Summary: An agent thought to have disinfectant properties and used as an expectorant. (From Martindale, The Extra Pharmacopoeia, 30th ed, p747)

Top Publications

  1. Chang S, Kang D. Alicyclobacillus spp. in the fruit juice industry: history, characteristics, and current isolation/detection procedures. Crit Rev Microbiol. 2004;30:55-74 pubmed
    ..The fruit juice industry has acknowledged Alicyclobacillus spp. as a major quality control target microorganism. Guaiacol and halophenols were identified as the offensive smelling agent in many Alicyclobacillus spp. related spoilage...
  2. Gocmen D, Elston A, Williams T, Parish M, Rouseff R. Identification of medicinal off-flavours generated by Alicyclobacillus species in orange juice using GC-olfactometry and GC-MS. Lett Appl Microbiol. 2005;40:172-7 pubmed
  3. Doerge D, Divi R, Churchwell M. Identification of the colored guaiacol oxidation product produced by peroxidases. Anal Biochem. 1997;250:10-7 pubmed
    Oxidation of guaiacol by peroxidases in the presence of H2O2 is the basis for a widely used colorimetric assay. However, the nature of the assay product, which has an absorption maximum around 470 nm, had not been determined...
  4. Mimurai T, Yazaki K, Sawaki K, Ozawa T, Kawaguchi M. Hydroxyl radical scavenging effects of guaiacol used in traditional dental pulp sedation: reaction kinetic study. Biomed Res. 2005;26:139-45 pubmed
    b>Guaiacol, which is a phenolic compound with a methoxy group and used in traditional dental pulp sedation, has the property of inducing cell proliferation...
  5. Ordoudi S, Tsimidou M, Vafiadis A, Bakalbassis E. Structure-DPPH* scavenging activity relationships: parallel study of catechol and guaiacol acid derivatives. J Agric Food Chem. 2006;54:5763-8 pubmed
    The scavenging behavior of a series of catechol and guaiacol acid derivatives toward DPPH(*) was examined having as a starting point the order of activity derived on the basis of theoretically calculated BDE values...
  6. Jhumur U, Dötterl S, Jürgens A. Naive and conditioned responses of Culex pipiens pipiens biotype molestus (Diptera: Culicidae) to flower odors. J Med Entomol. 2006;43:1164-70 pubmed
    ..These results indicate that naive mosquitoes are effectively attracted by appropriate floral scent compounds and that learning can increase the attractiveness of these compounds...
  7. Capeillere Blandin C. Oxidation of guaiacol by myeloperoxidase: a two-electron-oxidized guaiacol transient species as a mediator of NADPH oxidation. Biochem J. 1998;336 ( Pt 2):395-404 pubmed
    The present study was first aimed at a complete steady-state kinetic analysis of the reaction between guaiacol (2-methoxyphenol) and the myeloperoxidase (MPO)/H2O2 system, including a description of the isolation and purification of MPO ..
  8. Chun K, Kang J, Kim O, Kang H, Surh Y. Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin. J Environ Pathol Toxicol Oncol. 2002;21:131-9 pubmed
    ..These findings suggest that diarylheptanoids contained in Alpinia oxyphylla down-regulate COX-2 and iNOS expression through suppression of NF-kappaB activation in the TPA-treated mouse skin. ..
  9. Goto K, Nishibori A, Wasada Y, Furuhata K, Fukuyama M, Hara M. Identification of thermo-acidophilic bacteria isolated from the soil of several Japanese fruit orchards. Lett Appl Microbiol. 2008;46:289-94 pubmed publisher
    To investigate the occurrence and distribution of thermo-acidophilic bacteria (TAB) associated with various commercial fruit crop soils in Japan and to assess their ability to produce the odorous phenolic compound, guaiacol.

More Information

Publications110 found, 100 shown here

  1. Mageroy M, Tieman D, Floystad A, Taylor M, Klee H. A Solanum lycopersicum catechol-O-methyltransferase involved in synthesis of the flavor molecule guaiacol. Plant J. 2012;69:1043-51 pubmed publisher
    ..One such compound is guaiacol, a small volatile molecule with a smoky aroma that contributes to tomato flavor...
  2. Wong K, Cheung M, Au C, Kwan H. A novel Lentinula edodes laccase and its comparative enzymology suggest guaiacol-based laccase engineering for bioremediation. PLoS ONE. 2013;8:e66426 pubmed publisher
    ..On the other hand, correlation analyses revealed that guaiacol is much better associated with the decolorization of multiple structurally different dyes than are the two common ..
  3. Chen M, Qin X, Zeng G. Single-walled carbon nanotube release affects the microbial enzyme-catalyzed oxidation processes of organic pollutants and lignin model compounds in nature. Chemosphere. 2016;163:217-226 pubmed publisher
    ..of polycyclic aromatic hydrocarbons (benzo(a)pyrene, acenaphthene and anthracene), LMCs (2,6-dimethoxyphenol, guaiacol and veratryl alcohol) and ?-hexachlorocyclohexane, including the behaviour of water molecules, hydrogen bonds (..
  4. Rao B, Rao B, Aithal B, Kumar M. Radiomodifying and anticlastogenic effect of Zingerone on Swiss albino mice exposed to whole body gamma radiation. Mutat Res. 2009;677:33-41 pubmed publisher
  5. Velho A, Rockenbach M, Mondino P, Stadnik M. Modulation of oxidative responses by a virulent isolate of Colletotrichum fructicola in apple leaves. Fungal Biol. 2016;120:1184-93 pubmed publisher
    ..b>Guaiacol peroxidase, catalase, and glutathione reductase had activity peaks within 24 h after inoculation (HAI)...
