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Chemical Compound Review

Acetaal     1,1-diethoxyethane

Synonyms: Acetale, Acetal, polyacetal, Diethylacetal, Diaethylacetal, ...
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Disease relevance of Acetol

  • These studies imply that at least part of the insulin resistance indigenous to fasting and diabetic ketosis may be attributed to the metabolic influence of acetone and/or acetol in body fluids.(ABSTRACT TRUNCATED AT 250 WORDS)[1]
  • A new integrative model of diabetic complications is proposed that combines the aldose reductase/polyol pathway theory and the nonenzymatic glycation theory except that emphasis is placed both on methylglyoxal/acetol metabolism and on glucose metabolism [2].
  • Oligo(U) derivatives with [14C]-4-(N-2-chloroethyl-N-methylamino)benzaldehyde attached to 3'-end cis-diol group via acetal bond, p(Up)n-1UCHRCl as well as with [14C]-4-(N-2-chloroethyl-N-methylamino)benzylamine attached to 5'-phosphate via amide bond, ClRCH2NHpU(pU)6 were used to modify 70S E. coli ribosomes near mRNA binding centre [3].
  • Three of the major phospholipids of the cell membrane of Clostridium butyricum are phosphatidylethanolamine (PE), plasmenylethanolamine (PlaE), and the glycerol acetal of plasmenylethanolamine [4].
  • Hydrophobic acetal and ketal derivatives of mannopeptimycin-alpha and desmethylhexahydromannopeptimycin-alpha: semisynthetic glycopeptides with potent activity against Gram-positive bacteria [5].

Psychiatry related information on Acetol

  • In a modified procedure, where acetic anhydride is used as the reaction solvent, the simultaneous cleavage of the benzylidene acetal and the peracetylation of the substrates is obtained in quantitative yields and very short reaction times [6].

High impact information on Acetol

  • Like bryostatin, acetal 7c exhibited significant levels of in vitro growth inhibitory activity (1.8-170 ng/ml) against several human cancer cell lines, providing an important step toward the development of simplified, synthetically accessible analogs of the bryostatins [7].
  • Fisher 344 rats were used to test wound healing responses in the orbiting Space Shuttle Endeavour by preflight implantation of polyvinyl acetal sponge disks in which pellets were placed to release either platelet-derived growth factor (PDGF-BB), basic fibroblast growth factor (bFGF), or placebo [8].
  • A diacetoxy acetal derivative of santonin (DAAS) was found to induce significant HL-60 cell differentiation in a dose-dependent manner, whereas santonin in its original form did not [9].
  • Chemical Modification of Santonin into a Diacetoxy Acetal Form Confers the Ability to Induce Differentiation of Human Promyelocytic Leukemia Cells via the Down-regulation of NF-{kappa}B DNA Binding Activity [9].
  • Isozyme 3a was the most active enzyme in the hydroxylation of acetol, but isozymes 2, 3b, and 4 also were able to catalyze the reaction [10].

Chemical compound and disease context of Acetol


Biological context of Acetol

  • The rate of release was strongly correlated with the rate of acetal hydrolysis and was therefore controlled by the chemical structure of the copolymer [16].
  • Electron transfer initiated cyclizations: cyclic acetal synthesis through carbon-carbon sigma-bond activation [17].
  • The synthesis highlights the use of several new methods, including camphor auxiliary-directed asymmetric alkylation and the enantioselective preparation of acyclic mixed acetals bearing chirality at the acetal center, and the highly efficient connection of the two major precursors via a ketene-trapping/intramolecular [4 + 2] cycloaddition strategy [18].
  • With a 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetal protected thioglycoside, excellent beta-selectivity was obtained in glycosylation reactions, and subsequent treatment with tributyltin hydride and azoisobutyronitrile brought about clean fragmentation to the 6-deoxy-glycero-beta-D-manno-heptopyranosides [19].
  • The 3-mercapto analogue was obtained by removal of the acetal groups of the acetylthio analogue, followed by acetylation and purification of the peracetate, and subsequent O-demethylation and deacetylation [20].

