2,6-Dimethoxyphenol (BioDeep_00000002660)

 

Secondary id: BioDeep_00001871703

human metabolite blood metabolite natural product


代谢物信息卡片


2,6-Dimethoxyphenol (syringol)

化学式: C8H10O3 (154.063)
中文名称: 2,6-二甲氧基苯酚
谱图信息: 最多检出来源 Homo sapiens(blood) 84.74%

分子结构信息

SMILES: COC1=C(C(=CC=C1)OC)O
InChI: InChI=1S/C8H10O3/c1-10-6-4-3-5-7(11-2)8(6)9/h3-5,9H,1-2H3

描述信息

2,6-Dimethoxyphenol, also known as syringol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2,6-Dimethoxyphenol is a bacon, balsamic, and medicine tasting compound.
Isolated from maople syrup. Flavouring ingredient.

同义名列表

17 个代谢物同义名

2,6-Dimethoxyphenol (syringol); 1,3-Dimethoxy-2-hydroxybenzene; 2-Hydroxy-1,3-dimethoxybenzene; Pyrogallol 1,3-dimethyl ether; 1,3-Dimethyl pyrogallic acid; 1,3-Di-O-methylpyrogallol; 1,3-Dimethyl pyrogallate; Pyrogallol dimethylether; 2,6-Dimethoxy-phenol; 2,6-DIMETHOXYPHENOL; 2,6-Dwumetoksyfenol; 2,6-Dimethoxyphenyl; dimethoxyphenol; FEMA 3137; syringol; Aldrich; 2,6-Dimethoxyphenol



数据库引用编号

22 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

32 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 12 ALOX5, AOX1, BLNK, CA2, CAT, COPA, GZMB, KAT5, LMLN, PFDN5, TCF3, TYR
Peripheral membrane protein 4 ALOX5, COPA, CYP1B1, MBP
Endoplasmic reticulum membrane 2 COPA, CYP1B1
Nucleus 5 GZMB, KAT5, MBP, PFDN5, TCF3
cytosol 13 ALOX5, AOX1, BLNK, CA2, CAT, COPA, GZMB, KAT5, LIPE, LMLN, MBP, PFDN5, TCF3
nucleoplasm 3 ALOX5, KAT5, TCF3
RNA polymerase II transcription regulator complex 1 TCF3
Cell membrane 3 BLNK, CA2, LIPE
Cytoplasmic side 2 COPA, MBP
Multi-pass membrane protein 3 F2RL1, SLC9C1, TMEM245
Golgi apparatus membrane 1 COPA
Synapse 1 MBP
cell surface 1 MBP
Golgi apparatus 1 F2RL1
Golgi membrane 1 COPA
growth cone 1 COPA
lysosomal membrane 1 CP
neuronal cell body 1 MBP
Cytoplasm, cytosol 2 ALOX5, LIPE
Lysosome 2 CTSV, TYR
plasma membrane 6 BLNK, CA2, CP, F2RL1, MBP, SLC9C1
Membrane 10 BLNK, CAT, COPA, CYP1B1, F2RL1, GZMB, LIPE, LMLN, SLC9C1, TMEM245
caveola 1 LIPE
extracellular exosome 6 AOX1, CA2, CAT, COPA, CP, MBP
extracellular space 4 ALOX5, COPA, CP, CTSV
lysosomal lumen 1 CTSV
perinuclear region of cytoplasm 3 ALOX5, KAT5, TYR
mitochondrion 2 CAT, CYP1B1
protein-containing complex 3 CAT, MBP, TCF3
intracellular membrane-bounded organelle 6 BLNK, CAT, CYP1B1, GZMB, KAT5, TYR
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 1 TYR
Secreted 2 CP, GZMB
extracellular region 6 ALOX5, CAT, CP, CTSV, GZMB, MBP
mitochondrial matrix 1 CAT
transcription regulator complex 2 KAT5, TCF3
motile cilium 1 SLC9C1
Nucleus membrane 1 ALOX5
nuclear membrane 1 ALOX5
nucleolus 1 KAT5
Melanosome membrane 1 TYR
Early endosome 1 F2RL1
apical part of cell 1 CA2
Golgi-associated vesicle 1 TYR
Cytoplasm, perinuclear region 2 ALOX5, KAT5
focal adhesion 2 CAT, LMLN
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 MBP
chromatin 2 KAT5, TCF3
cell periphery 1 MBP
Chromosome 1 KAT5
[Isoform 3]: Nucleus 1 MBP
Nucleus, nucleolus 1 KAT5
blood microparticle 1 CP
NuA4 histone acetyltransferase complex 1 KAT5
site of double-strand break 1 KAT5
Cytoplasm, cytoskeleton, spindle pole 1 KAT5
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Lipid droplet 2 LIPE, LMLN
Membrane, caveola 1 LIPE
Chromosome, centromere, kinetochore 1 KAT5
Cell projection, cilium, flagellum membrane 1 SLC9C1
Melanosome 1 TYR
euchromatin 1 TCF3
myelin sheath 2 CA2, MBP
pseudopodium 1 F2RL1
intermediate filament cytoskeleton 1 PFDN5
ficolin-1-rich granule lumen 3 ALOX5, CAT, MBP
secretory granule lumen 2 ALOX5, CAT
endoplasmic reticulum lumen 1 CP
nuclear matrix 1 ALOX5
kinetochore 1 KAT5
mitotic spindle pole 1 KAT5
transport vesicle 2 COPA, MBP
beta-catenin-TCF complex 1 TCF3
immunological synapse 1 GZMB
Cytoplasmic vesicle, COPI-coated vesicle membrane 1 COPA
COPI vesicle coat 1 COPA
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
prefoldin complex 1 PFDN5
histone acetyltransferase complex 1 KAT5
nucleosome 1 KAT5
Swr1 complex 1 KAT5
membrane coat 1 COPA
COPI-coated vesicle membrane 1 COPA
compact myelin 1 MBP
internode region of axon 1 MBP
catalase complex 1 CAT
Nucleus intermembrane space 1 ALOX5
Cytolytic granule 1 GZMB
cytolytic granule lumen 1 GZMB
[Bone marrow proteoglycan]: Secreted 1 MBP
[Xenin]: Secreted 1 COPA
Myelin membrane 1 MBP
piccolo histone acetyltransferase complex 1 KAT5


