Methacrylic acid
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MedKoo CAT#: 558650

CAS#: 79-41-4

Description: Methacrylic acid is an organic compound that prepares polymers. It is a precursor for the preparation of methyl methacrylate, N-substituted methacryl amides, methacrylamide, N-substituted methacryl amides and acryloyl chloride.

Chemical Structure

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Methacrylic acid
CAS# 79-41-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 558650
Name: Methacrylic acid
CAS#: 79-41-4
Chemical Formula: C4H6O2
Exact Mass: 86.04
Molecular Weight: 86.090
Elemental Analysis: C, 55.81; H, 7.03; O, 37.17

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Synonym: Methacrylic acid; Kyselina methakrylova; Acide methacrylique;

IUPAC/Chemical Name: 2-Propenoic acid, 2-methyl-

InChi Key: CERQOIWHTDAKMF-UHFFFAOYSA-N

InChi Code: InChI=1S/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)

SMILES Code: C=C(C)C(O)=O

Appearance: Liquid (stabilized with MEHQ)

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Methacrylic acid is an organic compound that prepares polymers.
In vitro activity: The effects of PMAA-AgNPs-fluconazole (poly(methacrylic acid)-silver nanoparticles)combination was analysed by checkerboard methodology. PMAA-AgNPs showed a dose-dependent decrease in viability for cells tested, with 50% cytotoxic concentration (CC50 ) values of 6.5, 4.9 and 6.8 μg ml-1 for macrophages, fibroblasts and Vero cells, respectively. Reference: J Appl Microbiol. 2022 Jun;132(6):4300-4309. https://pubmed.ncbi.nlm.nih.gov/35338561/
In vivo activity: This study shows a new role for MAA (methacrylic acid)-based biomaterials in promoting terminal axon nerve growth. MAA was also able to increase the expression of key neuronal markers and growth factors in a peripheral neuropathy model, the diabetic db/db mouse, suggesting that MAA-based biomaterials may be relevant to treatment of peripheral neuropathy. Reference: Biomaterials. 2022 Oct;289:121764. https://pubmed.ncbi.nlm.nih.gov/36067565/

Preparing Stock Solutions

The following data is based on the product molecular weight 86.09 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Falcão CMC, Andrade A, Holanda VN, de Figueiredo RCBQ, Ximenes EA, Gomes ASL. Activity of poly(methacrylic acid)-silver nanoparticles on fluconazole-resistant Candida albicans strains: Synergistic and cytotoxic effects. J Appl Microbiol. 2022 Jun;132(6):4300-4309. doi: 10.1111/jam.15542. Epub 2022 Mar 31. PMID: 35338561. 2. Xu W, Wu Y, Lu H, Zhu Y, Ye J, Yang W. Sustained delivery of vascular endothelial growth factor mediated by bioactive methacrylic anhydride hydrogel accelerates peripheral nerve regeneration after crush injury. Neural Regen Res. 2022 Sep;17(9):2064-2071. doi: 10.4103/1673-5374.335166. PMID: 35142698; PMCID: PMC8848599. 3. Androschuk AM, Tam TH, Mahou R, Lo C, Salter MW, Sefton MV. Methacrylic acid-based biomaterials promote peripheral innervation in the subcutaneous space of mice. Biomaterials. 2022 Oct;289:121764. doi: 10.1016/j.biomaterials.2022.121764. Epub 2022 Aug 26. PMID: 36067565. 4. Zhukova OV, Arkhipova EV, Kovaleva TF, Zykova DA, Dubovskaya NA. Effect of Poly(methacrylic acid) on the Cytokine Level in an In Vivo Tumor Model. Molecules. 2022 Jul 18;27(14):4572. doi: 10.3390/molecules27144572. PMID: 35889444; PMCID: PMC9316288.
In vitro protocol: 1. Falcão CMC, Andrade A, Holanda VN, de Figueiredo RCBQ, Ximenes EA, Gomes ASL. Activity of poly(methacrylic acid)-silver nanoparticles on fluconazole-resistant Candida albicans strains: Synergistic and cytotoxic effects. J Appl Microbiol. 2022 Jun;132(6):4300-4309. doi: 10.1111/jam.15542. Epub 2022 Mar 31. PMID: 35338561. 2. Xu W, Wu Y, Lu H, Zhu Y, Ye J, Yang W. Sustained delivery of vascular endothelial growth factor mediated by bioactive methacrylic anhydride hydrogel accelerates peripheral nerve regeneration after crush injury. Neural Regen Res. 2022 Sep;17(9):2064-2071. doi: 10.4103/1673-5374.335166. PMID: 35142698; PMCID: PMC8848599.
In vivo protocol: 1. Androschuk AM, Tam TH, Mahou R, Lo C, Salter MW, Sefton MV. Methacrylic acid-based biomaterials promote peripheral innervation in the subcutaneous space of mice. Biomaterials. 2022 Oct;289:121764. doi: 10.1016/j.biomaterials.2022.121764. Epub 2022 Aug 26. PMID: 36067565. 2. Zhukova OV, Arkhipova EV, Kovaleva TF, Zykova DA, Dubovskaya NA. Effect of Poly(methacrylic acid) on the Cytokine Level in an In Vivo Tumor Model. Molecules. 2022 Jul 18;27(14):4572. doi: 10.3390/molecules27144572. PMID: 35889444; PMCID: PMC9316288.

