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Chemical Compound Review

Acetanhydride     ethanoyl ethanoate

Synonyms: CCRIS 688, Ac2O, HSDB 233, LS-456, Acetic oxide, ...
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Disease relevance of acetyl acetate

  • Acetic anhydride was used to label intact oncornaviruses, which consist of a complex ribonucleo-protein core within a lipid envelope [1].
  • Dehydration of the latter with acetic anhydride and glacial acetic acid yielded a mixture of 5beta-cholest-24ene-3alpha,7alpha-diol and the corresponding delta25 compound [2].
  • Modification of the alpha-amino group of Cys1 and of the epsilon-amino group of Lys4 by acetic anhydride or fluorescamine decreased toxicity only by a factor of 2.5-2 [3].
  • In this work, we have carried out the chemical modification (with acetic anhydride) of the amino groups of cyclodextrin glycosyltransferase from Thermoanaerobacter to assess their contributions to protein function [4].
  • Lys 109, Lys 112 and Glu 1 of cytochrome c2 from Rhodospirillum rubrum G-9 are about 4-fold less reactive towards acetic anhydride when cytochrome c2 is bound to the isolated photosynthetic reaction center from the same organism [5].

Psychiatry related information on acetyl acetate


High impact information on acetyl acetate


Chemical compound and disease context of acetyl acetate


Biological context of acetyl acetate


Anatomical context of acetyl acetate


Associations of acetyl acetate with other chemical compounds


Gene context of acetyl acetate


Analytical, diagnostic and therapeutic context of acetyl acetate

  • The minor, more polar product was sensitive to nitrous acid cleavage and was converted to the major product, as judged by TLC, after treatment with acetic anhydride [34].
  • Schizophrenia-related peptide (Thr-Val-Leu) was used as a model peptide and was treated with acetic anhydride and TMS-ITC at 50 degrees C for 30 min, and the peptidylthiohydantoin derivatives were isolated by reverse-phase HPLC and characterized by FAB-MS [35].
  • Samples are treated with either the H6 or the D6 form of acetic anhydride, peptides that contain C-terminal basic amino acids are isolated by affinity chromatography on anhydrotrypsin agarose, and the isolated peptides are analyzed by mass spectrometry [36].
  • Immobilization of the reducing sugars involves a simple incubation followed by trapping of the resulting glycosylamine with acetic anhydride and recovery of the unreacted sugar by filtration [37].
  • Acetic acid and acetic anhydride treated pericardial tissue grafts were stored in 75% ethanol for 18 to 27 months before implant [38].