文献列表

  • P Snega Priya, Ajay Guru, Ramu Meenatchi, B Haridevamuthu, Manikandan Velayutham, Boopathi Seenivasan, Raman Pachaiappan, Rajakrishnan Rajagopal, Palaniselvam Kuppusamy, Annie Juliet, Jesu Arockiaraj. Syringol, a wildfire residual methoxyphenol causes cytotoxicity and teratogenicity in zebrafish model. The Science of the total environment. 2023 Mar; 864(?):160968. doi: 10.1016/j.scitotenv.2022.160968. [PMID: 36549541]
  • M D Milan Gowda, K Jayachandra, Vikram Joshi, Vaddarahally N Manjuprasanna, Gotravalli V Rudresha, Devadasan Velmurugan, Raman Pachaiappan, Noor Mohamed Jameel, Bannikuppe S Vishwanath. Syringol isolated from Eleusine coracana (L.) Gaertn bran suppresses inflammatory response through the down-regulation of cPLA2, COX-2, IκBα, p38 and MPO signaling in sPLA2 induced mice paw oedema. Inflammopharmacology. 2022 Oct; 30(5):1853-1870. doi: 10.1007/s10787-022-00983-3. [PMID: 35639234]
  • Xinwen Zhang, Delphis F Levia, Elvis Osamudiamhen Ebikade, Jeffrey Chang, Dionisios G Vlachos, Changqing Wu. The impact of differential lignin S/G ratios on mutagenicity and chicken embryonic toxicity. Journal of applied toxicology : JAT. 2022 03; 42(3):423-435. doi: 10.1002/jat.4229. [PMID: 34448506]
  • Hafiz Saqib Ali, Richard H Henchman, Sam P de Visser. Lignin Biodegradation by a Cytochrome P450 Enzyme: A Computational Study into Syringol Activation by GcoA. Chemistry (Weinheim an der Bergstrasse, Germany). 2020 Oct; 26(57):13093-13102. doi: 10.1002/chem.202002203. [PMID: 32613677]
  • Sayuki Oka, Ryo Kuniba, Nozomi Tsuboi, Sayaka Tsuchida, Kazunari Ushida, Shusuke Tomoshige, Kouji Kuramochi. Isolation, synthesis, and biological activities of a bibenzyl from Empetrum nigrum var. japonicum. Bioscience, biotechnology, and biochemistry. 2020 Jan; 84(1):31-36. doi: 10.1080/09168451.2019.1662279. [PMID: 31794330]
  • Roland Wedekind, Pekka Keski-Rahkonen, Nivonirina Robinot, Vivian Viallon, Pietro Ferrari, Erwan Engel, Marie-Christine Boutron-Ruault, Yahya Mahamat-Saleh, Francesca Romana Mancini, Tilman Kühn, Theron Johnson, Heiner Boeing, Manuela Bergmann, Anna Karakatsani, Antonia Trichopoulou, Heleni Peppa, Claudia Agnoli, Maria Santucci de Magistris, Domenico Palli, Carlotta Sacerdote, Rosario Tumino, Marc J Gunter, Inge Huybrechts, Augustin Scalbert. Syringol metabolites as new biomarkers for smoked meat intake. The American journal of clinical nutrition. 2019 12; 110(6):1424-1433. doi: 10.1093/ajcn/nqz222. [PMID: 31559413]
  • Hongyu Rao, Peibo Li, Hao Wu, Chong Liu, Wei Peng, Weiwei Su. Simultaneous Determination of Six Compounds in Destructive Distillation Extracts of Hawthorn Seed by GC-MS and Evaluation of Their Antimicrobial Activity. Molecules (Basel, Switzerland). 2019 Nov; 24(23):. doi: 10.3390/molecules24234328. [PMID: 31783502]
  • Melodie M Machovina, Sam J B Mallinson, Brandon C Knott, Alexander W Meyers, Marc Garcia-Borràs, Lintao Bu, Japheth E Gado, April Oliver, Graham P Schmidt, Daniel J Hinchen, Michael F Crowley, Christopher W Johnson, Ellen L Neidle, Christina M Payne, Kendall N Houk, Gregg T Beckham, John E McGeehan, Jennifer L DuBois. Enabling microbial syringol conversion through structure-guided protein engineering. Proceedings of the National Academy of Sciences of the United States of America. 2019 07; 116(28):13970-13976. doi: 10.1073/pnas.1820001116. [PMID: 31235604]