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1: Le Nôtre J, Witte-van Dijk SC, van Haveren J, Scott EL, Sanders JP. Synthesis of bio-based methacrylic acid by decarboxylation of itaconic acid and citric acid catalyzed by solid transition-metal catalysts. ChemSusChem. 2014 Sep;7(9):2712-20. doi: 10.1002/cssc.201402117. Epub 2014 Jul 13. PubMed PMID: 25045161.

2: Zhang AQ, Yang YM, Li LP, Zhai GM, Jia HS, Liu XG, Xu BS. Syntheses and luminescent properties of a copolymer of terbium-p-aminobenzoic acid-methacrylic acid and styrene. Luminescence. 2015 Nov;30(7):1020-5. doi: 10.1002/bio.2853. Epub 2015 Feb 24. PubMed PMID: 25712787.

3: Marshall WG, Urquhart AJ, Oswald ID. Investigation of Methacrylic Acid at High Pressure Using Neutron Diffraction. J Phys Chem B. 2015 Sep 10;119(36):12147-54. doi: 10.1021/acs.jpcb.5b07106. Epub 2015 Aug 26. PubMed PMID: 26289930.

4: Hamori M, Shimizu Y, Yoshida K, Fukushima K, Sugioka N, Nishimura A, Naruhashi K, Shibata N. Preparation of methacrylic acid copolymer S nano-fibers using a solvent-based electrospinning method and their application in pharmaceutical formulations. Chem Pharm Bull (Tokyo). 2015;63(2):81-7. doi: 10.1248/cpb.c14-00563. PubMed PMID: 25748778.

5: Jun-Bo L, Yang S, Shan-Shan T, Rui-Fa J. Theoretical and experimental research on the self-assembled system of molecularly imprinted polymers formed by salbutamol and methacrylic acid. J Sep Sci. 2015 Mar;38(6):1065-71. doi: 10.1002/jssc.201401309. Epub 2015 Feb 4. PubMed PMID: 25580930.

6: Parisi OI, Puoci F, Iemma F, Curcio M, Cirillo G, Spizzirri UG, Picci N. Flavonoids preservation and release by methacrylic acid-grafted (N-vinyl-pyrrolidone). Pharm Dev Technol. 2013 Sep-Oct;18(5):1058-65. doi: 10.3109/10837450.2012.680595. Epub 2012 Apr 23. PubMed PMID: 22524466.

7: Clausen DN, Pires IM, Tarley CR. Improved selective cholesterol adsorption by molecularly imprinted poly(methacrylic acid)/silica (PMAA-SiO₂) hybrid material synthesized with different molar ratios. Mater Sci Eng C Mater Biol Appl. 2014 Nov;44:99-108. doi: 10.1016/j.msec.2014.08.008. Epub 2014 Aug 7. PubMed PMID: 25280685.

8: Huang Z, Qiu R, Liu T, Huang Y, Zhu Z, Wang L. Determination of methacrylic acid in food simulants by pyrolytic butylation-gas chromatography. J Chromatogr A. 2016 Jul 8;1454:101-6. doi: 10.1016/j.chroma.2016.05.068. Epub 2016 May 21. PubMed PMID: 27262371.

9: Taniguchi M, Nakashima K, Okamoto Y, Gong X, Kuroda C, Tori M. Constituents of Ligularia brassicoides Collected in China: A New Diels-Alder Adduct of Eremophilan-10β-ol and Methacrylic Acid. Nat Prod Commun. 2015 Jun;10(6):827-30. PubMed PMID: 26197491.