  6. Pérez Romero J, Idaszkin Y, Duarte B, Baeta A, Marques J, Redondo Gómez S, et al. Atmospheric CO2 enrichment effect on the Cu-tolerance of the C4 cordgrass Spartina densiflora. J Plant Physiol. 2018;220:155-166 pubmed publisher
    ..the lower values of ETRmax/AN ratio, malondialdehyde (MDA) and ascorbate peroxidase (APx), guaiacol peroxidase (GPx) and superoxide dismutase (SOD) activities under Cu excess, which could indicate a lower ..
  7. Su M, Chen W, Lo T, Wu T. Ionic mechanisms for the antiarrhythmic action of cinnamophilin in rat heart. J Biomed Sci. 1999;6:376-86 pubmed
    ..These results indicate that the inhibition of I(Na), I(Ca) and I(to) may contribute to the antiarrhythmic activity of Cinn against ischemia-reperfusion arrhythmia. ..
  8. Armand C, Thirion X, Saillard C, Lapeyre Mestre M, Lambert H. [Neocodion misuse: evolution between 1992 and 2002]. Therapie. 2004;59:547-53 pubmed
    ..Despite the reduction in the consumption of Neocodion, the changes observed in the consumption patterns for this medication suggest that vigilance is still required. ..
  9. Li Z, Wang Q, Feng Y, Luo X, Fan M, Yang S. [Chemical constituents from Coptis chinensis]. Zhong Yao Cai. 2012;35:1438-41 pubmed
    ..Compounds (3) is isolated from this genus for the first time, compounds (5), (6), (7) are isolated from this plant for the first time. ..
  10. Songulashvili G, Flahaut S, Demarez M, Tricot C, Bauvois C, Debaste F, et al. High yield production in seven days of Coriolopsis gallica 1184 laccase at 50 L scale; enzyme purification and molecular characterization. Fungal Biol. 2016;120:481-488 pubmed publisher
    ..The lowest Km values (17 and 20 ?M) were found for ABTS and guaiacol, respectively. Coriolopsis gallica 1184 laccase was characterized by mass spectrometry and shows that C...
  11. Gebicka L. Kinetic studies on the oxidation of nitrite by horseradish peroxidase and lactoperoxidase. Acta Biochim Pol. 1999;46:919-27 pubmed
    ..of lactoperoxidase with typical substrates like 2,2'-azino-bis[ethyl-benzothiazoline-(6)-sulphonic acid] (ABTS), guaiacol or thiocyanate (SCN-)...
  12. Lee E, Chen H, Hung Y, Chen T, Lee M, Yu S, et al. Therapeutic window for cinnamophilin following oxygen-glucose deprivation and transient focal cerebral ischemia. Exp Neurol. 2009;217:74-83 pubmed publisher
    ..Together, CINN protects against ischemic brain damage with a therapeutic window up to 6 h in vivo and in vitro, which may, at least in part, be attributed by its direct antioxidant and anti-inflammatory effects. ..
  13. Dória M, Sousa A, Barbosa C, Costa M, Gesteira A, Souza R, et al. Citrus tristeza virus (CTV) Causing Proteomic and Enzymatic Changes in Sweet Orange Variety "Westin". PLoS ONE. 2015;10:e0130950 pubmed publisher
    ..The activity of guaiacol peroxidase (GPX) did not vary significantly between samples...
  14. Spanic V, Viljevac Vuletic M, Abicic I, Marcek T. Early response of wheat antioxidant system with special reference to Fusarium head blight stress. Plant Physiol Biochem. 2017;115:34-43 pubmed publisher
    ..Moderately FHB resistant variety 'Kraljica' showed the higher guaiacol peroxidase (POD) activity and higher H2O2 content after 24 hai, increased malondialdehyde (..
  15. Murciano Martínez P, Punt A, Kabel M, Gruppen H. Deconstruction of lignin linked p-coumarates, ferulates and xylan by NaOH enhances the enzymatic conversion of glucan. Bioresour Technol. 2016;216:44-51 pubmed publisher
    ..compounds were assigned as p-coumarates and ferulates, analysed by pyrolysis-GC/MS as 4-vinyl phenol and 4-vinyl guaiacol, and designated as non-core lignin (NCL) compounds...
  16. Liu L, Simon S. The influence of removing extracellular Ca2+ in the desensitization responses to capsaicin, zingerone and olvanil in rat trigeminal ganglion neurons. Brain Res. 1998;809:246-52 pubmed
    ..These data analyses suggest the existence of calcium-independent pathways that can result in desensitization, and that pungency is not related to the phenomenon of desensitization. ..
  17. Reyes Melo K, Garcia A, Romo Mancillas A, Garza Gonzalez E, Rivas Galindo V, Miranda L, et al. meso-Dihydroguaiaretic acid derivatives with antibacterial and antimycobacterial activity. Bioorg Med Chem. 2017;25:5247-5259 pubmed publisher
    ..The amino-ether 31 exhibited a selectivity index value of 23, which indicate it was more toxic to M. tuberculosis than to mammalian cells. Therefore, 31 can be considered as a promising antitubercular agent for further studies. ..
  18. Matsubara H, Goto K, Matsumura T, Mochida K, Iwaki M, Niwa M, et al. Alicyclobacillus acidiphilus sp. nov., a novel thermo-acidophilic, omega-alicyclic fatty acid-containing bacterium isolated from acidic beverages. Int J Syst Evol Microbiol. 2002;52:1681-5 pubmed
    A novel thermo-acidophilic bacterium was isolated from an acidic beverage that had the odour of guaiacol. The cells are aerobic, gram-positive, spore-forming rods...
  19. Michałowicz J, Stufka Olczyk J, Milczarek A, Michniewicz M. Analysis of annual fluctuations in the content of phenol, chlorophenols and their derivatives in chlorinated drinking waters. Environ Sci Pollut Res Int. 2011;18:1174-83 pubmed publisher
    ..In this work, we analyzed annual fluctuations in the content of phenol, guaiacol, chlorophenols, chlorocatechols, and chlorinated methoxyphenols in drinking water collected in Warsaw and Tomaszó..
  20. Ubeda C, Callejón R, Troncoso A, Moreno Rojas J, Peña F, Morales M. A comparative study on aromatic profiles of strawberry vinegars obtained using different conditions in the production process. Food Chem. 2016;192:1051-9 pubmed publisher
    ..All strawberry vinegars retained certain impact odorants from strawberries: 3-nonen-2-one, (E,E)-2,4-decadienal, guaiacol, nerolidol, pantolactone+furaneol, eugenol, γ-dodecalactone and phenylacetic acid...
  21. Lettera V, Pezzella C, Cicatiello P, Piscitelli A, Giacobelli V, Galano E, et al. Efficient immobilization of a fungal laccase and its exploitation in fruit juice clarification. Food Chem. 2016;196:1272-8 pubmed publisher
    ..Furthermore, laccase treated juice displays an improved sensory profile, due to the reduction of vinyl guaiacol, a potent off-flavor possessing a peppery/spicy aroma.
  22. Hong E, Park J, Yoo I, Ryu K. Effects of structural difference of ionic liquids on the catalysis of horseradish peroxidase. J Microbiol Biotechnol. 2009;19:713-7 pubmed
    ..The oxidation of guaiacol (2-methoxyphenol) with H2O2 was used as a model reaction...
  23. Sánchez Rojo S, Cerda García Rojas C, Esparza García F, Plasencia J, Poggi Varaldo H, Ponce Noyola T, et al. Long-term response on growth, antioxidant enzymes, and secondary metabolites in salicylic acid pre-treated Uncaria tomentosa microplants. Biotechnol Lett. 2015;37:2489-96 pubmed publisher
    ..Both pre-treatments enhanced H2O2 and inhibited superoxide dismutase and catalase activities, while guaiacol peroxidase was increased only with 1 µM SA...
  24. Kaur R, Yadav P, Thukral A, Walia A, Bhardwaj R. Co-application of 6-ketone type brassinosteroid and metal chelator alleviates cadmium toxicity in B. juncea L. Environ Sci Pollut Res Int. 2017;24:685-700 pubmed publisher 39 % and reduced oxidative stress by enhancing the activities of antioxidant enzymes (superoxide dismutase, guaiacol peroxidase, catalase, ascorbate peroxidase, dehydroascorbate, glutathione reductase, glutathione peroxidase, ..
  25. Yamauchi S, Masuda T, Sugahara T, Kawaguchi Y, Ohuchi M, Someya T, et al. Antioxidant activity of butane type lignans, secoisolariciresinol, dihydroguaiaretic acid, and 7,7'-oxodihydroguaiaretic acid. Biosci Biotechnol Biochem. 2008;72:2981-6 pubmed
    ..SECO and DGA inhibited the oxidation of unsaturated fatty acid. Both enantiomers of DGA were also lipoxygenase inhibitors, but neither enantiomer of SECO inhibited the lipoxygenase activity. ..
  26. Pérez M, García M, Blustein G. Evaluation of low copper content antifouling paints containing natural phenolic compounds as bioactive additives. Mar Environ Res. 2015;109:177-84 pubmed publisher
    ..In the current study, we investigated the use of thymol, eugenol and guaiacol in this role combined with small quantities of copper...
  27. Li J, Zhang Y, Peng J, Wu X, Gao S, Mao L. The effect of dissolved organic matter on soybean peroxidase-mediated removal of triclosan in water. Chemosphere. 2017;172:399-407 pubmed publisher
    ..Cross-coupling between TCS and DOM was also verified using guaiacol as a model DOM constituent...
  28. Fernandez P, Gabaldon J, Periago M. Detection and quantification of Alicyclobacillus acidoterrestris by electrical impedance in apple juice. Food Microbiol. 2017;68:34-40 pubmed publisher
    ..In addition, a positive correlation (r = 0.98, R2 = 0.97) was observed between the classical microbiology (BAM agar) and the indirect impedance method. ..
  29. Michałowicz J, Duda W, Stufka Olczyk J. Transformation of phenol, catechol, guaiacol and syringol exposed to sodium hypochlorite. Chemosphere. 2007;66:657-63 pubmed
    ..The purpose of this work was to analyse the efficiency of transformation of phenol, catechol, guaiacol and syringol exposed to sodium hypochlorite and determine the intermediates formed during oxidative conversion of ..
  30. Jeong J, Hong S, Jeong H, Koo J. Anti-inflammatory effect of 2-methoxy-4-vinylphenol via the suppression of NF-?B and MAPK activation, and acetylation of histone H3. Arch Pharm Res. 2011;34:2109-16 pubmed publisher
    ..7 cells. These effects are mediated by suppression of NF-?B and MAPK activation and histone acetylation. ..
  31. Kitanovski Z, Grgic I, Yasmeen F, Claeys M, Cusak A. Development of a liquid chromatographic method based on ultraviolet-visible and electrospray ionization mass spectrometric detection for the identification of nitrocatechols and related tracers in biomass burning atmospheric organic aerosol. Rapid Commun Mass Spectrom. 2012;26:793-804 pubmed publisher
    ..The LC/MS peak intensity of the newly detected methyl nitrocatechols and nitroguaiacols is comparable to that of the methyl nitrocatechols, which also qualifies them as suitable molecular tracers for secondary biomass burning aerosol. ..
  32. Takahashi M, Sakamaki S, Fujita A. Simultaneous analysis of guaiacol and vanillin in a vanilla extract by using high-performance liquid chromatography with electrochemical detection. Biosci Biotechnol Biochem. 2013;77:595-600 pubmed
    We developed and validated a new high-performance liquid chromatographic analysis for electrochemically detecting guaiacol and vanillin as important components in vanilla extract...
  33. Hasebe A, Nishiwaki H, Akiyama K, Sugahara T, Kishida T, Yamauchi S. Quantitative structure-activity relationship analysis of antifungal (+)-dihydroguaiaretic acid using 7-phenyl derivatives. J Agric Food Chem. 2013;61:8548-55 pubmed publisher
    ..The whitening activity of 3-hydroxy-4-methoxyphenyl derivative 28, 3-hydroxy-4-ethoxyphenyl derivative 29, and 3-hydroxy-4-isopropoxyphenyl derivative 30 against A. alternata Japanese pear pathotype was also discovered. ..
  34. Jensen N, Varelis P, Whitfield F. Formation of guaiacol in chocolate milk by the psychrotrophic bacterium Rahnella aquatilis. Lett Appl Microbiol. 2001;33:339-43 pubmed
    ..The aim of this study was to identify the causative agent of a smoky/phenolic taint in refrigerated full cream chocolate milk...
  35. Fernandez García A, Butz P, Tauscher B. Mechanism-based irreversible inactivation of horseradish peroxidase at 500 MPa. Biotechnol Prog. 2002;18:1076-81 pubmed
    The effects of high-pressure treatment on the reaction rates of horseradish peroxidase (HRP) with guaethol or guaiacol as a hydrogen donor were evaluated from direct transmission measurements in a high-pressure optical cell at 435 nm...
  36. Tikunov Y, Molthoff J, De Vos R, Beekwilder J, van Houwelingen A, van der Hooft J, et al. Non-smoky glycosyltransferase1 prevents the release of smoky aroma from tomato fruit. Plant Cell. 2013;25:3067-78 pubmed publisher
    ..NSGT1 may be used in a precision breeding strategy toward development of tomato fruits with distinct flavor phenotypes. ..
  37. Diederix R, Fittipaldi M, Worrall J, Huber M, Ubbink M, Canters G. Kinetic stability of the peroxidase activity of unfolded cytochrome c: heme degradation and catalyst inactivation by hydrogen peroxide. Inorg Chem. 2003;42:7249-57 pubmed
    ..e. with heme hydroxylated at one of the heme meso positions. The occurrence of this species argues for the peroxo-iron species in the peroxidase mechanism as the labile intermediate leading to inactivated cytochrome c-550. ..
  38. Shi X, Liu Q, Ma J, Liao H, Xiong X, Zhang K, et al. An acid-stable bacterial laccase identified from the endophyte Pantoea ananatis Sd-1 genome exhibiting lignin degradation and dye decolorization abilities. Biotechnol Lett. 2015;37:2279-88 pubmed publisher
    ..5 and for guaiacol at pH 4.5 were 1 ± 0.15 and 6.1 ± 1.7 mM, respectively...
  39. Fukumori R, Nakamichi N, Takarada T, Kambe Y, Matsushima N, Moriguchi N, et al. Inhibition by 2-methoxy-4-ethylphenol of Ca2+ influx through acquired and native N-methyl-D-aspartate-receptor channels. J Pharmacol Sci. 2010;112:273-81 pubmed
    ..These results suggest that 2M4EP may protect neurons from excitotoxicity through inhibition of Ca(2+) influx across NMDAR channels composed of NR1/NR2B, rather than NR1/NR2A, subunits. ..
  40. Matsuo T, Fukumoto K, Watanabe T, Hayashi T. Precise design of artificial cofactors for enhancing peroxidase activity of myoglobin: myoglobin mutant H64D reconstituted with a "single-winged cofactor" is equivalent to native horseradish peroxidase in oxidation activity. Chem Asian J. 2011;6:2491-9 pubmed publisher
  41. Slaghenaufi D, Perello M, Marchand S, De Revel G. Quantification of megastigmatrienone, a potential contributor to tobacco aroma in spirits. Food Chem. 2016;203:41-48 pubmed publisher
    ..was adapted and validated in order to quantify 5 megastigmatrienones and related odorous compounds from oak wood: guaiacol, cis-whisky lactone, trans-whisky lactone, γ-nonalactone, eugenol, vanillin, and acetovanillone in a single ..
  42. Basiglini E, Pintore M, Forni C. Effects of treated industrial wastewaters and temperatures on growth and enzymatic activities of duckweed (Lemna minor L.). Ecotoxicol Environ Saf. 2018;153:54-59 pubmed publisher
    ..concentrations were determined, as well as the activities of catalase (CAT), ascorbate peroxidase (APX), guaiacol peroxidase (G-POD) and polyphenol oxidase (PPO)...
  43. Hsiao G, Teng C, Sheu J, Cheng Y, Lam K, Lee Y, et al. Cinnamophilin as a novel antiperoxidative cytoprotectant and free radical scavenger. Biochim Biophys Acta. 2001;1525:77-88 pubmed
    ..Furthermore, cinnamophilin exerted a divergent effect on the respiratory burst of human neutrophil by different stimulators. Our results show that cinnamophilin acts as a novel antioxidant and cytoprotectant against oxidative damage. ..
  44. Hsiang C, Lo H, Huang H, Li C, Wu S, Ho T. Ginger extract and zingerone ameliorated trinitrobenzene sulphonic acid-induced colitis in mice via modulation of nuclear factor-?B activity and interleukin-1? signalling pathway. Food Chem. 2013;136:170-7 pubmed publisher
    ..In conclusion, ginger improved TNBS-induced colitis via modulation of NF-?B activity and IL-1? signalling pathway. Moreover, zingerone might be the active component of ginger responsible for the amelioration of colitis induced by TNBS...
  45. Pollnitz A, Pardon K, Sykes M, Sefton M. The effects of sample preparation and gas chromatograph injection techniques on the accuracy of measuring guaiacol, 4-methylguaiacol and other volatile oak compounds in oak extracts by stable isotope dilution analyses. J Agric Food Chem. 2004;52:3244-52 pubmed
    The deuterium-labeled standards [(2)H(3)]-guaiacol and [(2)H(3)]-4-methylguaiacol were synthesized and utilized in a method employing gas chromatography-mass spectrometry to determine the concentration of guaiacol and 4-methylguaiacol in ..
  46. Kim Y, Song Y, Seo D, Kang D, Lee H, Rhee D, et al. Reversal of multidrug resistance by 4-chloro-N-(3-((E)-3-(4-hydroxy-3-methoxyphenyl)acryloyl)phenyl)benzamide through the reversible inhibition of P-glycoprotein. Biochem Biophys Res Commun. 2007;355:136-42 pubmed
    ..Collectively, our results describe the potential of C-4 to reverse the P-gp-mediated MDR phenotype through reversible inhibition of P-gp function, which may make it an attractive new agent for the chemosensitization of cancer cells. ..
  47. Lee W, Ku S, Bae J. Zingerone reduces HMGB1-mediated septic responses and improves survival in septic mice. Toxicol Appl Pharmacol. 2017;329:202-211 pubmed publisher
    ..In addition, treatment with ZGR reduced the CLP-induced release of HMGB1, sepsis-related mortality, and tissue injury in vivo. Our results indicated that ZGR might be useful in the treatment of sepsis by targeting HMGB1. ..
  48. Green B. Rapid recovery from capsaicin desensitization during recurrent stimulation. Pain. 1996;68:245-53 pubmed
    ..The implications these findings may have for hypotheses about the mechanisms of capsaicin desensitization and sensitization as well as for clinical applications of capsaicin as a topical analgesic are discussed. ..
  49. Gill K, Arora S. Effect of culture conditions on manganese peroxidase production and activity by some white rot fungi. J Ind Microbiol Biotechnol. 2003;30:28-33 pubmed
    ..Studies on enzyme production under different nutritional conditions revealed veratryl alcohol, guaiacol, Reax 80 and Polyfon H to be excellent MnP inducers.
  50. Selenski C, Pettus T. Enantioselective [4 + 2] cycloadditions of o-quinone methides: total synthesis of (+)-mimosifoliol and formal synthesis of (+)-tolterodine. J Org Chem. 2004;69:9196-203 pubmed
    ..Cycloadditions of various enol ethers and o-QMs are examined, and diastereoselectivities >95% are obtained with trans-2-phenyl-1-cyclohexanol and 2,2-diphenylcyclopentanol vinyl ethers. ..
  51. Härtl K, Huang F, Giri A, Franz Oberdorf K, Frotscher J, Shao Y, et al. Glucosylation of Smoke-Derived Volatiles in Grapevine (Vitis vinifera) is Catalyzed by a Promiscuous Resveratrol/Guaiacol Glucosyltransferase. J Agric Food Chem. 2017;65:5681-5689 pubmed publisher
    ..specificity constants (kcat/KM) of 114, 17, 9, 8, and 2 mM-1 s-1 for guaiacol, trans-resveratrol, syringol, methylsyringol, and methylguaiacol, respectively...
  52. Tantishaiyakul V, Wiwattanawongsa K, Pinsuwan S, Kasiwong S, Phadoongsombut N, Kaewnopparat S, et al. Characterization of mefenamic acid-guaiacol ester: stability and transport across Caco-2 cell monolayers. Pharm Res. 2002;19:1013-8 pubmed
    Prodrug of non-steroidal anti-inflammatory drugs (NSAIDs) or NSAIDs linked with guaiacol have been reported to suppress gastrointestinal (GI) toxicity or induce GI protective effect. In this study...
  53. Kellner H, Luis P, Buscot F. Diversity of laccase-like multicopper oxidase genes in Morchellaceae: identification of genes potentially involved in extracellular activities related to plant litter decay. FEMS Microbiol Ecol. 2007;61:153-63 pubmed
    ..showed the strongest LMCO activity enhancement in the presence of the naturally occurring phenolic compound guaiacol, and their expressed LMCO genes were identified by sequencing...
  54. Berna A, Trowell S, Cynkar W, Cozzolino D. Comparison of metal oxide-based electronic nose and mass spectrometry-based electronic nose for the prediction of red wine spoilage. J Agric Food Chem. 2008;56:3238-44 pubmed publisher
    ..It is concluded that, following ethanol removal, existing metal oxide sensors are sufficiently sensitive to detect brett taints in wine but lack the selectivity needed to perform this task when the aroma volatile background varies. ..
  55. Kennison K, Gibberd M, Pollnitz A, Wilkinson K. Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke. J Agric Food Chem. 2008;56:7379-83 pubmed publisher
    ..The concentrations of guaiacol, 4-methylguaiacol, 4-ethylguaiacol, 4-ethylphenol, and eugenol were determined by gas chromatography-mass ..
  56. Shimizu S, Yokoyama T, Akiyama T, Matsumoto Y. Reactivity of lignin with different composition of aromatic syringyl/guaiacyl structures and erythro/threo side chain structures in ?-O-4 type during alkaline delignification: as a basis for the different degradability of hardwood and softwood lignin. J Agric Food Chem. 2012;60:6471-6 pubmed publisher
    ..The effect of syringyl nucleus on the enhancement of the reaction rate appeared to be greater when the syringyl nucleus consists of the cleaving ether bond rather than being a member of the carbon framework. ..
  57. Nathwani S, Hughes L, Greene L, Carr M, O Boyle N, McDonnell S, et al. Novel cis-restricted ?-lactam combretastatin A-4 analogues display anti-vascular and anti-metastatic properties in vitro. Oncol Rep. 2013;29:585-94 pubmed publisher
  58. Ma C, Kim S, Kim J, Kim Y. Meso-dihydroguaiaretic acid and licarin A of Machilus thunbergii protect against glutamate-induced toxicity in primary cultures of a rat cortical cells. Br J Pharmacol. 2005;146:752-9 pubmed
    ..5 Thus, our results suggest that MDGA and licarin A significantly protect primary cultured neuronal cells against glutamate-induced oxidative stress, via antioxidative activities. ..
  59. Harris V, Ford C, Jiranek V, Grbin P. Dekkera and Brettanomyces growth and utilisation of hydroxycinnamic acids in synthetic media. Appl Microbiol Biotechnol. 2008;78:997-1006 pubmed publisher
    ..This study provides an insight into the spoilage potential of these organisms and possible control strategies involving hydroxycinnamic acids. ..
  60. Wang L, Zhang C, Wang Z, Zhang M, Shao L, Xu L. [Studies on chemical constituents of Dendrobium crystallinum]. Zhongguo Zhong Yao Za Zhi. 2008;33:1847-8 pubmed
    ..All these compounds were obtained from this plant for the first time, compounds 1 and 4 were isolated firstly from the genus. ..
  61. Jiang C, Ling S, Wang P, Liang A, Chen B, Wen G, et al. A new and sensitive catalytic resonance scattering spectral assay for the detection of laccase using guaiacol as substrate. Luminescence. 2011;26:500-5 pubmed publisher
    In pH 4.0 succinic acid-sodium hydroxide buffer solution, laccase catalyzed the oxidization of guaiacol substrate to form red particles, which exhibited a strong resonance scattering (RS) peak at 590 nm...
  62. Osopale B, Witthuhn C, Albertyn J, Oguntoyinbo F. Culture dependent and independent genomic identification of Alicyclobacillus species in contaminated commercial fruit juices. Food Microbiol. 2016;56:21-8 pubmed publisher
    ..endospore-forming, bacteria species which occasionally cause spoilage of heat-processed fruit juices by producing guaiacol taint...
  63. Yu S, Ko F, Wu T, Lee J, Teng C. Cinnamophilin, a novel thromboxane A2 receptor antagonist, isolated from Cinnamomum philippinense. Eur J Pharmacol. 1994;256:85-91 pubmed
    ..These results indicate that cinnamophilin is a selective thromboxane A2 receptor antagonist especially in rat aorta, and also possesses voltage-dependent Ca2+ channel blocking properties. ..
  64. Freyberger A, Ahr H. Studies on the goitrogenic mechanism of action of N,N,N',N'-tetramethylthiourea. Toxicology. 2006;217:169-75 pubmed
    ..propylthiouracil (PTU), and like ethylenethiourea (ETU), TMTU only marginally affected TPO-catalyzed oxidation of guaiacol. TMTU, like ETU, concentration-dependently suppressed TPO-catalyzed iodine formation with concomitant oxidative ..
  65. Lin C, Kuo S, Huang L, Gean P. Neuroprotective effect of N-acetylcysteine on neuronal apoptosis induced by a synthetic gingerdione compound: involvement of ERK and p38 phosphorylation. J Neurosci Res. 2006;84:1485-94 pubmed
    ..These results show that NAC serially activates ERKs and p38 MAPK, and ERKs and p38 work together to mediate the neuroprotective effect of NAC. ..
  66. Wang Z, Lin Y, Rosell F, Ni F, Lu H, Yang P, et al. Converting cytochrome C into a peroxidase-like metalloenzyme by molecular design. Chembiochem. 2007;8:607-9 pubmed
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    ..obtained by biomimetic oxidative coupling of caffeic acid derivatives, react efficiently with peroxyl radicals in both polar and non-polar solvents, thanks to the simultaneous presence of guaiacol-like and catechol-like OH-groups.
  68. Greene L, Carr M, Keeley N, Lawler M, Meegan M, Zisterer D. BubR1 is required for the mitotic block induced by combretastatin-A4 and a novel cis-restricted ß-lactam analogue in human cancer cells. Int J Mol Med. 2011;27:715-23 pubmed publisher
    ..Moreover, substitution of the ethylene bridge with 3,4-diaryl-2-azetidinone did not alter the tubulin depolymerising properties or the subsequent mitotic spindle checkpoint response to CA-4 in human cancer cells. ..
  69. Park J, Yoo I, Kwon O, Ryu K. Partial uncompetitive inhibition of horseradish peroxidase by a water-miscible ionic liquid [BMIM][MeSO4]. Biotechnol Lett. 2011;33:1657-62 pubmed publisher
    ..The ionic liquid decreased both K(m) and k(cat) values for the HRP-catalyzed oxidation of guaiacol (2-methoxyphenol) by H(2)O(2)...
  70. Iwami M, Shiina T, Hirayama H, Shimizu Y. Intraluminal administration of zingerol, a non-pungent analogue of zingerone, inhibits colonic motility in rats. Biomed Res. 2011;32:181-5 pubmed
    ..The non-pungent property of zingerol will be useful as an oral or suppository medicine for treating diarrhea and other gastrointestinal disorders. ..
  71. Stanzione J, Sadler J, La Scala J, Wool R. Lignin model compounds as bio-based reactive diluents for liquid molding resins. ChemSusChem. 2012;5:1291-7 pubmed publisher
    ..The single aromatic lignin model compounds, vanillin, guaiacol, and eugenol, were methacrylated by esterification with methacrylic anhydride and a catalytic amount of 4-..
  72. Gröblacher B, Maier V, Kunert O, Bucar F. Putative mycobacterial efflux inhibitors from the seeds of Aframomum melegueta. J Nat Prod. 2012;75:1393-9 pubmed publisher
    ..6-Paradol (3), 8-gingerol (6), and rac-6-dihydroparadol (7) were the most potent EtBr efflux inhibitors in M. smegmatis mc(2) 155, displaying EtBr efflux inhibiting activities comparable to reference inhibitors...
  73. Diederix R, Ubbink M, Canters G. The peroxidase activity of cytochrome c-550 from Paracoccus versutus. Eur J Biochem. 2001;268:4207-16 pubmed
    ..Steady-state conversion of a reducing substrate, guaiacol, is preceded by an activation phase, which is ascribed to the build-up of amino-acid radicals on the protein...
  74. Flynn B, Flynn G, Hamel E, Jung M. The synthesis and tubulin binding activity of thiophene-based analogues of combretastatin A-4. Bioorg Med Chem Lett. 2001;11:2341-3 pubmed
    ..Overall they are less active than 1 but exhibit comparable activity to the most active of the benzo[b]thiophenes 3-5. A structure-activity relationship of these compounds is considered. ..
  75. Samet Y, Elaoud S, Ammar S, Abdelhedi R. Electrochemical degradation of 4-chloroguaiacol for wastewater treatment using PbO2 anodes. J Hazard Mater. 2006;138:614-9 pubmed
    ..However, the increase of temperature has not a significant effect on the mineralization of carboxylic acids. Moreover, these products required long electrolysis time. ..
  76. Anderson K, Jaquinod L, Jensen M, Ngo N, Davis R. A novel catechol-based universal support for oligonucleotide synthesis. J Org Chem. 2007;72:9875-80 pubmed
    ..The flexibility of the universal support and the efficiency of 3'-dephosphorylation are expected to increase the use of universal supports in oligonucleotide synthesis. ..
  77. Katsuyama Y, Ohnishi Y, Horinouchi S. Production of dehydrogingerdione derivatives in Escherichia coli by exploiting a curcuminoid synthase from Oryza sativa and a ?-oxidation pathway from Saccharomyces cerevisiae. Chembiochem. 2010;11:2034-41 pubmed publisher
    ..sativa. To our knowledge, this is the first report of the microbial production of a plant metabolite the biosynthetic pathway of which has not yet been identified. ..
  78. Fudge A, Wilkinson K, Ristic R, Cozzolino D. Synchronous two-dimensional MIR correlation spectroscopy (2D-COS) as a novel method for screening smoke tainted wine. Food Chem. 2013;139:115-9 pubmed publisher
    ..2D-COS analysis was used to generate synchronous data maps for red and white cask wines spiked with guaiacol, a marker of smoke taint...
  79. Pérez Galende P, Hidalgo Cuadrado N, Kostetsky E, Roig M, Villar E, Shnyrov V, et al. Kinetics of Spanish broom peroxidase obeys a Ping-Pong Bi-Bi mechanism with competitive inhibition by substrates. Int J Biol Macromol. 2015;81:1005-11 pubmed publisher
  80. Wang L, Zhang M, Zhang C, Wang Z. Alkaloid and sesquiterpenes from the root tuber of Curcuma longa. Yao Xue Xue Bao. 2008;43:724-7 pubmed
    ..Their structures were identified by spectral evidence. Compound 1 is a new compound, compounds 6 -8 were isolated from this plant for the first time and compounds 9 - 10 from Curcuma for the first time. ..
  81. Baqueiro Peña I, Rodríguez Serrano G, González Zamora E, Augur C, Loera O, Saucedo Castañeda G. Biotransformation of ferulic acid to 4-vinylguaiacol by a wild and a diploid strain of Aspergillus niger. Bioresour Technol. 2010;101:4721-4 pubmed publisher
    ..Differential regulation of enzymes involved in the biotransformation of ferulic acid may explain the accumulation of 4VG by diploid DAR2. This strain produced both 4VG and VA. ..
  82. Iwami M, Mahmoud F, Shiina T, Hirayama H, Shima T, Sugita J, et al. Extract of grains of paradise and its active principle 6-paradol trigger thermogenesis of brown adipose tissue in rats. Auton Neurosci. 2011;161:63-7 pubmed publisher
    ..These results demonstrate that GP extracts and 6-paradol activate thermogenesis in brown adipose tissue, and may open up new avenues for the regulation of weight loss and weight maintenance. ..
  83. Koeduka T, Watanabe B, Suzuki S, Hiratake J, Mano J, Yazaki K. Characterization of raspberry ketone/zingerone synthase, catalyzing the alpha, beta-hydrogenation of phenylbutenones in raspberry fruits. Biochem Biophys Res Commun. 2011;412:104-8 pubmed publisher
    ..We conclude that RZS1 is responsible for hydrogenation of the ?,?-unsaturated double bond of phenylbutenones, the final step of the raspberry ketone biosynthesis, in the raspberry fruits. ..
  84. Yue H, Jiang C, Fujita T, Kumamoto E. Zingerone enhances glutamatergic spontaneous excitatory transmission by activating TRPA1 but not TRPV1 channels in the adult rat substantia gelatinosa. J Neurophysiol. 2013;110:658-71 pubmed publisher
  85. Liu L, Simon S. Similarities and differences in the currents activated by capsaicin, piperine, and zingerone in rat trigeminal ganglion cells. J Neurophysiol. 1996;76:1858-69 pubmed
    ..Their different physiological responses evoked by these compounds can be rationalized, in part, by their very different activation and desensitization kinetics, and perhaps by the existence of different subtypes of vanilloid receptors. ..
  86. Gebicka L, Gebicki J. Reactions of heme peroxidases with peroxynitrite. IUBMB Life. 2000;49:11-5 pubmed
    ..For example, in the presence of guaiacol the catalyzing effect was clear, but in the presence of trolox was only noticeable.
  87. Jelen H, Krawczyk J, Larsen T, Jarosz A, Gołebniak B. Main compounds responsible for off-odour of strawberries infected by Phytophthora cactorum. Lett Appl Microbiol. 2005;40:255-9 pubmed
    ..cactorum: 4-ethyl phenol and 4-ethyl-2-metoxy phenol (4-ethyl guaiacol). The content of these compounds in infected varieties ranged from 1.12 to 22.56 mg kg(-1) and 0.14-1...
  88. Guchu E, Díaz Maroto M, Díaz Maroto I, Vila Lameiro P, Pérez Coello M. Influence of the species and geographical location on volatile composition of Spanish oak wood (Quercus petraea Liebl. and Quercus robur L.). J Agric Food Chem. 2006;54:3062-6 pubmed
    ..Other important volatile components were furfural, 5-methylfurfural, guaiacol, eugenol, vanillin, or syringaldehyde...
  89. Helal M, Al Mudaris Z, Al Douh M, Osman H, Wahab H, Alnajjar B, et al. Diaminobenzene schiff base, a novel class of DNA minor groove binder. Int J Oncol. 2012;41:504-10 pubmed publisher
    ..Neither compound showed any significant cytotoxicity towards human breast, colon or liver cancer cell lines. ..
  90. Lu Y, Hsiao G, Lin K, Hsieh M, Jayakumar T, Wu T, et al. Cinnamophilin isolated from Cinnamomum philippinense protects against collagen degradation in human chondrocytes. Phytother Res. 2013;27:892-9 pubmed publisher
    ..Furthermore, these findings suggest that cinnamophilin may have the potential for chondroprotection against collagen matrix breakdown in cartilage of diseased tissues such as those found in arthritic disorders...
  91. Wukirsari T, Nishiwaki H, Hasebe A, Shuto Y, Yamauchi S. First discovery of insecticidal activity of 9,9'-epoxylignane and dihydroguaiaretic acid against houseflies and the structure-activity relationship. J Agric Food Chem. 2013;61:4318-25 pubmed publisher
    ..The activity of 1 was weaker than that of (-)-(8R,8'R)-dihydroguaiaretic acid ((-)-DGA) (4); however, compound 21 showed almost the same level of activity as 4. ..
  92. Dean J, Navotnaya P, Parobek A, Clayton R, Zwier T. Ultraviolet spectroscopy of fundamental lignin subunits: guaiacol, 4-methylguaiacol, syringol, and 4-methylsyringol. J Chem Phys. 2013;139:144313 pubmed publisher
    Ultraviolet spectroscopy of the G- and S-type lignin subunits, guaiacol (G) and syringol (S), along with their para-methylated derivatives 4-methylguaiacol (4-MG) and 4-methylsyringol (4-MS), has been carried out in the cold, isolated ..