  • R Sánchez-Gómez, A Zalacain, F Pardo, G L Alonso, M R Salinas. Moscatel vine-shoot extracts as a grapevine biostimulant to enhance wine quality. Food research international (Ottawa, Ont.). 2017 08; 98(?):40-49. doi: 10.1016/j.foodres.2017.01.004. [PMID: 28610731]
  • Magdalena Szejk, Tomasz Poplawski, Joanna Sarnik, Izabela Pawlaczyk-Graja, Franciszek Czechowski, Alicja Klaudia Olejnik, Roman Gancarz, Halina Malgorzata Zbikowska. Polyphenolic glycoconjugates from medical plants of Rosaceae/Asteraceae family protect human lymphocytes against γ-radiation-induced damage. International journal of biological macromolecules. 2017 Jan; 94(Pt A):585-593. doi: 10.1016/j.ijbiomac.2016.10.053. [PMID: 27769934]
  • S L Mathews, C E Smithson, A M Grunden. Purification and characterization of a recombinant laccase-like multi-copper oxidase from Paenibacillus glucanolyticus SLM1. Journal of applied microbiology. 2016 Nov; 121(5):1335-1345. doi: 10.1111/jam.13241. [PMID: 27451019]
  • Sindhu Mathew, Zainul Akmar Zakaria. Pyroligneous acid-the smoky acidic liquid from plant biomass. Applied microbiology and biotechnology. 2015 Jan; 99(2):611-22. doi: 10.1007/s00253-014-6242-1. [PMID: 25467926]
  • Jun Shigeto, Mariko Nagano, Koki Fujita, Yuji Tsutsumi. Catalytic profile of Arabidopsis peroxidases, AtPrx-2, 25 and 71, contributing to stem lignification. PloS one. 2014; 9(8):e105332. doi: 10.1371/journal.pone.0105332. [PMID: 25137070]
  • Martin Zabka, Roman Pavela. Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. Chemosphere. 2013 Oct; 93(6):1051-6. doi: 10.1016/j.chemosphere.2013.05.076. [PMID: 23800587]
  • Kwan Hee Park, Min Won Lee. Anti-oxidative, anti-inflammatory and whitening effects of phenolic compounds from Bambusae Caulis in Liquamen. Natural product research. 2012; 26(18):1687-91. doi: 10.1080/14786419.2011.593517. [PMID: 21985061]
  • Alberto P Macho, Adela Zumaquero, Juan J Gonzalez-Plaza, Inmaculada Ortiz-Martín, José S Rufián, Carmen R Beuzón. Genetic analysis of the individual contribution to virulence of the type III effector inventory of Pseudomonas syringae pv. phaseolicola. PloS one. 2012; 7(4):e35871. doi: 10.1371/journal.pone.0035871. [PMID: 22558247]
  • Erin D Scully, Kelli Hoover, John Carlson, Ming Tien, Scott M Geib. Proteomic analysis of Fusarium solani isolated from the Asian longhorned beetle, Anoplophora glabripennis. PloS one. 2012; 7(4):e32990. doi: 10.1371/journal.pone.0032990. [PMID: 22496740]
  • Jun Shigeto, Yoshitaka Itoh, Yuji Tsutsumi, Ryuichiro Kondo. Identification of Tyr74 and Tyr177 as substrate oxidation sites in cationic cell wall-bound peroxidase from Populus alba L. The FEBS journal. 2012 Jan; 279(2):348-57. doi: 10.1111/j.1742-4658.2011.08429.x. [PMID: 22099451]
  • Christiane Liers, René Ullrich, Martin Hofrichter, Farida V Minibayeva, Richard P Beckett. A heme peroxidase of the ascomyceteous lichen Leptogium saturninum oxidizes high-redox potential substrates. Fungal genetics and biology : FG & B. 2011 Dec; 48(12):1139-45. doi: 10.1016/j.fgb.2011.10.004. [PMID: 22056522]
  • Venugopal Mendu, Anne E Harman-Ware, Mark Crocker, Jungho Jae, Jozsef Stork, Samuel Morton, Andrew Placido, George Huber, Seth Debolt. Identification and thermochemical analysis of high-lignin feedstocks for biofuel and biochemical production. Biotechnology for biofuels. 2011 Oct; 4(?):43. doi: 10.1186/1754-6834-4-43. [PMID: 22018114]
  • Yi-Min Hsiao, Yu-Fan Liu, Pei-Yu Lee, Pei-Chi Hsu, Szu-Yu Tseng, Yu-Chien Pan. Functional characterization of copA gene encoding multicopper oxidase in Xanthomonas campestris pv. campestris. Journal of agricultural and food chemistry. 2011 Sep; 59(17):9290-302. doi: 10.1021/jf2024006. [PMID: 21790191]
  • David A Baltrus, Marc T Nishimura, Artur Romanchuk, Jeff H Chang, M Shahid Mukhtar, Karen Cherkis, Jeff Roach, Sarah R Grant, Corbin D Jones, Jeffery L Dangl. Dynamic evolution of pathogenicity revealed by sequencing and comparative genomics of 19 Pseudomonas syringae isolates. PLoS pathogens. 2011 Jul; 7(7):e1002132. doi: 10.1371/journal.ppat.1002132. [PMID: 21799664]
  • Gali Nirmal Kumar, Kotteazeth Srikumar. Thermophilic laccase from xerophyte species Opuntia vulgaris. Biomedical chromatography : BMC. 2011 Jun; 25(6):707-11. doi: 10.1002/bmc.1506. [PMID: 20812203]
  • Susanne Herter, Marlen Schmidt, Mark L Thompson, Annett Mikolasch, Frieder Schauer. A new phenol oxidase produced during melanogenesis and encystment stage in the nitrogen-fixing soil bacterium Azotobacter chroococcum. Applied microbiology and biotechnology. 2011 May; 90(3):1037-49. doi: 10.1007/s00253-011-3093-x. [PMID: 21327414]
  • Sara Fondevilla, Helge Küster, Franziska Krajinski, José I Cubero, Diego Rubiales. Identification of genes differentially expressed in a resistant reaction to Mycosphaerella pinodes in pea using microarray technology. BMC genomics. 2011 Jan; 12(?):28. doi: 10.1186/1471-2164-12-28. [PMID: 21226971]
  • Grazyna Bieniek, Krystyna Stepien. Occupational exposure to phenolic compounds at coke plants--urinary excretion of methoxyphenols as an indicator of exposure to methoxyphenols. Journal of occupational health. 2011; 53(2):110-4. doi: 10.1539/joh.o10005. [PMID: 21245652]
  • Leire Bardaji, Isabel Pérez-Martínez, Luis Rodríguez-Moreno, Pablo Rodríguez-Palenzuela, George W Sundin, Cayo Ramos, Jesús Murillo. Sequence and role in virulence of the three plasmid complement of the model tumor-inducing bacterium Pseudomonas savastanoi pv. savastanoi NCPPB 3335. PloS one. 2011; 6(10):e25705. doi: 10.1371/journal.pone.0025705. [PMID: 22022435]
  • Christian Lorenz, Daniela Büttner. Secretion of early and late substrates of the type III secretion system from Xanthomonas is controlled by HpaC and the C-terminal domain of HrcU. Molecular microbiology. 2011 Jan; 79(2):447-67. doi: 10.1111/j.1365-2958.2010.07461.x. [PMID: 21219463]
  • Tongming Yin, Xinye Zhang, Lee Gunter, Ranjan Priya, Robert Sykes, Mark Davis, Stan D Wullschleger, Gerald A Tuskan. Differential detection of genetic Loci underlying stem and root lignin content in Populus. PloS one. 2010 Nov; 5(11):e14021. doi: 10.1371/journal.pone.0014021. [PMID: 21151641]
  • Kai Bao, Yi Dai, Zhi-Bin Zhu, Feng-Juan Tu, Wei-Ge Zhang, Xin-Sheng Yao. Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors. Bioorganic & medicinal chemistry. 2010 Sep; 18(18):6708-14. doi: 10.1016/j.bmc.2010.07.062. [PMID: 20729091]
  • Rosario Díaz, Mario C N Saparrat, Miguel Jurado, Inmaculada García-Romera, Juan Antonio Ocampo, María Jesús Martínez. Biochemical and molecular characterization of Coriolopsis rigida laccases involved in transformation of the solid waste from olive oil production. Applied microbiology and biotechnology. 2010 Sep; 88(1):133-42. doi: 10.1007/s00253-010-2723-z. [PMID: 20607234]
  • Christiane Liers, Caroline Bobeth, Marek Pecyna, René Ullrich, Martin Hofrichter. DyP-like peroxidases of the jelly fungus Auricularia auricula-judae oxidize nonphenolic lignin model compounds and high-redox potential dyes. Applied microbiology and biotechnology. 2010 Feb; 85(6):1869-79. doi: 10.1007/s00253-009-2173-7. [PMID: 19756587]
  • S T Huang, S S Tzean, B Y Tsai, H J Hsieh. Cloning and heterologous expression of a novel ligninolytic peroxidase gene from poroid brown-rot fungus Antrodia cinnamomea. Microbiology (Reading, England). 2009 Feb; 155(Pt 2):424-433. doi: 10.1099/mic.0.022459-0. [PMID: 19202090]
  • Akira Yano, Sayaka Kikuchi, Yuko Nakagawa, Yuichi Sakamoto, Toshitsugu Sato. Secretory expression of the non-secretory-type Lentinula edodes laccase by Aspergillus oryzae. Microbiological research. 2009; 164(6):642-9. doi: 10.1016/j.micres.2008.12.001. [PMID: 19230633]
  • Radoslava Trifonova, Joeke Postma, Francel W A Verstappen, Harro J Bouwmeester, Jan J M H Ketelaars, Jan-Dirk van Elsas. Removal of phytotoxic compounds from torrefied grass fibres by plant-beneficial microorganisms. FEMS microbiology ecology. 2008 Oct; 66(1):158-66. doi: 10.1111/j.1574-6941.2008.00508.x. [PMID: 18537835]
  • Christian Lorenz, Steve Schulz, Thomas Wolsch, Ombeline Rossier, Ulla Bonas, Daniela Büttner. HpaC controls substrate specificity of the Xanthomonas type III secretion system. PLoS pathogens. 2008 Jun; 4(6):e1000094. doi: 10.1371/journal.ppat.1000094. [PMID: 18584024]
  • Jennifer A J Dungait, Natalie A Stear, Bart E van Dongen, Roland Bol, Richard P Evershed. Off-line pyrolysis and compound-specific stable carbon isotope analysis of lignin moieties: a new method for determining the fate of lignin residues in soil. Rapid communications in mass spectrometry : RCM. 2008 Jun; 22(11):1631-9. doi: 10.1002/rcm.3454. [PMID: 18446763]
  • Shinya Sasaki, Daisuke Nonaka, Hiroyuki Wariishi, Yuji Tsutsumi, Ryuichiro Kondo. Role of Tyr residues on the protein surface of cationic cell-wall-peroxidase (CWPO-C) from poplar: potential oxidation sites for oxidative polymerization of lignin. Phytochemistry. 2008 Jan; 69(2):348-55. doi: 10.1016/j.phytochem.2007.08.020. [PMID: 17910963]
  • Anita Zamboni, Leone Minoia, Alberto Ferrarini, Giovanni Battista Tornielli, Elisa Zago, Massimo Delledonne, Mario Pezzotti. Molecular analysis of post-harvest withering in grape by AFLP transcriptional profiling. Journal of experimental botany. 2008; 59(15):4145-59. doi: 10.1093/jxb/ern256. [PMID: 19010774]
  • Sangit Kumar, Lars Engman, Luca Valgimigli, Riccardo Amorati, Maria Grazia Fumo, Gian Franco Pedulli. Antioxidant profile of ethoxyquin and some of its S, Se, and Te analogues. The Journal of organic chemistry. 2007 Aug; 72(16):6046-55. doi: 10.1021/jo0705465. [PMID: 17602530]
  • Min Zhang, Zhiyi Wei, Shaojie Chang, Maikun Teng, Weimin Gong. Crystal structure of a papain-fold protein without the catalytic residue: a novel member in the cysteine proteinase family. Journal of molecular biology. 2006 Apr; 358(1):97-105. doi: 10.1016/j.jmb.2006.01.065. [PMID: 16497323]
  • Russell L Dills, Michael Paulsen, Jacqui Ahmad, David A Kalman, Fady N Elias, Christopher D Simpson. Evaluation of urinary methoxyphenols as biomarkers of woodsmoke exposure. Environmental science & technology. 2006 Apr; 40(7):2163-70. doi: 10.1021/es051886f. [PMID: 16646448]
  • Shinichi Tanimoto, Hitoshi Tominaga, Yoshiharu Okada, Masato Nomura. Synthesis and cosmetic whitening effect of glycosides derived from several phenylpropanoids. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2006 Mar; 126(3):173-7. doi: 10.1248/yakushi.126.173. [PMID: 16508241]
  • Mirjana Stajic, Limor Persky, Emanuel Cohen, Yitzhak Hadar, Ilija Brceski, Solomon P Wasser, Eviatar Nevo. Screening of laccase, manganese peroxidase, and versatile peroxidase activities of the genus Pleurotus in media with some raw plant materials as carbon sources. Applied biochemistry and biotechnology. 2004 Jun; 117(3):155-64. doi: 10.1385/abab:117:3:155. [PMID: 15304767]
  • Takuya Hagihara, Masaru Hashi, Yoji Takeuchi, Naoto Yamaoka. Cloning of soybean genes induced during hypersensitive cell death caused by syringolide elicitor. Planta. 2004 Feb; 218(4):606-14. doi: 10.1007/s00425-003-1136-y. [PMID: 14586656]
  • Grazyna Bieniek. Simultaneous determination of 2-methoxyphenol, 2-methoxy-4-methylphenol, 2,6-dimethoxyphenol and 4'-hydroxy-3'-methoxyacetophenone in urine by capillary gas chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Oct; 795(2):389-94. doi: 10.1016/s1570-0232(03)00593-2. [PMID: 14522045]
  • Jerzy Dec, Konrad Haider, Jean-Marc Bollag. Release of substituents from phenolic compounds during oxidative coupling reactions. Chemosphere. 2003 Jul; 52(3):549-56. doi: 10.1016/s0045-6535(03)00236-4. [PMID: 12738292]
  • Yasushi Okinaka, Ching-Hong Yang, Eliot Herman, Anthony Kinney, Noel T Keen. The P34 syringolide elicitor receptor interacts with a soybean photorespiration enzyme, NADH-dependent hydroxypyruvate reductase. Molecular plant-microbe interactions : MPMI. 2002 Dec; 15(12):1213-8. doi: 10.1094/mpmi.2002.15.12.1213. [PMID: 12481993]
  • R L Dills, X Zhu, D A Kalman. Measurement of urinary methoxyphenols and their use for biological monitoring of wood smoke exposure. Environmental research. 2001 Feb; 85(2):145-58. doi: 10.1006/enrs.2000.4107. [PMID: 11161664]
  • F Ikegami, T Sekine, Y Fujii. [Anti-dermaptophyte activity of phenolic compounds in "mokusaku-eki"]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1998 Jan; 118(1):27-30. doi: 10.1248/yakushi1947.118.1_27. [PMID: 9484039]
  • M M Häggblom, L J Nohynek, M S Salkinoja-Salonen. Degradation and O-methylation of chlorinated phenolic compounds by Rhodococcus and Mycobacterium strains. Applied and environmental microbiology. 1988 Dec; 54(12):3043-52. doi: 10.1128/aem.54.12.3043-3052.1988. [PMID: 3223768]