benzaldehydes

Summary

Summary: Compounds that consist of a benzene ring with a formyl group. They occur naturally in the seeds of many fruits and are used as FLAVORING AGENTS and fragrances, as well as precursors in pharmaceutical and plastics manufacturing.

Top Publications

  1. Itoh S, Tokunaga T, Sonoike S, Kitamura M, Yamano A, Aoki S. Asymmetric aldol reactions between acetone and benzaldehydes catalyzed by chiral Zn2+ complexes of aminoacyl 1,4,7,10-tetraazacyclododecane: fine-tuning of the amino-acid side chains and a revised reaction mechanism. Chem Asian J. 2013;8:2125-35 pubmed publisher
    ..The reaction mechanism of these aldol reactions is discussed and some corrections are made to our previous mechanistic hypothesis...
  2. Douglas J, Taylor J, Churchill G, Slawin A, Smith A. NHC-promoted asymmetric ?-lactone formation from arylalkylketenes and electron-deficient benzaldehydes or pyridinecarboxaldehydes. J Org Chem. 2013;78:3925-38 pubmed publisher
    ..NHC catalyzes the asymmetric formal [2 + 2] cycloaddition of alkylarylketenes with both electron-deficient benzaldehydes and 2- and 4-pyridinecarboxaldehydes to generate stereodefined ?-lactones...
  3. Kaur B, Chakraborty D. Biotechnological and molecular approaches for vanillin production: a review. Appl Biochem Biotechnol. 2013;169:1353-72 pubmed publisher
  4. Natsch A, Gfeller H, Haupt T, Brunner G. Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything?. Chem Res Toxicol. 2012;25:2203-15 pubmed publisher
    ..Here, we performed experimental studies on benzaldehydes of highly differing skin sensitization potential...
  5. Nguyen D, Le T, Bui T. Antioxidant activities of thiosemicarbazones from substituted benzaldehydes and N-(tetra-O-acetyl-?-D-galactopyranosyl)thiosemicarbazide. Eur J Med Chem. 2013;60:199-207 pubmed publisher
    Reaction of N-(2,3,4,6-tetra-O-acetyl-?-d-galactopyranosyl)thiosemicarbazide and different substituted benzaldehydes gave some new substituted benzaldehyde N-(2,3,4,6-tetra-O-acetyl-?-d-galactopyranosyl)thiosemicarbazones...
  6. Kaur B, Chakraborty D, Kaur G, Kaur G. Biotransformation of rice bran to ferulic acid by pediococcal isolates. Appl Biochem Biotechnol. 2013;170:854-67 pubmed publisher
    ..P. acidilactici M16, a probiotic isolate, has great potential for the production of FA from rice bran and could be exploited as starter culture in the food industry for the production of biovanillin...
  7. Plaggenborg R, Overhage J, Loos A, Archer J, Lessard P, Sinskey A, et al. Potential of Rhodococcus strains for biotechnological vanillin production from ferulic acid and eugenol. Appl Microbiol Biotechnol. 2006;72:745-55 pubmed
    ..HR199. The recombinant strain converted eugenol to ferulic acid. The obtained data suggest that genetically engineered strains of I24 and PD630 are suitable candidates for vanillin production from eugenol...
  8. Deb J, Dibra H, Shan S, Rajan S, Manneh J, Kankipati C, et al. Activity of aspirin analogues and vanillin in a human colorectal cancer cell line. Oncol Rep. 2011;26:557-65 pubmed publisher
    ..We propose that the anti-inflammatory and anticancer capacity of BCS and the other analogues described herein is worthy of investigation...
  9. Mohler E, Ballantyne C, Davidson M, Hanefeld M, Ruilope L, Johnson J, et al. The effect of darapladib on plasma lipoprotein-associated phospholipase A2 activity and cardiovascular biomarkers in patients with stable coronary heart disease or coronary heart disease risk equivalent: the results of a multicenter, randomized, doub. J Am Coll Cardiol. 2008;51:1632-41 pubmed publisher
    ..This study examined the effects of darapladib, a selective lipoprotein-associated phospholipase A(2) (Lp-PLA(2)) inhibitor, on biomarkers of cardiovascular (CV) risk...

More Information

Publications62

  1. Feng Y, Jadhav A, Rodighiero C, Fujinaga Y, Kirchhausen T, Lencer W. Retrograde transport of cholera toxin from the plasma membrane to the endoplasmic reticulum requires the trans-Golgi network but not the Golgi apparatus in Exo2-treated cells. EMBO Rep. 2004;5:596-601 pubmed
    ..We propose that even in the absence of Exo2 the glycolipid pathway that carries the toxin from plasma membrane into the ER bypasses the Golgi apparatus entirely...
  2. Song K, Chen Q, Wang Q, Qiu L, Huang H. Inhibitory effects of 4-vinylbenzaldehyde and 4-vinylbenzoic acid on the activity of mushroom tyrosinase. J Enzyme Inhib Med Chem. 2005;20:239-43 pubmed
    ..33 mM, respectively. Kinetic analyses showed that inhibition by both compounds was reversible and their mechanisms were mixed-II type; their inhibition constants were also determined and compared...
  3. Bloem A, Bertrand A, Lonvaud Funel A, de Revel G. Vanillin production from simple phenols by wine-associated lactic acid bacteria. Lett Appl Microbiol. 2007;44:62-7 pubmed
    ..The ability of lactic acid bacteria (LAB) to metabolize certain phenolic precursors to vanillin was investigated...
  4. Panoutsopoulos G, Beedham C. Kinetics and specificity of guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase towards substituted benzaldehydes. Acta Biochim Pol. 2004;51:649-63 pubmed
    ..The present investigation describes the interaction of eleven structurally related benzaldehydes with guinea pig liver aldehyde oxidase and bovine milk xanthine oxidase, since they have similar substrate ..
  5. Kromann H, Larsen M, Boesen T, Schønning K, Nielsen S. Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A. Eur J Med Chem. 2004;39:993-1000 pubmed
    In this paper, a general applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones is described...
  6. Hua D, Ma C, Song L, Lin S, Zhang Z, Deng Z, et al. Enhanced vanillin production from ferulic acid using adsorbent resin. Appl Microbiol Biotechnol. 2007;74:783-90 pubmed
    ..This yield was remarkable for exceeding the crystallization concentration of vanillin and therefore had far-reaching consequence in its downstream processing...
  7. White H, Held C, Stewart R, Watson D, Harrington R, Budaj A, et al. Study design and rationale for the clinical outcomes of the STABILITY Trial (STabilization of Atherosclerotic plaque By Initiation of darapLadIb TherapY) comparing darapladib versus placebo in patients with coronary heart disease. Am Heart J. 2010;160:655-61 pubmed publisher
    ..Direct inhibition of this proinflammatory enzyme with darapladib may benefit CV patients when given as an adjunct to standard of care, including lipid-lowering and antiplatelet therapies...
  8. Tai A, Sawano T, Yazama F, Ito H. Evaluation of antioxidant activity of vanillin by using multiple antioxidant assays. Biochim Biophys Acta. 2011;1810:170-7 pubmed publisher
    ..However, results of studies on the antioxidant activity of vanillin are not consistent...
  9. Pal S, Park D, Plapp B. Activity of yeast alcohol dehydrogenases on benzyl alcohols and benzaldehydes: characterization of ADH1 from Saccharomyces carlsbergensis and transition state analysis. Chem Biol Interact. 2009;178:16-23 pubmed publisher
    ..The reduction of a series of p-substituted benzaldehydes catalyzed by SceADH2 is significantly enhanced by electron-withdrawing groups, whereas the oxidation of p-..
  10. Endo A, Nakamura T, Shima J. Involvement of ergosterol in tolerance to vanillin, a potential inhibitor of bioethanol fermentation, in Saccharomyces cerevisiae. FEMS Microbiol Lett. 2009;299:95-9 pubmed publisher
    ..These findings provide a biotechnological basis for the molecular engineering of S. cerevisiae with increased tolerance to vanillin...
  11. Kim J, Campbell B, Mahoney N, Chan K, Molyneux R, May G. Chemosensitization prevents tolerance of Aspergillus fumigatus to antimycotic drugs. Biochem Biophys Res Commun. 2008;372:266-71 pubmed publisher
    ..The potential use of natural, safe chemosensitizing agents in antifungal chemotherapy of human mycoses as an alternative to combination therapy is discussed...
  12. Lee E, Yoon S, Das A, Lee S, Li C, Kim J, et al. Directing vanillin production from ferulic acid by increased acetyl-CoA consumption in recombinant Escherichia coli. Biotechnol Bioeng. 2009;102:200-8 pubmed publisher
    ..Vanillin of 5.14 g/L was produced in 24 h of the culture with molar conversion yield of 86.6%, which is the highest so far in vanillin production from ferulic acid using recombinant E. coli...
  13. Kang H, Choi J, Cho W, Park J, Choi J. A sphingolipid and tyrosinase inhibitors from the fruiting body of Phellinus linteus. Arch Pharm Res. 2004;27:742-50 pubmed
    ..40 and 90.8 microg/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a Ki of 1.1 microM and 1.4 mM, respectively...
  14. No J, Kim M, Kim Y, Bae S, Choi J, Chung H. Inhibition of tyrosinase by protocatechuic aldehyde. Am J Chin Med. 2004;32:97-103 pubmed
    ..The findings of our present study merit further research on the applicability of PCA as a potential agent for treatment of pigmentation disorder...
  15. Chen Q, Song K, Wang Q, Huang H. Inhibitory effects on mushroom tyrosinase by some alkylbenzaldehydes. J Enzyme Inhib Med Chem. 2003;18:491-6 pubmed
  16. Friedman M, Henika P, Mandrell R. Antibacterial activities of phenolic benzaldehydes and benzoic acids against Campylobacter jejuni, Escherichia coli, Listeria monocytogenes, and Salmonella enterica. J Food Prot. 2003;66:1811-21 pubmed
    We evaluated the bactericidal activities of 35 benzaldehydes, 34 benzoic acids, and 1 benzoic acid methyl ester against Campylobacter jejuni, Escherichia coli O157:H7, Listeria monocytogenes, and Salmonella enterica when these compounds ..
  17. Odoux E, Escoute J, Verdeil J, Brillouet J. Localization of beta-D-glucosidase activity and glucovanillin in vanilla bean (Vanilla planifolia Andrews). Ann Bot. 2003;92:437-44 pubmed
    ..A possible mechanism for the hydrolysis of glucovanillin and release of the aromatic aglycon vanillin involves the decompartmentation of cytoplasmic (and/or periplasmic) beta-glucosidase and vacuolar glucovanillin...
  18. Kim J, Chan K, Mahoney N, Campbell B. Antifungal activity of redox-active benzaldehydes that target cellular antioxidation. Ann Clin Microbiol Antimicrob. 2011;10:23 pubmed publisher
    ..The aim of this study was to identify benzaldehydes that disrupt the fungal antioxidation system...
  19. Lirdprapamongkol K, Sakurai H, Kawasaki N, Choo M, Saitoh Y, Aozuka Y, et al. Vanillin suppresses in vitro invasion and in vivo metastasis of mouse breast cancer cells. Eur J Pharm Sci. 2005;25:57-65 pubmed
    ..Since vanillin is generally regarded as safe, it may be of value in the development of anti-metastatic drugs for cancer treatment...
  20. Lin C, Yang J, Chang C, Kuo S, Lee M, Huang L. Synthesis and anticancer activity of benzyloxybenzaldehyde derivatives against HL-60 cells. Bioorg Med Chem. 2005;13:1537-44 pubmed
    ..They resulted in the loss of mitochondrial membrane potential after 12h of treatment...
  21. Xue C, Zhang L, Luo W, Xie X, Jiang L, Xiao T. 3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors. Bioorg Med Chem. 2007;15:2006-15 pubmed
    ..The best scored candidates were docked flexibly, and the interaction between the representative compound 4-butylbenzaldehyde thiosemicarbazone and the active site was elucidated in detail...
  22. Rollmann S, Yamamoto A, Goossens T, Zwarts L, Callaerts Vegh Z, Callaerts P, et al. The early developmental gene Semaphorin 5c contributes to olfactory behavior in adult Drosophila. Genetics. 2007;176:947-56 pubmed
    ..Our results demonstrate how hypomorphic mutation of an early developmental gene results in genomewide transcriptional consequences and alterations in brain structure accompanied by profound impairment of adult behavior...
  23. Wang B, Yu G, Hu H, Wang L. Quantitative structure-activity relationships and mixture toxicity of substituted benzaldehydes to Photobacterium phosphoreum. Bull Environ Contam Toxicol. 2007;78:503-9 pubmed
  24. Hansen E, Møller B, Kock G, Bünner C, Kristensen C, Jensen O, et al. De novo biosynthesis of vanillin in fission yeast (Schizosaccharomyces pombe) and baker's yeast (Saccharomyces cerevisiae). Appl Environ Microbiol. 2009;75:2765-74 pubmed publisher
    ..S. pombe yeast has not previously been metabolically engineered to produce any valuable, industrially scalable, white biotech commodity...
  25. Fitzgerald D, Stratford M, Narbad A. Analysis of the inhibition of food spoilage yeasts by vanillin. Int J Food Microbiol. 2003;86:113-22 pubmed
    ..It was observed that increased vanillin concentrations inhibited its own bioconversion suggesting that the activity required intact cells with metabolic capacity...
  26. Lirdprapamongkol K, Kramb J, Suthiphongchai T, Surarit R, Srisomsap C, Dannhardt G, et al. Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo. J Agric Food Chem. 2009;57:3055-63 pubmed publisher
    ..Vanillin and apocynin also inhibited angiogenesis, determined by the chick chorioallantoic membrane assay...
  27. Kim Y, Kim N, Lee S, Lee Y, Jang D, Kim J. Effect of protocatechualdehyde on receptor for advanced glycation end products and TGF-beta1 expression in human lens epithelial cells cultured under diabetic conditions and on lens opacity in streptozotocin-diabetic rats. Eur J Pharmacol. 2007;569:171-9 pubmed
    ..These results suggest that PCA is of therapeutic interest with respect to the prevention of diabetic complications such as diabetic cataract...
  28. Serruys P, Garcia Garcia H, Buszman P, Erne P, Verheye S, Aschermann M, et al. Effects of the direct lipoprotein-associated phospholipase A(2) inhibitor darapladib on human coronary atherosclerotic plaque. Circulation. 2008;118:1172-82 pubmed publisher
  29. Walton N, Mayer M, Narbad A. Vanillin. Phytochemistry. 2003;63:505-15 pubmed
    ..Finally, the significance of the latest biosynthetic and biotechnological developments is reviewed briefly in relation to authentication of vanillin...
  30. Menna Barreto R, Henriques Pons A, Pinto A, Morgado Diaz J, Soares M, de Castro S. Effect of a beta-lapachone-derived naphthoimidazole on Trypanosoma cruzi: identification of target organelles. J Antimicrob Chemother. 2005;56:1034-41 pubmed
    ..was one of the most active compounds against Trypanosoma cruzi trypomastigotes...
  31. Ye G, Wang C, Li Y, Ren H, Guo D. Simultaneous determination and pharmacokinetic studies on (3,4-Dihydroxyphenyl)-lactic acid and protocatechuic aldehyde in rat serum after oral administration of Radix Salviae miltiorrhizae extract. J Chromatogr Sci. 2003;41:327-30 pubmed
    ..This validated assay is applied to the determination of Dhpl and Pal concentrations and used to take a limited view of the pharmacokinetic profile in rat serum after oral administration of Radix Salviae miltiorrhizae extract...
  32. Nihei K, Yamagiwa Y, Kamikawa T, Kubo I. 2-hydroxy-4-isopropylbenzaldehyde, a potent partial tyrosinase inhibitor. Bioorg Med Chem Lett. 2004;14:681-3 pubmed
    ..3 microM. The inhibition kinetics analyzed by Dixon plots found that chamaecin is a mixed type inhibitor. This inhibition may come in part from its ability to form a Schiff base with a primary amino group in the enzyme...
  33. Park S, Sim Y, Choi S, Seo Y, Kwon M, Lee J, et al. Antinociceptive profiles and mechanisms of orally administered vanillin in the mice. Arch Pharm Res. 2009;32:1643-9 pubmed publisher
    ..Furthermore, this antinociceptive effect of vanillin may be mediated by alpha2-adrenergic and opioid receptors, but not alpha1-adrenergic and serotonergic receptors...
  34. Roston D, Kohen A. Elusive transition state of alcohol dehydrogenase unveiled. Proc Natl Acad Sci U S A. 2010;107:9572-7 pubmed publisher
    ..alcohol-like). The new picture of the TRS for this reaction identifies the principal components of the collective reaction coordinate and the average structure of the saddle point along that coordinate...
  35. Nakamura Y, Sugihara K, Sone T, Isobe M, Ohta S, Kitamura S. The in vitro metabolism of a pyrethroid insecticide, permethrin, and its hydrolysis products in rats. Toxicology. 2007;235:176-84 pubmed
    ..CYP 1A2, 2B1, 2C6, 2D1 and 3A1 exhibited significant oxidase activities in this reaction. Thus, permethrin was hydrolyzed by CES, and PBAlc formed was oxidized to PBAld and PBAcid by the cytochrome P450 system in rats...
  36. Brochado A, Matos C, Møller B, Hansen J, Mortensen U, Patil K. Improved vanillin production in baker's yeast through in silico design. Microb Cell Fact. 2010;9:84 pubmed publisher
    ..In this study we aimed at engineering this vanillin cell factory towards improved productivity and thereby at developing an attractive alternative to chemical synthesis...
  37. Kumar S, Priyadarsini K, Sainis K. Inhibition of peroxynitrite-mediated reactions by vanillin. J Agric Food Chem. 2004;52:139-45 pubmed
    ..The products of this reaction were analyzed by HPLC, and hydroxyvanillin was identified as one of the five products with absorption at 350 nm. These data demonstrate that vanillin effectively scavenges PON in cell-free systems...
  38. Huang X, Chen Q, You M, Wang Q, Song K, Wang J, et al. Inhibitory effects of fluorobenzaldehydes on the activity of mushroom tyrosinase. J Enzyme Inhib Med Chem. 2006;21:413-8 pubmed
    ..The inhibition constants for these three fluorobenzaldehydes on the diphenolase were determined and compared...
  39. Patil K, Rocha I, Forster J, Nielsen J. Evolutionary programming as a platform for in silico metabolic engineering. BMC Bioinformatics. 2005;6:308 pubmed
  40. Durant S, Karran P. Vanillins--a novel family of DNA-PK inhibitors. Nucleic Acids Res. 2003;31:5501-12 pubmed
    ..The inhibition of NHEJ is consistent with the antimutagenic and other biological properties of vanillin, possibly altering the balance between DSB repair by NHEJ and homologous recombination...
  41. Zhou Z, Liu Y, Miao A, Wang S. Protocatechuic aldehyde suppresses TNF-alpha-induced ICAM-1 and VCAM-1 expression in human umbilical vein endothelial cells. Eur J Pharmacol. 2005;513:1-8 pubmed
    ..Collectively, these results indicate that protocatechuic aldehyde inhibits TNF-alpha-stimulated VCAM-1 and ICAM-1expression in HUVECs through a mechanism that involves NF-kappaB and AP-1...
  42. Wilensky R, Shi Y, Mohler E, Hamamdzic D, Burgert M, Li J, et al. Inhibition of lipoprotein-associated phospholipase A2 reduces complex coronary atherosclerotic plaque development. Nat Med. 2008;14:1059-66 pubmed publisher
  43. King A, Shaughnessy D, Mure K, Leszczynska J, Ward W, Umbach D, et al. Antimutagenicity of cinnamaldehyde and vanillin in human cells: Global gene expression and possible role of DNA damage and repair. Mutat Res. 2007;616:60-9 pubmed
    ..These and other data lead us to propose that VAN and CIN may induce DNA damage that elicits recombinational DNA repair, which reduces spontaneous mutations...
  44. Asztalos Z, Arora N, Tully T. Olfactory jump reflex habituation in Drosophila and effects of classical conditioning mutations. J Neurogenet. 2007;21:1-18 pubmed
    ..We also show that the dunce and rutabaga memory mutants behave abnormally in this assay, suggesting that this assay might be used in behavioral screens for new mutants with defects in this simpler form of behavioral plasticity...
  45. Song M, Hang T, Zhang Z. [Pharmacokinetic interactions between the main components in the extracts of Salvia miltiorrhiza Bge. in rat]. Yao Xue Xue Bao. 2007;42:301-7 pubmed
    ..Therefore the traditional Chinese medicine was a complicated system, It should be taken a scientific and dialectic view in the research and development processes...
  46. Roeleveld K, David F, Lynen F. Comparison between polymerized ionic liquids synthesized using chain-growth and step-growth mechanisms used as stationary phase in gas chromatography. J Chromatogr A. 2016;1451:135-144 pubmed publisher
    ..The PIL phases and particularly the so far little studied condensation based polymer shows particular retention and satisfactory column performance for polar moieties such as esters, amine and carbonyl functionalities. ..
  47. El Sonbati A, Diab M, El Bindary A, Abd El Kader M. Supramolecular and structural modification on conformational by mixed ligand. Spectrochim Acta A Mol Biomol Spectrosc. 2012;99:211-7 pubmed publisher
    ..Various ligand and nephelouxetic parameter have been calculated for the complexes. The thermal decomposition for complexes was studied...
  48. Swarup S, Harbison S, Hahn L, Morozova T, Yamamoto A, Mackay T, et al. Extensive epistasis for olfactory behaviour, sleep and waking activity in Drosophila melanogaster. Genet Res (Camb). 2012;94:9-20 pubmed publisher
  49. Wang G, Qi H, Yang X. A ratiometric fluorescent probe for bisulphite anion, employing intramolecular charge transfer. Luminescence. 2013;28:97-101 pubmed publisher
    ..4 µmol/L. Probe 1 produces a ratiometric fluorescent response to bisulphite with a marked emission wavelength shift (130 nm) and displays high selectivity for bisulphite over other anions...
  50. Kocak N, Sahin M, Küçükkolbaşı S, Erdogan Z. Synthesis and characterization of novel nano-chitosan Schiff base and use of lead (II) sensor. Int J Biol Macromol. 2012;51:1159-66 pubmed publisher
    ..The modified electrode showed only one oxidation peak in the anodic scan at -0.34 V (vs. Ag/AgCl) for the oxidation of lead (II). The dedection limit (LOD) was calculated as 1.36×10(-7) for a 10-min preconcentration time at pH 6.0...
  51. Abdulmalik O, Ghatge M, Musayev F, Parikh A, Chen Q, Yang J, et al. Crystallographic analysis of human hemoglobin elucidates the structural basis of the potent and dual antisickling activity of pyridyl derivatives of vanillin. Acta Crystallogr D Biol Crystallogr. 2011;67:920-8 pubmed publisher
    ..These studies suggest that these compounds may act to prevent sickling of SS cells by increasing the fraction of the soluble high-affinity Hb S and/or by stereospecific inhibition of deoxygenated Hb S polymerization...
  52. Liu J, Zhou Y, Yi T, Zhao M, Xie N, Lei M, et al. Identification and role analysis of an intermediate produced by a polygenic mutant of Monascus pigments cluster in Monascus ruber M7. Appl Microbiol Biotechnol. 2016;100:7037-49 pubmed publisher
    ..The results in this study provide a line of action to unveil Monascus pigments biosynthesis pathway. ..
  53. Agus E, Lim M, Zhang L, Sedlak D. Odorous compounds in municipal wastewater effluent and potable water reuse systems. Environ Sci Technol. 2011;45:9347-55 pubmed publisher
    ..To avoid the presence of odorous compounds in drinking water derived from wastewater effluent, it is necessary to apply multiple barriers during advanced treatment or to dilute wastewater effluent with water from other sources...