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Chemical Compound Review

Salicylal     2-hydroxybenzaldehyde

Synonyms: Salicyladehyde, Salicylaldehyd, Salizylaldehyd, o-Formylphenol, S356_ALDRICH, ...
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Disease relevance of SALICYLALDEHYDE

  • We compared the effects of oil of basil (Ocimum basilicum) and essential oil components (thymol, carvacrol, and salicylaldehyde) to those of a placebo when placed in the ear canal of rats with experimental acute otitis media caused by pneumococci or Haemophilus influenzae [1].
  • In vapour phase toxicity tests with female lice, benzaldehyde and salicylaldehyde were much more effective in closed containers than in open ones, indicating that the mode of delivery of these compounds was largely due to action in the vapour phase [2].
  • Antiproliferative activities of iron and platinum conjugates of salicylaldehyde semi-/thiosemicarbazones against C6 glioma cells [3].
  • The acetone and salicylaldehyde derivatives showed similar potency to (-) ephedrine in the hyperthermia model [4].
  • A series of salicylaldehyde benzoylhydrazone derivatives, their copper(II) complexes and a range of transition metal complexes of the unsubstituted ligand has been synthesized and evaluated for cytotoxicity against a human adenocarcinoma cell line [5].

Psychiatry related information on SALICYLALDEHYDE


High impact information on SALICYLALDEHYDE

  • The catabolization of the host-plant O-glucoside salicin into salicylaldehyde is a character state that evolved later in two distinct lineages, which specialized on Salicaceae [7].
  • Other compounds (e.g., salicylaldehyde p-t-butyl-benzoyl hydrazone) redistributed ferritin-59Fe to different intracellular sites but had little net effect on hepatocyte iron levels [8].
  • In human reticulocytes (unlike those from rabbits), addition of ferric salicylaldehyde isonicotinoylhydrazone, to increase the pre-heme iron pool independently of the transferrin cycle, failed to promote heme synthesis or modify feedback inhibition induced by hematin [9].
  • Pyridoxal phosphate and salicylaldehyde were used as protein-labeling probes to study the organization of membrane proteins in the intact myelin sheath of the cat dorsal column [10].
  • Organization of membrane proteins in the intact myelin sheath. Pyridoxal phosphate and salicylaldehyde as probes of myelin structure [10].

Chemical compound and disease context of SALICYLALDEHYDE


Biological context of SALICYLALDEHYDE


Anatomical context of SALICYLALDEHYDE


Associations of SALICYLALDEHYDE with other chemical compounds



  • These products, formed in equimolar amounts, were the only ones detected that suggests that FMO1 catalyzes the oxidation of salicylaldehyde by Baeyer-Villiger chemistry [26].
  • EHT and CNDO calculations have been performed on a series on fungicidal salicylaldehyde derivatives [27].
  • A series of new bis[N-(2,6-di-tert-butyl-1-hyxyphenyl)salicylideneminato]zinc(II) complexes bearing one or two HO- and CH3O-substituents on the salicylaldehyde moiety were prepared, and their spectroscopic properties (IR, electronic, 1H NMR) as well as the ESR spectra of the one-electron oxidation products were examined [28].

