Numbers

HMDB32385

Metabolite Identification

Common Name

Methyl methacrylate

Description

Methyl methacrylate, also known as kallocryl or bone cement, zimmer, 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 is an acrylic, aromatic, and fruity tasting compound. Methyl methacrylate has been detected, but not quantified in, blackberries (Rubus) and evergreen blackberries (Rubus laciniatus). This could make methyl methacrylate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Methyl methacrylate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(Methoxycarbonyl)-1-propene	ChEBI
2-Methyl-2-propenoic acid methyl ester	ChEBI
2-Methylacrylic acid methyl ester	ChEBI
Methacrylate de methyle	ChEBI
Methacrylic acid methyl ester	ChEBI
Methacrylsaeuremethyl ester	ChEBI
Methyl 2-methyl-2-propenoate	ChEBI
Methyl 2-methylacrylate	ChEBI
Methyl 2-methylpropenoate	ChEBI
Methyl alpha-methylacrylate	ChEBI
Methyl methylacrylate	ChEBI
Methyl-methacrylat	ChEBI
Methylmethacrylate	ChEBI
MMA	ChEBI
2-Methyl-2-propenoate methyl ester	Generator
2-Methylacrylate methyl ester	Generator
Methacrylic acid de methyle	Generator
Methacrylate methyl ester	Generator
Methyl 2-methyl-2-propenoic acid	Generator
Methyl 2-methylacrylic acid	Generator
Methyl 2-methylpropenoic acid	Generator
Methyl a-methylacrylate	Generator
Methyl a-methylacrylic acid	Generator
Methyl alpha-methylacrylic acid	Generator
Methyl α-methylacrylate	Generator
Methyl α-methylacrylic acid	Generator
Methyl methylacrylic acid	Generator
Methylmethacrylic acid	Generator
Methyl methacrylic acid	Generator
Bone cement, zimmer	MeSH
Bone cements, zimmer	MeSH
Cement, zimmer bone	MeSH
Cements, zimmer bone	MeSH
Cranioplast	MeSH
Cranioplasts	MeSH
Kallocryl	MeSH
Kallocryl a	MeSH
Kallocryls	MeSH
Metaplex	MeSH
Metaplices	MeSH
Methacrylate methyl monomer	MeSH
Methacrylate methyl monomers	MeSH
Methyl monomer, methacrylate	MeSH
Methyl monomer, methylmethacrylate	MeSH
Methyl monomers, methacrylate	MeSH
Methyl monomers, methylmethacrylate	MeSH
Methylmethacrylate methyl monomer	MeSH
Methylmethacrylate methyl monomers	MeSH
Monomer, methacrylate methyl	MeSH
Monomer, methylmethacrylate methyl	MeSH
Monomers, methacrylate methyl	MeSH
Monomers, methylmethacrylate methyl	MeSH
Simplex p	MeSH
Sintex	MeSH
Sintices	MeSH
Zimmer bone cement	MeSH
Zimmer bone cements	MeSH
Polymethyl methacrylic acid	Generator, HMDB
2-Methyl-acrylic acid methyl ester	HMDB
2-Propenoic acid, 2-methyl-, methyl ester	HMDB
Acrylic acid, 2-methyl-, methyl ester	HMDB
Methyl ester OF 2-methyl-2-propenoic acid	HMDB

Chemical Formula

C₅H₈O₂

Average Molecular Weight

100.1158

Monoisotopic Molecular Weight

100.0524295

IUPAC Name

methyl 2-methylprop-2-enoate

Traditional Name

methyl methacrylate

CAS Registry Number

80-62-6

SMILES

COC(=O)C(C)=C

InChI Identifier

InChI=1S/C5H8O2/c1-4(2)5(6)7-3/h1H2,2-3H3

InChI Key

VVQNEPGJFQJSBK-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Enoate esters

Alternative Parents

Substituents

Enoate ester
Methyl ester
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enoate ester (CHEBI:34840 )

Ontology

Cellular substructure

Extracellular (HMDB: HMDB0032385)
Cytoplasm (HMDB: HMDB0032385)

Source

Endogenous

Endogenous (HMDB: HMDB0032385)

Exogenous

Food

Food (HMDB: HMDB0032385)

Fruit

Berry

Evergreen blackberry (FooDB: FOOD00901)
Blackberry (FooDB: FOOD00906)

Exogenous (HMDB: HMDB0032385)

Process

Not Available

Role

Environmental role

Hazardous air pollutant (HMDB: HMDB0032385)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-48 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15 mg/mL at 25 °C	Not Available
LogP	1.38	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	50.5 g/L	ALOGPS
logP	1.1	ALOGPS
logP	1.31	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.42 m³·mol⁻¹	ChemAxon
Polarizability	10.47 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	121.399	31661259
DarkChem	[M-H]-	115.412	31661259
DeepCCS	[M+H]+	122.428	30932474
DeepCCS	[M-H]-	120.17	30932474
DeepCCS	[M-2H]-	156.243	30932474
DeepCCS	[M+Na]+	130.758	30932474
AllCCS	[M+H]+	125.9	32859911
AllCCS	[M+H-H2O]+	121.6	32859911
AllCCS	[M+NH4]+	129.8	32859911
AllCCS	[M+Na]+	131.0	32859911
AllCCS	[M-H]-	122.9	32859911
AllCCS	[M+Na-2H]-	126.9	32859911
AllCCS	[M+HCOO]-	131.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.34 minutes	32390414
Predicted by Siyang on May 30, 2022	11.903 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1570.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	434.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	160.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	288.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	353.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	522.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	905.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	348.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1046.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	254.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	537.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	90.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl methacrylate	COC(=O)C(C)=C	950.8	Standard polar	33892256
Methyl methacrylate	COC(=O)C(C)=C	682.2	Standard non polar	33892256
Methyl methacrylate	COC(=O)C(C)=C	677.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methyl methacrylate EI-B (Non-derivatized)	splash10-00kf-9000000000-77a257ba815641d19301	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl methacrylate EI-B (Non-derivatized)	splash10-0006-9100000000-88f058bfbf5b9ed8387e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl methacrylate EI-B (Non-derivatized)	splash10-014i-9200000000-598b3051ae73088545da	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl methacrylate EI-B (Non-derivatized)	splash10-00kf-9000000000-77a257ba815641d19301	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl methacrylate EI-B (Non-derivatized)	splash10-0006-9100000000-88f058bfbf5b9ed8387e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl methacrylate EI-B (Non-derivatized)	splash10-014i-9200000000-598b3051ae73088545da	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl methacrylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-c7de093e2ae146122642	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl methacrylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl methacrylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 10V, Positive-QTOF	splash10-0udi-0900000000-2413b648229b3e94869a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 20V, Positive-QTOF	splash10-0udl-9700000000-81822add10a210995745	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 40V, Positive-QTOF	splash10-0006-9000000000-23cdc552bf98ca51da6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 10V, Negative-QTOF	splash10-0002-9000000000-4484d04b7eb3d4bfc616	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 20V, Negative-QTOF	splash10-0002-9000000000-790ff6ef8153c5b6c655	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 40V, Negative-QTOF	splash10-0gba-9000000000-5bccf026b5962d862db1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 10V, Negative-QTOF	splash10-0002-9000000000-5289cc75fe7aae11de79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 20V, Negative-QTOF	splash10-0002-9000000000-5289cc75fe7aae11de79	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 40V, Negative-QTOF	splash10-0a4l-9000000000-55bbf42d9273089147db	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 10V, Positive-QTOF	splash10-014l-9100000000-976d084532324d224dcb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 20V, Positive-QTOF	splash10-0006-9000000000-c0c1a83d7de830926fec	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl methacrylate 40V, Positive-QTOF	splash10-0006-9000000000-0842bd2bca109064cfcd	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009805

KNApSAcK ID

Not Available

Chemspider ID

6406

KEGG Compound ID

C19504

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl_methacrylate

METLIN ID

Not Available

PubChem Compound

6658

PDB ID

Not Available

ChEBI ID

34840

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
(). EAFUS: Everything Added to Food in the United States.. .

Showing metabocard for Methyl methacrylate (HMDB0032385)

MOL for HMDB0032385 (Methyl methacrylate)

3D MOL for HMDB0032385 (Methyl methacrylate)

3D SDF for HMDB0032385 (Methyl methacrylate)

3D-SDF for HMDB0032385 (Methyl methacrylate)

PDB for HMDB0032385 (Methyl methacrylate)

3D PDB for HMDB0032385 (Methyl methacrylate)

SMILES for HMDB0032385 (Methyl methacrylate)

INCHI for HMDB0032385 (Methyl methacrylate)

Structure for HMDB0032385 (Methyl methacrylate)

3D Structure for HMDB0032385 (Methyl methacrylate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra