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Chemical Compound Review

ACRYLATE     prop-2-enoate

Synonyms: Propenoate, AG-D-14300, CHEBI:37080, CTK4A2106, ZINC00895281, ...
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Disease relevance of acrylic acid


Psychiatry related information on acrylic acid

  • [reaction: see text] In homogeneous H(2)O/solvent medium, the reaction rate of aromatic aldehydes and acrylonitrile or acrylate was greatly accelerated, which led to shorter reaction time, lower reaction temperature, and higher yield [6].
  • The reaction conversion for different VA concentrations was greater than 57% after 96 h at 50 degrees C. The degree of substitution (DS, defined as the amount of acrylate groups per 100 inulin fructofuranoside residues) with acrylate moieties can be controlled by varying the molar ratio of VA to inulin [7].
  • Four-hour daily exposures (excluding weekends) of young adult male rats to 110 ppm methyl acrylate in air over a period of 32 d failed to produce significant differences in body or tissue weights, blood chemistries, gross metabolic performance, and spontaneous small-intestinal motor activities when compared with a sham-exposed group [8].

High impact information on acrylic acid

  • Here we report results that, together with those in the literature, show that DMSP and its breakdown products (DMS, acrylate, dimethylsulphoxide, and methane sulphinic acid) readily scavenge hydroxyl radicals and other reactive oxygen species, and thus may serve as an antioxidant system, regulated in part by enzymatic cleavage of DMSP [9].
  • Postgrafting hydrolysis of poly(tert-butyl acrylate) arms imparts amphiphilicity to the brush [10].
  • In the real systems the 2,1-insertion of acrylate is preferred by 0.5 kcal/mol [11].
  • It was thus demonstrated that the use of hexyl acrylate rather than butyl acrylate and lauryl methacrylate gives highly efficient monoliths (more than 300 000 plates per meter) with optimized EOF [12].
  • Grafting times of 30 and 60 s for AMPS and butyl acrylate, respectively, enabled the preparation of a monolith with full shielding of the analytes from the ionizable functionalities and excellent chromatographic performance [13].

Chemical compound and disease context of acrylic acid


Biological context of acrylic acid


Anatomical context of acrylic acid

  • N,N-Dimethylaminoethyl acrylate (acryl-DMA) was synthesized as a tertiary nitrogen choline acetyltransferase (ChAc) inhibitor which would be able to penetrate biological membranes to inhibit ChAc in the nerve terminal [24].
  • Data are presented showing increased T-lymphocyte proliferation following epicutaneous application of a variety of industrially important acrylate-like chemicals which appear to correlate well with their ability to sensitize in the guinea pig [25].
  • Popliteal artery occlusion as a late complication of liquid acrylate embolization for cerebral vascular malformation [4].
  • Pancreatic duct obstruction with an acrylate glue: a new method for producing pancreatic exocrine atrophy [26].
  • This may represent a true bioactive bond between the IOL and lens epithelial cells or between the IOL and the capsular bag and may be one reason the PCO and neodymium:YAG capsulotomy rates are lower in eyes with a soft acrylate IOL [27].

Associations of acrylic acid with other chemical compounds

  • The observation that the monoquaternary alcohol results from ester hydrolysis of the monoquaternary acrylate by plasma esterase(s) explains the presence of the monoquaternary alcohol metabolite in human plasma during clinical studies with cisatracurium [28].
  • Successful statistical copolymerization of an alpha-olefin (1-octene) with an acrylate (butyl acrylate, BA) and with a methacrylate (methyl methacrylate, MMA), employing reversible addition-fragmentation chain transfer (RAFT) mediated polymerization has been accomplished[29]
  • 13C nuclear magnetic resonance studies of [1,2,3-13C]acrylamide metabolism by actively growing cultures confirmed the rapid conversion of acrylamide to acrylate but failed to detect any subsequent intermediates of acrylate degradation [22].
  • The 1CU accommodative lens was used in 20 eyes, and conventional IOLs (polymethyl methacrylate, hydrophilic or hydrophobic acrylate) were used in the control group [30].
  • [Chemical reaction: see text] Time-resolved chemically induced dynamic nuclear polarization (TR-CIDNP) and laser flash photolysis (LFP) techniques have been used to measure rate constants for coupling between acrylate-type radicals and a series of newly synthesized stable imidazolidine N-oxyl radicals [31].

Gene context of acrylic acid


Analytical, diagnostic and therapeutic context of acrylic acid

  • BACKGROUND: The pioneering drug-delivery QuaDDS stent used four to six acrylate polymer sleeves, each loaded with 800 microg of the paclitaxel derivative 7-hexanoyltaxol [35].
  • Sphingomyelinase, SMase (EC, was coupled onto amino-derivatized acrylate microspheres and was shown to retain its catalytic activity [36].
  • Mildly hydrolyzed poly(AAEE) matrices still perform extremely well in both conventional isoelectric focusing and immobilized pH gradients, techniques which are quite sensitive to traces of acrylate in the polymer coil [37].
  • CONCLUSION: Intraocular lenses of acrylate/methacrylate polymers had excellent surface quality [38].
  • Separation and characterization of functional poly(n-butyl acrylate) by critical liquid chromatography [39].