Anatomical context of Acetol


Associations of Acetol with other chemical compounds

  • Microsomes isolated from the liver of animals maintained on drinking water supplemented with 1% acetone contained two previously unreported enzymatic activities, acetone monooxygenase which converts acetone to acetol and acetol monooxygenase which converts acetol to methylglyoxal [24].
  • On admission and 3 and 7 hours after admission, the combined serum osmolality of glycerol, acetone, acetol, and 1,2-propanediol accounted for 48%, 92%, and 62% of the increase in the osmolal gap above the highest normal level of 10 mOsm/kg H2O [25].
  • Gold nanoparticles (1-10 nm size range) were prepared with an appreciably narrow size distribution by in situ reduction of HAuCl(4) in the presence of heterobifunctional poly(ethylene glycol) (PEG) derivatives containing both mercapto and acetal groups (alpha-acetal-omega-mercapto-PEG) [26].
  • Other reducing agents, such as hydroxylamine, hydrazine, dihydroxymaleic acid, sodium bisulfite and acetol, were also effective for the hydroxylation reaction, as were metal-EDTA complexes (FeII-, SnII-, TiIII-, CuI-EDTA) [27].
  • The analog bearing a methyl group at C3 was prepared in a synthetic scheme beginning with the hydroxylation of acrolein dimethyl acetal [28].

Gene context of Acetol

  • In an effort to improve rates of catalysis of P450 1A2 enzymes, we considered a set of p-alkoxyacylanilide analogues of phenacetin and found that variations in the O-alkyl and N-acyl substituents altered the rates of the two oxidation reactions and the ratio of acetol/phenol products [29].
  • The irreversible lamellar-to-micellar transition observed with BD2-containing liposomes can possibly be attributed to acid-catalyzed hydrolysis of the acetal cross-linker, which generates two detergent monomers within the bilayer [30].
  • To address this issue, we have prepared two Gemini surfactants or 'bis-detergents' by cross-linking the headgroups of single-tailed, tertiary amine detergents through oxyethylene (BD1) or acid-labile acetal (BD2) moieties [30].
  • Bicycloillicinone asarone acetal: a novel prenylated C6-C3 compound increasing choline acetyltransferase (ChAT) activity from Illicium tashiroi [31].
  • Lewis Acid-promoted intermolecular acetal-initiated cationic polyene cyclizations [32].

Analytical, diagnostic and therapeutic context of Acetol


  1. Acetone and acetol inhibition of insulin-stimulated glucose oxidation in adipose tissue and isolated adipocytes. Skutches, C.L., Owen, O.E., Reichard, G.A. Diabetes (1990) [Pubmed]
  2. Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications. Vander Jagt, D.L., Robinson, B., Taylor, K.K., Hunsaker, L.A. J. Biol. Chem. (1992) [Pubmed]
  3. The proteins of the messenger RNA binding site of Escherichia coli ribosomes. Gimautdinova, O.I., Karpova, G.G., Knorre, D.G., Kobetz, N.D. Nucleic Acids Res. (1981) [Pubmed]
  4. Regulation of bilayer stability in Clostridium butyricum: studies on the polymorphic phase behavior of the ether lipids. Goldfine, H., Johnston, N.C., Mattai, J., Shipley, G.G. Biochemistry (1987) [Pubmed]
  5. Hydrophobic acetal and ketal derivatives of mannopeptimycin-alpha and desmethylhexahydromannopeptimycin-alpha: semisynthetic glycopeptides with potent activity against Gram-positive bacteria. Dushin, R.G., Wang, T.Z., Sum, P.E., He, H., Sutherland, A.G., Ashcroft, J.S., Graziani, E.I., Koehn, F.E., Bradford, P.A., Petersen, P.J., Wheless, K.L., How, D., Torres, N., Lenoy, E.B., Weiss, W.J., Lang, S.A., Projan, S.J., Shlaes, D.M., Mansour, T.S. J. Med. Chem. (2004) [Pubmed]
  6. Mild and efficient method for the cleavage of benzylidene acetals by using erbium (III) triflate. Procopio, A., Dalpozzo, R., De Nino, A., Maiuolo, L., Nardi, M., Romeo, G. Org. Biomol. Chem. (2005) [Pubmed]
  7. The design, computer modeling, solution structure, and biological evaluation of synthetic analogs of bryostatin 1. Wender, P.A., DeBrabander, J., Harran, P.G., Jimenez, J.M., Koehler, M.F., Lippa, B., Park, C.M., Siedenbiedel, C., Pettit, G.R. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  8. Sustained microgravity reduces intrinsic wound healing and growth factor responses in the rat. Davidson, J.M., Aquino, A.M., Woodward, S.C., Wilfinger, W.W. FASEB J. (1999) [Pubmed]
  9. Chemical Modification of Santonin into a Diacetoxy Acetal Form Confers the Ability to Induce Differentiation of Human Promyelocytic Leukemia Cells via the Down-regulation of NF-{kappa}B DNA Binding Activity. Kim, S.H., Song, J.H., Choi, B.G., Kim, H.J., Kim, T.S. J. Biol. Chem. (2006) [Pubmed]
  10. Identification of ethanol-inducible P-450 isozyme 3a as the acetone and acetol monooxygenase of rabbit microsomes. Koop, D.R., Casazza, J.P. J. Biol. Chem. (1985) [Pubmed]
  11. Conversion of methylglyoxal to acetol by Escherichia coli aldo-keto reductases. Ko, J., Kim, I., Yoo, S., Min, B., Kim, K., Park, C. J. Bacteriol. (2005) [Pubmed]
  12. Biosynthesis of phospholipids in Clostridium butyricum: kinetics of synthesis of plasmalogens and the glycerol acetal of ethanolamine plasmalogen. Koga, Y., Goldfine, H. J. Bacteriol. (1984) [Pubmed]
  13. Imidazole acetol phosphate aminotransferase in Zymomonas mobilis: molecular genetic, biochemical, and evolutionary analyses. Gu, W., Zhao, G., Eddy, C., Jensen, R.A. J. Bacteriol. (1995) [Pubmed]
  14. Immunochemical quantitation of thymine glycol in oxidized and X-irradiated DNA. Hubbard, K., Huang, H., Laspia, M.F., Ide, H., Erlanger, B.F., Wallace, S.S. Radiat. Res. (1989) [Pubmed]
  15. A novel method for the determination of the stereochemistry of pyruvate acetal substituents applied to the capsular polysaccharide from Streptococcus pneumoniae type 4. Jones, C. Carbohydr. Res. (1990) [Pubmed]
  16. Stimuli-responsive supramolecular assemblies of linear-dendritic copolymers. Gillies, E.R., Jonsson, T.B., Fréchet, J.M. J. Am. Chem. Soc. (2004) [Pubmed]
  17. Electron transfer initiated cyclizations: cyclic acetal synthesis through carbon-carbon sigma-bond activation. Kumar, V.S., Floreancig, P.E. J. Am. Chem. Soc. (2001) [Pubmed]
  18. Toward the development of a general chiral auxiliary. A total synthesis of (+)-tetronolide via a tandem ketene-trapping [4 + 2] cycloaddition strategy. Boeckman, R.K., Shao, P., Wrobleski, S.T., Boehmler, D.J., Heintzelman, G.R., Barbosa, A.J. J. Am. Chem. Soc. (2006) [Pubmed]