Analytical, diagnostic and therapeutic context of SALICYLALDEHYDE


  1. Effective treatment of experimental acute otitis media by application of volatile fluids into the ear canal. Kristinsson, K.G., Magnusdottir, A.B., Petersen, H., Hermansson, A. J. Infect. Dis. (2005) [Pubmed]
  2. Ovicidal and adulticidal activities of Cinnamomum zeylanicum bark essential oil compounds and related compounds against Pediculus humanus capitis (Anoplura: Pediculicidae). Yang, Y.C., Lee, H.S., Lee, S.H., Clark, J.M., Ahn, Y.J. Int. J. Parasitol. (2005) [Pubmed]
  3. Antiproliferative activities of iron and platinum conjugates of salicylaldehyde semi-/thiosemicarbazones against C6 glioma cells. Patole, J., Padhye, S., Moodbidri, M.S., Shirsat, N. European journal of medicinal chemistry. (2005) [Pubmed]
  4. Hyperthermic and anorectic effects of oxazolidines derived from L-ephedrine in rats. Walker, R.B., Wood, D.M., Akmal, M.M. Life Sci. (1990) [Pubmed]
  5. Cytotoxicity of salicylaldehyde benzoylhydrazone analogs and their transition metal complexes: quantitative structure-activity relationships. Ainscough, E.W., Brodie, A.M., Denny, W.A., Finlay, G.J., Gothe, S.A., Ranford, J.D. J. Inorg. Biochem. (1999) [Pubmed]
  6. The effect of ephedrine isomers and their oxazolidines on locomotor activity in rats. Walker, R.B., Fitz, L.D., Williams, L.M., Linton, H., Smith, C.C. Gen. Pharmacol. (1993) [Pubmed]
  7. Selective transport systems mediate sequestration of plant glucosides in leaf beetles: a molecular basis for adaptation and evolution. Kuhn, J., Pettersson, E.M., Feld, B.K., Burse, A., Termonia, A., Pasteels, J.M., Boland, W. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Evaluation of the iron chelation potential of hydrazones of pyridoxal, salicylaldehyde and 2-hydroxy-1-naphthylaldehyde using the hepatocyte in culture. Baker, E., Richardson, D., Gross, S., Ponka, P. Hepatology (1992) [Pubmed]
  9. Biosynthesis of heme in immature erythroid cells. The regulatory step for heme formation in the human erythron. Gardner, L.C., Cox, T.M. J. Biol. Chem. (1988) [Pubmed]
  10. Organization of membrane proteins in the intact myelin sheath. Pyridoxal phosphate and salicylaldehyde as probes of myelin structure. Golds, E.E., Braun, P.E. J. Biol. Chem. (1976) [Pubmed]
  11. Allergic contact dermatitis from salicyl alcohol and salicylaldehyde in aspen bark (Populus tremula). Aalto-Korte, K., Välimaa, J., Henriks-Eckerman, M.L., Jolanki, R. Contact Derm. (2005) [Pubmed]
  12. Inhibition of murine coronavirus RNA synthesis by hydroxyguanidine derivatives. Keck, J.G., Wang, P.H., Lien, E.J., Lai, M.M. Virus Res. (1989) [Pubmed]
  13. Fetal toxicity and hypocalcemia induced by acetylsalicylic acid analogues. Saito, H., Yokoyama, A., Takeno, S., Sakai, T., Ueno, K., Masumura, H., Kitagawa, H. Res. Commun. Chem. Pathol. Pharmacol. (1982) [Pubmed]
  14. Effect of 5-substituted benzylideneaminosalicylic acid on carrageenan-induced ulcerative colitis. Jaysekhar, P., Rao, S.B., Santhakumari, G. Bollettino chimico farmaceutico. (2004) [Pubmed]
  15. Complexes of salicylaldehyde acylhydrazones: cytotoxicity, QSAR and crystal structure of the sterically hindered t-butyl dimer. Koh, L.L., Kon, O.L., Loh, K.W., Long, Y.C., Ranford, J.D., Tan, A.L., Tjan, Y.Y. J. Inorg. Biochem. (1998) [Pubmed]
  16. synthesis of 2-deoxyfortimicins and 1-deamino-2-deoxy-2-epi-aminofortimicins via 2-O-methanesulfonylfortimicin B. Martin, J.R., Johnson, P., Tadanier, J., Goldstein, A.W. J. Antibiot. (1980) [Pubmed]
  17. Diamine preparation for synthesis of a water soluble Ni(II) salen complex. Shearer, J.M., Rokita, S.E. Bioorg. Med. Chem. Lett. (1999) [Pubmed]
  18. Food protective and color alteration effects of acaricidal aldehydes on Tyrophagus putrescentiae (Schrank). Sung, B.K., Lim, J.H., Lee, H.S. J. Food Prot. (2006) [Pubmed]
  19. Involvement of mammalian liver cytosols and aldehyde oxidase in reductive metabolism of zonisamide. Sugihara, K., Kitamura, S., Tatsumi, K. Drug Metab. Dispos. (1996) [Pubmed]
  20. Antimicrobial activity of exocrine glandular secretion of Chrysomela larvae. Gross, J., Podsiadlowski, L., Hilker, M. J. Chem. Ecol. (2002) [Pubmed]
  21. New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity. Xiang, Y., Tong, A., Jin, P., Ju, Y. Org. Lett. (2006) [Pubmed]
  22. Pyriform cortex beta-waves: odor-specific sensitization following repeated olfactory stimulation. Vanderwolf, C.H., Zibrowski, E.M. Brain Res. (2001) [Pubmed]
  23. The ability of various chemicals to elicit olfactory beta-waves in the pyriform cortex of meadow voles (Microtus pennsylvanicus) and laboratory rats (Rattus norvegicus). Vanderwolf, C.H., Zibrowski, E.M., Wakarchuk, D. Brain Res. (2002) [Pubmed]
  24. Synthesis, X-ray structure, single-crystal EPR and 1H NMR studies of a distorted square planar Cu(salEen)2(ClO4)2 complex in a novel bilayered architecture: salEen = N,N-diethylethylenesalicylidenamine. Subramanian, P.S., Suresh, E., Srinivas, D. Inorganic chemistry. (2000) [Pubmed]
  25. Electrospray ionization mass spectrometry in the structural characterization of some diphenyllead(IV) thiosemicarbazonates. Casas, J.S., García-Tasende, M.S., Sordo, J., Taboada, C., Tubaro, M., Traldi, P., Vidarte, M.J. Rapid Commun. Mass Spectrom. (2004) [Pubmed]
  26. Oxidation of aldehydes catalyzed by pig liver flavin-containing monooxygenase. Chen, G.P., Poulsen, L.L., Ziegler, D.M. Drug Metab. Dispos. (1995) [Pubmed]
  27. Determination of structure-activity relationships for salicylaldehydes using CNDO and EHT calculations. Tinland, B. Il Farmaco; edizione scientifica. (1975) [Pubmed]
  28. Preparation, spectral behaviour and oxidation of some new zinc(II) salicylaldimines containing sterically hindered phenol. Kasumov, V.T. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy. (2001) [Pubmed]
  29. Molecularly imprinted polymer with salicylaldehyde-Cu(OAc)2 as template. Yang, M.L., Li, Y.Z. J. Mol. Recognit. (2005) [Pubmed]
  30. Salicylaldehyde-metal-amino acid ternary complex: a new tool for immobilized metal affinity chromatography. Leibler, D., Rabinkov, A., Wilchek, M. J. Mol. Recognit. (1996) [Pubmed]
  31. Immobilized chymotrypsin by means of Schiff base copper(II) chelate. Moriya, K., Tanizawa, K., Kanaoka, Y. Biochem. Biophys. Res. Commun. (1989) [Pubmed]
  32. Determination of desmethyl nortriptyline in plasma by gas chromatography before and after treatment with salicylaldehyde. Burch, J.E., Raddats, M.A., Roberts, S.G. J. Chromatogr. (1983) [Pubmed]
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