  1. Duct obstruction with an acrylate glue for treatment of chronic alcoholic pancreatitis. Little, J.M., Stephen, M., Hogg, J. Lancet (1979) [Pubmed]
  2. Occupational respiratory hypersensitivity caused by preparations containing acrylates in dental personnel. Piirilä, P., Kanerva, L., Keskinen, H., Estlander, T., Hytönen, M., Tuppurainen, M., Nordman, H. Clin. Exp. Allergy (1998) [Pubmed]
  3. Relationship between the time of sustained ethyl acrylate forestomach hyperplasia and carcinogenicity. Ghanayem, B.I., Sanchez, I.M., Maronpot, R.R., Elwell, M.R., Matthews, H.B. Environ. Health Perspect. (1993) [Pubmed]
  4. Popliteal artery occlusion as a late complication of liquid acrylate embolization for cerebral vascular malformation. Rückert, R.I., Bender, A., Rogalla, P. J. Vasc. Surg. (1999) [Pubmed]
  5. Microbial oxidation and assimilation of propylene. Cerniglia, C.E., Blevins, W.T., Perry, J.J. Appl. Environ. Microbiol. (1976) [Pubmed]
  6. Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water. Cai, J., Zhou, Z., Zhao, G., Tang, C. Org. Lett. (2002) [Pubmed]
  7. Enzymatic synthesis of inulin-containing hydrogels. Ferreira, L., Carvalho, R., Gil, M.H., Dordick, J.S. Biomacromolecules (2002) [Pubmed]
  8. LC50 values for rats acutely exposed to vapors of acrylic and methacrylic acid esters. Oberly, R., Tansy, M.F. Journal of toxicology and environmental health. (1985) [Pubmed]
  9. An antioxidant function for DMSP and DMS in marine algae. Sunda, W., Kieber, D.J., Kiene, R.P., Huntsman, S. Nature (2002) [Pubmed]
  10. Y-shaped amphiphilic brushes with switchable micellar surface structures. Julthongpiput, D., Lin, Y.H., Teng, J., Zubarev, E.R., Tsukruk, V.V. J. Am. Chem. Soc. (2003) [Pubmed]
  11. DFT studies on the copolymerization of alpha-olefins with polar monomers: ethylene-methyl acrylate copolymerization catalyzed by a Pd-based diimine catalyst. Michalak, A., Ziegler, T. J. Am. Chem. Soc. (2001) [Pubmed]
  12. Development of acrylate-based monolithic stationary phases for electrochromatographic separations. Barrioulet, M.P., Delaunay-Bertoncini, N., Demesmay, C., Rocca, J.L. Electrophoresis (2005) [Pubmed]
  13. Shielded stationary phases based on porous polymer monoliths for the capillary electrochromatography of highly basic biomolecules. Hilder, E.F., Svec, F., Fréchet, J.M. Anal. Chem. (2004) [Pubmed]
  14. Identification of acrylate, the product of the dehydration of (R)-lactate catalysed by cell-free extracts from Clostridium propionicum. Schweiger, G., Buckel, W. FEBS Lett. (1985) [Pubmed]
  15. Ethyl acrylate-induced gastric toxicity. II. Structure-toxicity relationships and mechanism. Ghanayem, B.I., Maronpot, R.R., Matthews, H.B. Toxicol. Appl. Pharmacol. (1985) [Pubmed]
  16. 13C NMR studies of bacterial fermentations. Grivet, J.P., Durand, M., Tholozan, J.L. Biochimie (1992) [Pubmed]
  17. Clostridium neopropionicum sp. nov., a strict anaerobic bacterium fermenting ethanol to propionate through acrylate pathway. Tholozan, J.L., Touzel, J.P., Samain, E., Grivet, J.P., Prensier, G., Albagnac, G. Arch. Microbiol. (1992) [Pubmed]
  18. Antitumor agents LXII: synthesis and biological evaluation of podophyllotoxin esters and related derivatives. Levy, R.K., Hall, I.H., Lee, K.H. Journal of pharmaceutical sciences. (1983) [Pubmed]
  19. C(8) substituted 1-azabicyclo[3.3.1]non-3-enes and C(8) substituted 1-azabicyclo[3.3.1]nonan-4-ones: novel muscarinic receptor antagonists. Kim, M.G., Bodor, E.T., Wang, C., Harden, T.K., Kohn, H. J. Med. Chem. (2003) [Pubmed]
  20. Reversible collapse of brushlike macromolecules in ethanol and water vapours as revealed by real-time scanning force microscopy. Gallyamov, M.O., Tartsch, B., Khokhlov, A.R., Sheiko, S.S., Börner, H.G., Matyjaszewski, K., Möller, M. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  21. Metabolic pathways of 1-butyl [3-13C]acrylate. Identification of urinary metabolites in rat using nuclear magnetic resonance and mass spectroscopy. Linhart, I., Hrabal, R., Smejkal, J., Mitera, J. Chem. Res. Toxicol. (1994) [Pubmed]
  22. Photoheterotrophic metabolism of acrylamide by a newly isolated strain of Rhodopseudomonas palustris. Wampler, D.A., Ensign, S.A. Appl. Environ. Microbiol. (2005) [Pubmed]