  19. Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides. Crich, D., Banerjee, A. J. Am. Chem. Soc. (2006) [Pubmed]
  20. Synthesis and evaluation of 3-modified 1D-myo-inositols as inhibitors and substrates of phosphatidylinositol synthase and inhibitors of myo-inositol uptake by cells. Johnson, S.C., Dahl, J., Shih, T.L., Schedler, D.J., Anderson, L., Benjamin, T.L., Baker, D.C. J. Med. Chem. (1993) [Pubmed]
  21. Darmstoff analogues. 3. Actions of choline esters of acetal phosphatidic acids on visceral smooth muscle. Marx, M.H., Wiley, R.A., Satchell, D.G., Maguire, M.H. J. Med. Chem. (1989) [Pubmed]
  22. Suitability of a new stable acetal analogue of aldoifosphamide for purging leukemic cells from human bone marrow. Andersson, B.S., Wang, Y.Q., McCredie, K.B., Farquhar, D. Leukemia (1990) [Pubmed]
  23. In vivo formation and localization of 1,1-dichloroethylene epoxide in murine liver: identification of its glutathione conjugate 2-S-glutathionyl acetate. Forkert, P.G. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  24. The metabolism of acetone in rat. Casazza, J.P., Felver, M.E., Veech, R.L. J. Biol. Chem. (1984) [Pubmed]
  25. Increased osmolal gap in alcoholic acidosis. Braden, G.L., Strayhorn, C.H., Germain, M.J., Mulhern, J.G., Skutches, C.L. Arch. Intern. Med. (1993) [Pubmed]
  26. Quantitative and reversible lectin-induced association of gold nanoparticles modified with alpha-lactosyl-omega-mercapto-poly(ethylene glycol). Otsuka, H., Akiyama, Y., Nagasaki, Y., Kataoka, K. J. Am. Chem. Soc. (2001) [Pubmed]
  27. Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Kasai, H., Nishimura, S. Nucleic Acids Res. (1984) [Pubmed]
  28. Synthesis of phosphatidylcholine analogs with an alkyl group at C1 or C3 of the glycerol moiety. Witzke, N.M., Bittman, R. J. Lipid Res. (1985) [Pubmed]
  29. Oxidations of p-alkoxyacylanilides catalyzed by human cytochrome P450 1A2: structure-activity relationships and simulation of rate constants of individual steps in catalysis. Yun, C.H., Miller, G.P., Guengerich, F.P. Biochemistry (2001) [Pubmed]
  30. Cytosolic delivery of macromolecules. 3. Synthesis and characterization of acid-sensitive bis-detergents. Asokan, A., Cho, M.J. Bioconjug. Chem. (2004) [Pubmed]
  31. Bicycloillicinone asarone acetal: a novel prenylated C6-C3 compound increasing choline acetyltransferase (ChAT) activity from Illicium tashiroi. Fukuyama, Y., Hata, Y., Kodama, M. Planta Med. (1997) [Pubmed]
  32. Lewis Acid-promoted intermolecular acetal-initiated cationic polyene cyclizations. Zhao, Y.J., Chng, S.S., Loh, T.P. J. Am. Chem. Soc. (2007) [Pubmed]
  33. Uneven host tissue ongrowth and tissue detachment in stent mounted heart valve allografts and xenografts. Maxwell, L., Gavin, J.B., Barratt-Boyes, B.G. Cardiovasc. Res. (1989) [Pubmed]
  34. Stereochemical structures of synthesized and natural plasmalogalactosylceramides from equine brain. Yachida, Y., Kashiwagi, M., Mikami, T., Tsuchihashi, K., Daino, T., Akino, T., Gasa, S. J. Lipid Res. (1998) [Pubmed]
  35. A reactive poly(ethylene glycol) layer to achieve specific surface plasmon resonance sensing with a high S/N ratio: the substantial role of a short underbrushed PEG layer in minimizing nonspecific adsorption. Uchida, K., Otsuka, H., Kaneko, M., Kataoka, K., Nagasaki, Y. Anal. Chem. (2005) [Pubmed]
  36. Tether-controlled cycloadditions for the asymmetric synthesis of decalins: increased selectivity in acetonitrile solvent. Melekhov, A., Forgione, P., Legoupy, S., Fallis, A.G. Org. Lett. (2000) [Pubmed]
  37. Tissue reactions to wear products from polyacetal (Delrin) and UHMW polyethylene in total hip replacement. Mathiesen, E.B., Lindgren, J.U., Reinholt, F.P., Sudmann, E. J. Biomed. Mater. Res. (1987) [Pubmed]
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