10: Yan H, Wang M, Han Y, Qiao F, Row KH. Hybrid molecularly imprinted polymers synthesized with 3-aminopropyltriethoxysilane-methacrylic acid monomer for miniaturized solid-phase extraction: A new and economical sample preparation strategy for determination of acyclovir in urine. J Chromatogr A. 2014 Jun 13;1346:16-24. doi: 10.1016/j.chroma.2014.04.045. Epub 2014 Apr 21. PubMed PMID: 24811152.

11: Lisovsky A, Zhang DK, Sefton MV. Effect of methacrylic acid beads on the sonic hedgehog signaling pathway and macrophage polarization in a subcutaneous injection mouse model. Biomaterials. 2016 Aug;98:203-14. doi: 10.1016/j.biomaterials.2016.04.033. Epub 2016 May 4. PubMed PMID: 27264502.

12: Yuan H, Zhang L, Zhang Y. Preparation of high efficiency and low carry-over immobilized enzymatic reactor with methacrylic acid-silica hybrid monolith as matrix for on-line protein digestion. J Chromatogr A. 2014 Dec 5;1371:48-57. doi: 10.1016/j.chroma.2014.10.067. Epub 2014 Oct 30. PubMed PMID: 25456586.

13: Kurata S, Morishita K, Kawase T, Umemoto K. Cytotoxic effects of acrylic acid, methacrylic acid, their corresponding saturated carboxylic acids, HEMA, and hydroquinone on fibroblasts derived from human pulp. Dent Mater J. 2012;31(2):219-25. Epub 2012 Mar 23. PubMed PMID: 22447055.

14: Akkaya A, Pazarlioglu N. Thrombin immobilization to methacrylic acid grafted poly(3-hydroxybutyrate) and its in vitro application. Prep Biochem Biotechnol. 2013;43(1):48-59. doi: 10.1080/10826068.2012.693900. PubMed PMID: 23215654.

15: Dragan ES, Cocarta AI, Gierszewska M. Designing novel macroporous composite hydrogels based on methacrylic acid copolymers and chitosan and in vitro assessment of lysozyme controlled delivery. Colloids Surf B Biointerfaces. 2016 Mar 1;139:33-41. doi: 10.1016/j.colsurfb.2015.12.011. Epub 2015 Dec 8. PubMed PMID: 26700231.

16: Tao JX, Song XL, Yao YY, Chen FS, Su JS. [Self-cleaning and antimicrobial properties of methacrylic acid coupled TiO(2)/PMMA denture base resin]. Shanghai Kou Qiang Yi Xue. 2012 Apr;21(2):130-3. Chinese. PubMed PMID: 22610318.

17: Liu Z, Ge M, Wang W. Uptake of isoprene, methacrylic acid and methyl methacrylate into aqueous solutions of sulfuric acid and hydrogen peroxide. J Environ Sci (China). 2012;24(11):1947-53. PubMed PMID: 23534228.

18: Greim H, Ahlers J, Bias R, Broecker B, Hollander H, Gelbke HP, Jacobi S, Klimisch HJ, Mangelsdorf I, Mayr W, et al. Assessment of structurally related chemicals: toxicity and ecotoxicity of acrylic acid and acrylic acid alkyl esters (acrylates), methacrylic acid and methacrylic acid alkyl esters (methacrylates). Chemosphere. 1995 Jul;31(2):2637-59. Review. PubMed PMID: 7663949.

19: Horiguchi D, Ohyama K, Masunaga T, Fujita Y, Ali MF, Kishikawa N, Kuroda N. Characterization and comparison of methacrylic acid with 2-acrylamido-2-methyl-1-propanesulfonic acid in the preparation of monolithic column for capillary electrochromatography. J Chromatogr Sci. 2013 May-Jun;51(5):425-9. doi: 10.1093/chromsci/bms158. Epub 2012 Oct 5. PubMed PMID: 23042836.

20: Weeks A, Subbaraman LN, Jones L, Sheardown H. The Competing Effects of Hyaluronic and Methacrylic Acid in Model Contact Lenses. J Biomater Sci Polym Ed. 2012;23(8):1021-38. doi: 10.1163/092050611X569060. PubMed PMID: 21477462.