  23. Cluster analysis of acrylates to guide sampling for toxicity testing. Lawson, R.G., Jurs, P.C. Journal of chemical information and computer sciences. (1990) [Pubmed]
  24. Chemistry and biological activities of N,N-dimethylaminoethyl acrylate, a choline acetyltransferase inhibitor. Rowell, P.P., Chiou, C.Y. J. Med. Chem. (1976) [Pubmed]
  25. Predictive value of assessment of lymph node weight and T-lymphocyte proliferation in contact sensitivity in acrylates. Bull, J.E., Parker, D., Turk, J.L. J. Invest. Dermatol. (1985) [Pubmed]
  26. Pancreatic duct obstruction with an acrylate glue: a new method for producing pancreatic exocrine atrophy. Little, J.M., Lauer, C., Hogg, J. Surgery (1977) [Pubmed]
  27. Adhesion of fibronectin, vitronectin, laminin, and collagen type IV to intraocular lens materials in pseudophakic human autopsy eyes. Part 1: histological sections. Linnola, R.J., Werner, L., Pandey, S.K., Escobar-Gomez, M., Znoiko, S.L., Apple, D.J. Journal of cataract and refractive surgery. (2000) [Pubmed]
  28. The in vitro degradation of cisatracurium, the R, cis-R'-isomer of atracurium, in human and rat plasma. Welch, R.M., Brown, A., Ravitch, J., Dahl, R. Clin. Pharmacol. Ther. (1995) [Pubmed]
  29. Olefin copolymerization via reversible addition-fragmentation chain transfer. Venkatesh, R., Staal, B.B., Klumperman, B. Chem. Commun. (Camb.) (2004) [Pubmed]
  30. Comparison of 6-month results of implantation of the 1CU accommodative intraocular lens with conventional intraocular lenses. Küchle, M., Seitz, B., Langenbucher, A., Gusek-Schneider, G.C., Martus, P., Nguyen, N.X. Ophthalmology (2004) [Pubmed]
  31. Laser flash photolysis and CIDNP studies of steric effects on coupling rate constants of imidazolidine nitroxide with carbon-centered radicals, methyl isobutyrate-2-yl and tert-butyl propionate-2-yl. Zubenko, D., Tsentalovich, Y., Lebedeva, N., Kirilyuk, I., Roshchupkina, G., Zhurko, I., Reznikov, V., Marque, S.R., Bagryanskaya, E. J. Org. Chem. (2006) [Pubmed]
  32. Adhesion of fibronectin, vitronectin, laminin, and collagen type IV to intraocular lens materials in pseudophakic human autopsy eyes. Part 2: explanted intraocular lenses. Linnola, R.J., Werner, L., Pandey, S.K., Escobar-Gomez, M., Znoiko, S.L., Apple, D.J. Journal of cataract and refractive surgery. (2000) [Pubmed]
  33. Quantitative intra-individual monitoring of BCR-ABL transcript levels in archival bone marrow trephines of patients with chronic myeloid leukemia. Bock, O., Lehmann, U., Kreipe, H. The Journal of molecular diagnostics : JMD. (2003) [Pubmed]
  34. Homogeneous immunofluorometric assays of alpha-fetoprotein with macroporous, monosized particles and flow cytometry. Frengen, J., Schmid, R., Kierulf, B., Nustad, K., Paus, E., Berge, A., Lindmo, T. Clin. Chem. (1993) [Pubmed]
  35. High-dose 7-hexanoyltaxol-eluting stent with polymer sleeves for coronary revascularization: one-year results from the SCORE randomized trial. Grube, E., Lansky, A., Hauptmann, K.E., Di Mario, C., Di Sciascio, G., Colombo, A., Silber, S., Stumpf, J., Reifart, N., Fajadet, J., Marzocchi, A., Schofer, J., Dumas, P., Hoffmann, R., Guagliumi, G., Pitney, M., Russell, M.E. J. Am. Coll. Cardiol. (2004) [Pubmed]
  36. Observation of topical catalysis by sphingomyelinase coupled to microspheres. Nurminen, T.A., Holopainen, J.M., Zhao, H., Kinnunen, P.K. J. Am. Chem. Soc. (2002) [Pubmed]
  37. Towards new formulations for polyacrylamide matrices: N-acryloylaminoethoxyethanol, a novel monomer combining high hydrophilicity with extreme hydrolytic stability. Chiari, M., Micheletti, C., Nesi, M., Fazio, M., Righetti, P.G. Electrophoresis (1994) [Pubmed]
  38. Scanning electron microscopic analysis of foldable acrylic and hydrogel intraocular lenses. Kohnen, T., Magdowski, G., Koch, D.D. Journal of cataract and refractive surgery. (1996) [Pubmed]
  39. Separation and characterization of functional poly(n-butyl acrylate) by critical liquid chromatography. Jiang, X., Schoenmakers, P.J., Lou, X., Lima, V., van Dongen, J.L., Brokken-Zijp, J. Journal of chromatography. A. (2004) [Pubmed]
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