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Chemical Compound Review

Orthovanilline     2-hydroxy-3-methoxy- benzaldehyde

Synonyms: O-VANILLIN, o-Vanilline, CHEMBL13859, NSC-2150, ACMC-1C1I6, ...
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Disease relevance of Orthovanilline

  • In contrast, the vanillin study primarily showcases which non-native pathways need to be added into Escherichia coli [1].
  • A gene encoding a novel enoyl-SCoA hydratase/lyase enzyme for the hydration and nonoxidative cleavage of feruloyl-SCoA to vanillin and acetyl-SCoA was isolated and characterized from a strain of Pseudomonas fluorescens [2].
  • The olfactory threshold for vanillin was lower in migraine sufferers than in controls [3].
  • Production of vanillic acid from vanillin by resting cells of Serratia marcescens [4].
  • The conversions of vanillic acid and O-benzylvanillic acid to vanillin were examined by using whole cells and enzyme preparations of Nocardia sp. strain NRRL 5646 [5].

Psychiatry related information on Orthovanilline

  • The influence of early experience with vanillin on food preference later in life [6].
  • In olfaction, it is not possible to determine which nostril is being stimulated, i.e., lateralize, when a pure olfactory substance, e.g., phenylethyl alcohol or vanillin, is administered into one nostril, and, simultaneously, an odorless, solvent blank into the contralateral nostril [7].

High impact information on Orthovanilline


Chemical compound and disease context of Orthovanilline


Biological context of Orthovanilline


Anatomical context of Orthovanilline

  • To obtain OERPs, stimulants were chosen to stimulate specifically the olfactory nerve (2.1 ppm vanillin, 0.8 ppm H2S) [23].
  • Smelling of vanillin activated bilaterally the amygdala and piriform cortex [24].
  • These altered dormancy and tetrazolium uptake properties were related to defects in the pigmentation of the endothelium and its neighboring crushed parenchymatic layers, as determined by vanillin staining and microscopic observations [25].
  • In contrast to vanillin, which solely activates the olfactory cortex, acetone engages predominantly trigeminal projections from the nasal mucosa [24].
  • Suppression of mitomycin C-induced micronuclei in mouse bone marrow cells by post-treatment with vanillin [26].

Associations of Orthovanilline with other chemical compounds


Gene context of Orthovanilline


Analytical, diagnostic and therapeutic context of Orthovanilline


  1. OptStrain: a computational framework for redesign of microbial production systems. Pharkya, P., Burgard, A.P., Maranas, C.D. Genome Res. (2004) [Pubmed]
  2. Metabolism of ferulic acid to vanillin. A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester. Gasson, M.J., Kitamura, Y., McLauchlan, W.R., Narbad, A., Parr, A.J., Parsons, E.L., Payne, J., Rhodes, M.J., Walton, N.J. J. Biol. Chem. (1998) [Pubmed]
  3. Olfaction in migraine. Snyder, R.D., Drummond, P.D. Cephalalgia : an international journal of headache. (1997) [Pubmed]
  4. Production of vanillic acid from vanillin by resting cells of Serratia marcescens. Perestelo, F., Dalcón, M.A., de la Fuente, G. Appl. Environ. Microbiol. (1989) [Pubmed]
  5. Biocatalytic synthesis of vanillin. Li, T., Rosazza, J.P. Appl. Environ. Microbiol. (2000) [Pubmed]
  6. The influence of early experience with vanillin on food preference later in life. Haller, R., Rummel, C., Henneberg, S., Pollmer, U., Köster, E.P. Chem. Senses (1999) [Pubmed]
  7. Spatiotemporal masking in pure olfaction. Radil, T., Wysocki, C.J. Ann. N. Y. Acad. Sci. (1998) [Pubmed]
  8. Vanillin, a potential agent for the treatment of sickle cell anemia. Abraham, D.J., Mehanna, A.S., Wireko, F.C., Whitney, J., Thomas, R.P., Orringer, E.P. Blood (1991) [Pubmed]
  9. Reduction of carboxylic acids by nocardia aldehyde oxidoreductase requires a phosphopantetheinylated enzyme. Venkitasubramanian, P., Daniels, L., Rosazza, J.P. J. Biol. Chem. (2007) [Pubmed]
  10. Schiff base adducts of hemoglobin. Modifications that inhibit erythrocyte sickling. Zaugg, R.H., Walder, J.A., Klotz, I.M. J. Biol. Chem. (1977) [Pubmed]
  11. Novel approaches to the biosynthesis of vanillin. Walton, N.J., Narbad, A., Faulds, C., Williamson, G. Curr. Opin. Biotechnol. (2000) [Pubmed]
  12. Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Kulkarni, M.V., Kulkarni, G.M., Lin, C.H., Sun, C.M. Current medicinal chemistry. (2006) [Pubmed]
  13. Cloning and characterization of the ferulic acid catabolic genes of Sphingomonas paucimobilis SYK-6. Masai, E., Harada, K., Peng, X., Kitayama, H., Katayama, Y., Fukuda, M. Appl. Environ. Microbiol. (2002) [Pubmed]
  14. Whole-cell bioconversion of vanillin to vanillic acid by Streptomyces viridosporus. Pometto, A.L., Crawford, D.L. Appl. Environ. Microbiol. (1983) [Pubmed]
  15. Nitrate as a preferred electron sink for the acetogen Clostridium thermoaceticum. Seifritz, C., Daniel, S.L., Gössner, A., Drake, H.L. J. Bacteriol. (1993) [Pubmed]
  16. Inhibition of induction of adaptive response by o-vanillin in Escherichia coli B. Watanabe, K., Ohta, T., Watanabe, M., Kato, T., Shirasu, Y. Mutat. Res. (1990) [Pubmed]
  17. The 1.8 A resolution structure of hydroxycinnamoyl-coenzyme A hydratase-lyase (HCHL) from Pseudomonas fluorescens, an enzyme that catalyses the transformation of feruloyl-coenzyme A to vanillin. Leonard, P.M., Brzozowski, A.M., Lebedev, A., Marshall, C.M., Smith, D.J., Verma, C.S., Walton, N.J., Grogan, G. Acta Crystallogr. D Biol. Crystallogr. (2006) [Pubmed]
  18. Structural determinants for membrane trafficking and G protein selectivity of a mouse olfactory receptor. Katada, S., Tanaka, M., Touhara, K. J. Neurochem. (2004) [Pubmed]
  19. Molecular characterization of the genes pcaG and pcaH, encoding protocatechuate 3,4-dioxygenase, which are essential for vanillin catabolism in Pseudomonas sp. strain HR199. Overhage, J., Kresse, A.U., Priefert, H., Sommer, H., Krammer, G., Rabenhorst, J., Steinbüchel, A. Appl. Environ. Microbiol. (1999) [Pubmed]
  20. Antioxidant and pro-oxidant activities of p-hydroxybenzyl alcohol and vanillin: effects on free radicals, brain peroxidation and degradation of benzoate, deoxyribose, amino acids and DNA. Liu, J., Mori, A. Neuropharmacology (1993) [Pubmed]
  21. Different modifications by vanillin in cytotoxicity and genetic changes induced by EMS and H2O2 in cultured Chinese hamster cells. Tamai, K., Tezuka, H., Kuroda, Y. Mutat. Res. (1992) [Pubmed]
  22. Mass balance modeling of vanillin production from vanillic acid by cultures of the fungus Pycnoporus cinnabarinus in bioreactors. Bernard, O., Bastin, G., Stentelaire, C., Lesage-Meessen, L., Asther, M. Biotechnol. Bioeng. (1999) [Pubmed]
  23. Chemosensory event-related potentials in response to trigeminal and olfactory stimulation in idiopathic Parkinson's disease. Barz, S., Hummel, T., Pauli, E., Majer, M., Lang, C.J., Kobal, G. Neurology (1997) [Pubmed]
  24. Odorant differentiated pattern of cerebral activation: comparison of acetone and vanillin. Savic, I., Gulyás, B., Berglund, H. Human brain mapping. (2002) [Pubmed]
  25. Influence of the testa on seed dormancy, germination, and longevity in Arabidopsis. Debeaujon, I., Léon-Kloosterziel, K.M., Koornneef, M. Plant Physiol. (2000) [Pubmed]
  26. Suppression of mitomycin C-induced micronuclei in mouse bone marrow cells by post-treatment with vanillin. Inouye, T., Sasaki, Y.F., Imanishi, H., Watanebe, M., Ohta, T., Shirasu, Y. Mutat. Res. (1988) [Pubmed]
  27. Determination of site-specific carbon isotope ratios at natural abundance by carbon-13 nuclear magnetic resonance spectroscopy. Caer, V., Trierweiler, M., Martin, G.J., Martin, M.L. Anal. Chem. (1991) [Pubmed]
  28. Oxidation of benzaldehydes to benzoic acid derivatives by three Desulfovibrio strains. Zellner, G., Kneifel, H., Winter, J. Appl. Environ. Microbiol. (1990) [Pubmed]
  29. Protective activities of some phenolic 1,3-diketones against lipid peroxidation: possible involvement of the 1,3-diketone moiety. Patro, B.S., Rele, S., Chintalwar, G.J., Chattopadhyay, S., Adhikari, S., Mukherjee, T. Chembiochem (2002) [Pubmed]
  30. Mutation enhancing effect of o-vanillin in the lacZ gene of Escherichia coli: characterization of mutational spectrum. Watanabe, K., Ohta, T. Mutat. Res. (1993) [Pubmed]
  31. Post-replication repair and recombination in uvrA umuC strains of Escherichia coli are enhanced by vanillin, an antimutagenic compound. Ohta, T., Watanabe, M., Shirasu, Y., Inoue, T. Mutat. Res. (1988) [Pubmed]
  32. Vanillin (3-methoxy-4-hydroxybenzaldehyde) inhibits mutation induced by hydrogen peroxide, N-methyl-N-nitrosoguanidine and mitomycin C but not (137)Cs gamma-radiation at the CD59 locus in human-hamster hybrid A(L) cells. Gustafson, D.L., Franz, H.R., Ueno, A.M., Smith, C.J., Doolittle, D.J., Waldren, C.A. Mutagenesis (2000) [Pubmed]
  33. Determination of vanillin and related flavor compounds in cocoa drink by capillary electrophoresis. Ohashi, M., Omae, H., Hashida, M., Sowa, Y., Imai, S. Journal of chromatography. A (2007) [Pubmed]
  34. Determinants for nasal trigeminal detection of volatile organic compounds. Cometto-Muñiz, J.E., Cain, W.S., Abraham, M.H. Chem. Senses (2005) [Pubmed]
  35. Suppression of 6-TG-resistant mutations in V79 cells and recessive spot formations in mice by vanillin. Imanishi, H., Sasaki, Y.F., Matsumoto, K., Watanabe, M., Ohta, T., Shirasu, Y., Tutikawa, K. Mutat. Res. (1990) [Pubmed]
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