Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Show more...Show more...Show more...Show more...Show more...

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:45:06 UTC

Update Date

2023-02-21 17:23:51 UTC

HMDB ID

HMDB0033977

Secondary Accession Numbers

HMDB33977

Metabolite Identification

Common Name

Methyl acrylate

Description

Methyl acrylate belongs to the class of organic compounds known as acrylic acid esters. These are organic compounds containing and ester acrylic acid (CH2=CHC(=O)OH). Based on a literature review a significant number of articles have been published on Methyl acrylate.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl acrylic acid	Generator
2-Propenoic acid, methyl ester	HMDB
Acrylate de methyle	HMDB
Acrylic acid methyl ester	HMDB
Acrylic acid, methyl ester	HMDB
CH2=chcooch3	HMDB
Curithane 103	HMDB
Methacrylate	HMDB
Methoxycarbonylethylene	HMDB
Methyl 2-propenoate	HMDB
Methyl acrylate, inhibited	HMDB
Methyl acrylate, monomer	HMDB
Methyl ester acrylic acid	HMDB
Methyl ester OF 2-propenoic acid	HMDB
Methyl prop-2-enoate	HMDB
Methyl propenate	HMDB
Methyl propenoate	HMDB
Methyl-acrylat	HMDB
Methylacrylaat	HMDB
Methylacrylate	HMDB
Methylester kyseliny akrylove	HMDB
Metilacrilato	HMDB

Chemical Formula

C₄H₆O₂

Average Molecular Weight

86.0892

Monoisotopic Molecular Weight

86.036779436

IUPAC Name

methyl prop-2-enoate

Traditional Name

methyl acrylate

CAS Registry Number

96-33-3

SMILES

COC(=O)C=C

InChI Identifier

InChI=1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3

InChI Key

BAPJBEWLBFYGME-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acrylic acid esters. These are organic compounds containing and ester acrylic acid (CH2=CHC(=O)OH).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Acrylic acids and derivatives

Direct Parent

Acrylic acid esters

Alternative Parents

Substituents

Acrylic acid ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid 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:82482 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033977)
Cytoplasm (HMDB: HMDB0033977)

Source

Exogenous

Exogenous (HMDB: HMDB0033977)

Food

Food (HMDB: HMDB0033977)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033977)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	76.5 °C	Not Available
Boiling Point	80.00 to 81.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	49.4 mg/mL at 25 °C	Not Available
LogP	0.80	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	64.2 g/L	ALOGPS
logP	0.67	ALOGPS
logP	0.91	ChemAxon
logS	-0.13	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	22.06 m³·mol⁻¹	ChemAxon
Polarizability	8.49 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]+	116.607	31661259
DarkChem	[M-H]-	111.103	31661259
DeepCCS	[M+H]+	120.525	30932474
DeepCCS	[M-H]-	118.084	30932474
DeepCCS	[M-2H]-	154.043	30932474
DeepCCS	[M+Na]+	128.607	30932474
AllCCS	[M+H]+	123.9	32859911
AllCCS	[M+H-H2O]+	119.4	32859911
AllCCS	[M+NH4]+	128.1	32859911
AllCCS	[M+Na]+	129.3	32859911
AllCCS	[M-H]-	124.6	32859911
AllCCS	[M+Na-2H]-	129.3	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl acrylate	COC(=O)C=C	984.3	Standard polar	33892256
Methyl acrylate	COC(=O)C=C	616.9	Standard non polar	33892256
Methyl acrylate	COC(=O)C=C	632.3	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 acrylate EI-B (Non-derivatized)	splash10-0a4i-9000000000-369a2d051131a7bcebfb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a6r-9000000000-9c4b84fc68b2e0bb2cf1	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a4i-9000000000-e696fac186759df178cb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a4i-9000000000-0fb4f98d2839ab714433	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a4i-9000000000-369a2d051131a7bcebfb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a6r-9000000000-9c4b84fc68b2e0bb2cf1	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a4i-9000000000-e696fac186759df178cb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methyl acrylate EI-B (Non-derivatized)	splash10-0a4i-9000000000-0fb4f98d2839ab714433	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl acrylate GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-0a04d802cc1d0d092145	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl acrylate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl acrylate 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 acrylate 10V, Positive-QTOF	splash10-0a4r-9000000000-26700fa0b0cc1ef9ac71	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 20V, Positive-QTOF	splash10-0a4r-9000000000-4f0b53883a3c63c0c1b0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 40V, Positive-QTOF	splash10-0a4i-9000000000-446fec7696b712731704	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 10V, Negative-QTOF	splash10-000i-9000000000-c135071c33d8587df532	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 20V, Negative-QTOF	splash10-0f79-9000000000-29f94e0224b9b8c6bb77	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 40V, Negative-QTOF	splash10-0udi-9000000000-9f73a5d9dfd71243115c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 10V, Positive-QTOF	splash10-0a4i-9000000000-dc6fd85c31b3cd18f34d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 20V, Positive-QTOF	splash10-0a4i-9000000000-34ca0a63fa24408e0c45	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 40V, Positive-QTOF	splash10-0a4i-9000000000-033b227f9b35c5d4424d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 10V, Negative-QTOF	splash10-000i-9000000000-1ae9a8c0ae40e9051036	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 20V, Negative-QTOF	splash10-0udi-9000000000-946ed9e33faea9a54041	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl acrylate 40V, Negative-QTOF	splash10-0aor-9000000000-cdaf5ee1e39a36ad6902	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