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  2. Preparation of 24(R)- and 24(S)-5beta-cholestane-3alpha,7alpha,24-triols and 25(R)- and 25(S)-5beta-cholestane-3alpha,7alpha,26-triols by a hydroboration procedure. Dayal, B., Batta, A.K., Shefer, S., Tint, G.S., Salen, G., Mosbach, E.H. J. Lipid Res. (1978) [Pubmed]
  3. Structure-function relationships and site of action of apamin, a neurotoxic polypeptide of bee venom with an action on the central nervous system. Vincent, J.P., Schweitz, H., Lazdunski, M. Biochemistry (1975) [Pubmed]
  4. Chemical modification of lysine side chains of cyclodextrin glycosyltransferase from Thermoanaerobacter causes a shift from cyclodextrin glycosyltransferase to alpha-amylase specificity. Alcalde, M., Plou, F.J., Andersen, C., Martín, M.T., Pedersen, S., Ballesteros, A. FEBS Lett. (1999) [Pubmed]
  5. Binding of cytochrome c2 to the isolated reaction center of Rhodospirillum rubrum involves the "backside" of cytochrome c2. Rieder, R., Wiemken, V., Bachofen, R., Bosshard, H.R. Biochem. Biophys. Res. Commun. (1985) [Pubmed]
  6. Oxidized cellulose esters: I. Preparation and characterization of oxidized cellulose acetates--a new class of biodegradable polymers. Kumar, V., Yang, D. Journal of biomaterials science. Polymer edition. (2002) [Pubmed]
  7. Assembly and deacetylation of N-acetylglucosaminyl-plasmanylinositol in normal and affected paroxysmal nocturnal hemoglobinuria cells. Hirose, S., Ravi, L., Hazra, S.V., Medof, M.E. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  8. Physical properties of chemically acetylated rat liver chromatin. Wallace, R.B., Sargent, T.D., Murphy, R.F., Bonner, J. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  9. Activation of chromatin by acetylation of histone side chains. Marushige, K. Proc. Natl. Acad. Sci. U.S.A. (1976) [Pubmed]
  10. IgG-dependent generation of platelet-activating factor by normal and low density human eosinophils. Cromwell, O., Wardlaw, A.J., Champion, A., Moqbel, R., Osei, D., Kay, A.B. J. Immunol. (1990) [Pubmed]
  11. Role of lysines in mediating interaction of modified low density lipoproteins with the scavenger receptor of human monocyte macrophages. Haberland, M.E., Olch, C.L., Folgelman, A.M. J. Biol. Chem. (1984) [Pubmed]
  12. Biological activities of new poly(N-1-adamantylmaleimide) and poly(N-1-diamantylmaleimide). Wang, J.J., Chern, Y.T. Journal of biomaterials science. Polymer edition. (1996) [Pubmed]
  13. Rational design and synthesis of novel heparan sulfate mimetic compounds as antiadhesive agents. Ishida, K., Simizu, S., Teruya, T., Wierzba, M.K., Osada, H. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  14. Modification of isoleucine-16 acetylated delta-chymotrypsin. Kumar, S., Dar, K., Ganno, S., Hatano, H. J. Biol. Chem. (1975) [Pubmed]
  15. Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: an approach to kinetic resolution of secondary alcohols of broad structural scope. Copeland, G.T., Miller, S.J. J. Am. Chem. Soc. (2001) [Pubmed]
  16. Differential labeling of the catalytic subunit of cAMP-dependent protein kinase with acetic anhydride: substrate-induced conformational changes. Buechler, J.A., Vedvick, T.A., Taylor, S.S. Biochemistry (1989) [Pubmed]
  17. Site-specific interaction of ATPase-pumped protons with photosystem II in chloroplast thylakoid membranes. Baker, G.M., Bhatnagar, D., Dilley, R.A. J. Bioenerg. Biomembr. (1982) [Pubmed]
  18. Structural requirements for the activity of an immunologically generated lipid chemotactic factor. Valone, F.H., Goetzl, E.J. Immunology (1980) [Pubmed]
  19. Activation and inhibition of 3H-strychnine binding to the glycine receptor by Eccles' anions: modulatory effects of cations. Marvizón, J.C., García Calvo, M., Vázquez, J., Mayor, F., Ruíz Gómez, A., Valdiviesco, F., Benavides, J. Mol. Pharmacol. (1986) [Pubmed]
  20. Tropomyosin lysine reactivities and relationship to coiled-coil structure. Hitchcock-DeGregori, S.E., Lewis, S.F., Chou, T.M. Biochemistry (1985) [Pubmed]
  21. Biodegradable material for bladder reconstruction. Agishi, T., Nakazono, M., Kiraly, R.J., Picha, G., Nosé, Y. J. Biomed. Mater. Res. (1975) [Pubmed]
  22. Collagen at interfaces. I. In situ collagen adsorption at solution/air and solution/polymer interfaces. Deyme, M., Baszkin, A., Proust, J.E., Perez, E., Boissonnade, M.M. J. Biomed. Mater. Res. (1986) [Pubmed]
  23. Dissociation of single-stranded DNA from nucleosomes following modification with acetic anhydride. Jordano, J., Montero, F., Palacián, E. Biochem. Biophys. Res. Commun. (1984) [Pubmed]
  24. Acetylation and cleavage of purine nucleosides. Synthesis of 6-azauridine, 5-fluorouridine, and 5-methyluridine. Beránek, J., Hrebabecký, H. Nucleic Acids Res. (1976) [Pubmed]
  25. Mass spectral characterization of an endogenous digitalislike factor from human plasma. Mathews, W.R., DuCharme, D.W., Hamlyn, J.M., Harris, D.W., Mandel, F., Clark, M.A., Ludens, J.H. Hypertension (1991) [Pubmed]
  26. Gas chromatographic-mass spectrometric determination of myo-inositol in human cerebrospinal fluid. Swahn, C.G. J. Neurochem. (1985) [Pubmed]
  27. Identification of aspartate-184 as an essential residue in the catalytic subunit of cAMP-dependent protein kinase. Buechler, J.A., Taylor, S.S. Biochemistry (1988) [Pubmed]
  28. Lipoproteins of the extravascular space: enhanced macrophage degradation of low density lipoproteins from interstitial inflammatory fluid. Raymond, T.L., Reynolds, S.A., Swanson, J.A. J. Lipid Res. (1985) [Pubmed]
  29. Involvement of lysine and arginine residues in the binding of yeast ribosomal protein YL3 to 5S RNA. Vioque, A., Hernández, F., Palacián, E. Mol. Cell. Biochem. (1987) [Pubmed]
  30. Characterisation of the conformational and quaternary structure-dependent heparin-binding region of bovine seminal plasma protein PDC-109. Calvete, J.J., Campanero-Rhodes, M.A., Raida, M., Sanz, L. FEBS Lett. (1999) [Pubmed]
  31. The oligosaccharides of human alpha 1-antitrypsin. Hercz, A. Can. J. Biochem. Cell Biol. (1984) [Pubmed]
  32. Preferential induction of cell-mediated immunity by chemically modified carcinoembryonic antigen. Staab, H.J., Anderer, F.A. Int. Arch. Allergy Appl. Immunol. (1982) [Pubmed]
  33. Chemical treatment of macrophages increases their responsiveness to migration inhibitory factor (MIF). Remold, H.G. J. Immunol. (1977) [Pubmed]
  34. Defective glycosyl phosphatidylinositol biosynthesis in extracts of three Thy-1 negative lymphoma cell mutants. Stevens, V.L., Raetz, C.R. J. Biol. Chem. (1991) [Pubmed]
  35. Carboxy-terminal sequencing: formation and hydrolysis of C-terminal peptidylthiohydantoins. Bailey, J.M., Shively, J.E. Biochemistry (1990) [Pubmed]
  36. Quantitation of neuropeptides in Cpe(fat)/Cpe(fat) mice using differential isotopic tags and mass spectrometry. Che, F.Y., Fricker, L.D. Anal. Chem. (2002) [Pubmed]
  37. Immobilization of reducing sugars as toxin binding agents. Nilsson, U.J., Heerze, L.D., Liu, Y.C., Armstrong, G.D., Palcic, M.M., Hindsgaul, O. Bioconjug. Chem. (1997) [Pubmed]
  38. Biodegradable pericardial implants for bladder augmentation: a 2.5-year study in dogs. Kambic, H., Kay, R., Chen, J.F., Matsushita, M., Harasaki, H., Zilber, S. J. Urol. (1992) [Pubmed]
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