FDB012209

KNApSAcK ID

Not Available

Chemspider ID

7022

KEGG Compound ID

C19443

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methyl acrylate

METLIN ID

Not Available

PubChem Compound

7294

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1259551

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Falletta E, Ridi F, Fratini E, Vannucci C, Canton P, Bianchi S, Castelvetro V, Baglioni P: A tri-block copolymer templated synthesis of gold nanostructures. J Colloid Interface Sci. 2011 May 1;357(1):88-94. doi: 10.1016/j.jcis.2010.12.074. Epub 2011 Jan 27. [PubMed:21334634 ]
Dai X, He Y, Wei Y, Gong B: Preparation of hydrophilic polymer-grafted polystyrene beads for hydrophilic interaction chromatography via surface-initiated atom transfer radical polymerization. J Sep Sci. 2011 Nov;34(22):3115-22. doi: 10.1002/jssc.201100443. Epub 2011 Oct 4. [PubMed:21972137 ]
Haron MJ, Tiansin M, Ibrahim NA, Kassim A, Wan Yunus WM, Talebi SM: Sorption of Pb(ll) by poly(hydroxamic acid) grafted oil palm empty fruit bunch. Water Sci Technol. 2011;63(8):1788-93. [PubMed:21866782 ]
Graillot A, Bouyer D, Monge S, Robin JJ, Faur C: Removal of nickel ions from aqueous solution by low energy-consuming sorption process involving thermosensitive copolymers with phosphonic acid groups. J Hazard Mater. 2013 Jan 15;244-245:507-15. doi: 10.1016/j.jhazmat.2012.10.031. Epub 2012 Nov 6. [PubMed:23183346 ]
Yao Y, Zhao L, Yang J, Yang J: Glucose-responsive vehicles containing phenylborate ester for controlled insulin release at neutral pH. Biomacromolecules. 2012 Jun 11;13(6):1837-44. doi: 10.1021/bm3003286. Epub 2012 May 11. [PubMed:22537190 ]
Zhao H, Zheng C, Feng G, Zhao Y, Liang H, Wu H, Zhou G, Liang B, Wang Y, Xia X: Temperature-sensitive poly(N-isopropylacrylamide-co-butyl methylacrylate) nanogel as an embolic agent: distribution, durability of vascular occlusion, and inflammatory reactions in the renal artery of rabbits. AJNR Am J Neuroradiol. 2013 Jan;34(1):169-76. doi: 10.3174/ajnr.A3177. Epub 2012 Aug 2. [PubMed:22859278 ]
Mukhatyar VJ, Salmeron-Sanchez M, Rudra S, Mukhopadaya S, Barker TH, Garcia AJ, Bellamkonda RV: Role of fibronectin in topographical guidance of neurite extension on electrospun fibers. Biomaterials. 2011 Jun;32(16):3958-68. doi: 10.1016/j.biomaterials.2011.02.015. Epub 2011 Mar 5. [PubMed:21377726 ]
Zhao L, Xiang R, Ma R, Wang X, An Y, Shi L: Chiral conversion and memory of TPPS J-aggregates in complex micelles: PEG-b-PDMAEMA/TPPS. Langmuir. 2011 Sep 20;27(18):11554-9. doi: 10.1021/la201434r. Epub 2011 Aug 16. [PubMed:21846100 ]
Cook C, Liron F, Guinchard X, Roulland E: Study of the total synthesis of (-)-exiguolide. J Org Chem. 2012 Aug 17;77(16):6728-42. doi: 10.1021/jo301066p. Epub 2012 Aug 9. [PubMed:22849583 ]
Farrell RA, Kehagias N, Shaw MT, Reboud V, Zelsmann M, Holmes JD, Sotomayor Torres CM, Morris MA: Surface-directed dewetting of a block copolymer for fabricating highly uniform nanostructured microdroplets and concentric nanorings. ACS Nano. 2011 Feb 22;5(2):1073-85. doi: 10.1021/nn102720m. Epub 2011 Jan 12. [PubMed:21226483 ]
Vieira P, Banora MY, Castagnone-Sereno P, Rosso MN, Engler G, de Almeida Engler J: An immunocytochemical procedure for protein localization in various nematode life stages combined with plant tissues using methylacrylate-embedded specimens. Phytopathology. 2012 Oct;102(10):990-6. doi: 10.1094/PHYTO-02-12-0031-R. [PubMed:22690851 ]
Al-Issa SA: Synthesis of a new series of pyridine and fused pyridine derivatives. Molecules. 2012 Sep 11;17(9):10902-15. doi: 10.3390/molecules170910902. [PubMed:22968474 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl acrylate (HMDB0033977)

MOL for HMDB0033977 (Methyl acrylate)

3D MOL for HMDB0033977 (Methyl acrylate)

3D SDF for HMDB0033977 (Methyl acrylate)

3D-SDF for HMDB0033977 (Methyl acrylate)

PDB for HMDB0033977 (Methyl acrylate)

3D PDB for HMDB0033977 (Methyl acrylate)

SMILES for HMDB0033977 (Methyl acrylate)

INCHI for HMDB0033977 (Methyl acrylate)

Structure for HMDB0033977 (Methyl acrylate)

3D Structure for HMDB0033977 (Methyl acrylate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra